SmilesManager.ipynb: Knowledge Management

In [1]:

from xv.chemistry.physical import SmilesManager

In [2]:

ke = SmilesManager()
ke

Out[2]:

2867619582784@SmilesManager

Smiles code of molecules and conversion to rdkit molecule

Minimum Grade: 6
Maximum Grade: 12

Examples
--------
ke = SmilesManager()
ke

ke.printProblemTypes()

ke.getRandomProblem()
ke.getRandomProblem(problem_type = 0)
...

ke.printProblem()
ke.printAnswer()
ke.printSolution()

doc_style: xv_doc

In [3]:

ke.getRandomProblem(problem_type = 0, verbose = True)

Problem Template: _problem_examples_smiles

Out[3]:

Give some examples of the simplified molecular-input line-entry system (SMILES).

Note: Use input parameter 'search' to filter result.

In [4]:

from IPython.display import HTML
n = len(ke._problemTemplates)
max_loop = 1
for j in range(0, max_loop):
    for i in range(n):
        problem_type = i
        display(HTML(f"<h2>problem_type: {problem_type}/{n-1} (loop {j}/{max_loop-1})</h2>"))
        ke.getRandomProblem(problem_type = problem_type, verbose = True)
        display(ke.printProblem())

        display(HTML(f"<h6>Answer:</h6>"))
        display(ke.printAnswer())

        display(HTML(f"<h6>Solution:</h6>"))
        display(ke.printSolution())
        pass

problem_type: 0/25 (loop 0/0)

Problem Template: _problem_examples_smiles

[15:16:29] WARNING: Accepted unusual valence(s): Co(6); Metal was disconnected; Proton(s) added/removed

Give some examples of the simplified molecular-input line-entry system (SMILES).

Note: Use input parameter 'search' to filter result.

Answer:

Examples of SMILES:

Br:

S[Co@@](F)(Cl)(Br)(I)C=O:

[Zr]:

biphenyl: A ring closure digit may be reused if desired.: c1ccccc1c1ccccc1

Solution:

Examples of SMILES:

Br:

smiles_non_kekule:    Br
smiles_kekule:    Br
inchi:    InChI=1S/BrH/h1H
inchiKey:    CPELXLSAUQHCOX-UHFFFAOYSA-N
smarts:    [#35]
smarts_isomeric:    [#35]

S[Co@@](F)(Cl)(Br)(I)C=O:

smiles_non_kekule:    O=C[Co](F)(S)(Cl)(Br)I
smiles_kekule:    O=C[Co](F)(S)(Cl)(Br)I
inchi:    InChI=1S/CHO.BrH.ClH.Co.FH.HI.H2S/c1-2;;;;;;/h1H;2*1H;;2*1H;1H2/q;;;+5;;;/p-5
inchiKey:    OFLGBCHBKKTRSH-UHFFFAOYSA-I
smarts:    [#16]-[Co](-[#9])(-[#17])(-[#35])(-[#53])-[#6]=[#8]
smarts_isomeric:    [#16]-[Co](-[#9])(-[#17])(-[#35])(-[#53])-[#6]=[#8]

[Zr]:

smiles_non_kekule:    [Zr]
smiles_kekule:    [Zr]
inchi:    InChI=1S/Zr
inchiKey:    QCWXUUIWCKQGHC-UHFFFAOYSA-N
smarts:    [Zr]
smarts_isomeric:    [Zr]

biphenyl: A ring closure digit may be reused if desired.: c1ccccc1c1ccccc1

smiles_non_kekule:    c1ccc(-c2ccccc2)cc1
smiles_kekule:    C1=CC=C(C2=CC=CC=C2)C=C1
inchi:    InChI=1S/C12H10/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1-10H
inchiKey:    ZUOUZKKEUPVFJK-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

problem_type: 1/25 (loop 0/0)

Problem Template: _problem_search_smiles

Please pass input parameter 'search'.
For example:
search = "methane"

Answer:

None

Solution:

None

problem_type: 2/25 (loop 0/0)

Problem Template: _problem_draw_smiles

Draw the following smiles:
P

Note: Pass input smiles = 'YOUR SMILE CODE'

Answer:

Solution:

Code to draw smiles:

from rdkit import Chem
rdkit_molecule = Chem.MolFromSmiles('P')
if not rdkit_molecule is None:

display(rdkit_molecule)
pass

problem_type: 3/25 (loop 0/0)

Problem Template: _problem_draw_3d_from_smiles

Draw the following smiles:
N[C@H](C)C(=O)O

Note: Pass input smiles = 'YOUR SMILE CODE'

Answer:

N[C@H](C)C(=O)O

Solution:

N[C@H](C)C(=O)O

Code to draw smiles as 3d:

from xv.chemistry.helper import MoleculeVisualizationHelper
visual_helper = MoleculeVisualizationHelper()
visual_helper.mol_object_to_3d('N[C@H](C)C(=O)O')

problem_type: 4/25 (loop 0/0)

Problem Template: _problem_amino_acids

[15:16:31] WARNING: not removing hydrogen atom without neighbors

Write structure of amino acids molecules.

Answer:

structure of amino acids molecules:

alanine: C

arginine: CCCCNC(N)=N

asparagine: CCC(N)=O

aspartic acid: CC(O)=O

cysteine: CS

glutamic acid: CCC(O)=O

glutamine: CCC(N)=O

glycine: [H]

histidine: CC1=CNC=N1

isoleucine: C(CC)([H])C

leucine: CC(C)C

lysine: CCCCN

methionine: CCSC

phenylalanine: CC1=CC=CC=C1

proline: C2CCCN2

serine: CO

threonine: C(C)([H])O

tryptophan: CCC1=CNC2=C1C=CC=C2

tyrosine: CC1=CC=C(O)C=C1

valine: C(C)C

Solution:

structure of amino acids molecules:

alanine: C

smiles_non_kekule:    C
smiles_kekule:    C
inchi:    InChI=1S/CH4/h1H4
inchiKey:    VNWKTOKETHGBQD-UHFFFAOYSA-N
smarts:    [#6]
smarts_isomeric:    [#6]

arginine: CCCCNC(N)=N

smiles_non_kekule:    CCCCNC(=N)N
smiles_kekule:    CCCCNC(=N)N
inchi:    InChI=1S/C5H13N3/c1-2-3-4-8-5(6)7/h2-4H2,1H3,(H4,6,7,8)
inchiKey:    CGWBIHLHAGNJCX-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#7]-[#6](-[#7])=[#7]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#7]-[#6](-[#7])=[#7]

asparagine: CCC(N)=O

smiles_non_kekule:    CCC(N)=O
smiles_kekule:    CCC(N)=O
inchi:    InChI=1S/C3H7NO/c1-2-3(4)5/h2H2,1H3,(H2,4,5)
inchiKey:    QLNJFJADRCOGBJ-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](-[#7])=[#8]
smarts_isomeric:    [#6]-[#6]-[#6](-[#7])=[#8]

aspartic acid: CC(O)=O

smiles_non_kekule:    CC(=O)O
smiles_kekule:    CC(=O)O
inchi:    InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)
inchiKey:    QTBSBXVTEAMEQO-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#8])=[#8]
smarts_isomeric:    [#6]-[#6](-[#8])=[#8]

cysteine: CS

smiles_non_kekule:    CS
smiles_kekule:    CS
inchi:    InChI=1S/CH4S/c1-2/h2H,1H3
inchiKey:    LSDPWZHWYPCBBB-UHFFFAOYSA-N
smarts:    [#6]-[#16]
smarts_isomeric:    [#6]-[#16]

glutamic acid: CCC(O)=O

smiles_non_kekule:    CCC(=O)O
smiles_kekule:    CCC(=O)O
inchi:    InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)
inchiKey:    XBDQKXXYIPTUBI-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](-[#8])=[#8]
smarts_isomeric:    [#6]-[#6]-[#6](-[#8])=[#8]

glutamine: CCC(N)=O

glycine: [H]

smiles_non_kekule:    [H]
smiles_kekule:    [H]
inchi:    InChI=1S/H
inchiKey:    YZCKVEUIGOORGS-UHFFFAOYSA-N
smarts:    [H]
smarts_isomeric:    [H]

histidine: CC1=CNC=N1

smiles_non_kekule:    Cc1c[nH]cn1
smiles_kekule:    CC1=CNC=N1
inchi:    InChI=1S/C4H6N2/c1-4-2-5-3-6-4/h2-3H,1H3,(H,5,6)
inchiKey:    XLSZMDLNRCVEIJ-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#7H]:[#6]:[#7]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#7H]:[#6]:[#7]:1

isoleucine: C(CC)([H])C

smiles_non_kekule:    CCCC
smiles_kekule:    CCCC
inchi:    InChI=1S/C4H10/c1-3-4-2/h3-4H2,1-2H3
inchiKey:    IJDNQMDRQITEOD-UHFFFAOYSA-N
smarts:    [#6H](-[#6]-[#6])-[#6]
smarts_isomeric:    [#6H](-[#6]-[#6])-[#6]

leucine: CC(C)C

smiles_non_kekule:    CC(C)C
smiles_kekule:    CC(C)C
inchi:    InChI=1S/C4H10/c1-4(2)3/h4H,1-3H3
inchiKey:    NNPPMTNAJDCUHE-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6](-[#6])-[#6]

lysine: CCCCN

smiles_non_kekule:    CCCCN
smiles_kekule:    CCCCN
inchi:    InChI=1S/C4H11N/c1-2-3-4-5/h2-5H2,1H3
inchiKey:    HQABUPZFAYXKJW-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#7]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#7]

methionine: CCSC

smiles_non_kekule:    CCSC
smiles_kekule:    CCSC
inchi:    InChI=1S/C3H8S/c1-3-4-2/h3H2,1-2H3
inchiKey:    WXEHBUMAEPOYKP-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#16]-[#6]
smarts_isomeric:    [#6]-[#6]-[#16]-[#6]

phenylalanine: CC1=CC=CC=C1

smiles_non_kekule:    Cc1ccccc1
smiles_kekule:    CC1=CC=CC=C1
inchi:    InChI=1S/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3
inchiKey:    YXFVVABEGXRONW-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

proline: C2CCCN2

smiles_non_kekule:    C1CCNC1
smiles_kekule:    C1CCNC1
inchi:    InChI=1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2
inchiKey:    RWRDLPDLKQPQOW-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#6]-[#7]-1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#6]-[#7]-1

serine: CO

smiles_non_kekule:    CO
smiles_kekule:    CO
inchi:    InChI=1S/CH4O/c1-2/h2H,1H3
inchiKey:    OKKJLVBELUTLKV-UHFFFAOYSA-N
smarts:    [#6]-[#8]
smarts_isomeric:    [#6]-[#8]

threonine: C(C)([H])O

smiles_non_kekule:    CCO
smiles_kekule:    CCO
inchi:    InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3
inchiKey:    LFQSCWFLJHTTHZ-UHFFFAOYSA-N
smarts:    [#6H](-[#6])-[#8]
smarts_isomeric:    [#6H](-[#6])-[#8]

tryptophan: CCC1=CNC2=C1C=CC=C2

smiles_non_kekule:    CCc1c[nH]c2ccccc12
smiles_kekule:    CCC1=CNC2=C1C=CC=C2
inchi:    InChI=1S/C10H11N/c1-2-8-7-11-10-6-4-3-5-9(8)10/h3-7,11H,2H2,1H3
inchiKey:    GOVXKUCVZUROAN-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]1:[#6]:[#7H]:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#6]-[#6]-[#6]1:[#6]:[#7H]:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2

tyrosine: CC1=CC=C(O)C=C1

smiles_non_kekule:    Cc1ccc(O)cc1
smiles_kekule:    CC1=CC=C(O)C=C1
inchi:    InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3
inchiKey:    IWDCLRJOBJJRNH-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6](-[#8]):[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6](-[#8]):[#6]:[#6]:1

valine: C(C)C

smiles_non_kekule:    CCC
smiles_kekule:    CCC
inchi:    InChI=1S/C3H8/c1-3-2/h3H2,1-2H3
inchiKey:    ATUOYWHBWRKTHZ-UHFFFAOYSA-N
smarts:    [#6](-[#6])-[#6]
smarts_isomeric:    [#6](-[#6])-[#6]

problem_type: 5/25 (loop 0/0)

Problem Template: _problem_braf_kinase_inhibitors_for_cancer

Write structure of braf kinase inhibitors for cancer molecules.

Answer:

structure of braf kinase inhibitors for cancer molecules:

imidazole: C1=CN=CN1

pyrazole-1-ethanol: OCCN1N=CC=C1

acetonitrile: C#N

2-(tert-butyl)thiazole: CC(C)(C)C1=NC=CS1

pyridine: C1=CC=NC=C1

1-isopropyl-pyrazole: CC(C)N1N=CC=C1

isoindoline: C12=CC=CC=C1CNC2

pyrrolopyridine: C12=CC=CN=C1C=CN2

Solution:

structure of braf kinase inhibitors for cancer molecules:

imidazole: C1=CN=CN1

smiles_non_kekule:    c1c[nH]cn1
smiles_kekule:    C1=CNC=N1
inchi:    InChI=1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)
inchiKey:    RAXXELZNTBOGNW-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#7]:[#6]:[#7H]:1
smarts_isomeric:    [#6]1:[#6]:[#7]:[#6]:[#7H]:1

pyrazole-1-ethanol: OCCN1N=CC=C1

smiles_non_kekule:    OCCn1cccn1
smiles_kekule:    OCCN1C=CC=N1
inchi:    InChI=1S/C5H8N2O/c8-5-4-7-3-1-2-6-7/h1-3,8H,4-5H2
inchiKey:    DXFBKDSQMUFYLD-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]-[#7]1:[#7]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#8]-[#6]-[#6]-[#7]1:[#7]:[#6]:[#6]:[#6]:1

acetonitrile: C#N

smiles_non_kekule:    C#N
smiles_kekule:    C#N
inchi:    InChI=1S/CHN/c1-2/h1H
inchiKey:    LELOWRISYMNNSU-UHFFFAOYSA-N
smarts:    [#6]#[#7]
smarts_isomeric:    [#6]#[#7]

2-(tert-butyl)thiazole: CC(C)(C)C1=NC=CS1

smiles_non_kekule:    CC(C)(C)c1nccs1
smiles_kekule:    CC(C)(C)C1=NC=CS1
inchi:    InChI=1S/C7H11NS/c1-7(2,3)6-8-4-5-9-6/h4-5H,1-3H3
inchiKey:    DQAIZGWCKXJRSP-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])(-[#6])-[#6]1:[#7]:[#6]:[#6]:[#16]:1
smarts_isomeric:    [#6]-[#6](-[#6])(-[#6])-[#6]1:[#7]:[#6]:[#6]:[#16]:1

pyridine: C1=CC=NC=C1

smiles_non_kekule:    c1ccncc1
smiles_kekule:    C1=CC=NC=C1
inchi:    InChI=1S/C5H5N/c1-2-4-6-5-3-1/h1-5H
inchiKey:    JUJWROOIHBZHMG-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#7]:[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#7]:[#6]:[#6]:1

1-isopropyl-pyrazole: CC(C)N1N=CC=C1

smiles_non_kekule:    CC(C)n1cccn1
smiles_kekule:    CC(C)N1C=CC=N1
inchi:    InChI=1S/C6H10N2/c1-6(2)8-5-3-4-7-8/h3-6H,1-2H3
inchiKey:    ANMVTDVBEDVFRB-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])-[#7]1:[#7]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6](-[#6])-[#7]1:[#7]:[#6]:[#6]:[#6]:1

isoindoline: C12=CC=CC=C1CNC2

smiles_non_kekule:    c1ccc2c(c1)CNC2
smiles_kekule:    C1=CC=C2CNCC2=C1
inchi:    InChI=1S/C8H9N/c1-2-4-8-6-9-5-7(8)3-1/h1-4,9H,5-6H2
inchiKey:    GWVMLCQWXVFZCN-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#7]-[#6]-2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#7]-[#6]-2

pyrrolopyridine: C12=CC=CN=C1C=CN2

smiles_non_kekule:    c1cnc2cc[nH]c2c1
smiles_kekule:    C1=CN=C2C=CNC2=C1
inchi:    InChI=1S/C7H6N2/c1-2-6-7(8-4-1)3-5-9-6/h1-5,9H
inchiKey:    XWIYUCRMWCHYJR-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#7]:[#6]:1:[#6]:[#6]:[#7H]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#7]:[#6]:1:[#6]:[#6]:[#7H]:2

problem_type: 6/25 (loop 0/0)

[15:16:38] WARNING: Omitted undefined stereo

[15:16:38] WARNING: Omitted undefined stereo

[15:16:38] WARNING: Charges were rearranged

[15:16:38] WARNING: Omitted undefined stereo

[15:16:38] WARNING: Omitted undefined stereo

[15:16:38] WARNING: Omitted undefined stereo

[15:16:38] WARNING: Omitted undefined stereo

[15:16:38] WARNING: Omitted undefined stereo

Problem Template: _problem_chemical_adsorption_on_montmorillonite_clays

Write structure of chemical adsorption on montmorillonite clays molecules.

Answer:

structure of chemical adsorption on montmorillonite clays molecules:

3,3′,4,4′,5-pentachlorobiphenyl: C1=CC(=C(C=C1C2=CC(=C(C(=C2)Cl)Cl)Cl)Cl)Cl

3,4,3′,4′-tetrachlorobiphenyl: C1=CC(=C(C=C1C2=CC(=C(C=C2)Cl)Cl)Cl)Cl

2,2′,4,4′,5,5′-hexachlorobiphenyl: C1=C(C(=CC(=C1Cl)Cl)Cl)C2=CC(=C(C=C2Cl)Cl)Cl

bisphenol A: CC(C)(C1=CC=C(C=C1)O)C2=CC=C(C=C2)O

2,3,3′,4,4′,5′-hexachlorobiphenyl: C1=CC(=C(C=C1C2=CC(=C(C(=C2Cl)Cl)Cl)Cl)Cl)Cl

2,2′,4,4′,6,6′-hexachlorobiphenyl: C1=C(C=C(C(=C1Cl)C2=CC(=C(C=C2Cl)Cl)Cl)Cl)Cl

2,2′,4,4′,5,6′-hexachlorobiphenyl: C1=CC=C(C(=C1)C2=C(C(=C(C(=C2Cl)Cl)Cl)Cl)Cl)Cl

lindane: C1(C(C(C(C(C1Cl)Cl)Cl)Cl)Cl)Cl

naphthalene: C1=CC=C2C=CC=CC2=C1

benz[e]acephenanthrylene: C1=CC=C2C3=C4C(=CC=C3)C5=CC=CC=C5C4=CC2=C1

dieldrin: C1C2C3C(C1C4C2O4)C5(C(=C(C3(C5(Cl)Cl)Cl)Cl)Cl)Cl

linuron: CN(C(=O)NC1=CC(=C(C=C1)Cl)Cl)OC

trifluralin: CCCN(CCC)C1=C(C=C(C=C1[N+](=O)[O-])C(F)(F)F)[N+](=O)[O-]

toluene: CC1=CC=CC=C1

benzene: C1=CC=CC=C1

bisphenol S: C1=CC(=CC=C1O)S(=O)(=O)C2=CC=C(C=C2)O

bisphenol F: c1cc(ccc1Cc2ccc(cc2)O)O

benzo[a]pyrene: C1=CC=C2C3=C4C(=CC2=C1)C=CC5=C4C(=CC=C5)C=C3

2,4-dichlorophenoxyacetic acid: C1=CC(=C(C=C1Cl)Cl)OCC(=O)O

clofenotane (DDT): C1=CC(=CC=C1C(C2=CC=C(C=C2)Cl)C(Cl)(Cl)Cl)Cl

pyrene: C1=CC2=C3C(=C1)C=CC4=CC=CC(=C43)C=C2

deoxynivalenol (vomitoxin): CC1=CC2C(C(C1=O)O)(C3(CC(C(C34CO4)O2)O)C)CO

glyphosate: C(C(=O)O)NCP(=O)(O)O

fumonisin-B1: CCCCC(C)C(C(CC(C)CC(CCCCC(CC(C(C)N)O)O)O)OC(=O)CC(CC(=O)O)C(=O)O)OC(=O)CC(CC(=O)O)C(=O)O

aflatoxin-B1: COC1=C2C3=C(C(=O)CC3)C(=O)OC2=C4C5C=COC5OC4=C1

2,4,6-trichlorophenol: C1=C(C=C(C(=C1Cl)O)Cl)Cl

diazinon: CCOP(=S)(OCC)OC1=NC(=NC(=C1)C)C(C)C

paraquat: C[N+]1=CC=C(C=C1)C2=CC=[N+](C=C2)C

phenol: C1=CC=C(C=C1)O

aminomethylphosphonic acid: C(N)P(=O)(O)O

chlorpyriphos: CCOP(=S)(OCC)OC1=NC(=C(C=C1Cl)Cl)Cl

xearalenone: CC1CCCC(=O)CCCC=CC2=C(C(=CC(=C2)O)O)C(=O)O1

aldicarb: CC(C)(C=NOC(=O)NC)SC

Solution:

structure of chemical adsorption on montmorillonite clays molecules:

3,3′,4,4′,5-pentachlorobiphenyl: C1=CC(=C(C=C1C2=CC(=C(C(=C2)Cl)Cl)Cl)Cl)Cl

smiles_non_kekule:    Clc1ccc(-c2cc(Cl)c(Cl)c(Cl)c2)cc1Cl
smiles_kekule:    ClC1=C(Cl)C=C(C2=CC(Cl)=C(Cl)C(Cl)=C2)C=C1
inchi:    InChI=1S/C12H5Cl5/c13-8-2-1-6(3-9(8)14)7-4-10(15)12(17)11(16)5-7/h1-5H
inchiKey:    REHONNLQRWTIFF-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#6]1:[#6]:[#6](:[#6](:[#6](:[#6]:1)-[#17])-[#17])-[#17])-[#17])-[#17]
smarts_isomeric:    [#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#6]1:[#6]:[#6](:[#6](:[#6](:[#6]:1)-[#17])-[#17])-[#17])-[#17])-[#17]

3,4,3′,4′-tetrachlorobiphenyl: C1=CC(=C(C=C1C2=CC(=C(C=C2)Cl)Cl)Cl)Cl

smiles_non_kekule:    Clc1ccc(-c2ccc(Cl)c(Cl)c2)cc1Cl
smiles_kekule:    ClC1=C(Cl)C=C(C2=CC(Cl)=C(Cl)C=C2)C=C1
inchi:    InChI=1S/C12H6Cl4/c13-9-3-1-7(5-11(9)15)8-2-4-10(14)12(16)6-8/h1-6H
inchiKey:    UQMGJOKDKOLIDP-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1)-[#17])-[#17])-[#17])-[#17]
smarts_isomeric:    [#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1)-[#17])-[#17])-[#17])-[#17]

2,2′,4,4′,5,5′-hexachlorobiphenyl: C1=C(C(=CC(=C1Cl)Cl)Cl)C2=CC(=C(C=C2Cl)Cl)Cl

smiles_non_kekule:    Clc1cc(Cl)c(-c2cc(Cl)c(Cl)cc2Cl)cc1Cl
smiles_kekule:    ClC1=C(Cl)C=C(C2=CC(Cl)=C(Cl)C=C2Cl)C(Cl)=C1
inchi:    InChI=1S/C12H4Cl6/c13-7-3-11(17)9(15)1-5(7)6-2-10(16)12(18)4-8(6)14/h1-4H
inchiKey:    MVWHGTYKUMDIHL-UHFFFAOYSA-N
smarts:    [#6]1:[#6](:[#6](:[#6]:[#6](:[#6]:1-[#17])-[#17])-[#17])-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#17])-[#17])-[#17]
smarts_isomeric:    [#6]1:[#6](:[#6](:[#6]:[#6](:[#6]:1-[#17])-[#17])-[#17])-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#17])-[#17])-[#17]

bisphenol A: CC(C)(C1=CC=C(C=C1)O)C2=CC=C(C=C2)O

smiles_non_kekule:    CC(C)(c1ccc(O)cc1)c1ccc(O)cc1
smiles_kekule:    CC(C)(C1=CC=C(O)C=C1)C1=CC=C(O)C=C1
inchi:    InChI=1S/C15H16O2/c1-15(2,11-3-7-13(16)8-4-11)12-5-9-14(17)10-6-12/h3-10,16-17H,1-2H3
inchiKey:    IISBACLAFKSPIT-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])(-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#8])-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#8]
smarts_isomeric:    [#6]-[#6](-[#6])(-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#8])-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#8]

2,3,3′,4,4′,5′-hexachlorobiphenyl: C1=CC(=C(C=C1C2=CC(=C(C(=C2Cl)Cl)Cl)Cl)Cl)Cl

smiles_non_kekule:    Clc1ccc(-c2cc(Cl)c(Cl)c(Cl)c2Cl)cc1Cl
smiles_kekule:    ClC1=C(Cl)C=C(C2=CC(Cl)=C(Cl)C(Cl)=C2Cl)C=C1
inchi:    InChI=1S/C12H4Cl6/c13-7-2-1-5(3-8(7)14)6-4-9(15)11(17)12(18)10(6)16/h1-4H
inchiKey:    LCXMEXLGMKFLQO-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#6]1:[#6]:[#6](:[#6](:[#6](:[#6]:1-[#17])-[#17])-[#17])-[#17])-[#17])-[#17]
smarts_isomeric:    [#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#6]1:[#6]:[#6](:[#6](:[#6](:[#6]:1-[#17])-[#17])-[#17])-[#17])-[#17])-[#17]

2,2′,4,4′,6,6′-hexachlorobiphenyl: C1=C(C=C(C(=C1Cl)C2=CC(=C(C=C2Cl)Cl)Cl)Cl)Cl

smiles_non_kekule:    Clc1cc(Cl)c(-c2cc(Cl)c(Cl)cc2Cl)c(Cl)c1
smiles_kekule:    ClC1=CC(Cl)=C(C2=CC(Cl)=C(Cl)C=C2Cl)C(Cl)=C1
inchi:    InChI=1S/C12H4Cl6/c13-5-1-10(17)12(11(18)2-5)6-3-8(15)9(16)4-7(6)14/h1-4H
inchiKey:    QXZHEJWDLVUFFB-UHFFFAOYSA-N
smarts:    [#6]1:[#6](:[#6]:[#6](:[#6](:[#6]:1-[#17])-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#17])-[#17])-[#17])-[#17])-[#17]
smarts_isomeric:    [#6]1:[#6](:[#6]:[#6](:[#6](:[#6]:1-[#17])-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#17])-[#17])-[#17])-[#17])-[#17]

2,2′,4,4′,5,6′-hexachlorobiphenyl: C1=CC=C(C(=C1)C2=C(C(=C(C(=C2Cl)Cl)Cl)Cl)Cl)Cl

smiles_non_kekule:    Clc1ccccc1-c1c(Cl)c(Cl)c(Cl)c(Cl)c1Cl
smiles_kekule:    ClC1=CC=CC=C1C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl
inchi:    InChI=1S/C12H4Cl6/c13-6-4-2-1-3-5(6)7-8(14)10(16)12(18)11(17)9(7)15/h1-4H
inchiKey:    RUEIBQJFGMERJD-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](:[#6](:[#6]:1)-[#6]1:[#6](:[#6](:[#6](:[#6](:[#6]:1-[#17])-[#17])-[#17])-[#17])-[#17])-[#17]
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](:[#6](:[#6]:1)-[#6]1:[#6](:[#6](:[#6](:[#6](:[#6]:1-[#17])-[#17])-[#17])-[#17])-[#17])-[#17]

lindane: C1(C(C(C(C(C1Cl)Cl)Cl)Cl)Cl)Cl

smiles_non_kekule:    ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl
smiles_kekule:    ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl
inchi:    InChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H
inchiKey:    JLYXXMFPNIAWKQ-UHFFFAOYSA-N
smarts:    [#6]1(-[#6](-[#6](-[#6](-[#6](-[#6]-1-[#17])-[#17])-[#17])-[#17])-[#17])-[#17]
smarts_isomeric:    [#6]1(-[#6](-[#6](-[#6](-[#6](-[#6]-1-[#17])-[#17])-[#17])-[#17])-[#17])-[#17]

naphthalene: C1=CC=C2C=CC=CC2=C1

smiles_non_kekule:    c1ccc2ccccc2c1
smiles_kekule:    C1=CC=C2C=CC=CC2=C1
inchi:    InChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
inchiKey:    UFWIBTONFRDIAS-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#6]:1

benz[e]acephenanthrylene: C1=CC=C2C3=C4C(=CC=C3)C5=CC=CC=C5C4=CC2=C1

smiles_non_kekule:    c1ccc2c(c1)-c1cccc3c1c-2cc1ccccc13
smiles_kekule:    C1=CC=C2C(=C1)C1=CC=CC3=C1C2=CC1=CC=CC=C13
inchi:    InChI=1S/C20H12/c1-2-7-14-13(6-1)12-19-16-9-4-3-8-15(16)18-11-5-10-17(14)20(18)19/h1-12H
inchiKey:    FTOVXSOBNPWTSH-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]2:[#6]3:[#6]4:[#6](:[#6]:[#6]:[#6]:3)-[#6]3:[#6]:[#6]:[#6]:[#6]:[#6]:3-[#6]:4:[#6]:[#6]:2:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]2:[#6]3:[#6]4:[#6](:[#6]:[#6]:[#6]:3)-[#6]3:[#6]:[#6]:[#6]:[#6]:[#6]:3-[#6]:4:[#6]:[#6]:2:[#6]:1

dieldrin: C1C2C3C(C1C4C2O4)C5(C(=C(C3(C5(Cl)Cl)Cl)Cl)Cl)Cl

smiles_non_kekule:    ClC1=C(Cl)C2(Cl)C3C4CC(C5OC45)C3C1(Cl)C2(Cl)Cl
smiles_kekule:    ClC1=C(Cl)C2(Cl)C3C4CC(C5OC45)C3C1(Cl)C2(Cl)Cl
inchi:    InChI=1S/C12H8Cl6O/c13-8-9(14)11(16)5-3-1-2(6-7(3)19-6)4(5)10(8,15)12(11,17)18/h2-7H,1H2
inchiKey:    DFBKLUNHFCTMDC-UHFFFAOYSA-N
smarts:    [#6]1-[#6]2-[#6]3-[#6](-[#6]-1-[#6]1-[#6]-2-[#8]-1)-[#6]1(-[#6](=[#6](-[#6]-3(-[#6]-1(-[#17])-[#17])-[#17])-[#17])-[#17])-[#17]
smarts_isomeric:    [#6]1-[#6]2-[#6]3-[#6](-[#6]-1-[#6]1-[#6]-2-[#8]-1)-[#6]1(-[#6](=[#6](-[#6]-3(-[#6]-1(-[#17])-[#17])-[#17])-[#17])-[#17])-[#17]

linuron: CN(C(=O)NC1=CC(=C(C=C1)Cl)Cl)OC

smiles_non_kekule:    CON(C)C(=O)Nc1ccc(Cl)c(Cl)c1
smiles_kekule:    CON(C)C(=O)NC1=CC(Cl)=C(Cl)C=C1
inchi:    InChI=1S/C9H10Cl2N2O2/c1-13(15-2)9(14)12-6-3-4-7(10)8(11)5-6/h3-5H,1-2H3,(H,12,14)
inchiKey:    XKJMBINCVNINCA-UHFFFAOYSA-N
smarts:    [#6]-[#7](-[#6](=[#8])-[#7]-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1)-[#17])-[#17])-[#8]-[#6]
smarts_isomeric:    [#6]-[#7](-[#6](=[#8])-[#7]-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1)-[#17])-[#17])-[#8]-[#6]

trifluralin: CCCN(CCC)C1=C(C=C(C=C1[N+](=O)[O-])C(F)(F)F)[N+](=O)[O-]

smiles_non_kekule:    CCCN(CCC)c1c([N+](=O)[O-])cc(C(F)(F)F)cc1[N+](=O)[O-]
smiles_kekule:    CCCN(CCC)C1=C([N+](=O)[O-])C=C(C(F)(F)F)C=C1[N+](=O)[O-]
inchi:    InChI=1S/C13H16F3N3O4/c1-3-5-17(6-4-2)12-10(18(20)21)7-9(13(14,15)16)8-11(12)19(22)23/h7-8H,3-6H2,1-2H3
inchiKey:    ZSDSQXJSNMTJDA-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#7](-[#6]-[#6]-[#6])-[#6]1:[#6](:[#6]:[#6](:[#6]:[#6]:1-[#7+](=[#8])-[#8-])-[#6](-[#9])(-[#9])-[#9])-[#7+](=[#8])-[#8-]
smarts_isomeric:    [#6]-[#6]-[#6]-[#7](-[#6]-[#6]-[#6])-[#6]1:[#6](:[#6]:[#6](:[#6]:[#6]:1-[#7+](=[#8])-[#8-])-[#6](-[#9])(-[#9])-[#9])-[#7+](=[#8])-[#8-]

toluene: CC1=CC=CC=C1

benzene: C1=CC=CC=C1

smiles_non_kekule:    c1ccccc1
smiles_kekule:    C1=CC=CC=C1
inchi:    InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H
inchiKey:    UHOVQNZJYSORNB-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

bisphenol S: C1=CC(=CC=C1O)S(=O)(=O)C2=CC=C(C=C2)O

smiles_non_kekule:    O=S(=O)(c1ccc(O)cc1)c1ccc(O)cc1
smiles_kekule:    O=S(=O)(C1=CC=C(O)C=C1)C1=CC=C(O)C=C1
inchi:    InChI=1S/C12H10O4S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8,13-14H
inchiKey:    VPWNQTHUCYMVMZ-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1-[#8])-[#16](=[#8])(=[#8])-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#8]
smarts_isomeric:    [#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1-[#8])-[#16](=[#8])(=[#8])-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#8]

bisphenol F: c1cc(ccc1Cc2ccc(cc2)O)O

smiles_non_kekule:    Oc1ccc(Cc2ccc(O)cc2)cc1
smiles_kekule:    OC1=CC=C(CC2=CC=C(O)C=C2)C=C1
inchi:    InChI=1S/C13H12O2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8,14-15H,9H2
inchiKey:    PXKLMJQFEQBVLD-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#8])-[#8]
smarts_isomeric:    [#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#8])-[#8]

benzo[a]pyrene: C1=CC=C2C3=C4C(=CC2=C1)C=CC5=C4C(=CC=C5)C=C3

smiles_non_kekule:    c1ccc2c(c1)cc1ccc3cccc4ccc2c1c34
smiles_kekule:    C1=CC=C2C(=C1)C=C1C=CC3=C4C(=CC=C3)C=CC2=C14
inchi:    InChI=1S/C20H12/c1-2-7-17-15(4-1)12-16-9-8-13-5-3-6-14-10-11-18(17)20(16)19(13)14/h1-12H
inchiKey:    FMMWHPNWAFZXNH-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]2:[#6]3:[#6]4:[#6](:[#6]:[#6]:2:[#6]:1):[#6]:[#6]:[#6]1:[#6]:4:[#6](:[#6]:[#6]:[#6]:1):[#6]:[#6]:3
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]2:[#6]3:[#6]4:[#6](:[#6]:[#6]:2:[#6]:1):[#6]:[#6]:[#6]1:[#6]:4:[#6](:[#6]:[#6]:[#6]:1):[#6]:[#6]:3

2,4-dichlorophenoxyacetic acid: C1=CC(=C(C=C1Cl)Cl)OCC(=O)O

smiles_non_kekule:    O=C(O)COc1ccc(Cl)cc1Cl
smiles_kekule:    O=C(O)COC1=C(Cl)C=C(Cl)C=C1
inchi:    InChI=1S/C8H6Cl2O3/c9-5-1-2-7(6(10)3-5)13-4-8(11)12/h1-3H,4H2,(H,11,12)
inchiKey:    OVSKIKFHRZPJSS-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#17])-[#17])-[#8]-[#6]-[#6](=[#8])-[#8]
smarts_isomeric:    [#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#17])-[#17])-[#8]-[#6]-[#6](=[#8])-[#8]

clofenotane (DDT): C1=CC(=CC=C1C(C2=CC=C(C=C2)Cl)C(Cl)(Cl)Cl)Cl

smiles_non_kekule:    Clc1ccc(C(c2ccc(Cl)cc2)C(Cl)(Cl)Cl)cc1
smiles_kekule:    ClC1=CC=C(C(C2=CC=C(Cl)C=C2)C(Cl)(Cl)Cl)C=C1
inchi:    InChI=1S/C14H9Cl5/c15-11-5-1-9(2-6-11)13(14(17,18)19)10-3-7-12(16)8-4-10/h1-8,13H
inchiKey:    YVGGHNCTFXOJCH-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1-[#6](-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#17])-[#6](-[#17])(-[#17])-[#17])-[#17]
smarts_isomeric:    [#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1-[#6](-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#17])-[#6](-[#17])(-[#17])-[#17])-[#17]

pyrene: C1=CC2=C3C(=C1)C=CC4=CC=CC(=C43)C=C2

smiles_non_kekule:    c1cc2ccc3cccc4ccc(c1)c2c34
smiles_kekule:    C1=CC2=C3C(=C1)C=CC1=CC=CC(=C13)C=C2
inchi:    InChI=1S/C16H10/c1-3-11-7-9-13-5-2-6-14-10-8-12(4-1)15(11)16(13)14/h1-10H
inchiKey:    BBEAQIROQSPTKN-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]2:[#6]3:[#6](:[#6]:1):[#6]:[#6]:[#6]1:[#6]:[#6]:[#6]:[#6](:[#6]:3:1):[#6]:[#6]:2
smarts_isomeric:    [#6]1:[#6]:[#6]2:[#6]3:[#6](:[#6]:1):[#6]:[#6]:[#6]1:[#6]:[#6]:[#6]:[#6](:[#6]:3:1):[#6]:[#6]:2

deoxynivalenol (vomitoxin): CC1=CC2C(C(C1=O)O)(C3(CC(C(C34CO4)O2)O)C)CO

smiles_non_kekule:    CC1=CC2OC3C(O)CC(C)(C34CO4)C2(CO)C(O)C1=O
smiles_kekule:    CC1=CC2OC3C(O)CC(C)(C34CO4)C2(CO)C(O)C1=O
inchi:    InChI=1S/C15H20O6/c1-7-3-9-14(5-16,11(19)10(7)18)13(2)4-8(17)12(21-9)15(13)6-20-15/h3,8-9,11-12,16-17,19H,4-6H2,1-2H3
inchiKey:    LINOMUASTDIRTM-UHFFFAOYSA-N
smarts:    [#6]-[#6]1=[#6]-[#6]2-[#6](-[#6](-[#6]-1=[#8])-[#8])(-[#6]1(-[#6]-[#6](-[#6](-[#6]-13-[#6]-[#8]-3)-[#8]-2)-[#8])-[#6])-[#6]-[#8]
smarts_isomeric:    [#6]-[#6]1=[#6]-[#6]2-[#6](-[#6](-[#6]-1=[#8])-[#8])(-[#6]1(-[#6]-[#6](-[#6](-[#6]-13-[#6]-[#8]-3)-[#8]-2)-[#8])-[#6])-[#6]-[#8]

glyphosate: C(C(=O)O)NCP(=O)(O)O

smiles_non_kekule:    O=C(O)CNCP(=O)(O)O
smiles_kekule:    O=C(O)CNCP(=O)(O)O
inchi:    InChI=1S/C3H8NO5P/c5-3(6)1-4-2-10(7,8)9/h4H,1-2H2,(H,5,6)(H2,7,8,9)
inchiKey:    XDDAORKBJWWYJS-UHFFFAOYSA-N
smarts:    [#6](-[#6](=[#8])-[#8])-[#7]-[#6]-[#15](=[#8])(-[#8])-[#8]
smarts_isomeric:    [#6](-[#6](=[#8])-[#8])-[#7]-[#6]-[#15](=[#8])(-[#8])-[#8]

fumonisin-B1: CCCCC(C)C(C(CC(C)CC(CCCCC(CC(C(C)N)O)O)O)OC(=O)CC(CC(=O)O)C(=O)O)OC(=O)CC(CC(=O)O)C(=O)O

smiles_non_kekule:    CCCCC(C)C(OC(=O)CC(CC(=O)O)C(=O)O)C(CC(C)CC(O)CCCCC(O)CC(O)C(C)N)OC(=O)CC(CC(=O)O)C(=O)O
smiles_kekule:    CCCCC(C)C(OC(=O)CC(CC(=O)O)C(=O)O)C(CC(C)CC(O)CCCCC(O)CC(O)C(C)N)OC(=O)CC(CC(=O)O)C(=O)O
inchi:    InChI=1S/C34H59NO15/c1-5-6-9-20(3)32(50-31(44)17-23(34(47)48)15-29(41)42)27(49-30(43)16-22(33(45)46)14-28(39)40)13-19(2)12-24(36)10-7-8-11-25(37)18-26(38)21(4)35/h19-27,32,36-38H,5-18,35H2,1-4H3,(H,39,40)(H,41,42)(H,45,46)(H,47,48)
inchiKey:    UVBUBMSSQKOIBE-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6](-[#6])-[#6](-[#6](-[#6]-[#6](-[#6])-[#6]-[#6](-[#6]-[#6]-[#6]-[#6]-[#6](-[#6]-[#6](-[#6](-[#6])-[#7])-[#8])-[#8])-[#8])-[#8]-[#6](=[#8])-[#6]-[#6](-[#6]-[#6](=[#8])-[#8])-[#6](=[#8])-[#8])-[#8]-[#6](=[#8])-[#6]-[#6](-[#6]-[#6](=[#8])-[#8])-[#6](=[#8])-[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6](-[#6])-[#6](-[#6](-[#6]-[#6](-[#6])-[#6]-[#6](-[#6]-[#6]-[#6]-[#6]-[#6](-[#6]-[#6](-[#6](-[#6])-[#7])-[#8])-[#8])-[#8])-[#8]-[#6](=[#8])-[#6]-[#6](-[#6]-[#6](=[#8])-[#8])-[#6](=[#8])-[#8])-[#8]-[#6](=[#8])-[#6]-[#6](-[#6]-[#6](=[#8])-[#8])-[#6](=[#8])-[#8]

aflatoxin-B1: COC1=C2C3=C(C(=O)CC3)C(=O)OC2=C4C5C=COC5OC4=C1

smiles_non_kekule:    COc1cc2c(c3oc(=O)c4c(c13)CCC4=O)C1C=COC1O2
smiles_kekule:    COC1=C2C3=C(C(=O)CC3)C(=O)OC2=C2C(=C1)OC1OC=CC21
inchi:    InChI=1S/C17H12O6/c1-20-10-6-11-14(8-4-5-21-17(8)22-11)15-13(10)7-2-3-9(18)12(7)16(19)23-15/h4-6,8,17H,2-3H2,1H3
inchiKey:    OQIQSTLJSLGHID-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]1:[#6]2:[#6]3:[#6](-[#6](=[#8])-[#6]-[#6]-3):[#6](=[#8]):[#8]:[#6]:2:[#6]2-[#6]3-[#6]=[#6]-[#8]-[#6]-3-[#8]-[#6]:2:[#6]:1
smarts_isomeric:    [#6]-[#8]-[#6]1:[#6]2:[#6]3:[#6](-[#6](=[#8])-[#6]-[#6]-3):[#6](=[#8]):[#8]:[#6]:2:[#6]2-[#6]3-[#6]=[#6]-[#8]-[#6]-3-[#8]-[#6]:2:[#6]:1

2,4,6-trichlorophenol: C1=C(C=C(C(=C1Cl)O)Cl)Cl

smiles_non_kekule:    Oc1c(Cl)cc(Cl)cc1Cl
smiles_kekule:    OC1=C(Cl)C=C(Cl)C=C1Cl
inchi:    InChI=1S/C6H3Cl3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H
inchiKey:    LINPIYWFGCPVIE-UHFFFAOYSA-N
smarts:    [#6]1:[#6](:[#6]:[#6](:[#6](:[#6]:1-[#17])-[#8])-[#17])-[#17]
smarts_isomeric:    [#6]1:[#6](:[#6]:[#6](:[#6](:[#6]:1-[#17])-[#8])-[#17])-[#17]

diazinon: CCOP(=S)(OCC)OC1=NC(=NC(=C1)C)C(C)C

smiles_non_kekule:    CCOP(=S)(OCC)Oc1cc(C)nc(C(C)C)n1
smiles_kekule:    CCOP(=S)(OCC)OC1=NC(C(C)C)=NC(C)=C1
inchi:    InChI=1S/C12H21N2O3PS/c1-6-15-18(19,16-7-2)17-11-8-10(5)13-12(14-11)9(3)4/h8-9H,6-7H2,1-5H3
inchiKey:    FHIVAFMUCKRCQO-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]-[#15](=[#16])(-[#8]-[#6]-[#6])-[#8]-[#6]1:[#7]:[#6](:[#7]:[#6](:[#6]:1)-[#6])-[#6](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6]-[#8]-[#15](=[#16])(-[#8]-[#6]-[#6])-[#8]-[#6]1:[#7]:[#6](:[#7]:[#6](:[#6]:1)-[#6])-[#6](-[#6])-[#6]

paraquat: C[N+]1=CC=C(C=C1)C2=CC=[N+](C=C2)C

smiles_non_kekule:    C[n+]1ccc(-c2cc[n+](C)cc2)cc1
smiles_kekule:    C[N+]1=CC=C(C2=CC=[N+](C)C=C2)C=C1
inchi:    InChI=1S/C12H14N2/c1-13-7-3-11(4-8-13)12-5-9-14(2)10-6-12/h3-10H,1-2H3/q+2
inchiKey:    INFDPOAKFNIJBF-UHFFFAOYSA-N
smarts:    [#6]-[#7+]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#7+](:[#6]:[#6]:1)-[#6]
smarts_isomeric:    [#6]-[#7+]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#7+](:[#6]:[#6]:1)-[#6]

phenol: C1=CC=C(C=C1)O

smiles_non_kekule:    Oc1ccccc1
smiles_kekule:    OC1=CC=CC=C1
inchi:    InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
inchiKey:    ISWSIDIOOBJBQZ-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#8]
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#8]

aminomethylphosphonic acid: C(N)P(=O)(O)O

smiles_non_kekule:    NCP(=O)(O)O
smiles_kekule:    NCP(=O)(O)O
inchi:    InChI=1S/CH6NO3P/c2-1-6(3,4)5/h1-2H2,(H2,3,4,5)
inchiKey:    MGRVRXRGTBOSHW-UHFFFAOYSA-N
smarts:    [#6](-[#7])-[#15](=[#8])(-[#8])-[#8]
smarts_isomeric:    [#6](-[#7])-[#15](=[#8])(-[#8])-[#8]

chlorpyriphos: CCOP(=S)(OCC)OC1=NC(=C(C=C1Cl)Cl)Cl

smiles_non_kekule:    CCOP(=S)(OCC)Oc1nc(Cl)c(Cl)cc1Cl
smiles_kekule:    CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl
inchi:    InChI=1S/C9H11Cl3NO3PS/c1-3-14-17(18,15-4-2)16-9-7(11)5-6(10)8(12)13-9/h5H,3-4H2,1-2H3
inchiKey:    SBPBAQFWLVIOKP-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]-[#15](=[#16])(-[#8]-[#6]-[#6])-[#8]-[#6]1:[#7]:[#6](:[#6](:[#6]:[#6]:1-[#17])-[#17])-[#17]
smarts_isomeric:    [#6]-[#6]-[#8]-[#15](=[#16])(-[#8]-[#6]-[#6])-[#8]-[#6]1:[#7]:[#6](:[#6](:[#6]:[#6]:1-[#17])-[#17])-[#17]

xearalenone: CC1CCCC(=O)CCCC=CC2=C(C(=CC(=C2)O)O)C(=O)O1

smiles_non_kekule:    CC1CCCC(=O)CCCC=Cc2cc(O)cc(O)c2C(=O)O1
smiles_kekule:    CC1CCCC(=O)CCCC=CC2=C(C(=O)O1)C(O)=CC(O)=C2
inchi:    InChI=1S/C18H22O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h3,7,10-12,20-21H,2,4-6,8-9H2,1H3
inchiKey:    MBMQEIFVQACCCH-UHFFFAOYSA-N
smarts:    [#6]-[#6]1-[#6]-[#6]-[#6]-[#6](=[#8])-[#6]-[#6]-[#6]-[#6]=[#6]-[#6]2:[#6](:[#6](:[#6]:[#6](:[#6]:2)-[#8])-[#8])-[#6](=[#8])-[#8]-1
smarts_isomeric:    [#6]-[#6]1-[#6]-[#6]-[#6]-[#6](=[#8])-[#6]-[#6]-[#6]-[#6]=[#6]-[#6]2:[#6](:[#6](:[#6]:[#6](:[#6]:2)-[#8])-[#8])-[#6](=[#8])-[#8]-1

aldicarb: CC(C)(C=NOC(=O)NC)SC

smiles_non_kekule:    CNC(=O)ON=CC(C)(C)SC
smiles_kekule:    CNC(=O)ON=CC(C)(C)SC
inchi:    InChI=1S/C7H14N2O2S/c1-7(2,12-4)5-9-11-6(10)8-3/h5H,1-4H3,(H,8,10)
inchiKey:    QGLZXHRNAYXIBU-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])(-[#6]=[#7]-[#8]-[#6](=[#8])-[#7]-[#6])-[#16]-[#6]
smarts_isomeric:    [#6]-[#6](-[#6])(-[#6]=[#7]-[#8]-[#6](=[#8])-[#7]-[#6])-[#16]-[#6]

problem_type: 7/25 (loop 0/0)

Problem Template: _problem_common_amino_acid_protecting_groups

[15:16:45] WARNING: Charges were rearranged

Write structure of common amino acid protecting groups molecules.

Answer:

structure of common amino acid protecting groups molecules:

tert-butyloxycarbonyl: O=COC(C)(C)C

trityl: C(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3

3,5-dimethoxyphenylisoproxycarbonyl: COC1=CC(C(C)(OC=O)C)=CC(OC)=C1

2-(4-biphenyl)isopropoxycarbonyl: CC(C)(OC=O)C(C=C1)=CC=C1C2=CC=CC=C2

2-nitrophenylsulfenyl: SC1=CC=CC=C1[N+]([O-])=O

Solution:

structure of common amino acid protecting groups molecules:

tert-butyloxycarbonyl: O=COC(C)(C)C

smiles_non_kekule:    CC(C)(C)OC=O
smiles_kekule:    CC(C)(C)OC=O
inchi:    InChI=1S/C5H10O2/c1-5(2,3)7-4-6/h4H,1-3H3
inchiKey:    RUPAXCPQAAOIPB-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#8]-[#6](-[#6])(-[#6])-[#6]
smarts_isomeric:    [#8]=[#6]-[#8]-[#6](-[#6])(-[#6])-[#6]

trityl: C(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3

smiles_non_kekule:    c1ccc(C(c2ccccc2)c2ccccc2)cc1
smiles_kekule:    C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1
inchi:    InChI=1S/C19H16/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,19H
inchiKey:    AAAQKTZKLRYKHR-UHFFFAOYSA-N
smarts:    [#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

3,5-dimethoxyphenylisoproxycarbonyl: COC1=CC(C(C)(OC=O)C)=CC(OC)=C1

smiles_non_kekule:    COc1cc(OC)cc(C(C)(C)OC=O)c1
smiles_kekule:    COC1=CC(C(C)(C)OC=O)=CC(OC)=C1
inchi:    InChI=1S/C12H16O4/c1-12(2,16-8-13)9-5-10(14-3)7-11(6-9)15-4/h5-8H,1-4H3
inchiKey:    LROBWYQGENSLEK-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]1:[#6]:[#6](-[#6](-[#6])(-[#8]-[#6]=[#8])-[#6]):[#6]:[#6](-[#8]-[#6]):[#6]:1
smarts_isomeric:    [#6]-[#8]-[#6]1:[#6]:[#6](-[#6](-[#6])(-[#8]-[#6]=[#8])-[#6]):[#6]:[#6](-[#8]-[#6]):[#6]:1

2-(4-biphenyl)isopropoxycarbonyl: CC(C)(OC=O)C(C=C1)=CC=C1C2=CC=CC=C2

smiles_non_kekule:    CC(C)(OC=O)c1ccc(-c2ccccc2)cc1
smiles_kekule:    CC(C)(OC=O)C1=CC=C(C2=CC=CC=C2)C=C1
inchi:    InChI=1S/C16H16O2/c1-16(2,18-12-17)15-10-8-14(9-11-15)13-6-4-3-5-7-13/h3-12H,1-2H3
inchiKey:    VXLGMNUZTLZKHW-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])(-[#8]-[#6]=[#8])-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6](-[#6])(-[#8]-[#6]=[#8])-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

2-nitrophenylsulfenyl: SC1=CC=CC=C1[N+]([O-])=O

smiles_non_kekule:    O=[N+]([O-])c1ccccc1S
smiles_kekule:    O=[N+]([O-])C1=CC=CC=C1S
inchi:    InChI=1S/C6H5NO2S/c8-7(9)5-3-1-2-4-6(5)10/h1-4,10H
inchiKey:    JKIFPWHZEZQCQA-UHFFFAOYSA-N
smarts:    [#16]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#7+](-[#8-])=[#8]
smarts_isomeric:    [#16]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#7+](-[#8-])=[#8]

problem_type: 8/25 (loop 0/0)

Problem Template: _problem_common_electrophilic_warheads_for_kinases

[15:16:47] SMILES Parse Error: syntax error while parsing: C/C=N/\/NC(OC(C)(C)C)=O
[15:16:47] SMILES Parse Error: Failed parsing SMILES 'C/C=N/\/NC(OC(C)(C)C)=O' for input: 'C/C=N/\/NC(OC(C)(C)C)=O'
[15:16:47] WARNING: Omitted undefined stereo

[15:16:47] WARNING: Omitted undefined stereo

[15:16:47] WARNING: Omitted undefined stereo

Write structure of common electrophilic warheads for kinases molecules.

Answer:

structure of common electrophilic warheads for kinases molecules:

methylacrylamide: CNC(C=C)=O

methyl acrylate: COC(C=C)=O

methyl propiolate: COC(C#C)=O

2-cyanoacrylamide: N#CC(C(N)=O)=C

n-methylmaleimide: CN1C(C=CC1=O)=O

n-ethylmaleimide: O=C(C=CC1=O)N1CC

crotonamide: C/C=C/C(N)=O

ethyl crotonate: C/C=C/C(OCC)=O

crotononitrile: C/C=C/C#N

methyl methylpropiolate: CC#CC(OC)=O

isothiocyanatomethane: CN=C=S

isothiocyanatoethane: CCN=C=S

prop-1-ene: CC=C

prop-1-yne: CC#C

acetonitrile: CC#N

n-methylchloroacetamide: CNC(CCl)=O

n-methyl-2-chloropropanamide: CNC(C(C)Cl)=O

n-methyl-2-bromopropanamide: CNC(C(C)Br)=O

bromoacetone: CC(CBr)=O

2-methyloxirane: CC1OC1

fluoromethane: CF

methylsulfane: CS

aldehyde: CC=O

Solution:

structure of common electrophilic warheads for kinases molecules:

methylacrylamide: CNC(C=C)=O

smiles_non_kekule:    C=CC(=O)NC
smiles_kekule:    C=CC(=O)NC
inchi:    InChI=1S/C4H7NO/c1-3-4(6)5-2/h3H,1H2,2H3,(H,5,6)
inchiKey:    YPHQUSNPXDGUHL-UHFFFAOYSA-N
smarts:    [#6]-[#7]-[#6](-[#6]=[#6])=[#8]
smarts_isomeric:    [#6]-[#7]-[#6](-[#6]=[#6])=[#8]

methyl acrylate: COC(C=C)=O

smiles_non_kekule:    C=CC(=O)OC
smiles_kekule:    C=CC(=O)OC
inchi:    InChI=1S/C4H6O2/c1-3-4(5)6-2/h3H,1H2,2H3
inchiKey:    BAPJBEWLBFYGME-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6](-[#6]=[#6])=[#8]
smarts_isomeric:    [#6]-[#8]-[#6](-[#6]=[#6])=[#8]

methyl propiolate: COC(C#C)=O

smiles_non_kekule:    C#CC(=O)OC
smiles_kekule:    C#CC(=O)OC
inchi:    InChI=1S/C4H4O2/c1-3-4(5)6-2/h1H,2H3
inchiKey:    IMAKHNTVDGLIRY-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6](-[#6]#[#6])=[#8]
smarts_isomeric:    [#6]-[#8]-[#6](-[#6]#[#6])=[#8]

2-cyanoacrylamide: N#CC(C(N)=O)=C

smiles_non_kekule:    C=C(C#N)C(N)=O
smiles_kekule:    C=C(C#N)C(N)=O
inchi:    InChI=1S/C4H4N2O/c1-3(2-5)4(6)7/h1H2,(H2,6,7)
inchiKey:    HGBFVOSZYVRIHY-UHFFFAOYSA-N
smarts:    [#7]#[#6]-[#6](-[#6](-[#7])=[#8])=[#6]
smarts_isomeric:    [#7]#[#6]-[#6](-[#6](-[#7])=[#8])=[#6]

n-methylmaleimide: CN1C(C=CC1=O)=O

smiles_non_kekule:    CN1C(=O)C=CC1=O
smiles_kekule:    CN1C(=O)C=CC1=O
inchi:    InChI=1S/C5H5NO2/c1-6-4(7)2-3-5(6)8/h2-3H,1H3
inchiKey:    SEEYREPSKCQBBF-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6](-[#6]=[#6]-[#6]-1=[#8])=[#8]
smarts_isomeric:    [#6]-[#7]1-[#6](-[#6]=[#6]-[#6]-1=[#8])=[#8]

n-ethylmaleimide: O=C(C=CC1=O)N1CC

smiles_non_kekule:    CCN1C(=O)C=CC1=O
smiles_kekule:    CCN1C(=O)C=CC1=O
inchi:    InChI=1S/C6H7NO2/c1-2-7-5(8)3-4-6(7)9/h3-4H,2H2,1H3
inchiKey:    HDFGOPSGAURCEO-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#6]=[#6]-[#6](=[#8])-[#7]-1-[#6]-[#6]
smarts_isomeric:    [#8]=[#6]1-[#6]=[#6]-[#6](=[#8])-[#7]-1-[#6]-[#6]

crotonamide: C/C=C/C(N)=O

smiles_non_kekule:    C/C=C/C(N)=O
smiles_kekule:    C/C=C/C(N)=O
inchi:    InChI=1S/C4H7NO/c1-2-3-4(5)6/h2-3H,1H3,(H2,5,6)/b3-2+
inchiKey:    NQQRXZOPZBKCNF-NSCUHMNNSA-N
smarts:    [#6]-[#6]=[#6]-[#6](-[#7])=[#8]
smarts_isomeric:    [#6]/[#6]=[#6]/[#6](-[#7])=[#8]

ethyl crotonate: C/C=C/C(OCC)=O

smiles_non_kekule:    C/C=C/C(=O)OCC
smiles_kekule:    C/C=C/C(=O)OCC
inchi:    InChI=1S/C6H10O2/c1-3-5-6(7)8-4-2/h3,5H,4H2,1-2H3/b5-3+
inchiKey:    ZFDIRQKJPRINOQ-HWKANZROSA-N
smarts:    [#6]-[#6]=[#6]-[#6](-[#8]-[#6]-[#6])=[#8]
smarts_isomeric:    [#6]/[#6]=[#6]/[#6](-[#8]-[#6]-[#6])=[#8]

crotononitrile: C/C=C/C#N

smiles_non_kekule:    C/C=C/C#N
smiles_kekule:    C/C=C/C#N
inchi:    InChI=1S/C4H5N/c1-2-3-4-5/h2-3H,1H3/b3-2+
inchiKey:    NKKMVIVFRUYPLQ-NSCUHMNNSA-N
smarts:    [#6]-[#6]=[#6]-[#6]#[#7]
smarts_isomeric:    [#6]/[#6]=[#6]/[#6]#[#7]

methyl methylpropiolate: CC#CC(OC)=O

smiles_non_kekule:    CC#CC(=O)OC
smiles_kekule:    CC#CC(=O)OC
inchi:    InChI=1S/C5H6O2/c1-3-4-5(6)7-2/h1-2H3
inchiKey:    UJQCANQILFWSDJ-UHFFFAOYSA-N
smarts:    [#6]-[#6]#[#6]-[#6](-[#8]-[#6])=[#8]
smarts_isomeric:    [#6]-[#6]#[#6]-[#6](-[#8]-[#6])=[#8]

isothiocyanatomethane: CN=C=S

smiles_non_kekule:    CN=C=S
smiles_kekule:    CN=C=S
inchi:    InChI=1S/C2H3NS/c1-3-2-4/h1H3
inchiKey:    LGDSHSYDSCRFAB-UHFFFAOYSA-N
smarts:    [#6]-[#7]=[#6]=[#16]
smarts_isomeric:    [#6]-[#7]=[#6]=[#16]

isothiocyanatoethane: CCN=C=S

smiles_non_kekule:    CCN=C=S
smiles_kekule:    CCN=C=S
inchi:    InChI=1S/C3H5NS/c1-2-4-3-5/h2H2,1H3
inchiKey:    HBNYJWAFDZLWRS-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7]=[#6]=[#16]
smarts_isomeric:    [#6]-[#6]-[#7]=[#6]=[#16]

prop-1-ene: CC=C

smiles_non_kekule:    C=CC
smiles_kekule:    C=CC
inchi:    InChI=1S/C3H6/c1-3-2/h3H,1H2,2H3
inchiKey:    QQONPFPTGQHPMA-UHFFFAOYSA-N
smarts:    [#6]-[#6]=[#6]
smarts_isomeric:    [#6]-[#6]=[#6]

prop-1-yne: CC#C

smiles_non_kekule:    C#CC
smiles_kekule:    C#CC
inchi:    InChI=1S/C3H4/c1-3-2/h1H,2H3
inchiKey:    MWWATHDPGQKSAR-UHFFFAOYSA-N
smarts:    [#6]-[#6]#[#6]
smarts_isomeric:    [#6]-[#6]#[#6]

acetonitrile: CC#N

smiles_non_kekule:    CC#N
smiles_kekule:    CC#N
inchi:    InChI=1S/C2H3N/c1-2-3/h1H3
inchiKey:    WEVYAHXRMPXWCK-UHFFFAOYSA-N
smarts:    [#6]-[#6]#[#7]
smarts_isomeric:    [#6]-[#6]#[#7]

n-methylchloroacetamide: CNC(CCl)=O

smiles_non_kekule:    CNC(=O)CCl
smiles_kekule:    CNC(=O)CCl
inchi:    InChI=1S/C3H6ClNO/c1-5-3(6)2-4/h2H2,1H3,(H,5,6)
inchiKey:    HOZLOOPIXHWKCI-UHFFFAOYSA-N
smarts:    [#6]-[#7]-[#6](-[#6]-[#17])=[#8]
smarts_isomeric:    [#6]-[#7]-[#6](-[#6]-[#17])=[#8]

n-methyl-2-chloropropanamide: CNC(C(C)Cl)=O

smiles_non_kekule:    CNC(=O)C(C)Cl
smiles_kekule:    CNC(=O)C(C)Cl
inchi:    InChI=1S/C4H8ClNO/c1-3(5)4(7)6-2/h3H,1-2H3,(H,6,7)
inchiKey:    NKUQJMNRULPRAM-UHFFFAOYSA-N
smarts:    [#6]-[#7]-[#6](-[#6](-[#6])-[#17])=[#8]
smarts_isomeric:    [#6]-[#7]-[#6](-[#6](-[#6])-[#17])=[#8]

n-methyl-2-bromopropanamide: CNC(C(C)Br)=O

smiles_non_kekule:    CNC(=O)C(C)Br
smiles_kekule:    CNC(=O)C(C)Br
inchi:    InChI=1S/C4H8BrNO/c1-3(5)4(7)6-2/h3H,1-2H3,(H,6,7)
inchiKey:    ALSQAGFRBPHNIQ-UHFFFAOYSA-N
smarts:    [#6]-[#7]-[#6](-[#6](-[#6])-[#35])=[#8]
smarts_isomeric:    [#6]-[#7]-[#6](-[#6](-[#6])-[#35])=[#8]

bromoacetone: CC(CBr)=O

smiles_non_kekule:    CC(=O)CBr
smiles_kekule:    CC(=O)CBr
inchi:    InChI=1S/C3H5BrO/c1-3(5)2-4/h2H2,1H3
inchiKey:    VQFAIAKCILWQPZ-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#35])=[#8]
smarts_isomeric:    [#6]-[#6](-[#6]-[#35])=[#8]

2-methyloxirane: CC1OC1

smiles_non_kekule:    CC1CO1
smiles_kekule:    CC1CO1
inchi:    InChI=1S/C3H6O/c1-3-2-4-3/h3H,2H2,1H3
inchiKey:    GOOHAUXETOMSMM-UHFFFAOYSA-N
smarts:    [#6]-[#6]1-[#8]-[#6]-1
smarts_isomeric:    [#6]-[#6]1-[#8]-[#6]-1

fluoromethane: CF

smiles_non_kekule:    CF
smiles_kekule:    CF
inchi:    InChI=1S/CH3F/c1-2/h1H3
inchiKey:    NBVXSUQYWXRMNV-UHFFFAOYSA-N
smarts:    [#6]-[#9]
smarts_isomeric:    [#6]-[#9]

methylsulfane: CS

aldehyde: CC=O

smiles_non_kekule:    CC=O
smiles_kekule:    CC=O
inchi:    InChI=1S/C2H4O/c1-2-3/h2H,1H3
inchiKey:    IKHGUXGNUITLKF-UHFFFAOYSA-N
smarts:    [#6]-[#6]=[#8]
smarts_isomeric:    [#6]-[#6]=[#8]

problem_type: 9/25 (loop 0/0)

Problem Template: _problem_common_heterocyclic_rings_phase_2

Write structure of common heterocyclic rings phase 2 molecules.

Answer:

structure of common heterocyclic rings phase 2 molecules:

pyridine: C1=CC=NC=C1

indole: C12=CC=CC=C1C=CN2

imidazole: C1=CN=CN1

thiazol-2-amine: NC1=NC=CS1

tetrazole: C1=NN=NN1

1,2,4-triazole: C1=NC=NN1

thiophene: C1=CC=CS1

cytosine: O=C1N=C(N)C=CN1

adenine: NC1=NC=NC2=C1N=CN2

5-methylindole: CC1=CC=C2C(C=CN2)=C1

isocaffeine: O=C(N1C)NC2=C(N=CN2)C1=O

tetrazolethiol: SN1N=NN=C1

3-methylisoxazole: C1=CC=NO1

1-methylimidazole: CN1C=NC=C1

2-methylimidazole: CC1=NC=CN1

guanine: NC(N1)=NC2=C(N=CN2)C1=O

quinoline: C12=CC=CC=C1N=CC=C2

furan: C1=CC=CO1

tosufloxacin: NC1=C(F)C=C2C(NC=C(C(O)=O)C2=O)=N1

Solution:

structure of common heterocyclic rings phase 2 molecules:

pyridine: C1=CC=NC=C1

indole: C12=CC=CC=C1C=CN2

smiles_non_kekule:    c1ccc2[nH]ccc2c1
smiles_kekule:    C1=CC=C2NC=CC2=C1
inchi:    InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H
inchiKey:    SIKJAQJRHWYJAI-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#7H]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#7H]:2

imidazole: C1=CN=CN1

thiazol-2-amine: NC1=NC=CS1

smiles_non_kekule:    Nc1nccs1
smiles_kekule:    NC1=NC=CS1
inchi:    InChI=1S/C3H4N2S/c4-3-5-1-2-6-3/h1-2H,(H2,4,5)
inchiKey:    RAIPHJJURHTUIC-UHFFFAOYSA-N
smarts:    [#7]-[#6]1:[#7]:[#6]:[#6]:[#16]:1
smarts_isomeric:    [#7]-[#6]1:[#7]:[#6]:[#6]:[#16]:1

tetrazole: C1=NN=NN1

smiles_non_kekule:    c1nnn[nH]1
smiles_kekule:    C1=NN=NN1
inchi:    InChI=1S/CH2N4/c1-2-4-5-3-1/h1H,(H,2,3,4,5)
inchiKey:    KJUGUADJHNHALS-UHFFFAOYSA-N
smarts:    [#6]1:[#7]:[#7]:[#7]:[#7H]:1
smarts_isomeric:    [#6]1:[#7]:[#7]:[#7]:[#7H]:1

1,2,4-triazole: C1=NC=NN1

smiles_non_kekule:    c1nc[nH]n1
smiles_kekule:    C1=NNC=N1
inchi:    InChI=1S/C2H3N3/c1-3-2-5-4-1/h1-2H,(H,3,4,5)
inchiKey:    NSPMIYGKQJPBQR-UHFFFAOYSA-N
smarts:    [#6]1:[#7]:[#6]:[#7]:[#7H]:1
smarts_isomeric:    [#6]1:[#7]:[#6]:[#7]:[#7H]:1

thiophene: C1=CC=CS1

smiles_non_kekule:    c1ccsc1
smiles_kekule:    C1=CSC=C1
inchi:    InChI=1S/C4H4S/c1-2-4-5-3-1/h1-4H
inchiKey:    YTPLMLYBLZKORZ-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]:[#16]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]:[#16]:1

cytosine: O=C1N=C(N)C=CN1

smiles_non_kekule:    Nc1cc[nH]c(=O)n1
smiles_kekule:    NC1=NC(=O)NC=C1
inchi:    InChI=1S/C4H5N3O/c5-3-1-2-6-4(8)7-3/h1-2H,(H3,5,6,7,8)
inchiKey:    OPTASPLRGRRNAP-UHFFFAOYSA-N
smarts:    [#8]=[#6]1:[#7]:[#6](-[#7]):[#6]:[#6]:[#7H]:1
smarts_isomeric:    [#8]=[#6]1:[#7]:[#6](-[#7]):[#6]:[#6]:[#7H]:1

adenine: NC1=NC=NC2=C1N=CN2

smiles_non_kekule:    Nc1ncnc2[nH]cnc12
smiles_kekule:    NC1=NC=NC2=C1N=CN2
inchi:    InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)
inchiKey:    GFFGJBXGBJISGV-UHFFFAOYSA-N
smarts:    [#7]-[#6]1:[#7]:[#6]:[#7]:[#6]2:[#6]:1:[#7]:[#6]:[#7H]:2
smarts_isomeric:    [#7]-[#6]1:[#7]:[#6]:[#7]:[#6]2:[#6]:1:[#7]:[#6]:[#7H]:2

5-methylindole: CC1=CC=C2C(C=CN2)=C1

smiles_non_kekule:    Cc1ccc2[nH]ccc2c1
smiles_kekule:    CC1=CC=C2NC=CC2=C1
inchi:    InChI=1S/C9H9N/c1-7-2-3-9-8(6-7)4-5-10-9/h2-6,10H,1H3
inchiKey:    YPKBCLZFIYBSHK-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6]2:[#6](:[#6]:[#6]:[#7H]:2):[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6]2:[#6](:[#6]:[#6]:[#7H]:2):[#6]:1

isocaffeine: O=C(N1C)NC2=C(N=CN2)C1=O

smiles_non_kekule:    Cn1c(=O)[nH]c2[nH]cnc2c1=O
smiles_kekule:    CN1C(=O)NC2=C(N=CN2)C1=O
inchi:    InChI=1S/C6H6N4O2/c1-10-5(11)3-4(8-2-7-3)9-6(10)12/h2H,1H3,(H,7,8)(H,9,12)
inchiKey:    MVOYJPOZRLFTCP-UHFFFAOYSA-N
smarts:    [#8]=[#6]1:[#7](-[#6]):[#6](:[#6]2:[#6](:[#7H]:1):[#7H]:[#6]:[#7]:2)=[#8]
smarts_isomeric:    [#8]=[#6]1:[#7](-[#6]):[#6](:[#6]2:[#6](:[#7H]:1):[#7H]:[#6]:[#7]:2)=[#8]

tetrazolethiol: SN1N=NN=C1

smiles_non_kekule:    Sn1cnnn1
smiles_kekule:    SN1C=NN=N1
inchi:    InChI=1S/CH2N4S/c6-5-1-2-3-4-5/h1,6H
inchiKey:    DIGCWYGXBRVXIW-UHFFFAOYSA-N
smarts:    [#16]-[#7]1:[#7]:[#7]:[#7]:[#6]:1
smarts_isomeric:    [#16]-[#7]1:[#7]:[#7]:[#7]:[#6]:1

3-methylisoxazole: C1=CC=NO1

smiles_non_kekule:    c1cnoc1
smiles_kekule:    C1=CON=C1
inchi:    InChI=1S/C3H3NO/c1-2-4-5-3-1/h1-3H
inchiKey:    CTAPFRYPJLPFDF-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#7]:[#8]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#7]:[#8]:1

1-methylimidazole: CN1C=NC=C1

smiles_non_kekule:    Cn1ccnc1
smiles_kekule:    CN1C=CN=C1
inchi:    InChI=1S/C4H6N2/c1-6-3-2-5-4-6/h2-4H,1H3
inchiKey:    MCTWTZJPVLRJOU-UHFFFAOYSA-N
smarts:    [#6]-[#7]1:[#6]:[#7]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#7]1:[#6]:[#7]:[#6]:[#6]:1

2-methylimidazole: CC1=NC=CN1

smiles_non_kekule:    Cc1ncc[nH]1
smiles_kekule:    CC1=NC=CN1
inchi:    InChI=1S/C4H6N2/c1-4-5-2-3-6-4/h2-3H,1H3,(H,5,6)
inchiKey:    LXBGSDVWAMZHDD-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#7]:[#6]:[#6]:[#7H]:1
smarts_isomeric:    [#6]-[#6]1:[#7]:[#6]:[#6]:[#7H]:1

guanine: NC(N1)=NC2=C(N=CN2)C1=O

smiles_non_kekule:    Nc1nc2[nH]cnc2c(=O)[nH]1
smiles_kekule:    NC1=NC2=C(N=CN2)C(=O)N1
inchi:    InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
inchiKey:    UYTPUPDQBNUYGX-UHFFFAOYSA-N
smarts:    [#7]-[#6]1:[#7H]:[#6](:[#6]2:[#6](:[#7]:1):[#7H]:[#6]:[#7]:2)=[#8]
smarts_isomeric:    [#7]-[#6]1:[#7H]:[#6](:[#6]2:[#6](:[#7]:1):[#7H]:[#6]:[#7]:2)=[#8]

quinoline: C12=CC=CC=C1N=CC=C2

smiles_non_kekule:    c1ccc2ncccc2c1
smiles_kekule:    C1=CC=C2N=CC=CC2=C1
inchi:    InChI=1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H
inchiKey:    SMWDFEZZVXVKRB-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#7]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#7]:[#6]:[#6]:[#6]:2

furan: C1=CC=CO1

smiles_non_kekule:    c1ccoc1
smiles_kekule:    C1=COC=C1
inchi:    InChI=1S/C4H4O/c1-2-4-5-3-1/h1-4H
inchiKey:    YLQBMQCUIZJEEH-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]:[#8]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]:[#8]:1

tosufloxacin: NC1=C(F)C=C2C(NC=C(C(O)=O)C2=O)=N1

smiles_non_kekule:    Nc1nc2[nH]cc(C(=O)O)c(=O)c2cc1F
smiles_kekule:    NC1=C(F)C=C2C(=O)C(C(=O)O)=CNC2=N1
inchi:    InChI=1S/C9H6FN3O3/c10-5-1-3-6(14)4(9(15)16)2-12-8(3)13-7(5)11/h1-2H,(H,15,16)(H3,11,12,13,14)
inchiKey:    OJASIRGBHCFJPM-UHFFFAOYSA-N
smarts:    [#7]-[#6]1:[#6](-[#9]):[#6]:[#6]2:[#6](:[#7H]:[#6]:[#6](-[#6](-[#8])=[#8]):[#6]:2=[#8]):[#7]:1
smarts_isomeric:    [#7]-[#6]1:[#6](-[#9]):[#6]:[#6]2:[#6](:[#7H]:[#6]:[#6](-[#6](-[#8])=[#8]):[#6]:2=[#8]):[#7]:1

problem_type: 10/25 (loop 0/0)

Problem Template: _problem_common_organic_solvents

[15:16:56] WARNING: Charges were rearranged

Write structure of common organic solvents molecules.

Answer:

structure of common organic solvents molecules:

acetic acid: CC(=O)O

acetone: CC(=O)C

acetonitrile: CC#N

benzene: C1=CC=CC=C1

tert-butyl alcohol: CC(C)(C)O

tert-butyl methyl ether: CC(C)(C)OC

butylated hydroxytoluene: CC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C

chloroform: C(Cl)(Cl)Cl

18-crown-6: C1COCCOCCOCCOCCOCCO1

cyclohexane: C1CCCCC1

1,2-dichloroethane: C(CCl)Cl

dichloromethane: C(Cl)Cl

diethyl ether: CCOCC

diglyme: COCCOCCOC

1,2-dimethoxyethane: COCCOC

dimethylacetamide: CC(=O)N(C)C

dimethylformamide: CN(C)C=O

dimethyl sulfoxide: CS(=O)C

dioxane: C1COCCO1

ethanol: CCO

ethyl acetate: CCOC(=O)C

ethyl methyl ketone: CCC(=O)C

ethylene: C=C

ethylene glycol: C(CO)O

grease: C(C(F)(F)F)OCC(F)(F)F

n-hexane: CCCCCC

hexamethylbenzene: CC1=C(C(=C(C(=C1C)C)C)C)C

hexamethylphosphoramide: CN(C)P(=O)(N(C)C)N(C)C

hexamethyldisiloxane: O([Si](C)(C)C)[Si](C)(C)C

methanol: CO

nitromethane: C[N+](=O)[O-]

n-pentane: CCCCC

propylene: CC=C

2-propanol: CC(C)O

pyridine: C1=CC=NC=C1

pyrrole: C1=CNC=C1

pyrrolidine: C1CCNC1

silicon grease: C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C

tetrahydrofuran: C1CCOC1

toluene: CC1=CC=CC=C1

triethylamine: CCN(CC)CC

Solution:

structure of common organic solvents molecules:

acetic acid: CC(=O)O

smiles_non_kekule:    CC(=O)O
smiles_kekule:    CC(=O)O
inchi:    InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)
inchiKey:    QTBSBXVTEAMEQO-UHFFFAOYSA-N
smarts:    [#6]-[#6](=[#8])-[#8]
smarts_isomeric:    [#6]-[#6](=[#8])-[#8]

acetone: CC(=O)C

smiles_non_kekule:    CC(C)=O
smiles_kekule:    CC(C)=O
inchi:    InChI=1S/C3H6O/c1-3(2)4/h1-2H3
inchiKey:    CSCPPACGZOOCGX-UHFFFAOYSA-N
smarts:    [#6]-[#6](=[#8])-[#6]
smarts_isomeric:    [#6]-[#6](=[#8])-[#6]

acetonitrile: CC#N

benzene: C1=CC=CC=C1

tert-butyl alcohol: CC(C)(C)O

smiles_non_kekule:    CC(C)(C)O
smiles_kekule:    CC(C)(C)O
inchi:    InChI=1S/C4H10O/c1-4(2,3)5/h5H,1-3H3
inchiKey:    DKGAVHZHDRPRBM-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])(-[#6])-[#8]
smarts_isomeric:    [#6]-[#6](-[#6])(-[#6])-[#8]

tert-butyl methyl ether: CC(C)(C)OC

smiles_non_kekule:    COC(C)(C)C
smiles_kekule:    COC(C)(C)C
inchi:    InChI=1S/C5H12O/c1-5(2,3)6-4/h1-4H3
inchiKey:    BZLVMXJERCGZMT-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])(-[#6])-[#8]-[#6]
smarts_isomeric:    [#6]-[#6](-[#6])(-[#6])-[#8]-[#6]

butylated hydroxytoluene: CC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C

smiles_non_kekule:    Cc1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1
smiles_kekule:    CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1
inchi:    InChI=1S/C15H24O/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h8-9,16H,1-7H3
inchiKey:    NLZUEZXRPGMBCV-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6](:[#6](:[#6](:[#6]:1)-[#6](-[#6])(-[#6])-[#6])-[#8])-[#6](-[#6])(-[#6])-[#6]
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6](:[#6](:[#6](:[#6]:1)-[#6](-[#6])(-[#6])-[#6])-[#8])-[#6](-[#6])(-[#6])-[#6]

chloroform: C(Cl)(Cl)Cl

smiles_non_kekule:    ClC(Cl)Cl
smiles_kekule:    ClC(Cl)Cl
inchi:    InChI=1S/CHCl3/c2-1(3)4/h1H
inchiKey:    HEDRZPFGACZZDS-UHFFFAOYSA-N
smarts:    [#6](-[#17])(-[#17])-[#17]
smarts_isomeric:    [#6](-[#17])(-[#17])-[#17]

18-crown-6: C1COCCOCCOCCOCCOCCO1

smiles_non_kekule:    C1COCCOCCOCCOCCOCCO1
smiles_kekule:    C1COCCOCCOCCOCCOCCO1
inchi:    InChI=1S/C12H24O6/c1-2-14-5-6-16-9-10-18-12-11-17-8-7-15-4-3-13-1/h1-12H2
inchiKey:    XEZNGIUYQVAUSS-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#8]-[#6]-[#6]-[#8]-[#6]-[#6]-[#8]-[#6]-[#6]-[#8]-[#6]-[#6]-[#8]-[#6]-[#6]-[#8]-1
smarts_isomeric:    [#6]1-[#6]-[#8]-[#6]-[#6]-[#8]-[#6]-[#6]-[#8]-[#6]-[#6]-[#8]-[#6]-[#6]-[#8]-[#6]-[#6]-[#8]-1

cyclohexane: C1CCCCC1

smiles_non_kekule:    C1CCCCC1
smiles_kekule:    C1CCCCC1
inchi:    InChI=1S/C6H12/c1-2-4-6-5-3-1/h1-6H2
inchiKey:    XDTMQSROBMDMFD-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

1,2-dichloroethane: C(CCl)Cl

smiles_non_kekule:    ClCCCl
smiles_kekule:    ClCCCl
inchi:    InChI=1S/C2H4Cl2/c3-1-2-4/h1-2H2
inchiKey:    WSLDOOZREJYCGB-UHFFFAOYSA-N
smarts:    [#6](-[#6]-[#17])-[#17]
smarts_isomeric:    [#6](-[#6]-[#17])-[#17]

dichloromethane: C(Cl)Cl

smiles_non_kekule:    ClCCl
smiles_kekule:    ClCCl
inchi:    InChI=1S/CH2Cl2/c2-1-3/h1H2
inchiKey:    YMWUJEATGCHHMB-UHFFFAOYSA-N
smarts:    [#6](-[#17])-[#17]
smarts_isomeric:    [#6](-[#17])-[#17]

diethyl ether: CCOCC

smiles_non_kekule:    CCOCC
smiles_kekule:    CCOCC
inchi:    InChI=1S/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3
inchiKey:    RTZKZFJDLAIYFH-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]-[#6]-[#6]
smarts_isomeric:    [#6]-[#6]-[#8]-[#6]-[#6]

diglyme: COCCOCCOC

smiles_non_kekule:    COCCOCCOC
smiles_kekule:    COCCOCCOC
inchi:    InChI=1S/C6H14O3/c1-7-3-5-9-6-4-8-2/h3-6H2,1-2H3
inchiKey:    SBZXBUIDTXKZTM-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]-[#6]-[#8]-[#6]-[#6]-[#8]-[#6]
smarts_isomeric:    [#6]-[#8]-[#6]-[#6]-[#8]-[#6]-[#6]-[#8]-[#6]

1,2-dimethoxyethane: COCCOC

smiles_non_kekule:    COCCOC
smiles_kekule:    COCCOC
inchi:    InChI=1S/C4H10O2/c1-5-3-4-6-2/h3-4H2,1-2H3
inchiKey:    XTHFKEDIFFGKHM-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]-[#6]-[#8]-[#6]
smarts_isomeric:    [#6]-[#8]-[#6]-[#6]-[#8]-[#6]

dimethylacetamide: CC(=O)N(C)C

smiles_non_kekule:    CC(=O)N(C)C
smiles_kekule:    CC(=O)N(C)C
inchi:    InChI=1S/C4H9NO/c1-4(6)5(2)3/h1-3H3
inchiKey:    FXHOOIRPVKKKFG-UHFFFAOYSA-N
smarts:    [#6]-[#6](=[#8])-[#7](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6](=[#8])-[#7](-[#6])-[#6]

dimethylformamide: CN(C)C=O

smiles_non_kekule:    CN(C)C=O
smiles_kekule:    CN(C)C=O
inchi:    InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3
inchiKey:    ZMXDDKWLCZADIW-UHFFFAOYSA-N
smarts:    [#6]-[#7](-[#6])-[#6]=[#8]
smarts_isomeric:    [#6]-[#7](-[#6])-[#6]=[#8]

dimethyl sulfoxide: CS(=O)C

smiles_non_kekule:    CS(C)=O
smiles_kekule:    CS(C)=O
inchi:    InChI=1S/C2H6OS/c1-4(2)3/h1-2H3
inchiKey:    IAZDPXIOMUYVGZ-UHFFFAOYSA-N
smarts:    [#6]-[#16](=[#8])-[#6]
smarts_isomeric:    [#6]-[#16](=[#8])-[#6]

dioxane: C1COCCO1

smiles_non_kekule:    C1COCCO1
smiles_kekule:    C1COCCO1
inchi:    InChI=1S/C4H8O2/c1-2-6-4-3-5-1/h1-4H2
inchiKey:    RYHBNJHYFVUHQT-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#8]-[#6]-[#6]-[#8]-1
smarts_isomeric:    [#6]1-[#6]-[#8]-[#6]-[#6]-[#8]-1

ethanol: CCO

smiles_non_kekule:    CCO
smiles_kekule:    CCO
inchi:    InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3
inchiKey:    LFQSCWFLJHTTHZ-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]
smarts_isomeric:    [#6]-[#6]-[#8]

ethyl acetate: CCOC(=O)C

smiles_non_kekule:    CCOC(C)=O
smiles_kekule:    CCOC(C)=O
inchi:    InChI=1S/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H3
inchiKey:    XEKOWRVHYACXOJ-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]
smarts_isomeric:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]

ethyl methyl ketone: CCC(=O)C

smiles_non_kekule:    CCC(C)=O
smiles_kekule:    CCC(C)=O
inchi:    InChI=1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3
inchiKey:    ZWEHNKRNPOVVGH-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#6]
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#6]

ethylene: C=C

smiles_non_kekule:    C=C
smiles_kekule:    C=C
inchi:    InChI=1S/C2H4/c1-2/h1-2H2
inchiKey:    VGGSQFUCUMXWEO-UHFFFAOYSA-N
smarts:    [#6]=[#6]
smarts_isomeric:    [#6]=[#6]

ethylene glycol: C(CO)O

smiles_non_kekule:    OCCO
smiles_kekule:    OCCO
inchi:    InChI=1S/C2H6O2/c3-1-2-4/h3-4H,1-2H2
inchiKey:    LYCAIKOWRPUZTN-UHFFFAOYSA-N
smarts:    [#6](-[#6]-[#8])-[#8]
smarts_isomeric:    [#6](-[#6]-[#8])-[#8]

grease: C(C(F)(F)F)OCC(F)(F)F

smiles_non_kekule:    FC(F)(F)COCC(F)(F)F
smiles_kekule:    FC(F)(F)COCC(F)(F)F
inchi:    InChI=1S/C4H4F6O/c5-3(6,7)1-11-2-4(8,9)10/h1-2H2
inchiKey:    KGPPDNUWZNWPSI-UHFFFAOYSA-N
smarts:    [#6](-[#6](-[#9])(-[#9])-[#9])-[#8]-[#6]-[#6](-[#9])(-[#9])-[#9]
smarts_isomeric:    [#6](-[#6](-[#9])(-[#9])-[#9])-[#8]-[#6]-[#6](-[#9])(-[#9])-[#9]

n-hexane: CCCCCC

smiles_non_kekule:    CCCCCC
smiles_kekule:    CCCCCC
inchi:    InChI=1S/C6H14/c1-3-5-6-4-2/h3-6H2,1-2H3
inchiKey:    VLKZOEOYAKHREP-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]

hexamethylbenzene: CC1=C(C(=C(C(=C1C)C)C)C)C

smiles_non_kekule:    Cc1c(C)c(C)c(C)c(C)c1C
smiles_kekule:    CC1=C(C)C(C)=C(C)C(C)=C1C
inchi:    InChI=1S/C12H18/c1-7-8(2)10(4)12(6)11(5)9(7)3/h1-6H3
inchiKey:    YUWFEBAXEOLKSG-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6](:[#6](:[#6](:[#6](:[#6]:1-[#6])-[#6])-[#6])-[#6])-[#6]
smarts_isomeric:    [#6]-[#6]1:[#6](:[#6](:[#6](:[#6](:[#6]:1-[#6])-[#6])-[#6])-[#6])-[#6]

hexamethylphosphoramide: CN(C)P(=O)(N(C)C)N(C)C

smiles_non_kekule:    CN(C)P(=O)(N(C)C)N(C)C
smiles_kekule:    CN(C)P(=O)(N(C)C)N(C)C
inchi:    InChI=1S/C6H18N3OP/c1-7(2)11(10,8(3)4)9(5)6/h1-6H3
inchiKey:    GNOIPBMMFNIUFM-UHFFFAOYSA-N
smarts:    [#6]-[#7](-[#6])-[#15](=[#8])(-[#7](-[#6])-[#6])-[#7](-[#6])-[#6]
smarts_isomeric:    [#6]-[#7](-[#6])-[#15](=[#8])(-[#7](-[#6])-[#6])-[#7](-[#6])-[#6]

hexamethyldisiloxane: O([Si](C)(C)C)[Si](C)(C)C

smiles_non_kekule:    C[Si](C)(C)O[Si](C)(C)C
smiles_kekule:    C[Si](C)(C)O[Si](C)(C)C
inchi:    InChI=1S/C6H18OSi2/c1-8(2,3)7-9(4,5)6/h1-6H3
inchiKey:    UQEAIHBTYFGYIE-UHFFFAOYSA-N
smarts:    [#8](-[Si](-[#6])(-[#6])-[#6])-[Si](-[#6])(-[#6])-[#6]
smarts_isomeric:    [#8](-[Si](-[#6])(-[#6])-[#6])-[Si](-[#6])(-[#6])-[#6]

methanol: CO

smiles_non_kekule:    CO
smiles_kekule:    CO
inchi:    InChI=1S/CH4O/c1-2/h2H,1H3
inchiKey:    OKKJLVBELUTLKV-UHFFFAOYSA-N
smarts:    [#6]-[#8]
smarts_isomeric:    [#6]-[#8]

nitromethane: C[N+](=O)[O-]

smiles_non_kekule:    C[N+](=O)[O-]
smiles_kekule:    C[N+](=O)[O-]
inchi:    InChI=1S/CH3NO2/c1-2(3)4/h1H3
inchiKey:    LYGJENNIWJXYER-UHFFFAOYSA-N
smarts:    [#6]-[#7+](=[#8])-[#8-]
smarts_isomeric:    [#6]-[#7+](=[#8])-[#8-]

n-pentane: CCCCC

smiles_non_kekule:    CCCCC
smiles_kekule:    CCCCC
inchi:    InChI=1S/C5H12/c1-3-5-4-2/h3-5H2,1-2H3
inchiKey:    OFBQJSOFQDEBGM-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]

propylene: CC=C

2-propanol: CC(C)O

smiles_non_kekule:    CC(C)O
smiles_kekule:    CC(C)O
inchi:    InChI=1S/C3H8O/c1-3(2)4/h3-4H,1-2H3
inchiKey:    KFZMGEQAYNKOFK-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])-[#8]
smarts_isomeric:    [#6]-[#6](-[#6])-[#8]

pyridine: C1=CC=NC=C1

pyrrole: C1=CNC=C1

smiles_non_kekule:    c1cc[nH]c1
smiles_kekule:    C1=CNC=C1
inchi:    InChI=1S/C4H5N/c1-2-4-5-3-1/h1-5H
inchiKey:    KAESVJOAVNADME-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#7H]:[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#7H]:[#6]:[#6]:1

pyrrolidine: C1CCNC1

smiles_non_kekule:    C1CCNC1
smiles_kekule:    C1CCNC1
inchi:    InChI=1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2
inchiKey:    RWRDLPDLKQPQOW-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#7]-[#6]-1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#7]-[#6]-1

silicon grease: C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C

smiles_non_kekule:    C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C
smiles_kekule:    C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C
inchi:    InChI=1S/C30H90O13Si14/c1-44(2,3)31-46(7,8)33-48(11,12)35-50(15,16)37-52(19,20)39-54(23,24)41-56(27,28)43-57(29,30)42-55(25,26)40-53(21,22)38-51(17,18)36-49(13,14)34-47(9,10)32-45(4,5)6/h1-30H3
inchiKey:    ZJPOEHJHMRBDHP-UHFFFAOYSA-N
smarts:    [#6]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#6]
smarts_isomeric:    [#6]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#8]-[Si](-[#6])(-[#6])-[#6]

tetrahydrofuran: C1CCOC1

smiles_non_kekule:    C1CCOC1
smiles_kekule:    C1CCOC1
inchi:    InChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2
inchiKey:    WYURNTSHIVDZCO-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#8]-[#6]-1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#8]-[#6]-1

toluene: CC1=CC=CC=C1

triethylamine: CCN(CC)CC

smiles_non_kekule:    CCN(CC)CC
smiles_kekule:    CCN(CC)CC
inchi:    InChI=1S/C6H15N/c1-4-7(5-2)6-3/h4-6H2,1-3H3
inchiKey:    ZMANZCXQSJIPKH-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7](-[#6]-[#6])-[#6]-[#6]
smarts_isomeric:    [#6]-[#6]-[#7](-[#6]-[#6])-[#6]-[#6]

problem_type: 11/25 (loop 0/0)

[15:17:05] ERROR: Empty structure

[15:17:05] Invalid InChI prefix in generating InChI Key
[15:17:05] WARNING: Accepted unusual valence(s): C(2)

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Accepted unusual valence(s): C(2)

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Accepted unusual valence(s): C(3)

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Charges were rearranged; Omitted undefined stereo

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Omitted undefined stereo

Problem Template: _problem_common_polymer_repeating_units

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Charges were rearranged; Omitted undefined stereo

[15:17:05] WARNING: Omitted undefined stereo

[15:17:05] WARNING: Omitted undefined stereo

Write structure of common polymer repeating units molecules.

Answer:

structure of common polymer repeating units molecules:

3′-bromo-2-chloro[1,1′:4′,1′′-terphenyl]-4,4′′: ClC1=CC=CC=C1C2=CC=C(C3=CC=CC=C3)C(Br)=C2

[3,3′-biquinoline]-6,6′: C1(C2=CC3=CC=CC=C3N=C2)=CC4=CC=CC=C4N=C1

[2,3′-bipyridine]-4,5′: C1(C2=CC=CN=C2)=NC=CC=C1

(Z)-but-1-enel: C=CCC

threo-(E)-3-(methoxycarbonyl)-4-methylbut-1-ene-1,4-diyl:

ethene-1,2-diyl: C=C

propane-1,3-diyl: CCC

methylmethylene: [CH]C

1-phenylethylene: C=CC1=CC=CC=C1

1,2-dioxobutane: CCC(C=O)=O

1,3-dioxohexane: CCCC(CC=O)=O

oxyoxalyl: O=CC(O)=O

oxysuccinyl: O=CCCC(O)=O

naphthalene: C12=CC=CC=C1C=CC=C2

2H-furo[3,2-b]pyran: C12=CCOC1=CC=CO2

pyridine: C1=NC=CC=C1

1-carboxylatoethylene: NC1(C(O)=O)CC1

x-iminocyclopentane: N=C1CCCC1

pyridine-3,5-diylpiperidine: N1(C2=CC3=CN=C2)C3CCCC1

(4-chloro[3,3′-bipyridine])methylene: [CH]C1=NC=CC(Cl)=C1C2=CC=CN=C2

imino[1-oxo-2-(phenylsulfanyl)ethylene]: O=C=C(N)SC1=CC=CC=C1

methylphenylsiloxane: [H]O[SiH](C)C1=CC=CC=C1

diethoxyphosphazene: CCO[PH2](N)OCC

piperidine-3,5-diylideneethanediylidene: C/C=C1CNCCC1

sulfanediylcarbonyl: O=[CH]S

spiro[4.5]decane-2,8-diylmethylene: C1(CC(CC2)CC3)CC32CC1

4H-1,2,4-triazole-3,5-diylmethylene: C1(C2)=NN=C2N1

(2-phenyl-1,3-phenylene)ethylene: C1(C=C2)=CC=CC2=C1C3=CC=CC=C3

(5′-chloro[1,2′-binaphthalene])methylene: CC1=CC=C2C=CC=CC2=C1C3=CC=C4C(Cl)=CC=CC4=C3

(6-chlorocyclohex-1-ene)(1-bromoethylene): ClC1C=CC(C(Br)C)CC1

oxy{[3-(trifluoromethyl)phenyl]methylene}: FC(C1=CC([CH]O)=CC=C1)(F)F

1,3-phenyleneethylene: C1(C=C2)=CC=CC2=C1

(tetramethoxy-1,4-phenylene)(1,2-diphenylethene): COC(C(OC)=CC(OC)=C1OC)=C1/C(C2=CC=CC=C2)=C/C3=CC=CC=C3

(1,1′,3,3′-tetraoxo[5,5′-biisoindoline]-2,2′-diyl)biphenyl: O=C(C1=C2C=CC(C3=CC=C4C(OCN(C5=CC=C(C6=CC=CC=C6)C=C5)CO4)=C3)=C1)NC2=O

morpholine-2,6-diylpyridine-3,5-diylthianthrene: C(C=C1S2)(C3=CN=CC(C4CNCCO4)=C3)=CC=C1SC5=C2C=CC=C5

naphthalene-1,4-phenylenecyclohexane: C12=CC=CC=C1C=C(C3=CC=CC(C4CCCCC4)=C3)C=C2

pyridine-1,4-phenylenecyclopentane: C1(C2=CC=CC(C3CCCC3)=C2)=CC=CN=C1

pyridine-4H-1,2,4-triazole-3,5-diylmethylene: CC(N1)=NN=C1C2=NC=CC=C2

oxyspiro[3.5]nona-2,5-diene-7,1-diylcyclohex-4-ene-1,3-diyl: OC1C=CC2(CCC2C3CC=CCC3)CC1

piperidine-oxymethylene: COC1NCCCC1

pyridine-methyleneoxy-1,4-phenylene: C1(OCC2=NC=CC=C2)=CC=CC=C1

imino(1-chloro-2-oxoethylene)(4-nitro-1,3-phenylene)(3-bromopropane): NC(C(C1=CC=C([N+]([O-])=O)C(CCBr)=C1)=O)Cl

pyridine-acenaphthylene-3,8-diylpyrrole-diylacenaphthylene: C1(C2=C(C=C3)C(C3=C(C4=CNC=C4C5=C(C=C6)C(C6=CC=C7)=C7C=C5)C=C8)=C8C=C2)=CC=CN=C1

pyridine-(phenylmethylene)iminocyclohexane: C1(C(NC2CCCCC2)C3=CC=CC=C3)=CC=CC=N1

(methylimino)methyleneimino-1,3-phenylene: CNCNC1=CC=CC=C1

pyridine-diyliminocyclohexane(phenylmethylene): C1(NC2CCC(CC3=CC=CC=C3)CC2)=CC=CC=N1

imino(1-oxoethylene)silanediylpropane: NC(C[Si](C)(C)C)=O

pyridine-cyclohexane-oxypropane: CCCOC(CCC1)CC1C2=CC=CN=C2

sulfaneethylenesulfanediyl(2-amino-4-carboxypentane): SCCSC(N)CC(C)C(O)=O

sulfaneethylenesulfanediyl(4-amino-1-carboxypentane): SCCSC(C(O)=O)CC(N)C

pyridine-methylenepyridine(tetrahydropyran): C1(CC2=CN=CC(C3COCCC3)=C2)=CC=CN=C1

sulfane(2-chloropropane)sulfanepropane: SCC(CSCCC)Cl

pyridine-carbonyloxymethylene: O=C(OC)C1=CC=CN=C1

1,3-phenylene(1-bromoethylene)cyclohexane(2-butylethylene): BrC(C1CCCC(C(CCC)C)C1)C2=CC=CC=C2

oxy(1,1-dichloroethylene)imino(1-oxoethylene): OC(Cl)(CNCOC)Cl

sulfane(1-chloroethylene)-1,3-phenylene(1-chloroethylene): SC(CC1=CC(C(C)Cl)=CC=C1)Cl

sulfane(1-iodoethylene)sulfane(5-bromo-3-chloropentane): SC(CSCCC(CCBr)Cl)I

oxymethylene-ONN-azoxy(chloromethylene): OCN(O)-NCCl

(3-chlorobiphenyl)methylene(3-chloro-1,4-phenylene)methylene: ClC1=CC(C2=CC=C(C3=CC=C(C)C(Cl)=C3)C=C2)=CC=C1

imino(x-methyl-1,3-phenylene)iminomalonyl: NC1=CC(C)=CC(NC(CC=O)=O)=C1

oxyhexane-oxycarbonylimino(methylphenylene)iminocarbonyl: OCCCCCCOC(NC1=CC(C)=C(NC=O)C=C1)=O

2,4,8,10-tetraoxaspiro[5.5]undecane-oxyhexane-1,6-diyloxy: CC1OCC2(COC(OCCCCCCO)OC2)CO1

pyridine-methylenepyrrole-oxymethylene: COC1=CNC=C1CC2=CC=CN=C2

oxymethyleneiminocarbonylsulfane-1,3-phenyleneethylene: COCNC(SC1=CC=CC(CC)=C1)=O

oxyiminomethylenehydrazine-methylene: ONCNNC

piperidine-methylenepiperidine-4,2-diylcyclopentane-ethylenecyclopentane-1,2-diylmethylene: CC(C1)CCC1CC(C2)CCC2C(C3)NCCC3CC4NCCCC4

1,3-dioxa-8-thia-5,10-diazadodecane: OCOCNCCSCNCC

oxymethyleneoxymethyleneoxymethyleneimino-1,3-phenylenemethyleneiminomethylene: OCOCOCNC1=CC(CNC)=CC=C1

pyridine-1,4-phenylenemethyleneoxymethyleneiminomethyleneoxy-1,4-phenylenemethylene: CC(C=C1)=CC=C1OCNCOCC(C=C2)=CC=C2C3=CC=CN=C3

sulfinylmethylenesulfanediylpropane-1,3-diylsulfonyl-1,4-phenylene: SOCSCCCS(=O)(C1=CC=CC=C1)=O

oxyterephthaloylhydrazine-terephthaloyl: OC(C1=CC=C(C(NNC(C2=CC=C(C=O)C=C2)=O)=O)C=C1)=O

nitrilo-1,4-phenylenenitriloprop-2-en-3-yl-1-ylidene-1,4-phenyleneprop-1-en-1-yl-3-ylidene: NC1=CC=C(N=CC=CC2=CC=C(C=CCC)C=C2)C=C1

oxycarbonylnitrilopropane-idenenitrilocarbonyl: OC(N=CCC=NC=O)=O

oxyethyleneiminomethylenesulfanediylethyleneiminocyclohexane: OCCCNCSCCNC1CCCCC1

iminomethyleneiminocarbonyl{2-[(2,4-dinitrophenyl)hydrazono]cyclopentane}carbonyl: OC(C1=CC=C(C(OCCCCCC)=O)C=C1)=O

oxyterephthaloyloxyhexane: NCCNC(C1/C(C(C=O)CC1)=N/NC2=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C2)=O

nitrilocyclohexa-2,5-diene-idenenitrilo-1,4-phenyleneimino-1,4-phenyleneimino1,4-phenylene: N=C1C=CC(C=C1)=NC2=CC=C(NC3=CC=C(NC4=CC=CC=C4)C=C3)C=C2

cyclohexane-methanylylidenecyclohexane-idenemethanylylidenecyclohexane-methylene: CC(CC1)CCC1C=C(CC2)CCC2=CC3CCCCC3

Solution:

structure of common polymer repeating units molecules:

3′-bromo-2-chloro[1,1′:4′,1′′-terphenyl]-4,4′′: ClC1=CC=CC=C1C2=CC=C(C3=CC=CC=C3)C(Br)=C2

smiles_non_kekule:    Clc1ccccc1-c1ccc(-c2ccccc2)c(Br)c1
smiles_kekule:    ClC1=CC=CC=C1C1=CC=C(C2=CC=CC=C2)C(Br)=C1
inchi:    InChI=1S/C18H12BrCl/c19-17-12-14(16-8-4-5-9-18(16)20)10-11-15(17)13-6-2-1-3-7-13/h1-12H
inchiKey:    RKTVVYVYQKZGBM-UHFFFAOYSA-N
smarts:    [#17]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]1:[#6]:[#6]:[#6](-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2):[#6](-[#35]):[#6]:1
smarts_isomeric:    [#17]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]1:[#6]:[#6]:[#6](-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2):[#6](-[#35]):[#6]:1

[3,3′-biquinoline]-6,6′: C1(C2=CC3=CC=CC=C3N=C2)=CC4=CC=CC=C4N=C1

smiles_non_kekule:    c1ccc2ncc(-c3cnc4ccccc4c3)cc2c1
smiles_kekule:    C1=CC=C2N=CC(C3=CC4=CC=CC=C4N=C3)=CC2=C1
inchi:    InChI=1S/C18H12N2/c1-3-7-17-13(5-1)9-15(11-19-17)16-10-14-6-2-4-8-18(14)20-12-16/h1-12H
inchiKey:    NOABOXDQMPHZSI-UHFFFAOYSA-N
smarts:    [#6]1(-[#6]2:[#6]:[#6]3:[#6]:[#6]:[#6]:[#6]:[#6]:3:[#7]:[#6]:2):[#6]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#7]:[#6]:1
smarts_isomeric:    [#6]1(-[#6]2:[#6]:[#6]3:[#6]:[#6]:[#6]:[#6]:[#6]:3:[#7]:[#6]:2):[#6]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#7]:[#6]:1

[2,3′-bipyridine]-4,5′: C1(C2=CC=CN=C2)=NC=CC=C1

smiles_non_kekule:    c1ccc(-c2cccnc2)nc1
smiles_kekule:    C1=CN=C(C2=CC=CN=C2)C=C1
inchi:    InChI=1S/C10H8N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h1-8H
inchiKey:    VEKIYFGCEAJDDT-UHFFFAOYSA-N
smarts:    [#6]1(-[#6]2:[#6]:[#6]:[#6]:[#7]:[#6]:2):[#7]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1(-[#6]2:[#6]:[#6]:[#6]:[#7]:[#6]:2):[#7]:[#6]:[#6]:[#6]:[#6]:1

(Z)-but-1-enel: C=CCC

smiles_non_kekule:    C=CCC
smiles_kekule:    C=CCC
inchi:    InChI=1S/C4H8/c1-3-4-2/h3H,1,4H2,2H3
inchiKey:    VXNZUUAINFGPBY-UHFFFAOYSA-N
smarts:    [#6]=[#6]-[#6]-[#6]
smarts_isomeric:    [#6]=[#6]-[#6]-[#6]

threo-(E)-3-(methoxycarbonyl)-4-methylbut-1-ene-1,4-diyl:

smiles_non_kekule:
smiles_kekule:
inchi:
inchiKey:
smarts:
smarts_isomeric:

ethene-1,2-diyl: C=C

smiles_non_kekule:    C=C
smiles_kekule:    C=C
inchi:    InChI=1S/C2H4/c1-2/h1-2H2
inchiKey:    VGGSQFUCUMXWEO-UHFFFAOYSA-N
smarts:    [#6]=[#6]
smarts_isomeric:    [#6]=[#6]

propane-1,3-diyl: CCC

smiles_non_kekule:    CCC
smiles_kekule:    CCC
inchi:    InChI=1S/C3H8/c1-3-2/h3H2,1-2H3
inchiKey:    ATUOYWHBWRKTHZ-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]

methylmethylene: [CH]C

smiles_non_kekule:    [CH]C
smiles_kekule:    [CH]C
inchi:    InChI=1S/C2H4/c1-2/h1H,2H3
inchiKey:    UUFQTNFCRMXOAE-UHFFFAOYSA-N
smarts:    [#6H]-[#6]
smarts_isomeric:    [#6H]-[#6]

1-phenylethylene: C=CC1=CC=CC=C1

smiles_non_kekule:    C=Cc1ccccc1
smiles_kekule:    C=CC1=CC=CC=C1
inchi:    InChI=1S/C8H8/c1-2-8-6-4-3-5-7-8/h2-7H,1H2
inchiKey:    PPBRXRYQALVLMV-UHFFFAOYSA-N
smarts:    [#6]=[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]=[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

1,2-dioxobutane: CCC(C=O)=O

smiles_non_kekule:    CCC(=O)C=O
smiles_kekule:    CCC(=O)C=O
inchi:    InChI=1S/C4H6O2/c1-2-4(6)3-5/h3H,2H2,1H3
inchiKey:    RWHQMRRVZJSKGX-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](-[#6]=[#8])=[#8]
smarts_isomeric:    [#6]-[#6]-[#6](-[#6]=[#8])=[#8]

1,3-dioxohexane: CCCC(CC=O)=O

smiles_non_kekule:    CCCC(=O)CC=O
smiles_kekule:    CCCC(=O)CC=O
inchi:    InChI=1S/C6H10O2/c1-2-3-6(8)4-5-7/h5H,2-4H2,1H3
inchiKey:    PVLKSJIUOKAUMV-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6](-[#6]-[#6]=[#8])=[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6](-[#6]-[#6]=[#8])=[#8]

oxyoxalyl: O=CC(O)=O

smiles_non_kekule:    O=CC(=O)O
smiles_kekule:    O=CC(=O)O
inchi:    InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)
inchiKey:    HHLFWLYXYJOTON-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#6](-[#8])=[#8]
smarts_isomeric:    [#8]=[#6]-[#6](-[#8])=[#8]

oxysuccinyl: O=CCCC(O)=O

smiles_non_kekule:    O=CCCC(=O)O
smiles_kekule:    O=CCCC(=O)O
inchi:    InChI=1S/C4H6O3/c5-3-1-2-4(6)7/h3H,1-2H2,(H,6,7)
inchiKey:    UIUJIQZEACWQSV-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#6]-[#6]-[#6](-[#8])=[#8]
smarts_isomeric:    [#8]=[#6]-[#6]-[#6]-[#6](-[#8])=[#8]

naphthalene: C12=CC=CC=C1C=CC=C2

smiles_non_kekule:    c1ccc2ccccc2c1
smiles_kekule:    C1=CC=C2C=CC=CC2=C1
inchi:    InChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
inchiKey:    UFWIBTONFRDIAS-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#6]:[#6]:2

2H-furo[3,2-b]pyran: C12=CCOC1=CC=CO2

smiles_non_kekule:    C1=COC2=CCOC2=C1
smiles_kekule:    C1=COC2=CCOC2=C1
inchi:    InChI=1S/C7H6O2/c1-2-6-7(8-4-1)3-5-9-6/h1-4H,5H2
inchiKey:    FXJVRYIFIVSWID-UHFFFAOYSA-N
smarts:    [#6]12=[#6]-[#6]-[#8]-[#6]-1=[#6]-[#6]=[#6]-[#8]-2
smarts_isomeric:    [#6]12=[#6]-[#6]-[#8]-[#6]-1=[#6]-[#6]=[#6]-[#8]-2

pyridine: C1=NC=CC=C1

smiles_non_kekule:    c1ccncc1
smiles_kekule:    C1=CC=NC=C1
inchi:    InChI=1S/C5H5N/c1-2-4-6-5-3-1/h1-5H
inchiKey:    JUJWROOIHBZHMG-UHFFFAOYSA-N
smarts:    [#6]1:[#7]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#7]:[#6]:[#6]:[#6]:[#6]:1

1-carboxylatoethylene: NC1(C(O)=O)CC1

smiles_non_kekule:    NC1(C(=O)O)CC1
smiles_kekule:    NC1(C(=O)O)CC1
inchi:    InChI=1S/C4H7NO2/c5-4(1-2-4)3(6)7/h1-2,5H2,(H,6,7)
inchiKey:    PAJPWUMXBYXFCZ-UHFFFAOYSA-N
smarts:    [#7]-[#6]1(-[#6](-[#8])=[#8])-[#6]-[#6]-1
smarts_isomeric:    [#7]-[#6]1(-[#6](-[#8])=[#8])-[#6]-[#6]-1

x-iminocyclopentane: N=C1CCCC1

smiles_non_kekule:    N=C1CCCC1
smiles_kekule:    N=C1CCCC1
inchi:    InChI=1S/C5H9N/c6-5-3-1-2-4-5/h6H,1-4H2
inchiKey:    HMZHPDZCVINDPO-UHFFFAOYSA-N
smarts:    [#7]=[#6]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#7]=[#6]1-[#6]-[#6]-[#6]-[#6]-1

pyridine-3,5-diylpiperidine: N1(C2=CC3=CN=C2)C3CCCC1

smiles_non_kekule:    c1ncc2cc1C1CCCCN21
smiles_kekule:    C1=C2C=C(C=N1)N1CCCCC21
inchi:    InChI=1S/C10H12N2/c1-2-4-12-9-5-8(6-11-7-9)10(12)3-1/h5-7,10H,1-4H2
inchiKey:    WPOMFSWMENVYHZ-UHFFFAOYSA-N
smarts:    [#7]12-[#6]3:[#6]:[#6](:[#6]:[#7]:[#6]:3)-[#6]-1-[#6]-[#6]-[#6]-[#6]-2
smarts_isomeric:    [#7]12-[#6]3:[#6]:[#6](:[#6]:[#7]:[#6]:3)-[#6]-1-[#6]-[#6]-[#6]-[#6]-2

(4-chloro[3,3′-bipyridine])methylene: [CH]C1=NC=CC(Cl)=C1C2=CC=CN=C2

smiles_non_kekule:    [CH]c1nccc(Cl)c1-c1cccnc1
smiles_kekule:    [CH]C1=NC=CC(Cl)=C1C1=CC=CN=C1
inchi:    InChI=1S/C11H7ClN2/c1-8-11(10(12)4-6-14-8)9-3-2-5-13-7-9/h1-7H
inchiKey:    VBAVYZMVFFFEKL-UHFFFAOYSA-N
smarts:    [#6H]-[#6]1:[#7]:[#6]:[#6]:[#6](-[#17]):[#6]:1-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1
smarts_isomeric:    [#6H]-[#6]1:[#7]:[#6]:[#6]:[#6](-[#17]):[#6]:1-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1

imino[1-oxo-2-(phenylsulfanyl)ethylene]: O=C=C(N)SC1=CC=CC=C1

smiles_non_kekule:    NC(=C=O)Sc1ccccc1
smiles_kekule:    NC(=C=O)SC1=CC=CC=C1
inchi:    InChI=1S/C8H7NOS/c9-8(6-10)11-7-4-2-1-3-5-7/h1-5H,9H2
inchiKey:    KAYNKJHYEJUOTN-UHFFFAOYSA-N
smarts:    [#8]=[#6]=[#6](-[#7])-[#16]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#8]=[#6]=[#6](-[#7])-[#16]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

methylphenylsiloxane: [H]O[SiH](C)C1=CC=CC=C1

smiles_non_kekule:    C[SiH](O)c1ccccc1
smiles_kekule:    C[SiH](O)C1=CC=CC=C1
inchi:    InChI=1S/C7H10OSi/c1-9(8)7-5-3-2-4-6-7/h2-6,8-9H,1H3
inchiKey:    LFEMHZIYNMLNEB-UHFFFAOYSA-N
smarts:    [#8H]-[SiH](-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#8H]-[SiH](-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

diethoxyphosphazene: CCO[PH2](N)OCC

smiles_non_kekule:    CCO[PH2](N)OCC
smiles_kekule:    CCO[PH2](N)OCC
inchi:    InChI=1S/C4H12NO2P/c1-3-6-8(5)7-4-2/h3-5H2,1-2H3
inchiKey:    SWPYNTWPIAZGLT-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]-[#15H2](-[#7])-[#8]-[#6]-[#6]
smarts_isomeric:    [#6]-[#6]-[#8]-[#15H2](-[#7])-[#8]-[#6]-[#6]

piperidine-3,5-diylideneethanediylidene: C/C=C1CNCCC1

smiles_non_kekule:    CC=C1CCCNC1
smiles_kekule:    CC=C1CCCNC1
inchi:    InChI=1S/C7H13N/c1-2-7-4-3-5-8-6-7/h2,8H,3-6H2,1H3
inchiKey:    KPDBFXIKMXHJEB-UHFFFAOYSA-N
smarts:    [#6]-[#6]=[#6]1-[#6]-[#7]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6]=[#6]1-[#6]-[#7]-[#6]-[#6]-[#6]-1

sulfanediylcarbonyl: O=[CH]S

smiles_non_kekule:    O=CS
smiles_kekule:    O=CS
inchi:    InChI=1S/CH2OS/c2-1-3/h1H,(H,2,3)
inchiKey:    AWIJRPNMLHPLNC-UHFFFAOYSA-N
smarts:    [#8]=[#6H]-[#16]
smarts_isomeric:    [#8]=[#6H]-[#16]

spiro[4.5]decane-2,8-diylmethylene: C1(CC(CC2)CC3)CC32CC1

smiles_non_kekule:    C1CC23CCC1CC(CC2)C3
smiles_kekule:    C1CC23CCC1CC(CC2)C3
inchi:    InChI=1S/C11H18/c1-4-11-5-2-9(1)7-10(8-11)3-6-11/h9-10H,1-8H2
inchiKey:    GTLJAVLRHSRDQL-UHFFFAOYSA-N
smarts:    [#6]12-[#6]-[#6]3-[#6]-[#6]-[#6](-[#6]-[#6]-3)(-[#6]-1)-[#6]-[#6]-2
smarts_isomeric:    [#6]12-[#6]-[#6]3-[#6]-[#6]-[#6](-[#6]-[#6]-3)(-[#6]-1)-[#6]-[#6]-2

4H-1,2,4-triazole-3,5-diylmethylene: C1(C2)=NN=C2N1

smiles_non_kekule:    C1c2nnc1[nH]2
smiles_kekule:    C1C2=NN=C1N2
inchi:    InChI=1S/C3H3N3/c1-2-4-3(1)6-5-2/h1H2,(H,4,5,6)
inchiKey:    BDSKHKFPMHMXCM-UHFFFAOYSA-N
smarts:    [#6]12-[#6]-[#6](:[#7]:[#7]:1):[#7H]:2
smarts_isomeric:    [#6]12-[#6]-[#6](:[#7]:[#7]:1):[#7H]:2

(2-phenyl-1,3-phenylene)ethylene: C1(C=C2)=CC=CC2=C1C3=CC=CC=C3

smiles_non_kekule:    C1=Cc2cccc1c2-c1ccccc1
smiles_kekule:    C1=CC2=C(C3=CC=CC=C3)C1=CC=C2
inchi:    InChI=1S/C14H10/c1-2-5-11(6-3-1)14-12-7-4-8-13(14)10-9-12/h1-10H
inchiKey:    DVESNTFKIGKDRD-UHFFFAOYSA-N
smarts:    [#6]12-[#6]=[#6]-[#6](:[#6]:[#6]:[#6]:1):[#6]:2-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]12-[#6]=[#6]-[#6](:[#6]:[#6]:[#6]:1):[#6]:2-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

(5′-chloro[1,2′-binaphthalene])methylene: CC1=CC=C2C=CC=CC2=C1C3=CC=C4C(Cl)=CC=CC4=C3

smiles_non_kekule:    Cc1ccc2ccccc2c1-c1ccc2c(Cl)cccc2c1
smiles_kekule:    CC1=CC=C2C=CC=CC2=C1C1=CC=C2C(Cl)=CC=CC2=C1
inchi:    InChI=1S/C21H15Cl/c1-14-9-10-15-5-2-3-7-19(15)21(14)17-11-12-18-16(13-17)6-4-8-20(18)22/h2-13H,1H3
inchiKey:    CZHZJCSFDUNEEY-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#6]:1-[#6]1:[#6]:[#6]:[#6]2:[#6](-[#17]):[#6]:[#6]:[#6]:[#6]:2:[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#6]:1-[#6]1:[#6]:[#6]:[#6]2:[#6](-[#17]):[#6]:[#6]:[#6]:[#6]:2:[#6]:1

(6-chlorocyclohex-1-ene)(1-bromoethylene): ClC1C=CC(C(Br)C)CC1

smiles_non_kekule:    CC(Br)C1C=CC(Cl)CC1
smiles_kekule:    CC(Br)C1C=CC(Cl)CC1
inchi:    InChI=1S/C8H12BrCl/c1-6(9)7-2-4-8(10)5-3-7/h2,4,6-8H,3,5H2,1H3
inchiKey:    JOKBCNIDLMTKQF-UHFFFAOYSA-N
smarts:    [#17]-[#6]1-[#6]=[#6]-[#6](-[#6](-[#35])-[#6])-[#6]-[#6]-1
smarts_isomeric:    [#17]-[#6]1-[#6]=[#6]-[#6](-[#6](-[#35])-[#6])-[#6]-[#6]-1

oxy{[3-(trifluoromethyl)phenyl]methylene}: FC(C1=CC([CH]O)=CC=C1)(F)F

smiles_non_kekule:    O[CH]c1cccc(C(F)(F)F)c1
smiles_kekule:    O[CH]C1=CC=CC(C(F)(F)F)=C1
inchi:    InChI=1S/C8H6F3O/c9-8(10,11)7-3-1-2-6(4-7)5-12/h1-5,12H
inchiKey:    GFPGMKFRSIGLJU-UHFFFAOYSA-N
smarts:    [#9]-[#6](-[#6]1:[#6]:[#6](-[#6H]-[#8]):[#6]:[#6]:[#6]:1)(-[#9])-[#9]
smarts_isomeric:    [#9]-[#6](-[#6]1:[#6]:[#6](-[#6H]-[#8]):[#6]:[#6]:[#6]:1)(-[#9])-[#9]

1,3-phenyleneethylene: C1(C=C2)=CC=CC2=C1

smiles_non_kekule:    C1=Cc2cccc1c2
smiles_kekule:    C1=CC2=CC1=CC=C2
inchi:    InChI=1S/C8H6/c1-2-7-4-5-8(3-1)6-7/h1-6H
inchiKey:    WXYHBEAVYULZEG-UHFFFAOYSA-N
smarts:    [#6]12-[#6]=[#6]-[#6](:[#6]:[#6]:[#6]:1):[#6]:2
smarts_isomeric:    [#6]12-[#6]=[#6]-[#6](:[#6]:[#6]:[#6]:1):[#6]:2

(tetramethoxy-1,4-phenylene)(1,2-diphenylethene): COC(C(OC)=CC(OC)=C1OC)=C1/C(C2=CC=CC=C2)=C/C3=CC=CC=C3

smiles_non_kekule:    COc1cc(OC)c(OC)c(/C(=C/c2ccccc2)c2ccccc2)c1OC
smiles_kekule:    COC1=C(OC)C(/C(=C/C2=CC=CC=C2)C2=CC=CC=C2)=C(OC)C(OC)=C1
inchi:    InChI=1S/C24H24O4/c1-25-20-16-21(26-2)24(28-4)22(23(20)27-3)19(18-13-9-6-10-14-18)15-17-11-7-5-8-12-17/h5-16H,1-4H3/b19-15+
inchiKey:    CFFRWIZIYQGVOD-XDJHFCHBSA-N
smarts:    [#6]-[#8]-[#6]1:[#6](-[#8]-[#6]):[#6]:[#6](-[#8]-[#6]):[#6](-[#8]-[#6]):[#6]:1-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)=[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#8]-[#6]1:[#6](-[#8]-[#6]):[#6]:[#6](-[#8]-[#6]):[#6](-[#8]-[#6]):[#6]:1/[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)=[#6]/[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

(1,1′,3,3′-tetraoxo[5,5′-biisoindoline]-2,2′-diyl)biphenyl: O=C(C1=C2C=CC(C3=CC=C4C(OCN(C5=CC=C(C6=CC=CC=C6)C=C5)CO4)=C3)=C1)NC2=O

smiles_non_kekule:    O=C1NC(=O)c2cc(-c3ccc4c(c3)OCN(c3ccc(-c5ccccc5)cc3)CO4)ccc21
smiles_kekule:    O=C1NC(=O)C2=C1C=CC(C1=CC=C3OCN(C4=CC=C(C5=CC=CC=C5)C=C4)COC3=C1)=C2
inchi:    InChI=1S/C28H20N2O4/c31-27-23-12-8-20(14-24(23)28(32)29-27)21-9-13-25-26(15-21)34-17-30(16-33-25)22-10-6-19(7-11-22)18-4-2-1-3-5-18/h1-15H,16-17H2,(H,29,31,32)
inchiKey:    RZWZJHDZHCGIEZ-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#6]2:[#6](:[#6]:[#6]:[#6](-[#6]3:[#6]:[#6]:[#6]4:[#6](-[#8]-[#6]-[#7](-[#6]5:[#6]:[#6]:[#6](-[#6]6:[#6]:[#6]:[#6]:[#6]:[#6]:6):[#6]:[#6]:5)-[#6]-[#8]-4):[#6]:3):[#6]:2)-[#6](-[#7]-1)=[#8]
smarts_isomeric:    [#8]=[#6]1-[#6]2:[#6](:[#6]:[#6]:[#6](-[#6]3:[#6]:[#6]:[#6]4:[#6](-[#8]-[#6]-[#7](-[#6]5:[#6]:[#6]:[#6](-[#6]6:[#6]:[#6]:[#6]:[#6]:[#6]:6):[#6]:[#6]:5)-[#6]-[#8]-4):[#6]:3):[#6]:2)-[#6](-[#7]-1)=[#8]

morpholine-2,6-diylpyridine-3,5-diylthianthrene: C(C=C1S2)(C3=CN=CC(C4CNCCO4)=C3)=CC=C1SC5=C2C=CC=C5

smiles_non_kekule:    c1ccc2c(c1)Sc1ccc(-c3cncc(C4CNCCO4)c3)cc1S2
smiles_kekule:    C1=CC2=C(C=C1)SC1=C(C=CC(C3=CN=CC(C4CNCCO4)=C3)=C1)S2
inchi:    InChI=1S/C21H18N2OS2/c1-2-4-19-18(3-1)25-20-6-5-14(10-21(20)26-19)15-9-16(12-23-11-15)17-13-22-7-8-24-17/h1-6,9-12,17,22H,7-8,13H2
inchiKey:    IVFOQLXSZCEFSE-UHFFFAOYSA-N
smarts:    [#6]1(:[#6]:[#6]2-[#16]-[#6]3:[#6](-[#16]-[#6]:2:[#6]:[#6]:1):[#6]:[#6]:[#6]:[#6]:3)-[#6]1:[#6]:[#7]:[#6]:[#6](-[#6]2-[#6]-[#7]-[#6]-[#6]-[#8]-2):[#6]:1
smarts_isomeric:    [#6]1(:[#6]:[#6]2-[#16]-[#6]3:[#6](-[#16]-[#6]:2:[#6]:[#6]:1):[#6]:[#6]:[#6]:[#6]:3)-[#6]1:[#6]:[#7]:[#6]:[#6](-[#6]2-[#6]-[#7]-[#6]-[#6]-[#8]-2):[#6]:1

naphthalene-1,4-phenylenecyclohexane: C12=CC=CC=C1C=C(C3=CC=CC(C4CCCCC4)=C3)C=C2

smiles_non_kekule:    c1cc(-c2ccc3ccccc3c2)cc(C2CCCCC2)c1
smiles_kekule:    C1=CC(C2CCCCC2)=CC(C2=CC3=CC=CC=C3C=C2)=C1
inchi:    InChI=1S/C22H22/c1-2-7-17(8-3-1)20-11-6-12-21(15-20)22-14-13-18-9-4-5-10-19(18)16-22/h4-6,9-17H,1-3,7-8H2
inchiKey:    JCFTXFUKSYJKDH-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6](-[#6]1:[#6]:[#6]:[#6]:[#6](-[#6]3-[#6]-[#6]-[#6]-[#6]-[#6]-3):[#6]:1):[#6]:[#6]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6](-[#6]1:[#6]:[#6]:[#6]:[#6](-[#6]3-[#6]-[#6]-[#6]-[#6]-[#6]-3):[#6]:1):[#6]:[#6]:2

pyridine-1,4-phenylenecyclopentane: C1(C2=CC=CC(C3CCCC3)=C2)=CC=CN=C1

smiles_non_kekule:    c1cncc(-c2cccc(C3CCCC3)c2)c1
smiles_kekule:    C1=CN=CC(C2=CC=CC(C3CCCC3)=C2)=C1
inchi:    InChI=1S/C16H17N/c1-2-6-13(5-1)14-7-3-8-15(11-14)16-9-4-10-17-12-16/h3-4,7-13H,1-2,5-6H2
inchiKey:    QIZVAWMKIHNKMA-UHFFFAOYSA-N
smarts:    [#6]1(-[#6]2:[#6]:[#6]:[#6]:[#6](-[#6]3-[#6]-[#6]-[#6]-[#6]-3):[#6]:2):[#6]:[#6]:[#6]:[#7]:[#6]:1
smarts_isomeric:    [#6]1(-[#6]2:[#6]:[#6]:[#6]:[#6](-[#6]3-[#6]-[#6]-[#6]-[#6]-3):[#6]:2):[#6]:[#6]:[#6]:[#7]:[#6]:1

pyridine-4H-1,2,4-triazole-3,5-diylmethylene: CC(N1)=NN=C1C2=NC=CC=C2

smiles_non_kekule:    Cc1nnc(-c2ccccn2)[nH]1
smiles_kekule:    CC1=NN=C(C2=NC=CC=C2)N1
inchi:    InChI=1S/C8H8N4/c1-6-10-8(12-11-6)7-4-2-3-5-9-7/h2-5H,1H3,(H,10,11,12)
inchiKey:    BJDVHKDTPXZGEZ-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#7H]:[#6](:[#7]:[#7]:1)-[#6]1:[#7]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#7H]:[#6](:[#7]:[#7]:1)-[#6]1:[#7]:[#6]:[#6]:[#6]:[#6]:1

oxyspiro[3.5]nona-2,5-diene-7,1-diylcyclohex-4-ene-1,3-diyl: OC1C=CC2(CCC2C3CC=CCC3)CC1

smiles_non_kekule:    OC1C=CC2(CC1)CCC2C1CC=CCC1
smiles_kekule:    OC1C=CC2(CC1)CCC2C1CC=CCC1
inchi:    InChI=1S/C15H22O/c16-13-6-9-15(10-7-13)11-8-14(15)12-4-2-1-3-5-12/h1-2,6,9,12-14,16H,3-5,7-8,10-11H2
inchiKey:    IBXDBPWPUFMAAA-UHFFFAOYSA-N
smarts:    [#8]-[#6]1-[#6]=[#6]-[#6]2(-[#6]-[#6]-[#6]-2-[#6]2-[#6]-[#6]=[#6]-[#6]-[#6]-2)-[#6]-[#6]-1
smarts_isomeric:    [#8]-[#6]1-[#6]=[#6]-[#6]2(-[#6]-[#6]-[#6]-2-[#6]2-[#6]-[#6]=[#6]-[#6]-[#6]-2)-[#6]-[#6]-1

piperidine-oxymethylene: COC1NCCCC1

smiles_non_kekule:    COC1CCCCN1
smiles_kekule:    COC1CCCCN1
inchi:    InChI=1S/C6H13NO/c1-8-6-4-2-3-5-7-6/h6-7H,2-5H2,1H3
inchiKey:    DNYWGUIJLFDIPD-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]1-[#7]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#8]-[#6]1-[#7]-[#6]-[#6]-[#6]-[#6]-1

pyridine-methyleneoxy-1,4-phenylene: C1(OCC2=NC=CC=C2)=CC=CC=C1

smiles_non_kekule:    c1ccc(OCc2ccccn2)cc1
smiles_kekule:    C1=CC=C(OCC2=NC=CC=C2)C=C1
inchi:    InChI=1S/C12H11NO/c1-2-7-12(8-3-1)14-10-11-6-4-5-9-13-11/h1-9H,10H2
inchiKey:    HEMZNKOBGSXYFU-UHFFFAOYSA-N
smarts:    [#6]1(-[#8]-[#6]-[#6]2:[#7]:[#6]:[#6]:[#6]:[#6]:2):[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1(-[#8]-[#6]-[#6]2:[#7]:[#6]:[#6]:[#6]:[#6]:2):[#6]:[#6]:[#6]:[#6]:[#6]:1

imino(1-chloro-2-oxoethylene)(4-nitro-1,3-phenylene)(3-bromopropane): NC(C(C1=CC=C([N+]([O-])=O)C(CCBr)=C1)=O)Cl

smiles_non_kekule:    NC(Cl)C(=O)c1ccc([N+](=O)[O-])c(CCBr)c1
smiles_kekule:    NC(Cl)C(=O)C1=CC=C([N+](=O)[O-])C(CCBr)=C1
inchi:    InChI=1S/C10H10BrClN2O3/c11-4-3-6-5-7(9(15)10(12)13)1-2-8(6)14(16)17/h1-2,5,10H,3-4,13H2
inchiKey:    YWUPCMZDFCNBCL-UHFFFAOYSA-N
smarts:    [#7]-[#6](-[#6](-[#6]1:[#6]:[#6]:[#6](-[#7+](-[#8-])=[#8]):[#6](-[#6]-[#6]-[#35]):[#6]:1)=[#8])-[#17]
smarts_isomeric:    [#7]-[#6](-[#6](-[#6]1:[#6]:[#6]:[#6](-[#7+](-[#8-])=[#8]):[#6](-[#6]-[#6]-[#35]):[#6]:1)=[#8])-[#17]

pyridine-acenaphthylene-3,8-diylpyrrole-diylacenaphthylene: C1(C2=C(C=C3)C(C3=C(C4=CNC=C4C5=C(C=C6)C(C6=CC=C7)=C7C=C5)C=C8)=C8C=C2)=CC=CN=C1

smiles_non_kekule:    C1=Cc2c(-c3c[nH]cc3-c3ccc4ccc(-c5cccnc5)c5c4c3C=C5)ccc3cccc1c23
smiles_kekule:    C1=CC2=C(C3=CNC=C3C3=CC=C4C=CC(C5=CC=CN=C5)=C5C=CC3=C54)C=CC3=CC=CC1=C23
inchi:    InChI=1S/C33H20N2/c1-3-20-7-11-25(28-13-9-21(4-1)32(20)28)30-18-35-19-31(30)26-12-8-22-6-10-24(23-5-2-16-34-17-23)27-14-15-29(26)33(22)27/h1-19,35H
inchiKey:    VGOXLDCDNOXBRQ-UHFFFAOYSA-N
smarts:    [#6]1(-[#6]2:[#6]3-[#6]=[#6]-[#6]4:[#6]:3:[#6](:[#6]:[#6]:[#6]:4-[#6]3:[#6]:[#7H]:[#6]:[#6]:3-[#6]3:[#6]4-[#6]=[#6]-[#6]5:[#6]:4:[#6](:[#6]:[#6]:[#6]:5):[#6]:[#6]:3):[#6]:[#6]:2):[#6]:[#6]:[#6]:[#7]:[#6]:1
smarts_isomeric:    [#6]1(-[#6]2:[#6]3-[#6]=[#6]-[#6]4:[#6]:3:[#6](:[#6]:[#6]:[#6]:4-[#6]3:[#6]:[#7H]:[#6]:[#6]:3-[#6]3:[#6]4-[#6]=[#6]-[#6]5:[#6]:4:[#6](:[#6]:[#6]:[#6]:5):[#6]:[#6]:3):[#6]:[#6]:2):[#6]:[#6]:[#6]:[#7]:[#6]:1

pyridine-(phenylmethylene)iminocyclohexane: C1(C(NC2CCCCC2)C3=CC=CC=C3)=CC=CC=N1

smiles_non_kekule:    c1ccc(C(NC2CCCCC2)c2ccccn2)cc1
smiles_kekule:    C1=CC=C(C(NC2CCCCC2)C2=CC=CC=N2)C=C1
inchi:    InChI=1S/C18H22N2/c1-3-9-15(10-4-1)18(17-13-7-8-14-19-17)20-16-11-5-2-6-12-16/h1,3-4,7-10,13-14,16,18,20H,2,5-6,11-12H2
inchiKey:    SDCGVWYLSKFYGT-UHFFFAOYSA-N
smarts:    [#6]1(-[#6](-[#7]-[#6]2-[#6]-[#6]-[#6]-[#6]-[#6]-2)-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2):[#6]:[#6]:[#6]:[#6]:[#7]:1
smarts_isomeric:    [#6]1(-[#6](-[#7]-[#6]2-[#6]-[#6]-[#6]-[#6]-[#6]-2)-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2):[#6]:[#6]:[#6]:[#6]:[#7]:1

(methylimino)methyleneimino-1,3-phenylene: CNCNC1=CC=CC=C1

smiles_non_kekule:    CNCNc1ccccc1
smiles_kekule:    CNCNC1=CC=CC=C1
inchi:    InChI=1S/C8H12N2/c1-9-7-10-8-5-3-2-4-6-8/h2-6,9-10H,7H2,1H3
inchiKey:    ZZPULERNRAIIFC-UHFFFAOYSA-N
smarts:    [#6]-[#7]-[#6]-[#7]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#7]-[#6]-[#7]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

pyridine-diyliminocyclohexane(phenylmethylene): C1(NC2CCC(CC3=CC=CC=C3)CC2)=CC=CC=N1

smiles_non_kekule:    c1ccc(CC2CCC(Nc3ccccn3)CC2)cc1
smiles_kekule:    C1=CC=C(CC2CCC(NC3=CC=CC=N3)CC2)C=C1
inchi:    InChI=1S/C18H22N2/c1-2-6-15(7-3-1)14-16-9-11-17(12-10-16)20-18-8-4-5-13-19-18/h1-8,13,16-17H,9-12,14H2,(H,19,20)
inchiKey:    WIWRDPNJQXJENN-UHFFFAOYSA-N
smarts:    [#6]1(-[#7]-[#6]2-[#6]-[#6]-[#6](-[#6]-[#6]3:[#6]:[#6]:[#6]:[#6]:[#6]:3)-[#6]-[#6]-2):[#6]:[#6]:[#6]:[#6]:[#7]:1
smarts_isomeric:    [#6]1(-[#7]-[#6]2-[#6]-[#6]-[#6](-[#6]-[#6]3:[#6]:[#6]:[#6]:[#6]:[#6]:3)-[#6]-[#6]-2):[#6]:[#6]:[#6]:[#6]:[#7]:1

imino(1-oxoethylene)silanediylpropane: NC(C[Si](C)(C)C)=O

smiles_non_kekule:    C[Si](C)(C)CC(N)=O
smiles_kekule:    C[Si](C)(C)CC(N)=O
inchi:    InChI=1S/C5H13NOSi/c1-8(2,3)4-5(6)7/h4H2,1-3H3,(H2,6,7)
inchiKey:    MDQHTWMXYBVSHU-UHFFFAOYSA-N
smarts:    [#7]-[#6](-[#6]-[Si](-[#6])(-[#6])-[#6])=[#8]
smarts_isomeric:    [#7]-[#6](-[#6]-[Si](-[#6])(-[#6])-[#6])=[#8]

pyridine-cyclohexane-oxypropane: CCCOC(CCC1)CC1C2=CC=CN=C2

smiles_non_kekule:    CCCOC1CCCC(c2cccnc2)C1
smiles_kekule:    CCCOC1CCCC(C2=CC=CN=C2)C1
inchi:    InChI=1S/C14H21NO/c1-2-9-16-14-7-3-5-12(10-14)13-6-4-8-15-11-13/h4,6,8,11-12,14H,2-3,5,7,9-10H2,1H3
inchiKey:    AEBPMIHETQWLIO-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#8]-[#6]1-[#6]-[#6]-[#6]-[#6](-[#6]-1)-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6]-[#8]-[#6]1-[#6]-[#6]-[#6]-[#6](-[#6]-1)-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1

sulfaneethylenesulfanediyl(2-amino-4-carboxypentane): SCCSC(N)CC(C)C(O)=O

smiles_non_kekule:    CC(CC(N)SCCS)C(=O)O
smiles_kekule:    CC(CC(N)SCCS)C(=O)O
inchi:    InChI=1S/C7H15NO2S2/c1-5(7(9)10)4-6(8)12-3-2-11/h5-6,11H,2-4,8H2,1H3,(H,9,10)
inchiKey:    LCRYPQJBTMKOQR-UHFFFAOYSA-N
smarts:    [#16]-[#6]-[#6]-[#16]-[#6](-[#7])-[#6]-[#6](-[#6])-[#6](-[#8])=[#8]
smarts_isomeric:    [#16]-[#6]-[#6]-[#16]-[#6](-[#7])-[#6]-[#6](-[#6])-[#6](-[#8])=[#8]

sulfaneethylenesulfanediyl(4-amino-1-carboxypentane): SCCSC(C(O)=O)CC(N)C

smiles_non_kekule:    CC(N)CC(SCCS)C(=O)O
smiles_kekule:    CC(N)CC(SCCS)C(=O)O
inchi:    InChI=1S/C7H15NO2S2/c1-5(8)4-6(7(9)10)12-3-2-11/h5-6,11H,2-4,8H2,1H3,(H,9,10)
inchiKey:    HEBYGZJJNUMGQE-UHFFFAOYSA-N
smarts:    [#16]-[#6]-[#6]-[#16]-[#6](-[#6](-[#8])=[#8])-[#6]-[#6](-[#7])-[#6]
smarts_isomeric:    [#16]-[#6]-[#6]-[#16]-[#6](-[#6](-[#8])=[#8])-[#6]-[#6](-[#7])-[#6]

pyridine-methylenepyridine(tetrahydropyran): C1(CC2=CN=CC(C3COCCC3)=C2)=CC=CN=C1

smiles_non_kekule:    c1cncc(Cc2cncc(C3CCCOC3)c2)c1
smiles_kekule:    C1=CN=CC(CC2=CN=CC(C3CCCOC3)=C2)=C1
inchi:    InChI=1S/C16H18N2O/c1-3-13(9-17-5-1)7-14-8-16(11-18-10-14)15-4-2-6-19-12-15/h1,3,5,8-11,15H,2,4,6-7,12H2
inchiKey:    KJPMMIJSBNEXIL-UHFFFAOYSA-N
smarts:    [#6]1(-[#6]-[#6]2:[#6]:[#7]:[#6]:[#6](-[#6]3-[#6]-[#8]-[#6]-[#6]-[#6]-3):[#6]:2):[#6]:[#6]:[#6]:[#7]:[#6]:1
smarts_isomeric:    [#6]1(-[#6]-[#6]2:[#6]:[#7]:[#6]:[#6](-[#6]3-[#6]-[#8]-[#6]-[#6]-[#6]-3):[#6]:2):[#6]:[#6]:[#6]:[#7]:[#6]:1

sulfane(2-chloropropane)sulfanepropane: SCC(CSCCC)Cl

smiles_non_kekule:    CCCSCC(Cl)CS
smiles_kekule:    CCCSCC(Cl)CS
inchi:    InChI=1S/C6H13ClS2/c1-2-3-9-5-6(7)4-8/h6,8H,2-5H2,1H3
inchiKey:    NOMBJGRFSLXLTD-UHFFFAOYSA-N
smarts:    [#16]-[#6]-[#6](-[#6]-[#16]-[#6]-[#6]-[#6])-[#17]
smarts_isomeric:    [#16]-[#6]-[#6](-[#6]-[#16]-[#6]-[#6]-[#6])-[#17]

pyridine-carbonyloxymethylene: O=C(OC)C1=CC=CN=C1

smiles_non_kekule:    COC(=O)c1cccnc1
smiles_kekule:    COC(=O)C1=CC=CN=C1
inchi:    InChI=1S/C7H7NO2/c1-10-7(9)6-3-2-4-8-5-6/h2-5H,1H3
inchiKey:    YNBADRVTZLEFNH-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#8]-[#6])-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1
smarts_isomeric:    [#8]=[#6](-[#8]-[#6])-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1

1,3-phenylene(1-bromoethylene)cyclohexane(2-butylethylene): BrC(C1CCCC(C(CCC)C)C1)C2=CC=CC=C2

smiles_non_kekule:    CCCC(C)C1CCCC(C(Br)c2ccccc2)C1
smiles_kekule:    CCCC(C)C1CCCC(C(Br)C2=CC=CC=C2)C1
inchi:    InChI=1S/C18H27Br/c1-3-8-14(2)16-11-7-12-17(13-16)18(19)15-9-5-4-6-10-15/h4-6,9-10,14,16-18H,3,7-8,11-13H2,1-2H3
inchiKey:    XRURTEIBZONPMB-UHFFFAOYSA-N
smarts:    [#35]-[#6](-[#6]1-[#6]-[#6]-[#6]-[#6](-[#6](-[#6]-[#6]-[#6])-[#6])-[#6]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#35]-[#6](-[#6]1-[#6]-[#6]-[#6]-[#6](-[#6](-[#6]-[#6]-[#6])-[#6])-[#6]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

oxy(1,1-dichloroethylene)imino(1-oxoethylene): OC(Cl)(CNCOC)Cl

smiles_non_kekule:    COCNCC(O)(Cl)Cl
smiles_kekule:    COCNCC(O)(Cl)Cl
inchi:    InChI=1S/C4H9Cl2NO2/c1-9-3-7-2-4(5,6)8/h7-8H,2-3H2,1H3
inchiKey:    HBGBRAOGPBNTFS-UHFFFAOYSA-N
smarts:    [#8]-[#6](-[#17])(-[#6]-[#7]-[#6]-[#8]-[#6])-[#17]
smarts_isomeric:    [#8]-[#6](-[#17])(-[#6]-[#7]-[#6]-[#8]-[#6])-[#17]

sulfane(1-chloroethylene)-1,3-phenylene(1-chloroethylene): SC(CC1=CC(C(C)Cl)=CC=C1)Cl

smiles_non_kekule:    CC(Cl)c1cccc(CC(S)Cl)c1
smiles_kekule:    CC(Cl)C1=CC=CC(CC(S)Cl)=C1
inchi:    InChI=1S/C10H12Cl2S/c1-7(11)9-4-2-3-8(5-9)6-10(12)13/h2-5,7,10,13H,6H2,1H3
inchiKey:    QYKLZLATABEILP-UHFFFAOYSA-N
smarts:    [#16]-[#6](-[#6]-[#6]1:[#6]:[#6](-[#6](-[#6])-[#17]):[#6]:[#6]:[#6]:1)-[#17]
smarts_isomeric:    [#16]-[#6](-[#6]-[#6]1:[#6]:[#6](-[#6](-[#6])-[#17]):[#6]:[#6]:[#6]:1)-[#17]

sulfane(1-iodoethylene)sulfane(5-bromo-3-chloropentane): SC(CSCCC(CCBr)Cl)I

smiles_non_kekule:    SC(I)CSCCC(Cl)CCBr
smiles_kekule:    SC(I)CSCCC(Cl)CCBr
inchi:    InChI=1S/C7H13BrClIS2/c8-3-1-6(9)2-4-12-5-7(10)11/h6-7,11H,1-5H2
inchiKey:    WAIFEYRKUWOXSB-UHFFFAOYSA-N
smarts:    [#16]-[#6](-[#6]-[#16]-[#6]-[#6]-[#6](-[#6]-[#6]-[#35])-[#17])-[#53]
smarts_isomeric:    [#16]-[#6](-[#6]-[#16]-[#6]-[#6]-[#6](-[#6]-[#6]-[#35])-[#17])-[#53]

oxymethylene-ONN-azoxy(chloromethylene): OCN(O)-NCCl

smiles_non_kekule:    OCN(O)NCCl
smiles_kekule:    OCN(O)NCCl
inchi:    InChI=1S/C2H7ClN2O2/c3-1-4-5(7)2-6/h4,6-7H,1-2H2
inchiKey:    ZPMWHEJSPIDKBH-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#7](-[#8])-[#7]-[#6]-[#17]
smarts_isomeric:    [#8]-[#6]-[#7](-[#8])-[#7]-[#6]-[#17]

(3-chlorobiphenyl)methylene(3-chloro-1,4-phenylene)methylene: ClC1=CC(C2=CC=C(C3=CC=C(C)C(Cl)=C3)C=C2)=CC=C1

smiles_non_kekule:    Cc1ccc(-c2ccc(-c3cccc(Cl)c3)cc2)cc1Cl
smiles_kekule:    CC1=CC=C(C2=CC=C(C3=CC=CC(Cl)=C3)C=C2)C=C1Cl
inchi:    InChI=1S/C19H14Cl2/c1-13-5-6-17(12-19(13)21)15-9-7-14(8-10-15)16-3-2-4-18(20)11-16/h2-12H,1H3
inchiKey:    WDFOXWNOFLFVFO-UHFFFAOYSA-N
smarts:    [#17]-[#6]1:[#6]:[#6](-[#6]2:[#6]:[#6]:[#6](-[#6]3:[#6]:[#6]:[#6](-[#6]):[#6](-[#17]):[#6]:3):[#6]:[#6]:2):[#6]:[#6]:[#6]:1
smarts_isomeric:    [#17]-[#6]1:[#6]:[#6](-[#6]2:[#6]:[#6]:[#6](-[#6]3:[#6]:[#6]:[#6](-[#6]):[#6](-[#17]):[#6]:3):[#6]:[#6]:2):[#6]:[#6]:[#6]:1

imino(x-methyl-1,3-phenylene)iminomalonyl: NC1=CC(C)=CC(NC(CC=O)=O)=C1

smiles_non_kekule:    Cc1cc(N)cc(NC(=O)CC=O)c1
smiles_kekule:    CC1=CC(NC(=O)CC=O)=CC(N)=C1
inchi:    InChI=1S/C10H12N2O2/c1-7-4-8(11)6-9(5-7)12-10(14)2-3-13/h3-6H,2,11H2,1H3,(H,12,14)
inchiKey:    ADQZDRXLCUKIFT-UHFFFAOYSA-N
smarts:    [#7]-[#6]1:[#6]:[#6](-[#6]):[#6]:[#6](-[#7]-[#6](-[#6]-[#6]=[#8])=[#8]):[#6]:1
smarts_isomeric:    [#7]-[#6]1:[#6]:[#6](-[#6]):[#6]:[#6](-[#7]-[#6](-[#6]-[#6]=[#8])=[#8]):[#6]:1

oxyhexane-oxycarbonylimino(methylphenylene)iminocarbonyl: OCCCCCCOC(NC1=CC(C)=C(NC=O)C=C1)=O

smiles_non_kekule:    Cc1cc(NC(=O)OCCCCCCO)ccc1NC=O
smiles_kekule:    CC1=C(NC=O)C=CC(NC(=O)OCCCCCCO)=C1
inchi:    InChI=1S/C15H22N2O4/c1-12-10-13(6-7-14(12)16-11-19)17-15(20)21-9-5-3-2-4-8-18/h6-7,10-11,18H,2-5,8-9H2,1H3,(H,16,19)(H,17,20)
inchiKey:    OCZPPQVKQUJRPA-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#8]-[#6](-[#7]-[#6]1:[#6]:[#6](-[#6]):[#6](-[#7]-[#6]=[#8]):[#6]:[#6]:1)=[#8]
smarts_isomeric:    [#8]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#8]-[#6](-[#7]-[#6]1:[#6]:[#6](-[#6]):[#6](-[#7]-[#6]=[#8]):[#6]:[#6]:1)=[#8]

2,4,8,10-tetraoxaspiro[5.5]undecane-oxyhexane-1,6-diyloxy: CC1OCC2(COC(OCCCCCCO)OC2)CO1

smiles_non_kekule:    CC1OCC2(CO1)COC(OCCCCCCO)OC2
smiles_kekule:    CC1OCC2(CO1)COC(OCCCCCCO)OC2
inchi:    InChI=1S/C14H26O6/c1-12-17-8-14(9-18-12)10-19-13(20-11-14)16-7-5-3-2-4-6-15/h12-13,15H,2-11H2,1H3
inchiKey:    NWQJOHGZOWSTBN-UHFFFAOYSA-N
smarts:    [#6]-[#6]1-[#8]-[#6]-[#6]2(-[#6]-[#8]-[#6](-[#8]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#8])-[#8]-[#6]-2)-[#6]-[#8]-1
smarts_isomeric:    [#6]-[#6]1-[#8]-[#6]-[#6]2(-[#6]-[#8]-[#6](-[#8]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#8])-[#8]-[#6]-2)-[#6]-[#8]-1

pyridine-methylenepyrrole-oxymethylene: COC1=CNC=C1CC2=CC=CN=C2

smiles_non_kekule:    COc1c[nH]cc1Cc1cccnc1
smiles_kekule:    COC1=CNC=C1CC1=CC=CN=C1
inchi:    InChI=1S/C11H12N2O/c1-14-11-8-13-7-10(11)5-9-3-2-4-12-6-9/h2-4,6-8,13H,5H2,1H3
inchiKey:    TWOYFVOAVSWQNC-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]1:[#6]:[#7H]:[#6]:[#6]:1-[#6]-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1
smarts_isomeric:    [#6]-[#8]-[#6]1:[#6]:[#7H]:[#6]:[#6]:1-[#6]-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1

oxymethyleneiminocarbonylsulfane-1,3-phenyleneethylene: COCNC(SC1=CC=CC(CC)=C1)=O

smiles_non_kekule:    CCc1cccc(SC(=O)NCOC)c1
smiles_kekule:    CCC1=CC(SC(=O)NCOC)=CC=C1
inchi:    InChI=1S/C11H15NO2S/c1-3-9-5-4-6-10(7-9)15-11(13)12-8-14-2/h4-7H,3,8H2,1-2H3,(H,12,13)
inchiKey:    STKHDCIRUNXPKS-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]-[#7]-[#6](-[#16]-[#6]1:[#6]:[#6]:[#6]:[#6](-[#6]-[#6]):[#6]:1)=[#8]
smarts_isomeric:    [#6]-[#8]-[#6]-[#7]-[#6](-[#16]-[#6]1:[#6]:[#6]:[#6]:[#6](-[#6]-[#6]):[#6]:1)=[#8]

oxyiminomethylenehydrazine-methylene: ONCNNC

smiles_non_kekule:    CNNCNO
smiles_kekule:    CNNCNO
inchi:    InChI=1S/C2H9N3O/c1-3-4-2-5-6/h3-6H,2H2,1H3
inchiKey:    SICMIUMDHKFUAR-UHFFFAOYSA-N
smarts:    [#8]-[#7]-[#6]-[#7]-[#7]-[#6]
smarts_isomeric:    [#8]-[#7]-[#6]-[#7]-[#7]-[#6]

piperidine-methylenepiperidine-4,2-diylcyclopentane-ethylenecyclopentane-1,2-diylmethylene: CC(C1)CCC1CC(C2)CCC2C(C3)NCCC3CC4NCCCC4

smiles_non_kekule:    CC1CCC(CC2CCC(C3CC(CC4CCCCN4)CCN3)C2)C1
smiles_kekule:    CC1CCC(CC2CCC(C3CC(CC4CCCCN4)CCN3)C2)C1
inchi:    InChI=1S/C23H42N2/c1-17-5-6-18(12-17)13-19-7-8-21(14-19)23-16-20(9-11-25-23)15-22-4-2-3-10-24-22/h17-25H,2-16H2,1H3
inchiKey:    DJIXAJFRPSVJQG-UHFFFAOYSA-N
smarts:    [#6]-[#6]1-[#6]-[#6](-[#6]-[#6]-1)-[#6]-[#6]1-[#6]-[#6](-[#6]-[#6]-1)-[#6]1-[#6]-[#6](-[#6]-[#6]-[#7]-1)-[#6]-[#6]1-[#7]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6]1-[#6]-[#6](-[#6]-[#6]-1)-[#6]-[#6]1-[#6]-[#6](-[#6]-[#6]-1)-[#6]1-[#6]-[#6](-[#6]-[#6]-[#7]-1)-[#6]-[#6]1-[#7]-[#6]-[#6]-[#6]-[#6]-1

1,3-dioxa-8-thia-5,10-diazadodecane: OCOCNCCSCNCC

smiles_non_kekule:    CCNCSCCNCOCO
smiles_kekule:    CCNCSCCNCOCO
inchi:    InChI=1S/C7H18N2O2S/c1-2-8-6-12-4-3-9-5-11-7-10/h8-10H,2-7H2,1H3
inchiKey:    HIOCIEWKGLONDM-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#8]-[#6]-[#7]-[#6]-[#6]-[#16]-[#6]-[#7]-[#6]-[#6]
smarts_isomeric:    [#8]-[#6]-[#8]-[#6]-[#7]-[#6]-[#6]-[#16]-[#6]-[#7]-[#6]-[#6]

oxymethyleneoxymethyleneoxymethyleneimino-1,3-phenylenemethyleneiminomethylene: OCOCOCNC1=CC(CNC)=CC=C1

smiles_non_kekule:    CNCc1cccc(NCOCOCO)c1
smiles_kekule:    CNCC1=CC=CC(NCOCOCO)=C1
inchi:    InChI=1S/C11H18N2O3/c1-12-6-10-3-2-4-11(5-10)13-7-15-9-16-8-14/h2-5,12-14H,6-9H2,1H3
inchiKey:    URAZGPZFSRDNKA-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#8]-[#6]-[#8]-[#6]-[#7]-[#6]1:[#6]:[#6](-[#6]-[#7]-[#6]):[#6]:[#6]:[#6]:1
smarts_isomeric:    [#8]-[#6]-[#8]-[#6]-[#8]-[#6]-[#7]-[#6]1:[#6]:[#6](-[#6]-[#7]-[#6]):[#6]:[#6]:[#6]:1

pyridine-1,4-phenylenemethyleneoxymethyleneiminomethyleneoxy-1,4-phenylenemethylene: CC(C=C1)=CC=C1OCNCOCC(C=C2)=CC=C2C3=CC=CN=C3

smiles_non_kekule:    Cc1ccc(OCNCOCc2ccc(-c3cccnc3)cc2)cc1
smiles_kekule:    CC1=CC=C(OCNCOCC2=CC=C(C3=CC=CN=C3)C=C2)C=C1
inchi:    InChI=1S/C21H22N2O2/c1-17-4-10-21(11-5-17)25-16-23-15-24-14-18-6-8-19(9-7-18)20-3-2-12-22-13-20/h2-13,23H,14-16H2,1H3
inchiKey:    SNCREANTGAVYCC-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#7]-[#6]-[#8]-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#7]-[#6]-[#8]-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1

sulfinylmethylenesulfanediylpropane-1,3-diylsulfonyl-1,4-phenylene: SOCSCCCS(=O)(C1=CC=CC=C1)=O

smiles_non_kekule:    O=S(=O)(CCCSCOS)c1ccccc1
smiles_kekule:    O=S(=O)(CCCSCOS)C1=CC=CC=C1
inchi:    InChI=1S/C10H14O3S3/c11-16(12,8-4-7-15-9-13-14)10-5-2-1-3-6-10/h1-3,5-6,14H,4,7-9H2
inchiKey:    LYQUDAZUDPGFJK-UHFFFAOYSA-N
smarts:    [#16]-[#8]-[#6]-[#16]-[#6]-[#6]-[#6]-[#16](=[#8])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)=[#8]
smarts_isomeric:    [#16]-[#8]-[#6]-[#16]-[#6]-[#6]-[#6]-[#16](=[#8])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)=[#8]

oxyterephthaloylhydrazine-terephthaloyl: OC(C1=CC=C(C(NNC(C2=CC=C(C=O)C=C2)=O)=O)C=C1)=O

smiles_non_kekule:    O=Cc1ccc(C(=O)NNC(=O)c2ccc(C(=O)O)cc2)cc1
smiles_kekule:    O=CC1=CC=C(C(=O)NNC(=O)C2=CC=C(C(=O)O)C=C2)C=C1
inchi:    InChI=1S/C16H12N2O5/c19-9-10-1-3-11(4-2-10)14(20)17-18-15(21)12-5-7-13(8-6-12)16(22)23/h1-9H,(H,17,20)(H,18,21)(H,22,23)
inchiKey:    XYNCOPJXFRTAFR-UHFFFAOYSA-N
smarts:    [#8]-[#6](-[#6]1:[#6]:[#6]:[#6](-[#6](-[#7]-[#7]-[#6](-[#6]2:[#6]:[#6]:[#6](-[#6]=[#8]):[#6]:[#6]:2)=[#8])=[#8]):[#6]:[#6]:1)=[#8]
smarts_isomeric:    [#8]-[#6](-[#6]1:[#6]:[#6]:[#6](-[#6](-[#7]-[#7]-[#6](-[#6]2:[#6]:[#6]:[#6](-[#6]=[#8]):[#6]:[#6]:2)=[#8])=[#8]):[#6]:[#6]:1)=[#8]

nitrilo-1,4-phenylenenitriloprop-2-en-3-yl-1-ylidene-1,4-phenyleneprop-1-en-1-yl-3-ylidene: NC1=CC=C(N=CC=CC2=CC=C(C=CCC)C=C2)C=C1

smiles_non_kekule:    CCC=Cc1ccc(C=CC=Nc2ccc(N)cc2)cc1
smiles_kekule:    CCC=CC1=CC=C(C=CC=NC2=CC=C(N)C=C2)C=C1
inchi:    InChI=1S/C19H20N2/c1-2-3-5-16-7-9-17(10-8-16)6-4-15-21-19-13-11-18(20)12-14-19/h3-15H,2,20H2,1H3
inchiKey:    IPLAWWNSDGZQLH-UHFFFAOYSA-N
smarts:    [#7]-[#6]1:[#6]:[#6]:[#6](-[#7]=[#6]-[#6]=[#6]-[#6]2:[#6]:[#6]:[#6](-[#6]=[#6]-[#6]-[#6]):[#6]:[#6]:2):[#6]:[#6]:1
smarts_isomeric:    [#7]-[#6]1:[#6]:[#6]:[#6](-[#7]=[#6]-[#6]=[#6]-[#6]2:[#6]:[#6]:[#6](-[#6]=[#6]-[#6]-[#6]):[#6]:[#6]:2):[#6]:[#6]:1

oxycarbonylnitrilopropane-idenenitrilocarbonyl: OC(N=CCC=NC=O)=O

smiles_non_kekule:    O=CN=CCC=NC(=O)O
smiles_kekule:    O=CN=CCC=NC(=O)O
inchi:    InChI=1S/C5H6N2O3/c8-4-6-2-1-3-7-5(9)10/h2-4H,1H2,(H,9,10)
inchiKey:    WPQIRAWVHPULNN-UHFFFAOYSA-N
smarts:    [#8]-[#6](-[#7]=[#6]-[#6]-[#6]=[#7]-[#6]=[#8])=[#8]
smarts_isomeric:    [#8]-[#6](-[#7]=[#6]-[#6]-[#6]=[#7]-[#6]=[#8])=[#8]

oxyethyleneiminomethylenesulfanediylethyleneiminocyclohexane: OCCCNCSCCNC1CCCCC1

smiles_non_kekule:    OCCCNCSCCNC1CCCCC1
smiles_kekule:    OCCCNCSCCNC1CCCCC1
inchi:    InChI=1S/C12H26N2OS/c15-9-4-7-13-11-16-10-8-14-12-5-2-1-3-6-12/h12-15H,1-11H2
inchiKey:    IVUWWOFONACZEH-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]-[#6]-[#7]-[#6]-[#16]-[#6]-[#6]-[#7]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#8]-[#6]-[#6]-[#6]-[#7]-[#6]-[#16]-[#6]-[#6]-[#7]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

iminomethyleneiminocarbonyl{2-[(2,4-dinitrophenyl)hydrazono]cyclopentane}carbonyl: OC(C1=CC=C(C(OCCCCCC)=O)C=C1)=O

smiles_non_kekule:    CCCCCCOC(=O)c1ccc(C(=O)O)cc1
smiles_kekule:    CCCCCCOC(=O)C1=CC=C(C(=O)O)C=C1
inchi:    InChI=1S/C14H18O4/c1-2-3-4-5-10-18-14(17)12-8-6-11(7-9-12)13(15)16/h6-9H,2-5,10H2,1H3,(H,15,16)
inchiKey:    VIRIXVXDDFUBLT-UHFFFAOYSA-N
smarts:    [#8]-[#6](-[#6]1:[#6]:[#6]:[#6](-[#6](-[#8]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6])=[#8]):[#6]:[#6]:1)=[#8]
smarts_isomeric:    [#8]-[#6](-[#6]1:[#6]:[#6]:[#6](-[#6](-[#8]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6])=[#8]):[#6]:[#6]:1)=[#8]

oxyterephthaloyloxyhexane: NCCNC(C1/C(C(C=O)CC1)=N/NC2=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C2)=O

smiles_non_kekule:    NCCNC(=O)C1CCC(C=O)/C1=N\Nc1ccc([N+](=O)[O-])cc1[N+](=O)[O-]
smiles_kekule:    NCCNC(=O)C1CCC(C=O)/C1=N\NC1=C([N+](=O)[O-])C=C([N+](=O)[O-])C=C1
inchi:    InChI=1S/C15H18N6O6/c16-5-6-17-15(23)11-3-1-9(8-22)14(11)19-18-12-4-2-10(20(24)25)7-13(12)21(26)27/h2,4,7-9,11,18H,1,3,5-6,16H2,(H,17,23)/b19-14+
inchiKey:    TZPOQQYUYAGYIY-XMHGGMMESA-N
smarts:    [#7]-[#6]-[#6]-[#7]-[#6](-[#6]1-[#6](-[#6](-[#6]=[#8])-[#6]-[#6]-1)=[#7]-[#7]-[#6]1:[#6](-[#7+](-[#8-])=[#8]):[#6]:[#6](-[#7+](-[#8-])=[#8]):[#6]:[#6]:1)=[#8]
smarts_isomeric:    [#7]-[#6]-[#6]-[#7]-[#6](-[#6]1/[#6](-[#6](-[#6]=[#8])-[#6]-[#6]-1)=[#7]/[#7]-[#6]1:[#6](-[#7+](-[#8-])=[#8]):[#6]:[#6](-[#7+](-[#8-])=[#8]):[#6]:[#6]:1)=[#8]

nitrilocyclohexa-2,5-diene-idenenitrilo-1,4-phenyleneimino-1,4-phenyleneimino1,4-phenylene: N=C1C=CC(C=C1)=NC2=CC=C(NC3=CC=C(NC4=CC=CC=C4)C=C3)C=C2

smiles_non_kekule:    N=C1C=CC(=Nc2ccc(Nc3ccc(Nc4ccccc4)cc3)cc2)C=C1
smiles_kekule:    N=C1C=CC(=NC2=CC=C(NC3=CC=C(NC4=CC=CC=C4)C=C3)C=C2)C=C1
inchi:    InChI=1S/C24H20N4/c25-18-6-8-20(9-7-18)27-22-14-16-24(17-15-22)28-23-12-10-21(11-13-23)26-19-4-2-1-3-5-19/h1-17,25-26,28H
inchiKey:    GRGREMRADIGHKE-UHFFFAOYSA-N
smarts:    [#7]=[#6]1-[#6]=[#6]-[#6](-[#6]=[#6]-1)=[#7]-[#6]1:[#6]:[#6]:[#6](-[#7]-[#6]2:[#6]:[#6]:[#6](-[#7]-[#6]3:[#6]:[#6]:[#6]:[#6]:[#6]:3):[#6]:[#6]:2):[#6]:[#6]:1
smarts_isomeric:    [#7]=[#6]1-[#6]=[#6]-[#6](-[#6]=[#6]-1)=[#7]-[#6]1:[#6]:[#6]:[#6](-[#7]-[#6]2:[#6]:[#6]:[#6](-[#7]-[#6]3:[#6]:[#6]:[#6]:[#6]:[#6]:3):[#6]:[#6]:2):[#6]:[#6]:1

cyclohexane-methanylylidenecyclohexane-idenemethanylylidenecyclohexane-methylene: CC(CC1)CCC1C=C(CC2)CCC2=CC3CCCCC3

smiles_non_kekule:    CC1CCC(C=C2CCC(=CC3CCCCC3)CC2)CC1
smiles_kekule:    CC1CCC(C=C2CCC(=CC3CCCCC3)CC2)CC1
inchi:    InChI=1S/C21H34/c1-17-7-9-19(10-8-17)16-21-13-11-20(12-14-21)15-18-5-3-2-4-6-18/h15-19H,2-14H2,1H3
inchiKey:    GYALTMNCWWOJMI-UHFFFAOYSA-N
smarts:    [#6]-[#6]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)-[#6]=[#6]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)=[#6]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)-[#6]=[#6]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)=[#6]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

problem_type: 12/25 (loop 0/0)

[15:17:23] WARNING: Omitted undefined stereo

[15:17:23] WARNING: Omitted undefined stereo

[15:17:23] WARNING: Omitted undefined stereo

[15:17:23] WARNING: Omitted undefined stereo

[15:17:23] WARNING: Omitted undefined stereo

[15:17:24] WARNING: Omitted undefined stereo

[15:17:24] WARNING: Omitted undefined stereo

[15:17:24] WARNING: Omitted undefined stereo

Problem Template: _problem_common_privileged_scaffolds

Write structure of common privileged scaffolds molecules.

Answer:

structure of common privileged scaffolds molecules:

indole: C12=CC=CC=C1C=CN2

quinoline: C12=CC=CC=C1N=CC=C2

isoquinoline: C12=C(C=NC=C2)C=CC=C1

purine: C12=NC=NC=C1NC=N2

quinoxaline: C12=CC=CC=C1N=CC=N2

quinazolinone: O=C1NC2=C(C=CC=C2)C=N1

tetrahydroisoquinoline: C12=C(CNCC2)C=CC=C1

tetrahydraquinoline: C12=C(NCCC2)C=CC=C1

benzoxazole: C12=CC=CC=C1OC=N2

benzofuran: C12=CC=CC=C1C=CO2

3,3-dimethylbenzopyran: CC1(C)C=CC2=CC=CC=C2O1

chromone: O=C1C=COC2=C1C=CC=C2

coumarin: O=C1OC2=C(C=CC=C2)C=C1

carbohydrate: OCC1OC(O)C(O)C(O)C1O

steroid: C12CCCCC1C3C(C(CCC4)C4CC3)CC2

prostanoic acid: CCCCCCCC[C@@H]1[C@H](CCC1)CCCCCCC(O)=O

benzodiazepine: O=C1CN=C(C2=CC=CC=C2)C3=C(C=CC=C3)N1

arylpiperidine: C1(C2CCNCC2)=CC=CC=C1

arylpiperizine: C1(N2CCNCC2)=CC=CC=C1

benzylpiperidine: N1(CC2=CC=CC=C2)CCCCC1

benzothiophene: C12=CC=CC=C1C=CS2

dihydropyridine: C1CC=CC=N1

benzimidazole: C12=CC=CC=C1NC=N2

biphenyltetrazole: C1(C2=C(C3=CC=CC=C3)C=CC=C2)=NN=NN1

3,3-hydroxy-2-oxindole: OC(C1=CC=CC=C1N2)C2=O

5,7,5-lactone: C=C1C2CCCC3C(CC3)C2OC1=O

6,6-spiroacetal: C1CCCC2(CCCCO2)O1

dihydropyrimidone: O=C1NCC=CN1

indolizine: N12C=CC=C1C=CC=C2

biphenyl: C1(C2=CC=CC=C2)=CC=CC=C1

triazaspirodecanone: O=C(NC1)C2(CCNCC2)N1C3=CC=CC=C3

N-acylhydrazone: [H]C(/N=N/CC)=O

pyrrolinone: O=C1C=CNC1

hydroxyamate: ONC(CCC(C)=O)=O

trans-lactam: O=C1NC2CCCC2C1

trans-lactone: O=C1OC2CCCC2C1

hexahydroisoindole: C12CNCC1CCCC2

benzimidazolone: O=C1N(C2CCNCC2)C3=CC=CC=C3N1

indoline: C12=C(NCC2)C=CC=C1

2-arylbenzothiazole: C12=CC=CC=C1N=C(C3=CC=CC=C3)S2

imidazolequinoxaline: C1(NC2)=CC=CC=C1N3C2=CN=C3

spiroindanylpiperidine: C12=CC=CC=C1C3(CCNCC3)CC2

aminopyridazine: NC1=NN=CC=C1

1,4-pyrazolodiazepin-8-one: O=C1NCCNC2=CNN=C21

rhodanine: S=C(N1)SCC1=O

pyranopyridone: O=C1C2=C(OCC=C2)C=CN1

pyranoquinolone: O=C1C=CC2=CC=CC=C2N1

Solution:

structure of common privileged scaffolds molecules:

indole: C12=CC=CC=C1C=CN2

quinoline: C12=CC=CC=C1N=CC=C2

isoquinoline: C12=C(C=NC=C2)C=CC=C1

smiles_non_kekule:    c1ccc2cnccc2c1
smiles_kekule:    C1=CC2=CC=NC=C2C=C1
inchi:    InChI=1S/C9H7N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-7H
inchiKey:    AWJUIBRHMBBTKR-UHFFFAOYSA-N
smarts:    [#6]12:[#6](:[#6]:[#7]:[#6]:[#6]:1):[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#6]12:[#6](:[#6]:[#7]:[#6]:[#6]:1):[#6]:[#6]:[#6]:[#6]:2

purine: C12=NC=NC=C1NC=N2

smiles_non_kekule:    c1ncc2[nH]cnc2n1
smiles_kekule:    C1=NC=C2NC=NC2=N1
inchi:    InChI=1S/C5H4N4/c1-4-5(8-2-6-1)9-3-7-4/h1-3H,(H,6,7,8,9)
inchiKey:    KDCGOANMDULRCW-UHFFFAOYSA-N
smarts:    [#6]12:[#7]:[#6]:[#7]:[#6]:[#6]:1:[#7H]:[#6]:[#7]:2
smarts_isomeric:    [#6]12:[#7]:[#6]:[#7]:[#6]:[#6]:1:[#7H]:[#6]:[#7]:2

quinoxaline: C12=CC=CC=C1N=CC=N2

smiles_non_kekule:    c1ccc2nccnc2c1
smiles_kekule:    C1=CC=C2N=CC=NC2=C1
inchi:    InChI=1S/C8H6N2/c1-2-4-8-7(3-1)9-5-6-10-8/h1-6H
inchiKey:    XSCHRSMBECNVNS-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#7]:[#6]:[#6]:[#7]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#7]:[#6]:[#6]:[#7]:2

quinazolinone: O=C1NC2=C(C=CC=C2)C=N1

smiles_non_kekule:    O=c1ncc2ccccc2[nH]1
smiles_kekule:    O=C1N=CC2=C(C=CC=C2)N1
inchi:    InChI=1S/C8H6N2O/c11-8-9-5-6-3-1-2-4-7(6)10-8/h1-5H,(H,9,10,11)
inchiKey:    AVRPFRMDMNDIDH-UHFFFAOYSA-N
smarts:    [#8]=[#6]1:[#7H]:[#6]2:[#6](:[#6]:[#6]:[#6]:[#6]:2):[#6]:[#7]:1
smarts_isomeric:    [#8]=[#6]1:[#7H]:[#6]2:[#6](:[#6]:[#6]:[#6]:[#6]:2):[#6]:[#7]:1

tetrahydroisoquinoline: C12=C(CNCC2)C=CC=C1

smiles_non_kekule:    c1ccc2c(c1)CCNC2
smiles_kekule:    C1=CC2=C(C=C1)CNCC2
inchi:    InChI=1S/C9H11N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-4,10H,5-7H2
inchiKey:    UWYZHKAOTLEWKK-UHFFFAOYSA-N
smarts:    [#6]12:[#6](-[#6]-[#7]-[#6]-[#6]-1):[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#6]12:[#6](-[#6]-[#7]-[#6]-[#6]-1):[#6]:[#6]:[#6]:[#6]:2

tetrahydraquinoline: C12=C(NCCC2)C=CC=C1

smiles_non_kekule:    c1ccc2c(c1)CCCN2
smiles_kekule:    C1=CC2=C(C=C1)NCCC2
inchi:    InChI=1S/C9H11N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-2,4,6,10H,3,5,7H2
inchiKey:    LBUJPTNKIBCYBY-UHFFFAOYSA-N
smarts:    [#6]12:[#6](-[#7]-[#6]-[#6]-[#6]-1):[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#6]12:[#6](-[#7]-[#6]-[#6]-[#6]-1):[#6]:[#6]:[#6]:[#6]:2

benzoxazole: C12=CC=CC=C1OC=N2

smiles_non_kekule:    c1ccc2ocnc2c1
smiles_kekule:    C1=CC=C2OC=NC2=C1
inchi:    InChI=1S/C7H5NO/c1-2-4-7-6(3-1)8-5-9-7/h1-5H
inchiKey:    BCMCBBGGLRIHSE-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#8]:[#6]:[#7]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#8]:[#6]:[#7]:2

benzofuran: C12=CC=CC=C1C=CO2

smiles_non_kekule:    c1ccc2occc2c1
smiles_kekule:    C1=CC=C2OC=CC2=C1
inchi:    InChI=1S/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
inchiKey:    IANQTJSKSUMEQM-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#8]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#8]:2

3,3-dimethylbenzopyran: CC1(C)C=CC2=CC=CC=C2O1

smiles_non_kekule:    CC1(C)C=Cc2ccccc2O1
smiles_kekule:    CC1(C)C=CC2=CC=CC=C2O1
inchi:    InChI=1S/C11H12O/c1-11(2)8-7-9-5-3-4-6-10(9)12-11/h3-8H,1-2H3
inchiKey:    SAXKWTPDZMBKSQ-UHFFFAOYSA-N
smarts:    [#6]-[#6]1(-[#6])-[#6]=[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2-[#8]-1
smarts_isomeric:    [#6]-[#6]1(-[#6])-[#6]=[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2-[#8]-1

chromone: O=C1C=COC2=C1C=CC=C2

smiles_non_kekule:    O=c1ccoc2ccccc12
smiles_kekule:    O=C1C=COC2=C1C=CC=C2
inchi:    InChI=1S/C9H6O2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6H
inchiKey:    OTAFHZMPRISVEM-UHFFFAOYSA-N
smarts:    [#8]=[#6]1:[#6]:[#6]:[#8]:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#8]=[#6]1:[#6]:[#6]:[#8]:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2

coumarin: O=C1OC2=C(C=CC=C2)C=C1

smiles_non_kekule:    O=c1ccc2ccccc2o1
smiles_kekule:    O=C1C=CC2=C(C=CC=C2)O1
inchi:    InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
inchiKey:    ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
smarts:    [#8]=[#6]1:[#8]:[#6]2:[#6](:[#6]:[#6]:[#6]:[#6]:2):[#6]:[#6]:1
smarts_isomeric:    [#8]=[#6]1:[#8]:[#6]2:[#6](:[#6]:[#6]:[#6]:[#6]:2):[#6]:[#6]:1

carbohydrate: OCC1OC(O)C(O)C(O)C1O

smiles_non_kekule:    OCC1OC(O)C(O)C(O)C1O
smiles_kekule:    OCC1OC(O)C(O)C(O)C1O
inchi:    InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2
inchiKey:    WQZGKKKJIJFFOK-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]1-[#8]-[#6](-[#8])-[#6](-[#8])-[#6](-[#8])-[#6]-1-[#8]
smarts_isomeric:    [#8]-[#6]-[#6]1-[#8]-[#6](-[#8])-[#6](-[#8])-[#6](-[#8])-[#6]-1-[#8]

steroid: C12CCCCC1C3C(C(CCC4)C4CC3)CC2

smiles_non_kekule:    C1CCC2C(C1)CCC1C3CCCC3CCC21
smiles_kekule:    C1CCC2C(C1)CCC1C3CCCC3CCC21
inchi:    InChI=1S/C17H28/c1-2-6-14-12(4-1)8-10-17-15-7-3-5-13(15)9-11-16(14)17/h12-17H,1-11H2
inchiKey:    UACIBCPNAKBWHX-UHFFFAOYSA-N
smarts:    [#6]12-[#6]-[#6]-[#6]-[#6]-[#6]-1-[#6]1-[#6](-[#6]3-[#6]-[#6]-[#6]-[#6]-3-[#6]-[#6]-1)-[#6]-[#6]-2
smarts_isomeric:    [#6]12-[#6]-[#6]-[#6]-[#6]-[#6]-1-[#6]1-[#6](-[#6]3-[#6]-[#6]-[#6]-[#6]-3-[#6]-[#6]-1)-[#6]-[#6]-2

prostanoic acid: CCCCCCCC[C@@H]1[C@H](CCC1)CCCCCCC(O)=O

smiles_non_kekule:    CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(=O)O
smiles_kekule:    CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(=O)O
inchi:    InChI=1S/C20H38O2/c1-2-3-4-5-6-9-13-18-15-12-16-19(18)14-10-7-8-11-17-20(21)22/h18-19H,2-17H2,1H3,(H,21,22)/t18-,19-/m0/s1
inchiKey:    WGJJROVFWIXTPA-OALUTQOASA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6H]1-[#6H](-[#6]-[#6]-[#6]-1)-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6](-[#8])=[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6@@H]1-[#6@H](-[#6]-[#6]-[#6]-1)-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6](-[#8])=[#8]

benzodiazepine: O=C1CN=C(C2=CC=CC=C2)C3=C(C=CC=C3)N1

smiles_non_kekule:    O=C1CN=C(c2ccccc2)c2ccccc2N1
smiles_kekule:    O=C1CN=C(C2=CC=CC=C2)C2=C(C=CC=C2)N1
inchi:    InChI=1S/C15H12N2O/c18-14-10-16-15(11-6-2-1-3-7-11)12-8-4-5-9-13(12)17-14/h1-9H,10H2,(H,17,18)
inchiKey:    IVUAAOBNUNMJQC-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#6]-[#7]=[#6](-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]2:[#6](:[#6]:[#6]:[#6]:[#6]:2)-[#7]-1
smarts_isomeric:    [#8]=[#6]1-[#6]-[#7]=[#6](-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]2:[#6](:[#6]:[#6]:[#6]:[#6]:2)-[#7]-1

arylpiperidine: C1(C2CCNCC2)=CC=CC=C1

smiles_non_kekule:    c1ccc(C2CCNCC2)cc1
smiles_kekule:    C1=CC=C(C2CCNCC2)C=C1
inchi:    InChI=1S/C11H15N/c1-2-4-10(5-3-1)11-6-8-12-9-7-11/h1-5,11-12H,6-9H2
inchiKey:    UTBULQCHEUWJNV-UHFFFAOYSA-N
smarts:    [#6]1(-[#6]2-[#6]-[#6]-[#7]-[#6]-[#6]-2):[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1(-[#6]2-[#6]-[#6]-[#7]-[#6]-[#6]-2):[#6]:[#6]:[#6]:[#6]:[#6]:1

arylpiperizine: C1(N2CCNCC2)=CC=CC=C1

smiles_non_kekule:    c1ccc(N2CCNCC2)cc1
smiles_kekule:    C1=CC=C(N2CCNCC2)C=C1
inchi:    InChI=1S/C10H14N2/c1-2-4-10(5-3-1)12-8-6-11-7-9-12/h1-5,11H,6-9H2
inchiKey:    YZTJYBJCZXZGCT-UHFFFAOYSA-N
smarts:    [#6]1(-[#7]2-[#6]-[#6]-[#7]-[#6]-[#6]-2):[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1(-[#7]2-[#6]-[#6]-[#7]-[#6]-[#6]-2):[#6]:[#6]:[#6]:[#6]:[#6]:1

benzylpiperidine: N1(CC2=CC=CC=C2)CCCCC1

smiles_non_kekule:    c1ccc(CN2CCCCC2)cc1
smiles_kekule:    C1=CC=C(CN2CCCCC2)C=C1
inchi:    InChI=1S/C12H17N/c1-3-7-12(8-4-1)11-13-9-5-2-6-10-13/h1,3-4,7-8H,2,5-6,9-11H2
inchiKey:    NZVZVGPYTICZBZ-UHFFFAOYSA-N
smarts:    [#7]1(-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#7]1(-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-[#6]-[#6]-[#6]-1

benzothiophene: C12=CC=CC=C1C=CS2

smiles_non_kekule:    c1ccc2sccc2c1
smiles_kekule:    C1=CC=C2SC=CC2=C1
inchi:    InChI=1S/C8H6S/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
inchiKey:    FCEHBMOGCRZNNI-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#16]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#16]:2

dihydropyridine: C1CC=CC=N1

smiles_non_kekule:    C1=CCCN=C1
smiles_kekule:    C1=CCCN=C1
inchi:    InChI=1S/C5H7N/c1-2-4-6-5-3-1/h1-2,4H,3,5H2
inchiKey:    NZHIIDNOLFOHSG-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]=[#6]-[#6]=[#7]-1
smarts_isomeric:    [#6]1-[#6]-[#6]=[#6]-[#6]=[#7]-1

benzimidazole: C12=CC=CC=C1NC=N2

smiles_non_kekule:    c1ccc2[nH]cnc2c1
smiles_kekule:    C1=CC=C2NC=NC2=C1
inchi:    InChI=1S/C7H6N2/c1-2-4-7-6(3-1)8-5-9-7/h1-5H,(H,8,9)
inchiKey:    HYZJCKYKOHLVJF-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#7H]:[#6]:[#7]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#7H]:[#6]:[#7]:2

biphenyltetrazole: C1(C2=C(C3=CC=CC=C3)C=CC=C2)=NN=NN1

smiles_non_kekule:    c1ccc(-c2ccccc2-c2nnn[nH]2)cc1
smiles_kekule:    C1=CC=C(C2=CC=CC=C2C2=NN=NN2)C=C1
inchi:    InChI=1S/C13H10N4/c1-2-6-10(7-3-1)11-8-4-5-9-12(11)13-14-16-17-15-13/h1-9H,(H,14,15,16,17)
inchiKey:    HLAYLOOJBAJIRU-UHFFFAOYSA-N
smarts:    [#6]1(-[#6]2:[#6](-[#6]3:[#6]:[#6]:[#6]:[#6]:[#6]:3):[#6]:[#6]:[#6]:[#6]:2):[#7]:[#7]:[#7]:[#7H]:1
smarts_isomeric:    [#6]1(-[#6]2:[#6](-[#6]3:[#6]:[#6]:[#6]:[#6]:[#6]:3):[#6]:[#6]:[#6]:[#6]:2):[#7]:[#7]:[#7]:[#7H]:1

3,3-hydroxy-2-oxindole: OC(C1=CC=CC=C1N2)C2=O

smiles_non_kekule:    O=C1Nc2ccccc2C1O
smiles_kekule:    O=C1NC2=CC=CC=C2C1O
inchi:    InChI=1S/C8H7NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4,7,10H,(H,9,11)
inchiKey:    SGZFJWQQBHYNNF-UHFFFAOYSA-N
smarts:    [#8]-[#6]1-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2-[#7]-[#6]-1=[#8]
smarts_isomeric:    [#8]-[#6]1-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2-[#7]-[#6]-1=[#8]

5,7,5-lactone: C=C1C2CCCC3C(CC3)C2OC1=O

smiles_non_kekule:    C=C1C(=O)OC2C1CCCC1CCC12
smiles_kekule:    C=C1C(=O)OC2C1CCCC1CCC12
inchi:    InChI=1S/C12H16O2/c1-7-9-4-2-3-8-5-6-10(8)11(9)14-12(7)13/h8-11H,1-6H2
inchiKey:    OLARWIRLXUNTNH-UHFFFAOYSA-N
smarts:    [#6]=[#6]1-[#6]2-[#6]-[#6]-[#6]-[#6]3-[#6](-[#6]-[#6]-3)-[#6]-2-[#8]-[#6]-1=[#8]
smarts_isomeric:    [#6]=[#6]1-[#6]2-[#6]-[#6]-[#6]-[#6]3-[#6](-[#6]-[#6]-3)-[#6]-2-[#8]-[#6]-1=[#8]

6,6-spiroacetal: C1CCCC2(CCCCO2)O1

smiles_non_kekule:    C1CCC2(CCCCO2)OC1
smiles_kekule:    C1CCC2(CCCCO2)OC1
inchi:    InChI=1S/C9H16O2/c1-3-7-10-9(5-1)6-2-4-8-11-9/h1-8H2
inchiKey:    GBBVHDGKDQAEOT-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#6]-[#6]2(-[#6]-[#6]-[#6]-[#6]-[#8]-2)-[#8]-1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#6]-[#6]2(-[#6]-[#6]-[#6]-[#6]-[#8]-2)-[#8]-1

dihydropyrimidone: O=C1NCC=CN1

smiles_non_kekule:    O=C1NC=CCN1
smiles_kekule:    O=C1NC=CCN1
inchi:    InChI=1S/C4H6N2O/c7-4-5-2-1-3-6-4/h1-2H,3H2,(H2,5,6,7)
inchiKey:    QGKGASXQTBQINX-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#7]-[#6]-[#6]=[#6]-[#7]-1
smarts_isomeric:    [#8]=[#6]1-[#7]-[#6]-[#6]=[#6]-[#7]-1

indolizine: N12C=CC=C1C=CC=C2

smiles_non_kekule:    c1ccn2cccc2c1
smiles_kekule:    C1=CC2=CC=CN2C=C1
inchi:    InChI=1S/C8H7N/c1-2-6-9-7-3-5-8(9)4-1/h1-7H
inchiKey:    HOBCFUWDNJPFHB-UHFFFAOYSA-N
smarts:    [#7]12:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#7]12:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#6]:[#6]:2

biphenyl: C1(C2=CC=CC=C2)=CC=CC=C1

smiles_non_kekule:    c1ccc(-c2ccccc2)cc1
smiles_kekule:    C1=CC=C(C2=CC=CC=C2)C=C1
inchi:    InChI=1S/C12H10/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1-10H
inchiKey:    ZUOUZKKEUPVFJK-UHFFFAOYSA-N
smarts:    [#6]1(-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2):[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1(-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2):[#6]:[#6]:[#6]:[#6]:[#6]:1

triazaspirodecanone: O=C(NC1)C2(CCNCC2)N1C3=CC=CC=C3

smiles_non_kekule:    O=C1NCN(c2ccccc2)C12CCNCC2
smiles_kekule:    O=C1NCN(C2=CC=CC=C2)C12CCNCC2
inchi:    InChI=1S/C13H17N3O/c17-12-13(6-8-14-9-7-13)16(10-15-12)11-4-2-1-3-5-11/h1-5,14H,6-10H2,(H,15,17)
inchiKey:    HTQWGIHCFPWKAS-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#7]-[#6]-[#7](-[#6]-12-[#6]-[#6]-[#7]-[#6]-[#6]-2)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#8]=[#6]1-[#7]-[#6]-[#7](-[#6]-12-[#6]-[#6]-[#7]-[#6]-[#6]-2)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

N-acylhydrazone: [H]C(/N=N/CC)=O

smiles_non_kekule:    CC/N=N/C=O
smiles_kekule:    CC/N=N/C=O
inchi:    InChI=1S/C3H6N2O/c1-2-4-5-3-6/h3H,2H2,1H3/b5-4+
inchiKey:    UWBYCIKVYDOQRI-SNAWJCMRSA-N
smarts:    [#6H](-[#7]=[#7]-[#6]-[#6])=[#8]
smarts_isomeric:    [#6H](/[#7]=[#7]/[#6]-[#6])=[#8]

pyrrolinone: O=C1C=CNC1

smiles_non_kekule:    O=C1C=CNC1
smiles_kekule:    O=C1C=CNC1
inchi:    InChI=1S/C4H5NO/c6-4-1-2-5-3-4/h1-2,5H,3H2
inchiKey:    HMXQIFUGFZEJEO-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#6]=[#6]-[#7]-[#6]-1
smarts_isomeric:    [#8]=[#6]1-[#6]=[#6]-[#7]-[#6]-1

hydroxyamate: ONC(CCC(C)=O)=O

smiles_non_kekule:    CC(=O)CCC(=O)NO
smiles_kekule:    CC(=O)CCC(=O)NO
inchi:    InChI=1S/C5H9NO3/c1-4(7)2-3-5(8)6-9/h9H,2-3H2,1H3,(H,6,8)
inchiKey:    BBBJZDFCWMSCLS-UHFFFAOYSA-N
smarts:    [#8]-[#7]-[#6](-[#6]-[#6]-[#6](-[#6])=[#8])=[#8]
smarts_isomeric:    [#8]-[#7]-[#6](-[#6]-[#6]-[#6](-[#6])=[#8])=[#8]

trans-lactam: O=C1NC2CCCC2C1

smiles_non_kekule:    O=C1CC2CCCC2N1
smiles_kekule:    O=C1CC2CCCC2N1
inchi:    InChI=1S/C7H11NO/c9-7-4-5-2-1-3-6(5)8-7/h5-6H,1-4H2,(H,8,9)
inchiKey:    PMGSPDVTAKHCLW-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#7]-[#6]2-[#6]-[#6]-[#6]-[#6]-2-[#6]-1
smarts_isomeric:    [#8]=[#6]1-[#7]-[#6]2-[#6]-[#6]-[#6]-[#6]-2-[#6]-1

trans-lactone: O=C1OC2CCCC2C1

smiles_non_kekule:    O=C1CC2CCCC2O1
smiles_kekule:    O=C1CC2CCCC2O1
inchi:    InChI=1S/C7H10O2/c8-7-4-5-2-1-3-6(5)9-7/h5-6H,1-4H2
inchiKey:    DICZUTMNXOMHQD-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#8]-[#6]2-[#6]-[#6]-[#6]-[#6]-2-[#6]-1
smarts_isomeric:    [#8]=[#6]1-[#8]-[#6]2-[#6]-[#6]-[#6]-[#6]-2-[#6]-1

hexahydroisoindole: C12CNCC1CCCC2

smiles_non_kekule:    C1CCC2CNCC2C1
smiles_kekule:    C1CCC2CNCC2C1
inchi:    InChI=1S/C8H15N/c1-2-4-8-6-9-5-7(8)3-1/h7-9H,1-6H2
inchiKey:    ODSNARDHJFFSRH-UHFFFAOYSA-N
smarts:    [#6]12-[#6]-[#7]-[#6]-[#6]-1-[#6]-[#6]-[#6]-[#6]-2
smarts_isomeric:    [#6]12-[#6]-[#7]-[#6]-[#6]-1-[#6]-[#6]-[#6]-[#6]-2

benzimidazolone: O=C1N(C2CCNCC2)C3=CC=CC=C3N1

smiles_non_kekule:    O=c1[nH]c2ccccc2n1C1CCNCC1
smiles_kekule:    O=C1NC2=CC=CC=C2N1C1CCNCC1
inchi:    InChI=1S/C12H15N3O/c16-12-14-10-3-1-2-4-11(10)15(12)9-5-7-13-8-6-9/h1-4,9,13H,5-8H2,(H,14,16)
inchiKey:    BYNBAMHAURJNTR-UHFFFAOYSA-N
smarts:    [#8]=[#6]1:[#7](-[#6]2-[#6]-[#6]-[#7]-[#6]-[#6]-2):[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#7H]:1
smarts_isomeric:    [#8]=[#6]1:[#7](-[#6]2-[#6]-[#6]-[#7]-[#6]-[#6]-2):[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#7H]:1

indoline: C12=C(NCC2)C=CC=C1

smiles_non_kekule:    c1ccc2c(c1)CCN2
smiles_kekule:    C1=CC2=C(C=C1)NCC2
inchi:    InChI=1S/C8H9N/c1-2-4-8-7(3-1)5-6-9-8/h1-4,9H,5-6H2
inchiKey:    LPAGFVYQRIESJQ-UHFFFAOYSA-N
smarts:    [#6]12:[#6](-[#7]-[#6]-[#6]-1):[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#6]12:[#6](-[#7]-[#6]-[#6]-1):[#6]:[#6]:[#6]:[#6]:2

2-arylbenzothiazole: C12=CC=CC=C1N=C(C3=CC=CC=C3)S2

smiles_non_kekule:    c1ccc(-c2nc3ccccc3s2)cc1
smiles_kekule:    C1=CC=C(C2=NC3=CC=CC=C3S2)C=C1
inchi:    InChI=1S/C13H9NS/c1-2-6-10(7-3-1)13-14-11-8-4-5-9-12(11)15-13/h1-9H
inchiKey:    XBHOUXSGHYZCNH-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#7]:[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1):[#16]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#7]:[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1):[#16]:2

imidazolequinoxaline: C1(NC2)=CC=CC=C1N3C2=CN=C3

smiles_non_kekule:    c1ccc2c(c1)NCc1cncn1-2
smiles_kekule:    C1=CC=C2C(=C1)NCC1=CN=CN21
inchi:    InChI=1S/C10H9N3/c1-2-4-10-9(3-1)12-6-8-5-11-7-13(8)10/h1-5,7,12H,6H2
inchiKey:    GZGCTIXIODMQIE-UHFFFAOYSA-N
smarts:    [#6]12-[#7]-[#6]-[#6]3:[#7](-[#6]:1:[#6]:[#6]:[#6]:[#6]:2):[#6]:[#7]:[#6]:3
smarts_isomeric:    [#6]12-[#7]-[#6]-[#6]3:[#7](-[#6]:1:[#6]:[#6]:[#6]:[#6]:2):[#6]:[#7]:[#6]:3

spiroindanylpiperidine: C12=CC=CC=C1C3(CCNCC3)CC2

smiles_non_kekule:    c1ccc2c(c1)CCC21CCNCC1
smiles_kekule:    C1=CC=C2C(=C1)CCC21CCNCC1
inchi:    InChI=1S/C13H17N/c1-2-4-12-11(3-1)5-6-13(12)7-9-14-10-8-13/h1-4,14H,5-10H2
inchiKey:    ZBYFQSPEUIVDTF-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]1(-[#6]-[#6]-[#7]-[#6]-[#6]-1)-[#6]-[#6]-2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]1(-[#6]-[#6]-[#7]-[#6]-[#6]-1)-[#6]-[#6]-2

aminopyridazine: NC1=NN=CC=C1

smiles_non_kekule:    Nc1cccnn1
smiles_kekule:    NC1=NN=CC=C1
inchi:    InChI=1S/C4H5N3/c5-4-2-1-3-6-7-4/h1-3H,(H2,5,7)
inchiKey:    LETVJWLLIMJADE-UHFFFAOYSA-N
smarts:    [#7]-[#6]1:[#7]:[#7]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#7]-[#6]1:[#7]:[#7]:[#6]:[#6]:[#6]:1

1,4-pyrazolodiazepin-8-one: O=C1NCCNC2=CNN=C21

smiles_non_kekule:    O=C1NCCNc2c[nH]nc21
smiles_kekule:    O=C1NCCNC2=CNN=C12
inchi:    InChI=1S/C6H8N4O/c11-6-5-4(3-9-10-5)7-1-2-8-6/h3,7H,1-2H2,(H,8,11)(H,9,10)
inchiKey:    DBUIQCDHTOJZDG-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#7]-[#6]-[#6]-[#7]-[#6]2:[#6]:[#7H]:[#7]:[#6]:2-1
smarts_isomeric:    [#8]=[#6]1-[#7]-[#6]-[#6]-[#7]-[#6]2:[#6]:[#7H]:[#7]:[#6]:2-1

rhodanine: S=C(N1)SCC1=O

smiles_non_kekule:    O=C1CSC(=S)N1
smiles_kekule:    O=C1CSC(=S)N1
inchi:    InChI=1S/C3H3NOS2/c5-2-1-7-3(6)4-2/h1H2,(H,4,5,6)
inchiKey:    KIWUVOGUEXMXSV-UHFFFAOYSA-N
smarts:    [#16]=[#6]1-[#7]-[#6](-[#6]-[#16]-1)=[#8]
smarts_isomeric:    [#16]=[#6]1-[#7]-[#6](-[#6]-[#16]-1)=[#8]

pyranopyridone: O=C1C2=C(OCC=C2)C=CN1

smiles_non_kekule:    O=c1[nH]ccc2c1C=CCO2
smiles_kekule:    O=C1NC=CC2=C1C=CCO2
inchi:    InChI=1S/C8H7NO2/c10-8-6-2-1-5-11-7(6)3-4-9-8/h1-4H,5H2,(H,9,10)
inchiKey:    QOLGILXLMNTCHE-UHFFFAOYSA-N
smarts:    [#8]=[#6]1:[#6]2:[#6](-[#8]-[#6]-[#6]=[#6]-2):[#6]:[#6]:[#7H]:1
smarts_isomeric:    [#8]=[#6]1:[#6]2:[#6](-[#8]-[#6]-[#6]=[#6]-2):[#6]:[#6]:[#7H]:1

pyranoquinolone: O=C1C=CC2=CC=CC=C2N1

smiles_non_kekule:    O=c1ccc2ccccc2[nH]1
smiles_kekule:    O=C1C=CC2=CC=CC=C2N1
inchi:    InChI=1S/C9H7NO/c11-9-6-5-7-3-1-2-4-8(7)10-9/h1-6H,(H,10,11)
inchiKey:    LISFMEBWQUVKPJ-UHFFFAOYSA-N
smarts:    [#8]=[#6]1:[#6]:[#6]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#7H]:1
smarts_isomeric:    [#8]=[#6]1:[#6]:[#6]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#7H]:1

problem_type: 13/25 (loop 0/0)

Problem Template: _problem_common_warhead_covalent_inhibitors

[15:17:33] WARNING: Omitted undefined stereo

[15:17:34] WARNING: Charges were rearranged

[15:17:34] WARNING: Accepted unusual valence(s): S(3)

Write structure of common warhead covalent inhibitors molecules.

Answer:

structure of common warhead covalent inhibitors molecules:

propiolamide: C#CC(N)=O

fumarate ester: NC(/C=C/CC(OC)=O)=O

allenamide: NC(C=C=C)=O

propiolonitrile: C#CC#N

propargylamide: C#CCC(N)=O

arylsulfonyl bicyclobutane: O=S(C12CC1C2)(C3=CC=CC=C3)=O

haloalkane: CBr

alpha-halomethyl: CC(CCl)=O

alpha-haloamide: NC(CCl)=O

alpha-haloester: O=C(CCl)OC

epoxide: C1CO1

aziridine: N1CC1

nitroalkane: CC[N+]([O-])=O

acrylamide: C=CC(N)=O

cyanoenone: O=C(C)C(C#N)=C

aldehyde: O=C(C)[H]

ketone: O=C(C)C

nitrile: N#CC

cyanamide: NC#N

isothicyanate: [N-]=C=S

sulfone: CS=O

sulfonyl fluoride: O=S(F)=O

sulfonimidoyl fluoride: N=S(F)(F)=O

aryl fluorosulfate: O=S(OCCCCC)(F)=O

ester: CC(OC)=O

sulfonamide: O=S(N)=O

2-carbonyl arylboronic acid: O=C(C1=CC=CC=C1B(O)O)C

n-methyl isoxazolium: C[N+]1=CC=CO1

oxaziridine: O1NC1

Solution:

structure of common warhead covalent inhibitors molecules:

propiolamide: C#CC(N)=O

smiles_non_kekule:    C#CC(N)=O
smiles_kekule:    C#CC(N)=O
inchi:    InChI=1S/C3H3NO/c1-2-3(4)5/h1H,(H2,4,5)
inchiKey:    HCJTYESURSHXNB-UHFFFAOYSA-N
smarts:    [#6]#[#6]-[#6](-[#7])=[#8]
smarts_isomeric:    [#6]#[#6]-[#6](-[#7])=[#8]

fumarate ester: NC(/C=C/CC(OC)=O)=O

smiles_non_kekule:    COC(=O)C/C=C/C(N)=O
smiles_kekule:    COC(=O)C/C=C/C(N)=O
inchi:    InChI=1S/C6H9NO3/c1-10-6(9)4-2-3-5(7)8/h2-3H,4H2,1H3,(H2,7,8)/b3-2+
inchiKey:    MNMCNGHQDACXMV-NSCUHMNNSA-N
smarts:    [#7]-[#6](-[#6]=[#6]-[#6]-[#6](-[#8]-[#6])=[#8])=[#8]
smarts_isomeric:    [#7]-[#6](/[#6]=[#6]/[#6]-[#6](-[#8]-[#6])=[#8])=[#8]

allenamide: NC(C=C=C)=O

smiles_non_kekule:    C=C=CC(N)=O
smiles_kekule:    C=C=CC(N)=O
inchi:    InChI=1S/C4H5NO/c1-2-3-4(5)6/h3H,1H2,(H2,5,6)
inchiKey:    QOYPXNPNQLIEIL-UHFFFAOYSA-N
smarts:    [#7]-[#6](-[#6]=[#6]=[#6])=[#8]
smarts_isomeric:    [#7]-[#6](-[#6]=[#6]=[#6])=[#8]

propiolonitrile: C#CC#N

smiles_non_kekule:    C#CC#N
smiles_kekule:    C#CC#N
inchi:    InChI=1S/C3HN/c1-2-3-4/h1H
inchiKey:    LNDJVIYUJOJFSO-UHFFFAOYSA-N
smarts:    [#6]#[#6]-[#6]#[#7]
smarts_isomeric:    [#6]#[#6]-[#6]#[#7]

propargylamide: C#CCC(N)=O

smiles_non_kekule:    C#CCC(N)=O
smiles_kekule:    C#CCC(N)=O
inchi:    InChI=1S/C4H5NO/c1-2-3-4(5)6/h1H,3H2,(H2,5,6)
inchiKey:    OTDADMIMLSDQCC-UHFFFAOYSA-N
smarts:    [#6]#[#6]-[#6]-[#6](-[#7])=[#8]
smarts_isomeric:    [#6]#[#6]-[#6]-[#6](-[#7])=[#8]

arylsulfonyl bicyclobutane: O=S(C12CC1C2)(C3=CC=CC=C3)=O

smiles_non_kekule:    O=S(=O)(c1ccccc1)C12CC1C2
smiles_kekule:    O=S(=O)(C1=CC=CC=C1)C12CC1C2
inchi:    InChI=1S/C10H10O2S/c11-13(12,10-6-8(10)7-10)9-4-2-1-3-5-9/h1-5,8H,6-7H2
inchiKey:    GJORDRKZOZLVKK-UHFFFAOYSA-N
smarts:    [#8]=[#16](-[#6]12-[#6]-[#6]-1-[#6]-2)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)=[#8]
smarts_isomeric:    [#8]=[#16](-[#6]12-[#6]-[#6]-1-[#6]-2)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)=[#8]

haloalkane: CBr

smiles_non_kekule:    CBr
smiles_kekule:    CBr
inchi:    InChI=1S/CH3Br/c1-2/h1H3
inchiKey:    GZUXJHMPEANEGY-UHFFFAOYSA-N
smarts:    [#6]-[#35]
smarts_isomeric:    [#6]-[#35]

alpha-halomethyl: CC(CCl)=O

smiles_non_kekule:    CC(=O)CCl
smiles_kekule:    CC(=O)CCl
inchi:    InChI=1S/C3H5ClO/c1-3(5)2-4/h2H2,1H3
inchiKey:    BULLHNJGPPOUOX-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#17])=[#8]
smarts_isomeric:    [#6]-[#6](-[#6]-[#17])=[#8]

alpha-haloamide: NC(CCl)=O

smiles_non_kekule:    NC(=O)CCl
smiles_kekule:    NC(=O)CCl
inchi:    InChI=1S/C2H4ClNO/c3-1-2(4)5/h1H2,(H2,4,5)
inchiKey:    VXIVSQZSERGHQP-UHFFFAOYSA-N
smarts:    [#7]-[#6](-[#6]-[#17])=[#8]
smarts_isomeric:    [#7]-[#6](-[#6]-[#17])=[#8]

alpha-haloester: O=C(CCl)OC

smiles_non_kekule:    COC(=O)CCl
smiles_kekule:    COC(=O)CCl
inchi:    InChI=1S/C3H5ClO2/c1-6-3(5)2-4/h2H2,1H3
inchiKey:    QABLOFMHHSOFRJ-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6]-[#17])-[#8]-[#6]
smarts_isomeric:    [#8]=[#6](-[#6]-[#17])-[#8]-[#6]

epoxide: C1CO1

smiles_non_kekule:    C1CO1
smiles_kekule:    C1CO1
inchi:    InChI=1S/C2H4O/c1-2-3-1/h1-2H2
inchiKey:    IAYPIBMASNFSPL-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#8]-1
smarts_isomeric:    [#6]1-[#6]-[#8]-1

aziridine: N1CC1

smiles_non_kekule:    C1CN1
smiles_kekule:    C1CN1
inchi:    InChI=1S/C2H5N/c1-2-3-1/h3H,1-2H2
inchiKey:    NOWKCMXCCJGMRR-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-1

nitroalkane: CC[N+]([O-])=O

smiles_non_kekule:    CC[N+](=O)[O-]
smiles_kekule:    CC[N+](=O)[O-]
inchi:    InChI=1S/C2H5NO2/c1-2-3(4)5/h2H2,1H3
inchiKey:    MCSAJNNLRCFZED-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7+](-[#8-])=[#8]
smarts_isomeric:    [#6]-[#6]-[#7+](-[#8-])=[#8]

acrylamide: C=CC(N)=O

smiles_non_kekule:    C=CC(N)=O
smiles_kekule:    C=CC(N)=O
inchi:    InChI=1S/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5)
inchiKey:    HRPVXLWXLXDGHG-UHFFFAOYSA-N
smarts:    [#6]=[#6]-[#6](-[#7])=[#8]
smarts_isomeric:    [#6]=[#6]-[#6](-[#7])=[#8]

cyanoenone: O=C(C)C(C#N)=C

smiles_non_kekule:    C=C(C#N)C(C)=O
smiles_kekule:    C=C(C#N)C(C)=O
inchi:    InChI=1S/C5H5NO/c1-4(3-6)5(2)7/h1H2,2H3
inchiKey:    KRTNCALJETZRGN-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6])-[#6](-[#6]#[#7])=[#6]
smarts_isomeric:    [#8]=[#6](-[#6])-[#6](-[#6]#[#7])=[#6]

aldehyde: O=C(C)[H]

smiles_non_kekule:    CC=O
smiles_kekule:    CC=O
inchi:    InChI=1S/C2H4O/c1-2-3/h2H,1H3
inchiKey:    IKHGUXGNUITLKF-UHFFFAOYSA-N
smarts:    [#8]=[#6H]-[#6]
smarts_isomeric:    [#8]=[#6H]-[#6]

ketone: O=C(C)C

smiles_non_kekule:    CC(C)=O
smiles_kekule:    CC(C)=O
inchi:    InChI=1S/C3H6O/c1-3(2)4/h1-2H3
inchiKey:    CSCPPACGZOOCGX-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6])-[#6]
smarts_isomeric:    [#8]=[#6](-[#6])-[#6]

nitrile: N#CC

smiles_non_kekule:    CC#N
smiles_kekule:    CC#N
inchi:    InChI=1S/C2H3N/c1-2-3/h1H3
inchiKey:    WEVYAHXRMPXWCK-UHFFFAOYSA-N
smarts:    [#7]#[#6]-[#6]
smarts_isomeric:    [#7]#[#6]-[#6]

cyanamide: NC#N

smiles_non_kekule:    N#CN
smiles_kekule:    N#CN
inchi:    InChI=1S/CH2N2/c2-1-3/h2H2
inchiKey:    XZMCDFZZKTWFGF-UHFFFAOYSA-N
smarts:    [#7]-[#6]#[#7]
smarts_isomeric:    [#7]-[#6]#[#7]

isothicyanate: [N-]=C=S

smiles_non_kekule:    [N-]=C=S
smiles_kekule:    [N-]=C=S
inchi:    InChI=1S/CNS/c2-1-3/q-1
inchiKey:    ZBKFYXZXZJPWNQ-UHFFFAOYSA-N
smarts:    [#7-]=[#6]=[#16]
smarts_isomeric:    [#7-]=[#6]=[#16]

sulfone: CS=O

smiles_non_kekule:    C[SH]=O
smiles_kekule:    C[SH]=O
inchi:    InChI=1S/CH3OS/c1-3-2/h1H3
inchiKey:    BSASGANESDGUBT-UHFFFAOYSA-N
smarts:    [#6]-[#16]=[#8]
smarts_isomeric:    [#6]-[#16]=[#8]

sulfonyl fluoride: O=S(F)=O

smiles_non_kekule:    O=[SH](=O)F
smiles_kekule:    O=[SH](=O)F
inchi:    InChI=1S/FHO2S/c1-4(2)3/h4H
inchiKey:    KRVPQYLAPLFQNB-UHFFFAOYSA-N
smarts:    [#8]=[#16](-[#9])=[#8]
smarts_isomeric:    [#8]=[#16](-[#9])=[#8]

sulfonimidoyl fluoride: N=S(F)(F)=O

smiles_non_kekule:    N=S(=O)(F)F
smiles_kekule:    N=S(=O)(F)F
inchi:    InChI=1S/F2HNOS/c1-5(2,3)4/h3H
inchiKey:    LHXNDZQKLAXNKX-UHFFFAOYSA-N
smarts:    [#7]=[#16](-[#9])(-[#9])=[#8]
smarts_isomeric:    [#7]=[#16](-[#9])(-[#9])=[#8]

aryl fluorosulfate: O=S(OCCCCC)(F)=O

smiles_non_kekule:    CCCCCOS(=O)(=O)F
smiles_kekule:    CCCCCOS(=O)(=O)F
inchi:    InChI=1S/C5H11FO3S/c1-2-3-4-5-9-10(6,7)8/h2-5H2,1H3
inchiKey:    XTFDSIUWLQNMDA-UHFFFAOYSA-N
smarts:    [#8]=[#16](-[#8]-[#6]-[#6]-[#6]-[#6]-[#6])(-[#9])=[#8]
smarts_isomeric:    [#8]=[#16](-[#8]-[#6]-[#6]-[#6]-[#6]-[#6])(-[#9])=[#8]

ester: CC(OC)=O

smiles_non_kekule:    COC(C)=O
smiles_kekule:    COC(C)=O
inchi:    InChI=1S/C3H6O2/c1-3(4)5-2/h1-2H3
inchiKey:    KXKVLQRXCPHEJC-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#8]-[#6])=[#8]
smarts_isomeric:    [#6]-[#6](-[#8]-[#6])=[#8]

sulfonamide: O=S(N)=O

smiles_non_kekule:    N[SH](=O)=O
smiles_kekule:    N[SH](=O)=O
inchi:    InChI=1S/H3NO2S/c1-4(2)3/h4H,(H2,1,2,3)
inchiKey:    AHZVGADFMXTGBU-UHFFFAOYSA-N
smarts:    [#8]=[#16](-[#7])=[#8]
smarts_isomeric:    [#8]=[#16](-[#7])=[#8]

2-carbonyl arylboronic acid: O=C(C1=CC=CC=C1B(O)O)C

smiles_non_kekule:    CC(=O)c1ccccc1B(O)O
smiles_kekule:    CC(=O)C1=CC=CC=C1B(O)O
inchi:    InChI=1S/C8H9BO3/c1-6(10)7-4-2-3-5-8(7)9(11)12/h2-5,11-12H,1H3
inchiKey:    ZKAOVABYLXQUTI-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#5](-[#8])-[#8])-[#6]
smarts_isomeric:    [#8]=[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#5](-[#8])-[#8])-[#6]

n-methyl isoxazolium: C[N+]1=CC=CO1

smiles_non_kekule:    C[n+]1ccco1
smiles_kekule:    C[N+]1=CC=CO1
inchi:    InChI=1S/C4H6NO/c1-5-3-2-4-6-5/h2-4H,1H3/q+1
inchiKey:    LEOYNSMUKJJRLA-UHFFFAOYSA-N
smarts:    [#6]-[#7+]1:[#6]:[#6]:[#6]:[#8]:1
smarts_isomeric:    [#6]-[#7+]1:[#6]:[#6]:[#6]:[#8]:1

oxaziridine: O1NC1

smiles_non_kekule:    C1NO1
smiles_kekule:    C1NO1
inchi:    InChI=1S/CH3NO/c1-2-3-1/h2H,1H2
inchiKey:    SJGALSBBFTYSBA-UHFFFAOYSA-N
smarts:    [#8]1-[#7]-[#6]-1
smarts_isomeric:    [#8]1-[#7]-[#6]-1

problem_type: 14/25 (loop 0/0)

[15:17:40] WARNING: Accepted unusual valence(s): N+1(3)

[15:17:40] Can't kekulize mol.  Unkekulized atoms: 0 1 2 3 4
[15:17:40] WARNING: Charges were rearranged

[15:17:40] WARNING: Omitted undefined stereo

[15:17:40] Can't kekulize mol.  Unkekulized atoms: 0 1 2 3 4
[15:17:40] WARNING: Omitted undefined stereo

[15:17:40] WARNING: Omitted undefined stereo

[15:17:40] Can't kekulize mol.  Unkekulized atoms: 0 1 2 3 4
[15:17:40] WARNING: Omitted undefined stereo

[15:17:40] Can't kekulize mol.  Unkekulized atoms: 0 1 2 3 4
[15:17:40] WARNING: Omitted undefined stereo

[15:17:41] WARNING: Omitted undefined stereo

[15:17:41] WARNING: Omitted undefined stereo

[15:17:41] WARNING: Omitted undefined stereo

[15:17:41] WARNING: Omitted undefined stereo

[15:17:41] WARNING: Omitted undefined stereo

[15:17:41] WARNING: Omitted undefined stereo

[15:17:41] WARNING: Omitted undefined stereo

[15:17:41] WARNING: Omitted undefined stereo

Problem Template: _problem_commonly_used_r_group_replacements

Write structure of commonly used r group replacements molecules.

Answer:

structure of commonly used r group replacements molecules:

water: O

methanol: OC

ammonia: N

hydrogen chloride: Cl

hydrogen fluoride: F

ethane: CC

hydrogen cyanide: C#N

formic acid: C(=O)O

hydrogen bromide: Br

fluroform: C(F)(F)F

propane: C(C)C

toulene: Cc1ccccc1

pyridine: c1cccnc1

dimethylamine: N(C)C

ethanol: OCC

formamide: C(N)=O

morpholine: N1CCOCC1

nitro: [N+](=O)[O-]

isobutane: C(C)(C)C

anisole: c1ccc(OC)cc1

flurobenzene: c1ccc(F)cc1

cyclohexane: C1CCCCC1

acetic acid: CC(=O)O

methyl formate: C(=O)OC

butane: CCCC

acetamide: NC(C)=O

methanamine: NC

acetaldehyde: C(C)=O

chlorobenzene: c1ccc(Cl)cc1

1-methylpiperazine: N1CCN(C)CC1

phenylmethanol: OCc1ccccc1

ethylbenzene: CCc1ccccc1

piperidine: N1CCCCC1

thiophene: c1cccs1

cyclopropane: C1CC1

phenol: Oc1ccccc1

aniline: Nc1ccccc1

hydrosulfonylmethane: S(C)(=O)=O

piperazine: N1CCNCC1

pyrrolidine: N1CCCC1

4-methylmorpholine: CN1CCOCC1

hydrogen iodide: I

ethyl formate: C(=O)OCC

sulfonic amide: S(N)(=O)=O

phenylmethanamine: NCc1ccccc1

N-methylformamide: C(=O)NC

trimethylamine: CN(C)C

N,N-dimethylformamide: C(=O)N(C)C

thiol: SC

benzaldehyde: C(=O)c1ccccc1

1-methylpiperidine: CN1CCCCC1

cyclopentane: C1CCCC1

N-hydroxyformamide: C(=O)NO

pyrimidine: c1cncnc1

furan: c1ccco1

ethanamine: CCN

benzonitrile: c1ccc(C#N)cc1

propionic acid: CCC(=O)O

propan-2-ol: OC(C)C

methanesulfonamide: NS(C)(=O)=O

pentane: CCCCC

morpholine-4-carbaldehyde: C(=O)N1CCOCC1

trifluoromethanol: OC(F)(F)F

methoxymethane: COC

cyclohexanamine: NC1CCCCC1

formaldehyde: C=O

N-phenylformamide: C(=O)Nc1ccccc1

butan-1-ol: OCCCC

pyrazine: c1cnccn1

naphthalene: c1ccc2ccccc2c1

propan-1-ol: OCCC

benzamide: NC(=O)c1ccccc1

1-methyl-1H-pyrazole: c1cnn(C)c1

N-benzylformamide: C(=O)NCc1ccccc1

propan-2-amine: NC(C)C

1,3-Benzodioxole: c1ccc2c(c1)OCO2

1-methylpyrrolidine: CN1CCCC1

methylcyclohexane: CC1CCCCC1

ethyne: C#C

2-methoxypyridine: c1ccc(OC)nc1

N,N-dimethylethanamine: CCN(C)C

thiazole: c1nccs1

bromobenzene: c1ccc(Br)cc1

4-methylpyridine: Cc1ccncc1

2-methoxyethan-1-ol: OCCOC

hexane: CCCCCC

Tetrahydropyran: C1CCOCC1

1H-pyrazole: c1cn[nH]c1

1-methyl-1H-imidazole: Cn1ccnc1

benzoic acid: c1ccc(C(=O)O)cc1

boronic acid: B(O)O

2-hydroxyacetic acid: OCC(=O)O

ethene: C=C

piperidine-1-carbaldehyde: C(=O)N1CCCCC1

styrene: C=Cc1ccccc1

1-fluoro-4-methylbenzene: Cc1ccc(F)cc1

ethylene glycol: OCCO

2-(dimethylamino)ethan-1-ol: OCCN(C)C

(trifluoromethyl)benzene: c1ccc(C(F)(F)F)cc1

diethylamine: N(CC)CC

N-cyclohexylformamide: C(=O)NC1CCCCC1

benzothiazole: c1nc2ccccc2s1

methylcyclopropane: CC1CC1

N-ethyl-N-methylethanamine: CN(CC)CC

1H-benzoimidazole: c1nc2ccccc2[nH]1

N-isopropylformamide: C(=O)NC(C)C

2-aminoethan-1-ol: NCCO

N-(2-hydroxyethyl)formamide: C(=O)NCCO

2,3-dihydrobenzo[b][1,4]dioxine: c1ccc2c(c1)OCCO2

benzothiophene: c1cc2ccccc2s1

propylbenzene: CCCc1ccccc1

pyrrolidine-1-carbaldehyde: C(=O)N1CCCC1

1,4-dimethylpiperazine: CN1CCN(C)CC1

N-ethylformamide: C(=O)NCC

2-morpholinoethan-1-ol: OCCN1CCOCC1

4-ethylmorpholine: CCN1CCOCC1

indole: c1c[nH]c2ccccc12

quinoline: c1cnc2ccccc2c1

3-(dimethylamino)propan-1-ol: OCCCN(C)C

3-methylpyridine: Cc1cccnc1

cyclobutane: C1CCC1

formimidamide: C(=N)N

benzofuran: c1cc2ccccc2o1

1-methoxy-4-methylbenzene: Cc1ccc(OC)cc1

2-methylpyridine: Cc1ccccn1

acetonitrile: CC#N

1,2-dichlorobenzene: c1ccc(Cl)c(Cl)c1

N,N-dimethylaniline: c1ccc(N(C)C)cc1

hydrosulfonylbenzene: S(=O)(=O)c1ccccc1

N-methylacetamide: CNC(C)=O

hydrogen sulfide: S

2-phenylethan-1-amine: NCCc1ccccc1

2-(pyrrolidin-1-yl)ethan-1-ol: OCCN1CCCC1

methoxyethane: CCOC

1,2-dimethoxybenzene: c1ccc(OC)c(OC)c1

nitrobenzene: c1ccc([N+](=O)[O-])cc1

ethynylbenzene: C#Cc1ccccc1

N-(pyridin-3-yl)formamide: C(=O)Nc1cccnc1

2-(piperidin-1-yl)ethan-1-ol: OCCN1CCCCC1

benzenesulfonamide: c1ccc(S(N)(=O)=O)cc1

1-ethylpyrrolidine: CCN1CCCC1

pyrazole: c1cc[nH]n1

3-(piperidin-1-yl)propan-1-ol: OCCCN1CCCCC1

N,N-diethylformamide: C(=O)N(CC)CC

acetophenone: c1ccc(C(C)=O)cc1

benzooxazole: c1nc2ccccc2o1

4-methylpiperazine-1-carbaldehyde: C(=O)N1CCN(C)CC1

benzenethiol: Sc1ccccc1

sulfuric diamide: NS(N)(=O)=O

4-methoxyaniline: Nc1ccc(OC)cc1

1-chloro-4-methylbenzene: Cc1ccc(Cl)cc1

propan-1-amine: CCCN

ethoxybenzene: c1ccc(OCC)cc1

5-methylene-2-thioxothiazolidin-4-one: C=C1SC(=S)NC1=O

1,3-difluorobenzene: c1ccc(F)cc1F

(trifluoromethoxy)benzene: c1ccc(OC(F)(F)F)cc1

heptane: CCCCCCC

pyridin-2-amine: c1ccc(N)nc1

1-ethylpiperidine: CCN1CCCCC1

formohydrazide: C(=O)NN

2-chlorothiophene: c1ccc(Cl)s1

piperidin-4-ol: N1CCC(O)CC1

2-methylthiazole: c1csc(C)n1

N-cyclopropylformamide: C(=O)NC1CC1

prop-2-en-1-ol: OCC=C

cyclopentanamine: NC1CCCC1

urea: NC(N)=O

prop-1-ene: CC=C

(methylsulfonyl)benzene: c1ccc(S(C)(=O)=O)cc1

difluoromethanol: OC(F)F

2-phenylacetamide: NC(=O)Cc1ccccc1

4-fluorobenzaldehyde: C(=O)c1ccc(F)cc1

N-propylformamide: C(=O)NCCC

N-tert-butylformamide: C(=O)NC(C)(C)C

tetrazole: c1nnn[nH]1

pyrrolidin-3-ol: N1CCC(O)C1

biphenyl: c1ccc(-c2ccccc2)cc1

cyclopropanamine: NC1CC1

formaldehyde oxime: C=NO

furan-2-carboxamide: NC(=O)c1ccco1

3-morpholinopropan-1-ol: OCCCN1CCOCC1

propionamide: NC(=O)CC

2-(piperazin-1-yl)ethan-1-ol: N1CCN(CCO)CC1

pyridin-3-ylmethanamine: NCc1cccnc1

N-hydroxyacrylamide: C=CC(=O)NO

N-(2-methoxyethyl)formamide: C(=O)NCCOC

2-methylthiophene: Cc1cccs1

tert-butylbenzene: c1ccc(C(C)(C)C)cc1

cyclohexanecarboxamide: NC(=O)C1CCCCC1

4-fluorophenol: Oc1ccc(F)cc1

2-ethynylpyridine: C#Cc1ccccn1

(4-methoxyphenyl)methanamine: NCc1ccc(OC)cc1

butyric acid: CCCC(=O)O

1-Acetylpiperazine: N1CCN(C(C)=O)CC1

3,5-dimethylisoxazole: c1c(C)noc1C

1-ethylpiperazine: N1CCN(CC)CC1

adamantane: C12CC3CC(CC(C3)C1)C2

1-chloro-3-methylbenzene: Cc1cccc(Cl)c1

1,2-difluorobenzene: c1ccc(F)c(F)c1

1-phenylurea: NC(=O)Nc1ccccc1

2-methylpropan-2-ol: OC(C)(C)C

1-chloro-2-methylbenzene: Cc1ccccc1Cl

N-phenethylformamide: C(=O)NCCc1ccccc1

isonicotinamide: NC(=O)c1ccncc1

N-methylcyclopentanamine: CNC1CCCC1

2-methoxyethan-1-amine: NCCOC

propionaldehyde: C(=O)CC

N-(4-chlorophenyl)formamide: C(=O)Nc1ccc(Cl)cc1

2-chloropyridine: c1ccc(Cl)nc1

N,N-dimethylpropan-1-amine: CCCN(C)C

5-methylenethiazolidine-2,4-dione: C=C1SC(=O)NC1=O

3-methoxypyridine: c1cncc(OC)c1

3-(trifluoromethyl)pyridine: c1ncccc1C(F)(F)F

4-methylbenzenesulfonamide: NS(=O)(=O)c1ccc(C)cc1

2-phenylethan-1-ol: OCCc1ccccc1

N-cyclopentylformamide: C(=O)NC1CCCC1

indazole: c1ccc2[nH]ncc2c1

cyclopentanol: OC1CCCC1

nicotinamide: NC(=O)c1cccnc1

isopentane: CCC(C)C

hydrosulfonylethane: S(=O)(=O)CC

tert-butyl carbamate: NC(=O)OC(C)(C)C

(tetrahydrofuran-2-yl)methanol: OCC1CCCO1

N,N-dimethylacetamide: CC(=O)N(C)C

1-phenylpiperazine: N1CCN(c2ccccc2)CC1

2-methylpropan-1-ol: C(C)(C)CO

N-methylethanamine: CCNC

1,3-dichlorobenzene: c1ccc(Cl)cc1Cl

tert-butyl formate: C(=O)OC(C)(C)C

thiophene-2-carbaldehyde: C(=O)c1cccs1

1-methyl-1,4-diazepane: N1CCCN(C)CC1

N-phenylacetamide: c1ccc(NC(C)=O)cc1

octane: CCCCCCCC

1-methoxy-2-methylbenzene: Cc1ccccc1OC

1H-pyrrole-2,5-dione: N1C(=O)C=CC1=O

sulfamic acid: OS(N)(=O)=O

2-methylisoindoline-1,3-dione: CN1C(=O)c2ccccc2C1=O

(difluoromethyl)phosphonic acid: C(F)(F)P(=O)(O)O

pyrimidin-2-amine: c1ccnc(N)n1

1H-benzo[d]imidazole-5-carboxamide: c1nc2cc(C(N)=O)ccc2[nH]1

2-methylpropan-2-amine: NC(C)(C)C

N-(4-fluorophenyl)formamide: C(=O)Nc1ccc(F)cc1

oxazole: c1cnco1

pyridin-3-ylmethanol: OCc1cccnc1

pyridin-3-ol: Oc1cccnc1

picolinamide: NC(=O)c1ccccn1

cyclopropylmethanol: OCC1CC1

ethyl carbamate: NC(=O)OCC

2-(diethylamino)ethan-1-ol: OCCN(CC)CC

pyrocatechol: c1ccc(O)c(O)c1

acrylamide: NC(=O)C=C

azetidine: N1CCC1

p-xylene: Cc1ccc(C)cc1

1-methylpiperidin-4-ol: OC1CCN(C)CC1

4-hydrosulfonylmorpholine: S(=O)(=O)N1CCOCC1

4-methyl-1H-imidazole: Cc1c[nH]cn1

N-(pyridin-4-yl)formamide: C(=O)Nc1ccncc1

4-methoxyphenol: Oc1ccc(OC)cc1

fluoromethane: CF

N-methylbenzamide: CNC(=O)c1ccccc1

pyridin-3-amine: Nc1cccnc1

pyridin-4-ylmethanamine: NCc1ccncc1

imidazole: c1ncc[nH]1

3-chlorophenol: Oc1cccc(Cl)c1

1-ethylurea: NC(=O)NCC

methyl benzoate: c1ccc(C(=O)OC)cc1

(aminomethylene)bis(phosphonic acid): NC(P(=O)(O)O)P(=O)(O)O

pyridin-4-amine: Nc1ccncc1

N-methyl-2-phenylcyclopropan-1-amine: CNC1CC1c1ccccc1

5-methoxy-3-methyl-1,3,4-oxadiazol-2(3H)-one: Cn1nc(OC)oc1=O

(methylsulfonyl)methane: CS(C)(=O)=O

1-(piperidin-1-yl)ethan-1-one: C1CCN(C(C)=O)CC1

methyl acetate: CC(=O)OC

4-chlorophenol: Oc1ccc(Cl)cc1

ethane-1,2-diamine: NCCN

4-methylpiperidine: N1CCC(C)CC1

benzyl formate: C(=O)OCc1ccccc1

N,N-dimethylsulfonic amide: S(=O)(=O)N(C)C

4-methoxybenzaldehyde: C(=O)c1ccc(OC)cc1

N-hydroxyacetamide: CC(=O)NO

2-fluoroethan-1-ol: OCCF

2-aminobenzamide: Nc1ccccc1C(N)=O

N-hydroxypropionamide: CCC(=O)NO

2H-tetrazole: c1nn[nH]n1

prop-2-yn-1-ol: OCC#C

piperidin-4-ylmethanol: N1CCC(CO)CC1

3-ethynylpyridine: C#Cc1cccnc1

4-chlorobenzaldehyde: C(=O)c1ccc(Cl)cc1

methylphosphonic acid: CP(=O)(O)O

isobutyramide: NC(=O)C(C)C

cyclopropylmethanamine: NCC1CC1

N,N-dimethylpyrrolidin-3-amine: N1CCC(N(C)C)C1

4,5-dihydrooxazol-2-amine: C1COC(N)=N1

1,2,3,4-tetrahydroisoquinoline: N1CCc2ccccc2C1

4-phenylmorpholine: c1ccc(N2CCOCC2)cc1

4,5-dihydro-1H-imidazole: C1=NCCN1

3-aminopropan-1-ol: NCCCO

2,2,2-trifluoroacetaldehyde: C(=O)C(F)(F)F

trifluoromethanethiol: SC(F)(F)F

N-ethylacetamide: CCNC(C)=O

N-methylaniline: N(C)c1ccccc1

phenylmethanethiol: SCc1ccccc1

4-(pyrrolidin-1-yl)piperidine: N1CCC(N2CCCC2)CC1

4-(trifluoromethyl)pyrimidine: c1nccc(C(F)(F)F)n1

1-methoxy-3-methylbenzene: Cc1cccc(OC)c1

N-butylformamide: C(=O)NCCCC

2,2,2-trifluoroethan-1-ol: OCC(F)(F)F

p-toluidine: Nc1ccc(C)cc1

1,3-dimethoxybenzene: c1cc(OC)cc(OC)c1

N,N-dimethyl-1-phenylmethanamine: CN(C)Cc1ccccc1

2-methylnaphthalene: Cc1ccc2ccccc2c1

tetrahydrofuran: C1CCCO1

acrylic acid: C=CC(=O)O

2-(methylamino)ethan-1-ol: CNCCO

4-methylbenzaldehyde: C(=O)c1ccc(C)cc1

3,4-dimethyl-1H-pyrazole-5-carboxylic acid: Cc1c(C)n[nH]c1C(=O)O

chloromethane: CCl

butyramide: NC(=O)CCC

1-chloro-4-hydrosulfonylbenzene: S(=O)(=O)c1ccc(Cl)cc1

difluoromethane: C(F)F

3-(pyrrolidin-1-yl)propan-1-ol: OCCCN1CCCC1

cyclopropylbenzene: C1CC1c1ccccc1

cumene: c1ccc(C(C)C)cc1

2-methyltetrahydrofuran: CC1CCCO1

N-methylpropan-2-amine: CNC(C)C

alanine: CC(N)C(=O)O

1,2,3,6-tetrahydropyridine: C1=CCNCC1

2-(trifluoromethyl)pyridine: c1ccc(C(F)(F)F)nc1

hydroquinone: Oc1ccc(O)cc1

4-fluoroaniline: Nc1ccc(F)cc1

1-fluoro-2-methoxybenzene: c1ccc(OC)c(F)c1

2-ethylidenehydrazine-1-carbothioamide: C(C)=NNC(N)=S

furan-2-carbaldehyde: C(=O)c1ccco1

butan-1-amine: NCCCC

triaza-1,2-dien-2-ium: N=[N+]=N

pyridin-2-ylmethanol: OCc1ccccn1

resorcinol: c1cc(O)cc(O)c1

piperidin-3-ol: N1CCCC(O)C1

cyclopropanecarboxamide: NC(=O)C1CC1

1-methyl-1H-1,2,4-triazole: Cn1cncn1

4-chlorobenzene-1,2-diol: Oc1ccc(Cl)cc1O

N-methyl-1-phenylmethanamine: N(C)Cc1ccccc1

pyrazin-2-amine: c1cnc(N)cn1

thiophen-2-ylmethanamine: NCc1cccs1

2-morpholinoethan-1-amine: NCCN1CCOCC1

thiomorpholine 1,1-dioxide: N1CCS(=O)(=O)CC1

2-isopropoxypyridine: c1ccc(OC(C)C)nc1

pyridazine: c1ccnnc1

3-fluoropyridine: c1ccc(F)cn1

isoquinoline: c1cncc2ccccc12

4-chloroaniline: Nc1ccc(Cl)cc1

pyrrolidin-2-one: N1CCCC1=O

5-methyloctahydropyrrolo[3,4-b]pyrrole: N1CCC2CN(C)CC21

4-methoxybenzamide: NC(=O)c1ccc(OC)cc1

m-cresol: Oc1cccc(C)c1

4,4,5,5-tetramethyl-1,3,2-dioxaborolane: B1OC(C)(C)C(C)(C)O1

N1,N1-dimethylethane-1,2-diamine: NCCN(C)C

1-phenylthiourea: NC(=S)Nc1ccccc1

1-methyl-4-(trifluoromethyl)benzene: Cc1ccc(C(F)(F)F)cc1

isopropoxybenzene: c1ccc(OC(C)C)cc1

4-methoxypiperidine: N1CCC(OC)CC1

1,2-dichloro-4-methylbenzene: Cc1ccc(Cl)c(Cl)c1

1-(4-chlorophenyl)urea: NC(=O)Nc1ccc(Cl)cc1

thiazol-2-amine: Nc1nccs1

o-xylene: c1ccc(C)c(C)c1

2-methyl-1,3,4-oxadiazole: c1nnc(C)o1

1-fluoro-3-methylbenzene: Cc1cccc(F)c1

(methoxymethyl)benzene: COCc1ccccc1

hydrazine: NN

1-cyclohexylurea: NC(=O)NC1CCCCC1

ethanethiol: SCC

N-hydroxypentanamide: CCCCC(=O)NO

thiophene-2-carboxamide: NC(=O)c1cccs1

N-(cyclopropylmethyl)formamide: C(=O)NCC1CC1

1-ethyl-2-methylpyrrolidine: CCN1CCCC1C

pyridin-4-ylmethanol: OCc1ccncc1

triethylamine: CCN(CC)CC

4-hydroxy-2-oxobut-3-enoic acid: C(O)=CC(=O)C(=O)O

isonicotinaldehyde: C(=O)c1ccncc1

1,1,1-trifluoroethane: CC(F)(F)F

isothiocyanic acid: N=C=S

phosphonic acid: P(=O)(O)O

2-hydroxy-4-oxobut-2-enoic acid: C(=O)C=C(O)C(=O)O

N,N-dimethylpiperidin-4-amine: CN(C)C1CCNCC1

1-(pyridin-2-yl)piperazine: N1CCN(c2ccccn2)CC1

Solution:

structure of commonly used r group replacements molecules:

water: O

smiles_non_kekule:    O
smiles_kekule:    O
inchi:    InChI=1S/H2O/h1H2
inchiKey:    XLYOFNOQVPJJNP-UHFFFAOYSA-N
smarts:    [#8]
smarts_isomeric:    [#8]

methanol: OC

smiles_non_kekule:    CO
smiles_kekule:    CO
inchi:    InChI=1S/CH4O/c1-2/h2H,1H3
inchiKey:    OKKJLVBELUTLKV-UHFFFAOYSA-N
smarts:    [#8]-[#6]
smarts_isomeric:    [#8]-[#6]

ammonia: N

smiles_non_kekule:    N
smiles_kekule:    N
inchi:    InChI=1S/H3N/h1H3
inchiKey:    QGZKDVFQNNGYKY-UHFFFAOYSA-N
smarts:    [#7]
smarts_isomeric:    [#7]

hydrogen chloride: Cl

smiles_non_kekule:    Cl
smiles_kekule:    Cl
inchi:    InChI=1S/ClH/h1H
inchiKey:    VEXZGXHMUGYJMC-UHFFFAOYSA-N
smarts:    [#17]
smarts_isomeric:    [#17]

hydrogen fluoride: F

smiles_non_kekule:    F
smiles_kekule:    F
inchi:    InChI=1S/FH/h1H
inchiKey:    KRHYYFGTRYWZRS-UHFFFAOYSA-N
smarts:    [#9]
smarts_isomeric:    [#9]

ethane: CC

smiles_non_kekule:    CC
smiles_kekule:    CC
inchi:    InChI=1S/C2H6/c1-2/h1-2H3
inchiKey:    OTMSDBZUPAUEDD-UHFFFAOYSA-N
smarts:    [#6]-[#6]
smarts_isomeric:    [#6]-[#6]

hydrogen cyanide: C#N

smiles_non_kekule:    C#N
smiles_kekule:    C#N
inchi:    InChI=1S/CHN/c1-2/h1H
inchiKey:    LELOWRISYMNNSU-UHFFFAOYSA-N
smarts:    [#6]#[#7]
smarts_isomeric:    [#6]#[#7]

formic acid: C(=O)O

smiles_non_kekule:    O=CO
smiles_kekule:    O=CO
inchi:    InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3)
inchiKey:    BDAGIHXWWSANSR-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#8]
smarts_isomeric:    [#6](=[#8])-[#8]

hydrogen bromide: Br

smiles_non_kekule:    Br
smiles_kekule:    Br
inchi:    InChI=1S/BrH/h1H
inchiKey:    CPELXLSAUQHCOX-UHFFFAOYSA-N
smarts:    [#35]
smarts_isomeric:    [#35]

fluroform: C(F)(F)F

smiles_non_kekule:    FC(F)F
smiles_kekule:    FC(F)F
inchi:    InChI=1S/CHF3/c2-1(3)4/h1H
inchiKey:    XPDWGBQVDMORPB-UHFFFAOYSA-N
smarts:    [#6](-[#9])(-[#9])-[#9]
smarts_isomeric:    [#6](-[#9])(-[#9])-[#9]

propane: C(C)C

toulene: Cc1ccccc1

pyridine: c1cccnc1

smiles_non_kekule:    c1ccncc1
smiles_kekule:    C1=CC=NC=C1
inchi:    InChI=1S/C5H5N/c1-2-4-6-5-3-1/h1-5H
inchiKey:    JUJWROOIHBZHMG-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1

dimethylamine: N(C)C

smiles_non_kekule:    CNC
smiles_kekule:    CNC
inchi:    InChI=1S/C2H7N/c1-3-2/h3H,1-2H3
inchiKey:    ROSDSFDQCJNGOL-UHFFFAOYSA-N
smarts:    [#7](-[#6])-[#6]
smarts_isomeric:    [#7](-[#6])-[#6]

ethanol: OCC

smiles_non_kekule:    CCO
smiles_kekule:    CCO
inchi:    InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3
inchiKey:    LFQSCWFLJHTTHZ-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]
smarts_isomeric:    [#8]-[#6]-[#6]

formamide: C(N)=O

smiles_non_kekule:    NC=O
smiles_kekule:    NC=O
inchi:    InChI=1S/CH3NO/c2-1-3/h1H,(H2,2,3)
inchiKey:    ZHNUHDYFZUAESO-UHFFFAOYSA-N
smarts:    [#6](-[#7])=[#8]
smarts_isomeric:    [#6](-[#7])=[#8]

morpholine: N1CCOCC1

smiles_non_kekule:    C1COCCN1
smiles_kekule:    C1COCCN1
inchi:    InChI=1S/C4H9NO/c1-3-6-4-2-5-1/h5H,1-4H2
inchiKey:    YNAVUWVOSKDBBP-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1

nitro: [N+](=O)[O-]

smiles_non_kekule:    O=[N+][O-]
smiles_kekule:    O=[N+][O-]
inchi:    InChI=1S/NO2/c2-1-3
inchiKey:    JCXJVPUVTGWSNB-UHFFFAOYSA-N
smarts:    [#7+](=[#8])-[#8-]
smarts_isomeric:    [#7+](=[#8])-[#8-]

isobutane: C(C)(C)C

smiles_non_kekule:    CC(C)C
smiles_kekule:    CC(C)C
inchi:    InChI=1S/C4H10/c1-4(2)3/h4H,1-3H3
inchiKey:    NNPPMTNAJDCUHE-UHFFFAOYSA-N
smarts:    [#6](-[#6])(-[#6])-[#6]
smarts_isomeric:    [#6](-[#6])(-[#6])-[#6]

anisole: c1ccc(OC)cc1

smiles_non_kekule:    COc1ccccc1
smiles_kekule:    COC1=CC=CC=C1
inchi:    InChI=1S/C7H8O/c1-8-7-5-3-2-4-6-7/h2-6H,1H3
inchiKey:    RDOXTESZEPMUJZ-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6]:[#6]:1

flurobenzene: c1ccc(F)cc1

smiles_non_kekule:    Fc1ccccc1
smiles_kekule:    FC1=CC=CC=C1
inchi:    InChI=1S/C6H5F/c7-6-4-2-1-3-5-6/h1-5H
inchiKey:    PYLWMHQQBFSUBP-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#9]):[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#9]):[#6]:[#6]:1

cyclohexane: C1CCCCC1

acetic acid: CC(=O)O

smiles_non_kekule:    CC(=O)O
smiles_kekule:    CC(=O)O
inchi:    InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)
inchiKey:    QTBSBXVTEAMEQO-UHFFFAOYSA-N
smarts:    [#6]-[#6](=[#8])-[#8]
smarts_isomeric:    [#6]-[#6](=[#8])-[#8]

methyl formate: C(=O)OC

smiles_non_kekule:    COC=O
smiles_kekule:    COC=O
inchi:    InChI=1S/C2H4O2/c1-4-2-3/h2H,1H3
inchiKey:    TZIHFWKZFHZASV-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#8]-[#6]
smarts_isomeric:    [#6](=[#8])-[#8]-[#6]

butane: CCCC

smiles_non_kekule:    CCCC
smiles_kekule:    CCCC
inchi:    InChI=1S/C4H10/c1-3-4-2/h3-4H2,1-2H3
inchiKey:    IJDNQMDRQITEOD-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]

acetamide: NC(C)=O

smiles_non_kekule:    CC(N)=O
smiles_kekule:    CC(N)=O
inchi:    InChI=1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4)
inchiKey:    DLFVBJFMPXGRIB-UHFFFAOYSA-N
smarts:    [#7]-[#6](-[#6])=[#8]
smarts_isomeric:    [#7]-[#6](-[#6])=[#8]

methanamine: NC

smiles_non_kekule:    CN
smiles_kekule:    CN
inchi:    InChI=1S/CH5N/c1-2/h2H2,1H3
inchiKey:    BAVYZALUXZFZLV-UHFFFAOYSA-N
smarts:    [#7]-[#6]
smarts_isomeric:    [#7]-[#6]

acetaldehyde: C(C)=O

smiles_non_kekule:    CC=O
smiles_kekule:    CC=O
inchi:    InChI=1S/C2H4O/c1-2-3/h2H,1H3
inchiKey:    IKHGUXGNUITLKF-UHFFFAOYSA-N
smarts:    [#6](-[#6])=[#8]
smarts_isomeric:    [#6](-[#6])=[#8]

chlorobenzene: c1ccc(Cl)cc1

smiles_non_kekule:    Clc1ccccc1
smiles_kekule:    ClC1=CC=CC=C1
inchi:    InChI=1S/C6H5Cl/c7-6-4-2-1-3-5-6/h1-5H
inchiKey:    MVPPADPHJFYWMZ-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1

1-methylpiperazine: N1CCN(C)CC1

smiles_non_kekule:    CN1CCNCC1
smiles_kekule:    CN1CCNCC1
inchi:    InChI=1S/C5H12N2/c1-7-4-2-6-3-5-7/h6H,2-5H2,1H3
inchiKey:    PVOAHINGSUIXLS-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#7](-[#6])-[#6]-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#7](-[#6])-[#6]-[#6]-1

phenylmethanol: OCc1ccccc1

smiles_non_kekule:    OCc1ccccc1
smiles_kekule:    OCC1=CC=CC=C1
inchi:    InChI=1S/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2
inchiKey:    WVDDGKGOMKODPV-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#8]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

ethylbenzene: CCc1ccccc1

smiles_non_kekule:    CCc1ccccc1
smiles_kekule:    CCC1=CC=CC=C1
inchi:    InChI=1S/C8H10/c1-2-8-6-4-3-5-7-8/h3-7H,2H2,1H3
inchiKey:    YNQLUTRBYVCPMQ-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

piperidine: N1CCCCC1

smiles_non_kekule:    C1CCNCC1
smiles_kekule:    C1CCNCC1
inchi:    InChI=1S/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2
inchiKey:    NQRYJNQNLNOLGT-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

thiophene: c1cccs1

cyclopropane: C1CC1

smiles_non_kekule:    C1CC1
smiles_kekule:    C1CC1
inchi:    InChI=1S/C3H6/c1-2-3-1/h1-3H2
inchiKey:    LVZWSLJZHVFIQJ-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-1
smarts_isomeric:    [#6]1-[#6]-[#6]-1

phenol: Oc1ccccc1

smiles_non_kekule:    Oc1ccccc1
smiles_kekule:    OC1=CC=CC=C1
inchi:    InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
inchiKey:    ISWSIDIOOBJBQZ-UHFFFAOYSA-N
smarts:    [#8]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#8]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

aniline: Nc1ccccc1

smiles_non_kekule:    Nc1ccccc1
smiles_kekule:    NC1=CC=CC=C1
inchi:    InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
inchiKey:    PAYRUJLWNCNPSJ-UHFFFAOYSA-N
smarts:    [#7]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#7]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

hydrosulfonylmethane: S(C)(=O)=O

smiles_non_kekule:    C[SH](=O)=O
smiles_kekule:    C[SH](=O)=O
inchi:    InChI=1S/CH4O2S/c1-4(2)3/h4H,1H3
inchiKey:    KEIVLHIFSZBKGU-UHFFFAOYSA-N
smarts:    [#16](-[#6])(=[#8])=[#8]
smarts_isomeric:    [#16](-[#6])(=[#8])=[#8]

piperazine: N1CCNCC1

smiles_non_kekule:    C1CNCCN1
smiles_kekule:    C1CNCCN1
inchi:    InChI=1S/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2
inchiKey:    GLUUGHFHXGJENI-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#7]-[#6]-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#7]-[#6]-[#6]-1

pyrrolidine: N1CCCC1

smiles_non_kekule:    C1CCNC1
smiles_kekule:    C1CCNC1
inchi:    InChI=1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2
inchiKey:    RWRDLPDLKQPQOW-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#6]-[#6]-1

4-methylmorpholine: CN1CCOCC1

smiles_non_kekule:    CN1CCOCC1
smiles_kekule:    CN1CCOCC1
inchi:    InChI=1S/C5H11NO/c1-6-2-4-7-5-3-6/h2-5H2,1H3
inchiKey:    SJRJJKPEHAURKC-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1

hydrogen iodide: I

smiles_non_kekule:    I
smiles_kekule:    I
inchi:    InChI=1S/HI/h1H
inchiKey:    XMBWDFGMSWQBCA-UHFFFAOYSA-N
smarts:    [#53]
smarts_isomeric:    [#53]

ethyl formate: C(=O)OCC

smiles_non_kekule:    CCOC=O
smiles_kekule:    CCOC=O
inchi:    InChI=1S/C3H6O2/c1-2-5-3-4/h3H,2H2,1H3
inchiKey:    WBJINCZRORDGAQ-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#8]-[#6]-[#6]
smarts_isomeric:    [#6](=[#8])-[#8]-[#6]-[#6]

sulfonic amide: S(N)(=O)=O

smiles_non_kekule:    N[SH](=O)=O
smiles_kekule:    N[SH](=O)=O
inchi:    InChI=1S/H3NO2S/c1-4(2)3/h4H,(H2,1,2,3)
inchiKey:    AHZVGADFMXTGBU-UHFFFAOYSA-N
smarts:    [#16](-[#7])(=[#8])=[#8]
smarts_isomeric:    [#16](-[#7])(=[#8])=[#8]

phenylmethanamine: NCc1ccccc1

smiles_non_kekule:    NCc1ccccc1
smiles_kekule:    NCC1=CC=CC=C1
inchi:    InChI=1S/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H2
inchiKey:    WGQKYBSKWIADBV-UHFFFAOYSA-N
smarts:    [#7]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#7]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

N-methylformamide: C(=O)NC

smiles_non_kekule:    CNC=O
smiles_kekule:    CNC=O
inchi:    InChI=1S/C2H5NO/c1-3-2-4/h2H,1H3,(H,3,4)
inchiKey:    ATHHXGZTWNVVOU-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]-[#6]
smarts_isomeric:    [#6](=[#8])-[#7]-[#6]

trimethylamine: CN(C)C

smiles_non_kekule:    CN(C)C
smiles_kekule:    CN(C)C
inchi:    InChI=1S/C3H9N/c1-4(2)3/h1-3H3
inchiKey:    GETQZCLCWQTVFV-UHFFFAOYSA-N
smarts:    [#6]-[#7](-[#6])-[#6]
smarts_isomeric:    [#6]-[#7](-[#6])-[#6]

N,N-dimethylformamide: C(=O)N(C)C

smiles_non_kekule:    CN(C)C=O
smiles_kekule:    CN(C)C=O
inchi:    InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3
inchiKey:    ZMXDDKWLCZADIW-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7](-[#6])-[#6]
smarts_isomeric:    [#6](=[#8])-[#7](-[#6])-[#6]

thiol: SC

smiles_non_kekule:    CS
smiles_kekule:    CS
inchi:    InChI=1S/CH4S/c1-2/h2H,1H3
inchiKey:    LSDPWZHWYPCBBB-UHFFFAOYSA-N
smarts:    [#16]-[#6]
smarts_isomeric:    [#16]-[#6]

benzaldehyde: C(=O)c1ccccc1

smiles_non_kekule:    O=Cc1ccccc1
smiles_kekule:    O=CC1=CC=CC=C1
inchi:    InChI=1S/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H
inchiKey:    HUMNYLRZRPPJDN-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

1-methylpiperidine: CN1CCCCC1

smiles_non_kekule:    CN1CCCCC1
smiles_kekule:    CN1CCCCC1
inchi:    InChI=1S/C6H13N/c1-7-5-3-2-4-6-7/h2-6H2,1H3
inchiKey:    PAMIQIKDUOTOBW-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

cyclopentane: C1CCCC1

smiles_non_kekule:    C1CCCC1
smiles_kekule:    C1CCCC1
inchi:    InChI=1S/C5H10/c1-2-4-5-3-1/h1-5H2
inchiKey:    RGSFGYAAUTVSQA-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#6]-[#6]-1

N-hydroxyformamide: C(=O)NO

smiles_non_kekule:    O=CNO
smiles_kekule:    O=CNO
inchi:    InChI=1S/CH3NO2/c3-1-2-4/h1,4H,(H,2,3)
inchiKey:    KDGKTJGPFXIBEB-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]-[#8]
smarts_isomeric:    [#6](=[#8])-[#7]-[#8]

pyrimidine: c1cncnc1

smiles_non_kekule:    c1cncnc1
smiles_kekule:    C1=CN=CN=C1
inchi:    InChI=1S/C4H4N2/c1-2-5-4-6-3-1/h1-4H
inchiKey:    CZPWVGJYEJSRLH-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#7]:[#6]:[#7]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#7]:[#6]:[#7]:[#6]:1

furan: c1ccco1

ethanamine: CCN

smiles_non_kekule:    CCN
smiles_kekule:    CCN
inchi:    InChI=1S/C2H7N/c1-2-3/h2-3H2,1H3
inchiKey:    QUSNBJAOOMFDIB-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7]
smarts_isomeric:    [#6]-[#6]-[#7]

benzonitrile: c1ccc(C#N)cc1

smiles_non_kekule:    N#Cc1ccccc1
smiles_kekule:    N#CC1=CC=CC=C1
inchi:    InChI=1S/C7H5N/c8-6-7-4-2-1-3-5-7/h1-5H
inchiKey:    JFDZBHWFFUWGJE-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#6]#[#7]):[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#6]#[#7]):[#6]:[#6]:1

propionic acid: CCC(=O)O

smiles_non_kekule:    CCC(=O)O
smiles_kekule:    CCC(=O)O
inchi:    InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)
inchiKey:    XBDQKXXYIPTUBI-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#8]
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#8]

propan-2-ol: OC(C)C

smiles_non_kekule:    CC(C)O
smiles_kekule:    CC(C)O
inchi:    InChI=1S/C3H8O/c1-3(2)4/h3-4H,1-2H3
inchiKey:    KFZMGEQAYNKOFK-UHFFFAOYSA-N
smarts:    [#8]-[#6](-[#6])-[#6]
smarts_isomeric:    [#8]-[#6](-[#6])-[#6]

methanesulfonamide: NS(C)(=O)=O

smiles_non_kekule:    CS(N)(=O)=O
smiles_kekule:    CS(N)(=O)=O
inchi:    InChI=1S/CH5NO2S/c1-5(2,3)4/h1H3,(H2,2,3,4)
inchiKey:    HNQIVZYLYMDVSB-UHFFFAOYSA-N
smarts:    [#7]-[#16](-[#6])(=[#8])=[#8]
smarts_isomeric:    [#7]-[#16](-[#6])(=[#8])=[#8]

pentane: CCCCC

morpholine-4-carbaldehyde: C(=O)N1CCOCC1

smiles_non_kekule:    O=CN1CCOCC1
smiles_kekule:    O=CN1CCOCC1
inchi:    InChI=1S/C5H9NO2/c7-5-6-1-3-8-4-2-6/h5H,1-4H2
inchiKey:    LCEDQNDDFOCWGG-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1
smarts_isomeric:    [#6](=[#8])-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1

trifluoromethanol: OC(F)(F)F

smiles_non_kekule:    OC(F)(F)F
smiles_kekule:    OC(F)(F)F
inchi:    InChI=1S/CHF3O/c2-1(3,4)5/h5H
inchiKey:    WZCZNEGTXVXAAS-UHFFFAOYSA-N
smarts:    [#8]-[#6](-[#9])(-[#9])-[#9]
smarts_isomeric:    [#8]-[#6](-[#9])(-[#9])-[#9]

methoxymethane: COC

smiles_non_kekule:    COC
smiles_kekule:    COC
inchi:    InChI=1S/C2H6O/c1-3-2/h1-2H3
inchiKey:    LCGLNKUTAGEVQW-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]
smarts_isomeric:    [#6]-[#8]-[#6]

cyclohexanamine: NC1CCCCC1

smiles_non_kekule:    NC1CCCCC1
smiles_kekule:    NC1CCCCC1
inchi:    InChI=1S/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2
inchiKey:    PAFZNILMFXTMIY-UHFFFAOYSA-N
smarts:    [#7]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#7]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

formaldehyde: C=O

smiles_non_kekule:    C=O
smiles_kekule:    C=O
inchi:    InChI=1S/CH2O/c1-2/h1H2
inchiKey:    WSFSSNUMVMOOMR-UHFFFAOYSA-N
smarts:    [#6]=[#8]
smarts_isomeric:    [#6]=[#8]

N-phenylformamide: C(=O)Nc1ccccc1

smiles_non_kekule:    O=CNc1ccccc1
smiles_kekule:    O=CNC1=CC=CC=C1
inchi:    InChI=1S/C7H7NO/c9-6-8-7-4-2-1-3-5-7/h1-6H,(H,8,9)
inchiKey:    DYDNPESBYVVLBO-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6](=[#8])-[#7]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

butan-1-ol: OCCCC

smiles_non_kekule:    CCCCO
smiles_kekule:    CCCCO
inchi:    InChI=1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3
inchiKey:    LRHPLDYGYMQRHN-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]-[#6]-[#6]
smarts_isomeric:    [#8]-[#6]-[#6]-[#6]-[#6]

pyrazine: c1cnccn1

smiles_non_kekule:    c1cnccn1
smiles_kekule:    C1=CN=CC=N1
inchi:    InChI=1S/C4H4N2/c1-2-6-4-3-5-1/h1-4H
inchiKey:    KYQCOXFCLRTKLS-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#7]:[#6]:[#6]:[#7]:1
smarts_isomeric:    [#6]1:[#6]:[#7]:[#6]:[#6]:[#7]:1

naphthalene: c1ccc2ccccc2c1

propan-1-ol: OCCC

smiles_non_kekule:    CCCO
smiles_kekule:    CCCO
inchi:    InChI=1S/C3H8O/c1-2-3-4/h4H,2-3H2,1H3
inchiKey:    BDERNNFJNOPAEC-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]-[#6]
smarts_isomeric:    [#8]-[#6]-[#6]-[#6]

benzamide: NC(=O)c1ccccc1

smiles_non_kekule:    NC(=O)c1ccccc1
smiles_kekule:    NC(=O)C1=CC=CC=C1
inchi:    InChI=1S/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9)
inchiKey:    KXDAEFPNCMNJSK-UHFFFAOYSA-N
smarts:    [#7]-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#7]-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

1-methyl-1H-pyrazole: c1cnn(C)c1

smiles_non_kekule:    Cn1cccn1
smiles_kekule:    CN1C=CC=N1
inchi:    InChI=1S/C4H6N2/c1-6-4-2-3-5-6/h2-4H,1H3
inchiKey:    UQFQONCQIQEYPJ-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#7]:[#7](-[#6]):[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#7]:[#7](-[#6]):[#6]:1

N-benzylformamide: C(=O)NCc1ccccc1

smiles_non_kekule:    O=CNCc1ccccc1
smiles_kekule:    O=CNCC1=CC=CC=C1
inchi:    InChI=1S/C8H9NO/c10-7-9-6-8-4-2-1-3-5-8/h1-5,7H,6H2,(H,9,10)
inchiKey:    IIBOGKHTXBPGEI-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6](=[#8])-[#7]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

propan-2-amine: NC(C)C

smiles_non_kekule:    CC(C)N
smiles_kekule:    CC(C)N
inchi:    InChI=1S/C3H9N/c1-3(2)4/h3H,4H2,1-2H3
inchiKey:    JJWLVOIRVHMVIS-UHFFFAOYSA-N
smarts:    [#7]-[#6](-[#6])-[#6]
smarts_isomeric:    [#7]-[#6](-[#6])-[#6]

1,3-Benzodioxole: c1ccc2c(c1)OCO2

smiles_non_kekule:    c1ccc2c(c1)OCO2
smiles_kekule:    C1=CC=C2OCOC2=C1
inchi:    InChI=1S/C7H6O2/c1-2-4-7-6(3-1)8-5-9-7/h1-4H,5H2
inchiKey:    FTNJQNQLEGKTGD-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]2:[#6](:[#6]:1)-[#8]-[#6]-[#8]-2
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]2:[#6](:[#6]:1)-[#8]-[#6]-[#8]-2

1-methylpyrrolidine: CN1CCCC1

smiles_non_kekule:    CN1CCCC1
smiles_kekule:    CN1CCCC1
inchi:    InChI=1S/C5H11N/c1-6-4-2-3-5-6/h2-5H2,1H3
inchiKey:    AVFZOVWCLRSYKC-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-1

methylcyclohexane: CC1CCCCC1

smiles_non_kekule:    CC1CCCCC1
smiles_kekule:    CC1CCCCC1
inchi:    InChI=1S/C7H14/c1-7-5-3-2-4-6-7/h7H,2-6H2,1H3
inchiKey:    UAEPNZWRGJTJPN-UHFFFAOYSA-N
smarts:    [#6]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

ethyne: C#C

smiles_non_kekule:    C#C
smiles_kekule:    C#C
inchi:    InChI=1S/C2H2/c1-2/h1-2H
inchiKey:    HSFWRNGVRCDJHI-UHFFFAOYSA-N
smarts:    [#6]#[#6]
smarts_isomeric:    [#6]#[#6]

2-methoxypyridine: c1ccc(OC)nc1

smiles_non_kekule:    COc1ccccn1
smiles_kekule:    COC1=CC=CC=N1
inchi:    InChI=1S/C6H7NO/c1-8-6-4-2-3-5-7-6/h2-5H,1H3
inchiKey:    IWTFOFMTUOBLHG-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#7]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#7]:[#6]:1

N,N-dimethylethanamine: CCN(C)C

smiles_non_kekule:    CCN(C)C
smiles_kekule:    CCN(C)C
inchi:    InChI=1S/C4H11N/c1-4-5(2)3/h4H2,1-3H3
inchiKey:    DAZXVJBJRMWXJP-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6]-[#7](-[#6])-[#6]

thiazole: c1nccs1

smiles_non_kekule:    c1cscn1
smiles_kekule:    C1=CSC=N1
inchi:    InChI=1S/C3H3NS/c1-2-5-3-4-1/h1-3H
inchiKey:    FZWLAAWBMGSTSO-UHFFFAOYSA-N
smarts:    [#6]1:[#7]:[#6]:[#6]:[#16]:1
smarts_isomeric:    [#6]1:[#7]:[#6]:[#6]:[#16]:1

bromobenzene: c1ccc(Br)cc1

smiles_non_kekule:    Brc1ccccc1
smiles_kekule:    BrC1=CC=CC=C1
inchi:    InChI=1S/C6H5Br/c7-6-4-2-1-3-5-6/h1-5H
inchiKey:    QARVLSVVCXYDNA-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#35]):[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#35]):[#6]:[#6]:1

4-methylpyridine: Cc1ccncc1

smiles_non_kekule:    Cc1ccncc1
smiles_kekule:    CC1=CC=NC=C1
inchi:    InChI=1S/C6H7N/c1-6-2-4-7-5-3-6/h2-5H,1H3
inchiKey:    FKNQCJSGGFJEIZ-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#7]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#7]:[#6]:[#6]:1

2-methoxyethan-1-ol: OCCOC

smiles_non_kekule:    COCCO
smiles_kekule:    COCCO
inchi:    InChI=1S/C3H8O2/c1-5-3-2-4/h4H,2-3H2,1H3
inchiKey:    XNWFRZJHXBZDAG-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]-[#8]-[#6]
smarts_isomeric:    [#8]-[#6]-[#6]-[#8]-[#6]

hexane: CCCCCC

Tetrahydropyran: C1CCOCC1

smiles_non_kekule:    C1CCOCC1
smiles_kekule:    C1CCOCC1
inchi:    InChI=1S/C5H10O/c1-2-4-6-5-3-1/h1-5H2
inchiKey:    DHXVGJBLRPWPCS-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#8]-[#6]-[#6]-1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#8]-[#6]-[#6]-1

1H-pyrazole: c1cn[nH]c1

smiles_non_kekule:    c1cn[nH]c1
smiles_kekule:    C1=CNN=C1
inchi:    InChI=1S/C3H4N2/c1-2-4-5-3-1/h1-3H,(H,4,5)
inchiKey:    WTKZEGDFNFYCGP-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#7]:[#7H]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#7]:[#7H]:[#6]:1

1-methyl-1H-imidazole: Cn1ccnc1

smiles_non_kekule:    Cn1ccnc1
smiles_kekule:    CN1C=CN=C1
inchi:    InChI=1S/C4H6N2/c1-6-3-2-5-4-6/h2-4H,1H3
inchiKey:    MCTWTZJPVLRJOU-UHFFFAOYSA-N
smarts:    [#6]-[#7]1:[#6]:[#6]:[#7]:[#6]:1
smarts_isomeric:    [#6]-[#7]1:[#6]:[#6]:[#7]:[#6]:1

benzoic acid: c1ccc(C(=O)O)cc1

smiles_non_kekule:    O=C(O)c1ccccc1
smiles_kekule:    O=C(O)C1=CC=CC=C1
inchi:    InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
inchiKey:    WPYMKLBDIGXBTP-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#6](=[#8])-[#8]):[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#6](=[#8])-[#8]):[#6]:[#6]:1

boronic acid: B(O)O

smiles_non_kekule:    OBO
smiles_kekule:    OBO
inchi:    InChI=1S/BH3O2/c2-1-3/h1-3H
inchiKey:    ZADPBFCGQRWHPN-UHFFFAOYSA-N
smarts:    [#5](-[#8])-[#8]
smarts_isomeric:    [#5](-[#8])-[#8]

2-hydroxyacetic acid: OCC(=O)O

smiles_non_kekule:    O=C(O)CO
smiles_kekule:    O=C(O)CO
inchi:    InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)
inchiKey:    AEMRFAOFKBGASW-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6](=[#8])-[#8]
smarts_isomeric:    [#8]-[#6]-[#6](=[#8])-[#8]

ethene: C=C

smiles_non_kekule:    C=C
smiles_kekule:    C=C
inchi:    InChI=1S/C2H4/c1-2/h1-2H2
inchiKey:    VGGSQFUCUMXWEO-UHFFFAOYSA-N
smarts:    [#6]=[#6]
smarts_isomeric:    [#6]=[#6]

piperidine-1-carbaldehyde: C(=O)N1CCCCC1

smiles_non_kekule:    O=CN1CCCCC1
smiles_kekule:    O=CN1CCCCC1
inchi:    InChI=1S/C6H11NO/c8-6-7-4-2-1-3-5-7/h6H,1-5H2
inchiKey:    FEWLNYSYJNLUOO-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6](=[#8])-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

styrene: C=Cc1ccccc1

1-fluoro-4-methylbenzene: Cc1ccc(F)cc1

smiles_non_kekule:    Cc1ccc(F)cc1
smiles_kekule:    CC1=CC=C(F)C=C1
inchi:    InChI=1S/C7H7F/c1-6-2-4-7(8)5-3-6/h2-5H,1H3
inchiKey:    WRWPPGUCZBJXKX-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6](-[#9]):[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6](-[#9]):[#6]:[#6]:1

ethylene glycol: OCCO

smiles_non_kekule:    OCCO
smiles_kekule:    OCCO
inchi:    InChI=1S/C2H6O2/c3-1-2-4/h3-4H,1-2H2
inchiKey:    LYCAIKOWRPUZTN-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]-[#8]
smarts_isomeric:    [#8]-[#6]-[#6]-[#8]

2-(dimethylamino)ethan-1-ol: OCCN(C)C

smiles_non_kekule:    CN(C)CCO
smiles_kekule:    CN(C)CCO
inchi:    InChI=1S/C4H11NO/c1-5(2)3-4-6/h6H,3-4H2,1-2H3
inchiKey:    UEEJHVSXFDXPFK-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]-[#7](-[#6])-[#6]
smarts_isomeric:    [#8]-[#6]-[#6]-[#7](-[#6])-[#6]

(trifluoromethyl)benzene: c1ccc(C(F)(F)F)cc1

smiles_non_kekule:    FC(F)(F)c1ccccc1
smiles_kekule:    FC(F)(F)C1=CC=CC=C1
inchi:    InChI=1S/C7H5F3/c8-7(9,10)6-4-2-1-3-5-6/h1-5H
inchiKey:    GETTZEONDQJALK-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#6](-[#9])(-[#9])-[#9]):[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#6](-[#9])(-[#9])-[#9]):[#6]:[#6]:1

diethylamine: N(CC)CC

smiles_non_kekule:    CCNCC
smiles_kekule:    CCNCC
inchi:    InChI=1S/C4H11N/c1-3-5-4-2/h5H,3-4H2,1-2H3
inchiKey:    HPNMFZURTQLUMO-UHFFFAOYSA-N
smarts:    [#7](-[#6]-[#6])-[#6]-[#6]
smarts_isomeric:    [#7](-[#6]-[#6])-[#6]-[#6]

N-cyclohexylformamide: C(=O)NC1CCCCC1

smiles_non_kekule:    O=CNC1CCCCC1
smiles_kekule:    O=CNC1CCCCC1
inchi:    InChI=1S/C7H13NO/c9-6-8-7-4-2-1-3-5-7/h6-7H,1-5H2,(H,8,9)
inchiKey:    SWGXDLRCJNEEGZ-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6](=[#8])-[#7]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

benzothiazole: c1nc2ccccc2s1

smiles_non_kekule:    c1ccc2scnc2c1
smiles_kekule:    C1=CC=C2SC=NC2=C1
inchi:    InChI=1S/C7H5NS/c1-2-4-7-6(3-1)8-5-9-7/h1-5H
inchiKey:    IOJUPLGTWVMSFF-UHFFFAOYSA-N
smarts:    [#6]1:[#7]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#16]:1
smarts_isomeric:    [#6]1:[#7]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#16]:1

methylcyclopropane: CC1CC1

smiles_non_kekule:    CC1CC1
smiles_kekule:    CC1CC1
inchi:    InChI=1S/C4H8/c1-4-2-3-4/h4H,2-3H2,1H3
inchiKey:    VNXBKJFUJUWOCW-UHFFFAOYSA-N
smarts:    [#6]-[#6]1-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6]1-[#6]-[#6]-1

N-ethyl-N-methylethanamine: CN(CC)CC

smiles_non_kekule:    CCN(C)CC
smiles_kekule:    CCN(C)CC
inchi:    InChI=1S/C5H13N/c1-4-6(3)5-2/h4-5H2,1-3H3
inchiKey:    GNVRJGIVDSQCOP-UHFFFAOYSA-N
smarts:    [#6]-[#7](-[#6]-[#6])-[#6]-[#6]
smarts_isomeric:    [#6]-[#7](-[#6]-[#6])-[#6]-[#6]

1H-benzoimidazole: c1nc2ccccc2[nH]1

smiles_non_kekule:    c1ccc2[nH]cnc2c1
smiles_kekule:    C1=CC=C2NC=NC2=C1
inchi:    InChI=1S/C7H6N2/c1-2-4-7-6(3-1)8-5-9-7/h1-5H,(H,8,9)
inchiKey:    HYZJCKYKOHLVJF-UHFFFAOYSA-N
smarts:    [#6]1:[#7]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#7H]:1
smarts_isomeric:    [#6]1:[#7]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#7H]:1

N-isopropylformamide: C(=O)NC(C)C

smiles_non_kekule:    CC(C)NC=O
smiles_kekule:    CC(C)NC=O
inchi:    InChI=1S/C4H9NO/c1-4(2)5-3-6/h3-4H,1-2H3,(H,5,6)
inchiKey:    KVTGAKFJRLBHLU-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]-[#6](-[#6])-[#6]
smarts_isomeric:    [#6](=[#8])-[#7]-[#6](-[#6])-[#6]

2-aminoethan-1-ol: NCCO

smiles_non_kekule:    NCCO
smiles_kekule:    NCCO
inchi:    InChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2
inchiKey:    HZAXFHJVJLSVMW-UHFFFAOYSA-N
smarts:    [#7]-[#6]-[#6]-[#8]
smarts_isomeric:    [#7]-[#6]-[#6]-[#8]

N-(2-hydroxyethyl)formamide: C(=O)NCCO

smiles_non_kekule:    O=CNCCO
smiles_kekule:    O=CNCCO
inchi:    InChI=1S/C3H7NO2/c5-2-1-4-3-6/h3,5H,1-2H2,(H,4,6)
inchiKey:    BAMUPQJDKBGDPU-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]-[#6]-[#6]-[#8]
smarts_isomeric:    [#6](=[#8])-[#7]-[#6]-[#6]-[#8]

2,3-dihydrobenzo[b][1,4]dioxine: c1ccc2c(c1)OCCO2

smiles_non_kekule:    c1ccc2c(c1)OCCO2
smiles_kekule:    C1=CC=C2OCCOC2=C1
inchi:    InChI=1S/C8H8O2/c1-2-4-8-7(3-1)9-5-6-10-8/h1-4H,5-6H2
inchiKey:    BNBQRQQYDMDJAH-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]2:[#6](:[#6]:1)-[#8]-[#6]-[#6]-[#8]-2
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]2:[#6](:[#6]:1)-[#8]-[#6]-[#6]-[#8]-2

benzothiophene: c1cc2ccccc2s1

smiles_non_kekule:    c1ccc2sccc2c1
smiles_kekule:    C1=CC=C2SC=CC2=C1
inchi:    InChI=1S/C8H6S/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
inchiKey:    FCEHBMOGCRZNNI-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#16]:1
smarts_isomeric:    [#6]1:[#6]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#16]:1

propylbenzene: CCCc1ccccc1

smiles_non_kekule:    CCCc1ccccc1
smiles_kekule:    CCCC1=CC=CC=C1
inchi:    InChI=1S/C9H12/c1-2-6-9-7-4-3-5-8-9/h3-5,7-8H,2,6H2,1H3
inchiKey:    ODLMAHJVESYWTB-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

pyrrolidine-1-carbaldehyde: C(=O)N1CCCC1

smiles_non_kekule:    O=CN1CCCC1
smiles_kekule:    O=CN1CCCC1
inchi:    InChI=1S/C5H9NO/c7-5-6-3-1-2-4-6/h5H,1-4H2
inchiKey:    AGRIQBHIKABLPJ-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6](=[#8])-[#7]1-[#6]-[#6]-[#6]-[#6]-1

1,4-dimethylpiperazine: CN1CCN(C)CC1

smiles_non_kekule:    CN1CCN(C)CC1
smiles_kekule:    CN1CCN(C)CC1
inchi:    InChI=1S/C6H14N2/c1-7-3-5-8(2)6-4-7/h3-6H2,1-2H3
inchiKey:    RXYPXQSKLGGKOL-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#7](-[#6])-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#7](-[#6])-[#6]-[#6]-1

N-ethylformamide: C(=O)NCC

smiles_non_kekule:    CCNC=O
smiles_kekule:    CCNC=O
inchi:    InChI=1S/C3H7NO/c1-2-4-3-5/h3H,2H2,1H3,(H,4,5)
inchiKey:    KERBAAIBDHEFDD-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]-[#6]-[#6]
smarts_isomeric:    [#6](=[#8])-[#7]-[#6]-[#6]

2-morpholinoethan-1-ol: OCCN1CCOCC1

smiles_non_kekule:    OCCN1CCOCC1
smiles_kekule:    OCCN1CCOCC1
inchi:    InChI=1S/C6H13NO2/c8-4-1-7-2-5-9-6-3-7/h8H,1-6H2
inchiKey:    KKFDCBRMNNSAAW-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1
smarts_isomeric:    [#8]-[#6]-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1

4-ethylmorpholine: CCN1CCOCC1

smiles_non_kekule:    CCN1CCOCC1
smiles_kekule:    CCN1CCOCC1
inchi:    InChI=1S/C6H13NO/c1-2-7-3-5-8-6-4-7/h2-6H2,1H3
inchiKey:    HVCNXQOWACZAFN-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1

indole: c1c[nH]c2ccccc12

smiles_non_kekule:    c1ccc2[nH]ccc2c1
smiles_kekule:    C1=CC=C2NC=CC2=C1
inchi:    InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H
inchiKey:    SIKJAQJRHWYJAI-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#7H]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2
smarts_isomeric:    [#6]1:[#6]:[#7H]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2

quinoline: c1cnc2ccccc2c1

smiles_non_kekule:    c1ccc2ncccc2c1
smiles_kekule:    C1=CC2=CC=CN=C2C=C1
inchi:    InChI=1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H
inchiKey:    SMWDFEZZVXVKRB-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#7]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#7]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#6]:1

3-(dimethylamino)propan-1-ol: OCCCN(C)C

smiles_non_kekule:    CN(C)CCCO
smiles_kekule:    CN(C)CCCO
inchi:    InChI=1S/C5H13NO/c1-6(2)4-3-5-7/h7H,3-5H2,1-2H3
inchiKey:    PYSGFFTXMUWEOT-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]-[#6]-[#7](-[#6])-[#6]
smarts_isomeric:    [#8]-[#6]-[#6]-[#6]-[#7](-[#6])-[#6]

3-methylpyridine: Cc1cccnc1

smiles_non_kekule:    Cc1cccnc1
smiles_kekule:    CC1=CC=CN=C1
inchi:    InChI=1S/C6H7N/c1-6-3-2-4-7-5-6/h2-5H,1H3
inchiKey:    ITQTTZVARXURQS-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1

cyclobutane: C1CCC1

smiles_non_kekule:    C1CCC1
smiles_kekule:    C1CCC1
inchi:    InChI=1S/C4H8/c1-2-4-3-1/h1-4H2
inchiKey:    PMPVIKIVABFJJI-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#6]-1

formimidamide: C(=N)N

smiles_non_kekule:    N=CN
smiles_kekule:    N=CN
inchi:    InChI=1S/CH4N2/c2-1-3/h1H,(H3,2,3)
inchiKey:    PNKUSGQVOMIXLU-UHFFFAOYSA-N
smarts:    [#6](=[#7])-[#7]
smarts_isomeric:    [#6](=[#7])-[#7]

benzofuran: c1cc2ccccc2o1

smiles_non_kekule:    c1ccc2occc2c1
smiles_kekule:    C1=CC=C2OC=CC2=C1
inchi:    InChI=1S/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
inchiKey:    IANQTJSKSUMEQM-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#8]:1
smarts_isomeric:    [#6]1:[#6]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#8]:1

1-methoxy-4-methylbenzene: Cc1ccc(OC)cc1

smiles_non_kekule:    COc1ccc(C)cc1
smiles_kekule:    COC1=CC=C(C)C=C1
inchi:    InChI=1S/C8H10O/c1-7-3-5-8(9-2)6-4-7/h3-6H,1-2H3
inchiKey:    CHLICZRVGGXEOD-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6]:[#6]:1

2-methylpyridine: Cc1ccccn1

smiles_non_kekule:    Cc1ccccn1
smiles_kekule:    CC1=CC=CC=N1
inchi:    InChI=1S/C6H7N/c1-6-4-2-3-5-7-6/h2-5H,1H3
inchiKey:    BSKHPKMHTQYZBB-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#7]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#7]:1

acetonitrile: CC#N

1,2-dichlorobenzene: c1ccc(Cl)c(Cl)c1

smiles_non_kekule:    Clc1ccccc1Cl
smiles_kekule:    ClC1=CC=CC=C1Cl
inchi:    InChI=1S/C6H4Cl2/c7-5-3-1-2-4-6(5)8/h1-4H
inchiKey:    RFFLAFLAYFXFSW-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#17]):[#6](-[#17]):[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#17]):[#6](-[#17]):[#6]:1

N,N-dimethylaniline: c1ccc(N(C)C)cc1

smiles_non_kekule:    CN(C)c1ccccc1
smiles_kekule:    CN(C)C1=CC=CC=C1
inchi:    InChI=1S/C8H11N/c1-9(2)8-6-4-3-5-7-8/h3-7H,1-2H3
inchiKey:    JLTDJTHDQAWBAV-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#7](-[#6])-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#7](-[#6])-[#6]):[#6]:[#6]:1

hydrosulfonylbenzene: S(=O)(=O)c1ccccc1

smiles_non_kekule:    O=[SH](=O)c1ccccc1
smiles_kekule:    O=[SH](=O)C1=CC=CC=C1
inchi:    InChI=1S/C6H6O2S/c7-9(8)6-4-2-1-3-5-6/h1-5,9H
inchiKey:    XYUAXZDQSDTCHO-UHFFFAOYSA-N
smarts:    [#16](=[#8])(=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#16](=[#8])(=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

N-methylacetamide: CNC(C)=O

smiles_non_kekule:    CNC(C)=O
smiles_kekule:    CNC(C)=O
inchi:    InChI=1S/C3H7NO/c1-3(5)4-2/h1-2H3,(H,4,5)
inchiKey:    OHLUUHNLEMFGTQ-UHFFFAOYSA-N
smarts:    [#6]-[#7]-[#6](-[#6])=[#8]
smarts_isomeric:    [#6]-[#7]-[#6](-[#6])=[#8]

hydrogen sulfide: S

smiles_non_kekule:    S
smiles_kekule:    S
inchi:    InChI=1S/H2S/h1H2
inchiKey:    RWSOTUBLDIXVET-UHFFFAOYSA-N
smarts:    [#16]
smarts_isomeric:    [#16]

2-phenylethan-1-amine: NCCc1ccccc1

smiles_non_kekule:    NCCc1ccccc1
smiles_kekule:    NCCC1=CC=CC=C1
inchi:    InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2
inchiKey:    BHHGXPLMPWCGHP-UHFFFAOYSA-N
smarts:    [#7]-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#7]-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

2-(pyrrolidin-1-yl)ethan-1-ol: OCCN1CCCC1

smiles_non_kekule:    OCCN1CCCC1
smiles_kekule:    OCCN1CCCC1
inchi:    InChI=1S/C6H13NO/c8-6-5-7-3-1-2-4-7/h8H,1-6H2
inchiKey:    XBRDBODLCHKXHI-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#8]-[#6]-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-1

methoxyethane: CCOC

smiles_non_kekule:    CCOC
smiles_kekule:    CCOC
inchi:    InChI=1S/C3H8O/c1-3-4-2/h3H2,1-2H3
inchiKey:    XOBKSJJDNFUZPF-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]-[#6]
smarts_isomeric:    [#6]-[#6]-[#8]-[#6]

1,2-dimethoxybenzene: c1ccc(OC)c(OC)c1

smiles_non_kekule:    COc1ccccc1OC
smiles_kekule:    COC1=CC=CC=C1OC
inchi:    InChI=1S/C8H10O2/c1-9-7-5-3-4-6-8(7)10-2/h3-6H,1-2H3
inchiKey:    ABDKAPXRBAPSQN-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6](-[#8]-[#6]):[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6](-[#8]-[#6]):[#6]:1

nitrobenzene: c1ccc([N+](=O)[O-])cc1

smiles_non_kekule:    O=[N+]([O-])c1ccccc1
smiles_kekule:    O=[N+]([O-])C1=CC=CC=C1
inchi:    InChI=1S/C6H5NO2/c8-7(9)6-4-2-1-3-5-6/h1-5H
inchiKey:    LQNUZADURLCDLV-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#7+](=[#8])-[#8-]):[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#7+](=[#8])-[#8-]):[#6]:[#6]:1

ethynylbenzene: C#Cc1ccccc1

smiles_non_kekule:    C#Cc1ccccc1
smiles_kekule:    C#CC1=CC=CC=C1
inchi:    InChI=1S/C8H6/c1-2-8-6-4-3-5-7-8/h1,3-7H
inchiKey:    UEXCJVNBTNXOEH-UHFFFAOYSA-N
smarts:    [#6]#[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]#[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

N-(pyridin-3-yl)formamide: C(=O)Nc1cccnc1

smiles_non_kekule:    O=CNc1cccnc1
smiles_kekule:    O=CNC1=CC=CN=C1
inchi:    InChI=1S/C6H6N2O/c9-5-8-6-2-1-3-7-4-6/h1-5H,(H,8,9)
inchiKey:    CBKFHSNATJJWQK-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1
smarts_isomeric:    [#6](=[#8])-[#7]-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1

2-(piperidin-1-yl)ethan-1-ol: OCCN1CCCCC1

smiles_non_kekule:    OCCN1CCCCC1
smiles_kekule:    OCCN1CCCCC1
inchi:    InChI=1S/C7H15NO/c9-7-6-8-4-2-1-3-5-8/h9H,1-7H2
inchiKey:    KZTWONRVIPPDKH-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#8]-[#6]-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

benzenesulfonamide: c1ccc(S(N)(=O)=O)cc1

smiles_non_kekule:    NS(=O)(=O)c1ccccc1
smiles_kekule:    NS(=O)(=O)C1=CC=CC=C1
inchi:    InChI=1S/C6H7NO2S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H2,7,8,9)
inchiKey:    KHBQMWCZKVMBLN-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#16](-[#7])(=[#8])=[#8]):[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#16](-[#7])(=[#8])=[#8]):[#6]:[#6]:1

1-ethylpyrrolidine: CCN1CCCC1

smiles_non_kekule:    CCN1CCCC1
smiles_kekule:    CCN1CCCC1
inchi:    InChI=1S/C6H13N/c1-2-7-5-3-4-6-7/h2-6H2,1H3
inchiKey:    ONQBOTKLCMXPOF-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-1

pyrazole: c1cc[nH]n1

smiles_non_kekule:    c1cn[nH]c1
smiles_kekule:    C1=CNN=C1
inchi:    InChI=1S/C3H4N2/c1-2-4-5-3-1/h1-3H,(H,4,5)
inchiKey:    WTKZEGDFNFYCGP-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#7H]:[#7]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#7H]:[#7]:1

3-(piperidin-1-yl)propan-1-ol: OCCCN1CCCCC1

smiles_non_kekule:    OCCCN1CCCCC1
smiles_kekule:    OCCCN1CCCCC1
inchi:    InChI=1S/C8H17NO/c10-8-4-7-9-5-2-1-3-6-9/h10H,1-8H2
inchiKey:    PLRXAFVBCHEMGD-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#8]-[#6]-[#6]-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

N,N-diethylformamide: C(=O)N(CC)CC

smiles_non_kekule:    CCN(C=O)CC
smiles_kekule:    CCN(C=O)CC
inchi:    InChI=1S/C5H11NO/c1-3-6(4-2)5-7/h5H,3-4H2,1-2H3
inchiKey:    SUAKHGWARZSWIH-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7](-[#6]-[#6])-[#6]-[#6]
smarts_isomeric:    [#6](=[#8])-[#7](-[#6]-[#6])-[#6]-[#6]

acetophenone: c1ccc(C(C)=O)cc1

smiles_non_kekule:    CC(=O)c1ccccc1
smiles_kekule:    CC(=O)C1=CC=CC=C1
inchi:    InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3
inchiKey:    KWOLFJPFCHCOCG-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#6](-[#6])=[#8]):[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#6](-[#6])=[#8]):[#6]:[#6]:1

benzooxazole: c1nc2ccccc2o1

smiles_non_kekule:    c1ccc2ocnc2c1
smiles_kekule:    C1=CC=C2OC=NC2=C1
inchi:    InChI=1S/C7H5NO/c1-2-4-7-6(3-1)8-5-9-7/h1-5H
inchiKey:    BCMCBBGGLRIHSE-UHFFFAOYSA-N
smarts:    [#6]1:[#7]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#8]:1
smarts_isomeric:    [#6]1:[#7]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#8]:1

4-methylpiperazine-1-carbaldehyde: C(=O)N1CCN(C)CC1

smiles_non_kekule:    CN1CCN(C=O)CC1
smiles_kekule:    CN1CCN(C=O)CC1
inchi:    InChI=1S/C6H12N2O/c1-7-2-4-8(6-9)5-3-7/h6H,2-5H2,1H3
inchiKey:    JQTMGOLZSBTZMS-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]1-[#6]-[#6]-[#7](-[#6])-[#6]-[#6]-1
smarts_isomeric:    [#6](=[#8])-[#7]1-[#6]-[#6]-[#7](-[#6])-[#6]-[#6]-1

benzenethiol: Sc1ccccc1

smiles_non_kekule:    Sc1ccccc1
smiles_kekule:    SC1=CC=CC=C1
inchi:    InChI=1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H
inchiKey:    RMVRSNDYEFQCLF-UHFFFAOYSA-N
smarts:    [#16]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#16]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

sulfuric diamide: NS(N)(=O)=O

smiles_non_kekule:    NS(N)(=O)=O
smiles_kekule:    NS(N)(=O)=O
inchi:    InChI=1S/H4N2O2S/c1-5(2,3)4/h(H4,1,2,3,4)
inchiKey:    NVBFHJWHLNUMCV-UHFFFAOYSA-N
smarts:    [#7]-[#16](-[#7])(=[#8])=[#8]
smarts_isomeric:    [#7]-[#16](-[#7])(=[#8])=[#8]

4-methoxyaniline: Nc1ccc(OC)cc1

smiles_non_kekule:    COc1ccc(N)cc1
smiles_kekule:    COC1=CC=C(N)C=C1
inchi:    InChI=1S/C7H9NO/c1-9-7-4-2-6(8)3-5-7/h2-5H,8H2,1H3
inchiKey:    BHAAPTBBJKJZER-UHFFFAOYSA-N
smarts:    [#7]-[#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#7]-[#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6]:[#6]:1

1-chloro-4-methylbenzene: Cc1ccc(Cl)cc1

smiles_non_kekule:    Cc1ccc(Cl)cc1
smiles_kekule:    CC1=CC=C(Cl)C=C1
inchi:    InChI=1S/C7H7Cl/c1-6-2-4-7(8)5-3-6/h2-5H,1H3
inchiKey:    NPDACUSDTOMAMK-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1

propan-1-amine: CCCN

smiles_non_kekule:    CCCN
smiles_kekule:    CCCN
inchi:    InChI=1S/C3H9N/c1-2-3-4/h2-4H2,1H3
inchiKey:    WGYKZJWCGVVSQN-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#7]
smarts_isomeric:    [#6]-[#6]-[#6]-[#7]

ethoxybenzene: c1ccc(OCC)cc1

smiles_non_kekule:    CCOc1ccccc1
smiles_kekule:    CCOC1=CC=CC=C1
inchi:    InChI=1S/C8H10O/c1-2-9-8-6-4-3-5-7-8/h3-7H,2H2,1H3
inchiKey:    DLRJIFUOBPOJNS-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#8]-[#6]-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#8]-[#6]-[#6]):[#6]:[#6]:1

5-methylene-2-thioxothiazolidin-4-one: C=C1SC(=S)NC1=O

smiles_non_kekule:    C=C1SC(=S)NC1=O
smiles_kekule:    C=C1SC(=S)NC1=O
inchi:    InChI=1S/C4H3NOS2/c1-2-3(6)5-4(7)8-2/h1H2,(H,5,6,7)
inchiKey:    ALDXAQBFSDSZJR-UHFFFAOYSA-N
smarts:    [#6]=[#6]1-[#16]-[#6](=[#16])-[#7]-[#6]-1=[#8]
smarts_isomeric:    [#6]=[#6]1-[#16]-[#6](=[#16])-[#7]-[#6]-1=[#8]

1,3-difluorobenzene: c1ccc(F)cc1F

smiles_non_kekule:    Fc1cccc(F)c1
smiles_kekule:    FC1=CC=CC(F)=C1
inchi:    InChI=1S/C6H4F2/c7-5-2-1-3-6(8)4-5/h1-4H
inchiKey:    UEMGWPRHOOEKTA-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#9]):[#6]:[#6]:1-[#9]
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#9]):[#6]:[#6]:1-[#9]

(trifluoromethoxy)benzene: c1ccc(OC(F)(F)F)cc1

smiles_non_kekule:    FC(F)(F)Oc1ccccc1
smiles_kekule:    FC(F)(F)OC1=CC=CC=C1
inchi:    InChI=1S/C7H5F3O/c8-7(9,10)11-6-4-2-1-3-5-6/h1-5H
inchiKey:    GQHWSLKNULCZGI-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#8]-[#6](-[#9])(-[#9])-[#9]):[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#8]-[#6](-[#9])(-[#9])-[#9]):[#6]:[#6]:1

heptane: CCCCCCC

smiles_non_kekule:    CCCCCCC
smiles_kekule:    CCCCCCC
inchi:    InChI=1S/C7H16/c1-3-5-7-6-4-2/h3-7H2,1-2H3
inchiKey:    IMNFDUFMRHMDMM-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]

pyridin-2-amine: c1ccc(N)nc1

smiles_non_kekule:    Nc1ccccn1
smiles_kekule:    NC1=CC=CC=N1
inchi:    InChI=1S/C5H6N2/c6-5-3-1-2-4-7-5/h1-4H,(H2,6,7)
inchiKey:    ICSNLGPSRYBMBD-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#7]):[#7]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#7]):[#7]:[#6]:1

1-ethylpiperidine: CCN1CCCCC1

smiles_non_kekule:    CCN1CCCCC1
smiles_kekule:    CCN1CCCCC1
inchi:    InChI=1S/C7H15N/c1-2-8-6-4-3-5-7-8/h2-7H2,1H3
inchiKey:    HTLZVHNRZJPSMI-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

formohydrazide: C(=O)NN

smiles_non_kekule:    NNC=O
smiles_kekule:    NNC=O
inchi:    InChI=1S/CH4N2O/c2-3-1-4/h1H,2H2,(H,3,4)
inchiKey:    XZBIXDPGRMLSTC-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]-[#7]
smarts_isomeric:    [#6](=[#8])-[#7]-[#7]

2-chlorothiophene: c1ccc(Cl)s1

smiles_non_kekule:    Clc1cccs1
smiles_kekule:    ClC1=CC=CS1
inchi:    InChI=1S/C4H3ClS/c5-4-2-1-3-6-4/h1-3H
inchiKey:    GSFNQBFZFXUTBN-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#17]):[#16]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#17]):[#16]:1

piperidin-4-ol: N1CCC(O)CC1

smiles_non_kekule:    OC1CCNCC1
smiles_kekule:    OC1CCNCC1
inchi:    InChI=1S/C5H11NO/c7-5-1-3-6-4-2-5/h5-7H,1-4H2
inchiKey:    HDOWRFHMPULYOA-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#6](-[#8])-[#6]-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#6](-[#8])-[#6]-[#6]-1

2-methylthiazole: c1csc(C)n1

smiles_non_kekule:    Cc1nccs1
smiles_kekule:    CC1=NC=CS1
inchi:    InChI=1S/C4H5NS/c1-4-5-2-3-6-4/h2-3H,1H3
inchiKey:    VZWOXDYRBDIHMA-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#16]:[#6](-[#6]):[#7]:1
smarts_isomeric:    [#6]1:[#6]:[#16]:[#6](-[#6]):[#7]:1

N-cyclopropylformamide: C(=O)NC1CC1

smiles_non_kekule:    O=CNC1CC1
smiles_kekule:    O=CNC1CC1
inchi:    InChI=1S/C4H7NO/c6-3-5-4-1-2-4/h3-4H,1-2H2,(H,5,6)
inchiKey:    AWQVKAURKXXOCG-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]-[#6]1-[#6]-[#6]-1
smarts_isomeric:    [#6](=[#8])-[#7]-[#6]1-[#6]-[#6]-1

prop-2-en-1-ol: OCC=C

smiles_non_kekule:    C=CCO
smiles_kekule:    C=CCO
inchi:    InChI=1S/C3H6O/c1-2-3-4/h2,4H,1,3H2
inchiKey:    XXROGKLTLUQVRX-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]=[#6]
smarts_isomeric:    [#8]-[#6]-[#6]=[#6]

cyclopentanamine: NC1CCCC1

smiles_non_kekule:    NC1CCCC1
smiles_kekule:    NC1CCCC1
inchi:    InChI=1S/C5H11N/c6-5-3-1-2-4-5/h5H,1-4,6H2
inchiKey:    NISGSNTVMOOSJQ-UHFFFAOYSA-N
smarts:    [#7]-[#6]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#7]-[#6]1-[#6]-[#6]-[#6]-[#6]-1

urea: NC(N)=O

smiles_non_kekule:    NC(N)=O
smiles_kekule:    NC(N)=O
inchi:    InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4)
inchiKey:    XSQUKJJJFZCRTK-UHFFFAOYSA-N
smarts:    [#7]-[#6](-[#7])=[#8]
smarts_isomeric:    [#7]-[#6](-[#7])=[#8]

prop-1-ene: CC=C

(methylsulfonyl)benzene: c1ccc(S(C)(=O)=O)cc1

smiles_non_kekule:    CS(=O)(=O)c1ccccc1
smiles_kekule:    CS(=O)(=O)C1=CC=CC=C1
inchi:    InChI=1S/C7H8O2S/c1-10(8,9)7-5-3-2-4-6-7/h2-6H,1H3
inchiKey:    JCDWETOKTFWTHA-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#16](-[#6])(=[#8])=[#8]):[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#16](-[#6])(=[#8])=[#8]):[#6]:[#6]:1

difluoromethanol: OC(F)F

smiles_non_kekule:    OC(F)F
smiles_kekule:    OC(F)F
inchi:    InChI=1S/CH2F2O/c2-1(3)4/h1,4H
inchiKey:    FMLSOUMOHNIGAA-UHFFFAOYSA-N
smarts:    [#8]-[#6](-[#9])-[#9]
smarts_isomeric:    [#8]-[#6](-[#9])-[#9]

2-phenylacetamide: NC(=O)Cc1ccccc1

smiles_non_kekule:    NC(=O)Cc1ccccc1
smiles_kekule:    NC(=O)CC1=CC=CC=C1
inchi:    InChI=1S/C8H9NO/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H2,9,10)
inchiKey:    LSBDFXRDZJMBSC-UHFFFAOYSA-N
smarts:    [#7]-[#6](=[#8])-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#7]-[#6](=[#8])-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

4-fluorobenzaldehyde: C(=O)c1ccc(F)cc1

smiles_non_kekule:    O=Cc1ccc(F)cc1
smiles_kekule:    O=CC1=CC=C(F)C=C1
inchi:    InChI=1S/C7H5FO/c8-7-3-1-6(5-9)2-4-7/h1-5H
inchiKey:    UOQXIWFBQSVDPP-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#6]1:[#6]:[#6]:[#6](-[#9]):[#6]:[#6]:1
smarts_isomeric:    [#6](=[#8])-[#6]1:[#6]:[#6]:[#6](-[#9]):[#6]:[#6]:1

N-propylformamide: C(=O)NCCC

smiles_non_kekule:    CCCNC=O
smiles_kekule:    CCCNC=O
inchi:    InChI=1S/C4H9NO/c1-2-3-5-4-6/h4H,2-3H2,1H3,(H,5,6)
inchiKey:    SUUDTPGCUKBECW-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]-[#6]-[#6]-[#6]
smarts_isomeric:    [#6](=[#8])-[#7]-[#6]-[#6]-[#6]

N-tert-butylformamide: C(=O)NC(C)(C)C

smiles_non_kekule:    CC(C)(C)NC=O
smiles_kekule:    CC(C)(C)NC=O
inchi:    InChI=1S/C5H11NO/c1-5(2,3)6-4-7/h4H,1-3H3,(H,6,7)
inchiKey:    SDLAKRCBYGZJRW-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]-[#6](-[#6])(-[#6])-[#6]
smarts_isomeric:    [#6](=[#8])-[#7]-[#6](-[#6])(-[#6])-[#6]

tetrazole: c1nnn[nH]1

pyrrolidin-3-ol: N1CCC(O)C1

smiles_non_kekule:    OC1CCNC1
smiles_kekule:    OC1CCNC1
inchi:    InChI=1S/C4H9NO/c6-4-1-2-5-3-4/h4-6H,1-3H2
inchiKey:    JHHZLHWJQPUNKB-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#6](-[#8])-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#6](-[#8])-[#6]-1

biphenyl: c1ccc(-c2ccccc2)cc1

smiles_non_kekule:    c1ccc(-c2ccccc2)cc1
smiles_kekule:    C1=CC=C(C2=CC=CC=C2)C=C1
inchi:    InChI=1S/C12H10/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1-10H
inchiKey:    ZUOUZKKEUPVFJK-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2):[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2):[#6]:[#6]:1

cyclopropanamine: NC1CC1

smiles_non_kekule:    NC1CC1
smiles_kekule:    NC1CC1
inchi:    InChI=1S/C3H7N/c4-3-1-2-3/h3H,1-2,4H2
inchiKey:    HTJDQJBWANPRPF-UHFFFAOYSA-N
smarts:    [#7]-[#6]1-[#6]-[#6]-1
smarts_isomeric:    [#7]-[#6]1-[#6]-[#6]-1

formaldehyde oxime: C=NO

smiles_non_kekule:    C=NO
smiles_kekule:    C=NO
inchi:    InChI=1S/CH3NO/c1-2-3/h3H,1H2
inchiKey:    SQDFHQJTAWCFIB-UHFFFAOYSA-N
smarts:    [#6]=[#7]-[#8]
smarts_isomeric:    [#6]=[#7]-[#8]

furan-2-carboxamide: NC(=O)c1ccco1

smiles_non_kekule:    NC(=O)c1ccco1
smiles_kekule:    NC(=O)C1=CC=CO1
inchi:    InChI=1S/C5H5NO2/c6-5(7)4-2-1-3-8-4/h1-3H,(H2,6,7)
inchiKey:    TVFIYRKPCACCNL-UHFFFAOYSA-N
smarts:    [#7]-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#8]:1
smarts_isomeric:    [#7]-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#8]:1

3-morpholinopropan-1-ol: OCCCN1CCOCC1

smiles_non_kekule:    OCCCN1CCOCC1
smiles_kekule:    OCCCN1CCOCC1
inchi:    InChI=1S/C7H15NO2/c9-5-1-2-8-3-6-10-7-4-8/h9H,1-7H2
inchiKey:    VZKSLWJLGAGPIU-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1
smarts_isomeric:    [#8]-[#6]-[#6]-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1

propionamide: NC(=O)CC

smiles_non_kekule:    CCC(N)=O
smiles_kekule:    CCC(N)=O
inchi:    InChI=1S/C3H7NO/c1-2-3(4)5/h2H2,1H3,(H2,4,5)
inchiKey:    QLNJFJADRCOGBJ-UHFFFAOYSA-N
smarts:    [#7]-[#6](=[#8])-[#6]-[#6]
smarts_isomeric:    [#7]-[#6](=[#8])-[#6]-[#6]

2-(piperazin-1-yl)ethan-1-ol: N1CCN(CCO)CC1

smiles_non_kekule:    OCCN1CCNCC1
smiles_kekule:    OCCN1CCNCC1
inchi:    InChI=1S/C6H14N2O/c9-6-5-8-3-1-7-2-4-8/h7,9H,1-6H2
inchiKey:    WFCSWCVEJLETKA-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#8])-[#6]-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#8])-[#6]-[#6]-1

pyridin-3-ylmethanamine: NCc1cccnc1

smiles_non_kekule:    NCc1cccnc1
smiles_kekule:    NCC1=CC=CN=C1
inchi:    InChI=1S/C6H8N2/c7-4-6-2-1-3-8-5-6/h1-3,5H,4,7H2
inchiKey:    HDOUGSFASVGDCS-UHFFFAOYSA-N
smarts:    [#7]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1
smarts_isomeric:    [#7]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1

N-hydroxyacrylamide: C=CC(=O)NO

smiles_non_kekule:    C=CC(=O)NO
smiles_kekule:    C=CC(=O)NO
inchi:    InChI=1S/C3H5NO2/c1-2-3(5)4-6/h2,6H,1H2,(H,4,5)
inchiKey:    HQVFKSDWNYVAQD-UHFFFAOYSA-N
smarts:    [#6]=[#6]-[#6](=[#8])-[#7]-[#8]
smarts_isomeric:    [#6]=[#6]-[#6](=[#8])-[#7]-[#8]

N-(2-methoxyethyl)formamide: C(=O)NCCOC

smiles_non_kekule:    COCCNC=O
smiles_kekule:    COCCNC=O
inchi:    InChI=1S/C4H9NO2/c1-7-3-2-5-4-6/h4H,2-3H2,1H3,(H,5,6)
inchiKey:    SSQTXMAIJVOVIP-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]-[#6]-[#6]-[#8]-[#6]
smarts_isomeric:    [#6](=[#8])-[#7]-[#6]-[#6]-[#8]-[#6]

2-methylthiophene: Cc1cccs1

smiles_non_kekule:    Cc1cccs1
smiles_kekule:    CC1=CC=CS1
inchi:    InChI=1S/C5H6S/c1-5-3-2-4-6-5/h2-4H,1H3
inchiKey:    XQQBUAPQHNYYRS-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#16]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#16]:1

tert-butylbenzene: c1ccc(C(C)(C)C)cc1

smiles_non_kekule:    CC(C)(C)c1ccccc1
smiles_kekule:    CC(C)(C)C1=CC=CC=C1
inchi:    InChI=1S/C10H14/c1-10(2,3)9-7-5-4-6-8-9/h4-8H,1-3H3
inchiKey:    YTZKOQUCBOVLHL-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#6](-[#6])(-[#6])-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#6](-[#6])(-[#6])-[#6]):[#6]:[#6]:1

cyclohexanecarboxamide: NC(=O)C1CCCCC1

smiles_non_kekule:    NC(=O)C1CCCCC1
smiles_kekule:    NC(=O)C1CCCCC1
inchi:    InChI=1S/C7H13NO/c8-7(9)6-4-2-1-3-5-6/h6H,1-5H2,(H2,8,9)
inchiKey:    PNZXMIKHJXIPEK-UHFFFAOYSA-N
smarts:    [#7]-[#6](=[#8])-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#7]-[#6](=[#8])-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

4-fluorophenol: Oc1ccc(F)cc1

smiles_non_kekule:    Oc1ccc(F)cc1
smiles_kekule:    OC1=CC=C(F)C=C1
inchi:    InChI=1S/C6H5FO/c7-5-1-3-6(8)4-2-5/h1-4,8H
inchiKey:    RHMPLDJJXGPMEX-UHFFFAOYSA-N
smarts:    [#8]-[#6]1:[#6]:[#6]:[#6](-[#9]):[#6]:[#6]:1
smarts_isomeric:    [#8]-[#6]1:[#6]:[#6]:[#6](-[#9]):[#6]:[#6]:1

2-ethynylpyridine: C#Cc1ccccn1

smiles_non_kekule:    C#Cc1ccccn1
smiles_kekule:    C#CC1=CC=CC=N1
inchi:    InChI=1S/C7H5N/c1-2-7-5-3-4-6-8-7/h1,3-6H
inchiKey:    NHUBNHMFXQNNMV-UHFFFAOYSA-N
smarts:    [#6]#[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#7]:1
smarts_isomeric:    [#6]#[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#7]:1

(4-methoxyphenyl)methanamine: NCc1ccc(OC)cc1

smiles_non_kekule:    COc1ccc(CN)cc1
smiles_kekule:    COC1=CC=C(CN)C=C1
inchi:    InChI=1S/C8H11NO/c1-10-8-4-2-7(6-9)3-5-8/h2-5H,6,9H2,1H3
inchiKey:    IDPURXSQCKYKIJ-UHFFFAOYSA-N
smarts:    [#7]-[#6]-[#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#7]-[#6]-[#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6]:[#6]:1

butyric acid: CCCC(=O)O

smiles_non_kekule:    CCCC(=O)O
smiles_kekule:    CCCC(=O)O
inchi:    InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)
inchiKey:    FERIUCNNQQJTOY-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6](=[#8])-[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6](=[#8])-[#8]

1-Acetylpiperazine: N1CCN(C(C)=O)CC1

smiles_non_kekule:    CC(=O)N1CCNCC1
smiles_kekule:    CC(=O)N1CCNCC1
inchi:    InChI=1S/C6H12N2O/c1-6(9)8-4-2-7-3-5-8/h7H,2-5H2,1H3
inchiKey:    PKDPUENCROCRCH-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#7](-[#6](-[#6])=[#8])-[#6]-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#7](-[#6](-[#6])=[#8])-[#6]-[#6]-1

3,5-dimethylisoxazole: c1c(C)noc1C

smiles_non_kekule:    Cc1cc(C)on1
smiles_kekule:    CC1=NOC(C)=C1
inchi:    InChI=1S/C5H7NO/c1-4-3-5(2)7-6-4/h3H,1-2H3
inchiKey:    FICAQKBMCKEFDI-UHFFFAOYSA-N
smarts:    [#6]1:[#6](-[#6]):[#7]:[#8]:[#6]:1-[#6]
smarts_isomeric:    [#6]1:[#6](-[#6]):[#7]:[#8]:[#6]:1-[#6]

1-ethylpiperazine: N1CCN(CC)CC1

smiles_non_kekule:    CCN1CCNCC1
smiles_kekule:    CCN1CCNCC1
inchi:    InChI=1S/C6H14N2/c1-2-8-5-3-7-4-6-8/h7H,2-6H2,1H3
inchiKey:    WGCYRFWNGRMRJA-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#7](-[#6]-[#6])-[#6]-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#7](-[#6]-[#6])-[#6]-[#6]-1

adamantane: C12CC3CC(CC(C3)C1)C2

smiles_non_kekule:    C1C2CC3CC1CC(C2)C3
smiles_kekule:    C1C2CC3CC1CC(C2)C3
inchi:    InChI=1S/C10H16/c1-7-2-9-4-8(1)5-10(3-7)6-9/h7-10H,1-6H2
inchiKey:    ORILYTVJVMAKLC-UHFFFAOYSA-N
smarts:    [#6]12-[#6]-[#6]3-[#6]-[#6](-[#6]-[#6](-[#6]-3)-[#6]-1)-[#6]-2
smarts_isomeric:    [#6]12-[#6]-[#6]3-[#6]-[#6](-[#6]-[#6](-[#6]-3)-[#6]-1)-[#6]-2

1-chloro-3-methylbenzene: Cc1cccc(Cl)c1

smiles_non_kekule:    Cc1cccc(Cl)c1
smiles_kekule:    CC1=CC=CC(Cl)=C1
inchi:    InChI=1S/C7H7Cl/c1-6-3-2-4-7(8)5-6/h2-5H,1H3
inchiKey:    OSOUNOBYRMOXQQ-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6](-[#17]):[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6](-[#17]):[#6]:1

1,2-difluorobenzene: c1ccc(F)c(F)c1

smiles_non_kekule:    Fc1ccccc1F
smiles_kekule:    FC1=CC=CC=C1F
inchi:    InChI=1S/C6H4F2/c7-5-3-1-2-4-6(5)8/h1-4H
inchiKey:    GOYDNIKZWGIXJT-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#9]):[#6](-[#9]):[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#9]):[#6](-[#9]):[#6]:1

1-phenylurea: NC(=O)Nc1ccccc1

smiles_non_kekule:    NC(=O)Nc1ccccc1
smiles_kekule:    NC(=O)NC1=CC=CC=C1
inchi:    InChI=1S/C7H8N2O/c8-7(10)9-6-4-2-1-3-5-6/h1-5H,(H3,8,9,10)
inchiKey:    LUBJCRLGQSPQNN-UHFFFAOYSA-N
smarts:    [#7]-[#6](=[#8])-[#7]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#7]-[#6](=[#8])-[#7]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

2-methylpropan-2-ol: OC(C)(C)C

smiles_non_kekule:    CC(C)(C)O
smiles_kekule:    CC(C)(C)O
inchi:    InChI=1S/C4H10O/c1-4(2,3)5/h5H,1-3H3
inchiKey:    DKGAVHZHDRPRBM-UHFFFAOYSA-N
smarts:    [#8]-[#6](-[#6])(-[#6])-[#6]
smarts_isomeric:    [#8]-[#6](-[#6])(-[#6])-[#6]

1-chloro-2-methylbenzene: Cc1ccccc1Cl

smiles_non_kekule:    Cc1ccccc1Cl
smiles_kekule:    CC1=CC=CC=C1Cl
inchi:    InChI=1S/C7H7Cl/c1-6-4-2-3-5-7(6)8/h2-5H,1H3
inchiKey:    IBSQPLPBRSHTTG-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17]
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17]

N-phenethylformamide: C(=O)NCCc1ccccc1

smiles_non_kekule:    O=CNCCc1ccccc1
smiles_kekule:    O=CNCCC1=CC=CC=C1
inchi:    InChI=1S/C9H11NO/c11-8-10-7-6-9-4-2-1-3-5-9/h1-5,8H,6-7H2,(H,10,11)
inchiKey:    NOOOMJZHMKSKBF-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6](=[#8])-[#7]-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

isonicotinamide: NC(=O)c1ccncc1

smiles_non_kekule:    NC(=O)c1ccncc1
smiles_kekule:    NC(=O)C1=CC=NC=C1
inchi:    InChI=1S/C6H6N2O/c7-6(9)5-1-3-8-4-2-5/h1-4H,(H2,7,9)
inchiKey:    VFQXVTODMYMSMJ-UHFFFAOYSA-N
smarts:    [#7]-[#6](=[#8])-[#6]1:[#6]:[#6]:[#7]:[#6]:[#6]:1
smarts_isomeric:    [#7]-[#6](=[#8])-[#6]1:[#6]:[#6]:[#7]:[#6]:[#6]:1

N-methylcyclopentanamine: CNC1CCCC1

smiles_non_kekule:    CNC1CCCC1
smiles_kekule:    CNC1CCCC1
inchi:    InChI=1S/C6H13N/c1-7-6-4-2-3-5-6/h6-7H,2-5H2,1H3
inchiKey:    KKTBUCVHSCATGB-UHFFFAOYSA-N
smarts:    [#6]-[#7]-[#6]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#7]-[#6]1-[#6]-[#6]-[#6]-[#6]-1

2-methoxyethan-1-amine: NCCOC

smiles_non_kekule:    COCCN
smiles_kekule:    COCCN
inchi:    InChI=1S/C3H9NO/c1-5-3-2-4/h2-4H2,1H3
inchiKey:    ASUDFOJKTJLAIK-UHFFFAOYSA-N
smarts:    [#7]-[#6]-[#6]-[#8]-[#6]
smarts_isomeric:    [#7]-[#6]-[#6]-[#8]-[#6]

propionaldehyde: C(=O)CC

smiles_non_kekule:    CCC=O
smiles_kekule:    CCC=O
inchi:    InChI=1S/C3H6O/c1-2-3-4/h3H,2H2,1H3
inchiKey:    NBBJYMSMWIIQGU-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#6]-[#6]
smarts_isomeric:    [#6](=[#8])-[#6]-[#6]

N-(4-chlorophenyl)formamide: C(=O)Nc1ccc(Cl)cc1

smiles_non_kekule:    O=CNc1ccc(Cl)cc1
smiles_kekule:    O=CNC1=CC=C(Cl)C=C1
inchi:    InChI=1S/C7H6ClNO/c8-6-1-3-7(4-2-6)9-5-10/h1-5H,(H,9,10)
inchiKey:    LMLFHXMNNHGRRO-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]-[#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1
smarts_isomeric:    [#6](=[#8])-[#7]-[#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1

2-chloropyridine: c1ccc(Cl)nc1

smiles_non_kekule:    Clc1ccccn1
smiles_kekule:    ClC1=CC=CC=N1
inchi:    InChI=1S/C5H4ClN/c6-5-3-1-2-4-7-5/h1-4H
inchiKey:    OKDGRDCXVWSXDC-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#17]):[#7]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#17]):[#7]:[#6]:1

N,N-dimethylpropan-1-amine: CCCN(C)C

smiles_non_kekule:    CCCN(C)C
smiles_kekule:    CCCN(C)C
inchi:    InChI=1S/C5H13N/c1-4-5-6(2)3/h4-5H2,1-3H3
inchiKey:    ZUHZZVMEUAUWHY-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#7](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]-[#7](-[#6])-[#6]

5-methylenethiazolidine-2,4-dione: C=C1SC(=O)NC1=O

smiles_non_kekule:    C=C1SC(=O)NC1=O
smiles_kekule:    C=C1SC(=O)NC1=O
inchi:    InChI=1S/C4H3NO2S/c1-2-3(6)5-4(7)8-2/h1H2,(H,5,6,7)
inchiKey:    GXITUSCERRRNDI-UHFFFAOYSA-N
smarts:    [#6]=[#6]1-[#16]-[#6](=[#8])-[#7]-[#6]-1=[#8]
smarts_isomeric:    [#6]=[#6]1-[#16]-[#6](=[#8])-[#7]-[#6]-1=[#8]

3-methoxypyridine: c1cncc(OC)c1

smiles_non_kekule:    COc1cccnc1
smiles_kekule:    COC1=CC=CN=C1
inchi:    InChI=1S/C6H7NO/c1-8-6-3-2-4-7-5-6/h2-5H,1H3
inchiKey:    UMJSCPRVCHMLSP-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#7]:[#6]:[#6](-[#8]-[#6]):[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#7]:[#6]:[#6](-[#8]-[#6]):[#6]:1

3-(trifluoromethyl)pyridine: c1ncccc1C(F)(F)F

smiles_non_kekule:    FC(F)(F)c1cccnc1
smiles_kekule:    FC(F)(F)C1=CC=CN=C1
inchi:    InChI=1S/C6H4F3N/c7-6(8,9)5-2-1-3-10-4-5/h1-4H
inchiKey:    JTZSFNHHVULOGJ-UHFFFAOYSA-N
smarts:    [#6]1:[#7]:[#6]:[#6]:[#6]:[#6]:1-[#6](-[#9])(-[#9])-[#9]
smarts_isomeric:    [#6]1:[#7]:[#6]:[#6]:[#6]:[#6]:1-[#6](-[#9])(-[#9])-[#9]

4-methylbenzenesulfonamide: NS(=O)(=O)c1ccc(C)cc1

smiles_non_kekule:    Cc1ccc(S(N)(=O)=O)cc1
smiles_kekule:    CC1=CC=C(S(N)(=O)=O)C=C1
inchi:    InChI=1S/C7H9NO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3,(H2,8,9,10)
inchiKey:    LMYRWZFENFIFIT-UHFFFAOYSA-N
smarts:    [#7]-[#16](=[#8])(=[#8])-[#6]1:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#7]-[#16](=[#8])(=[#8])-[#6]1:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:1

2-phenylethan-1-ol: OCCc1ccccc1

smiles_non_kekule:    OCCc1ccccc1
smiles_kekule:    OCCC1=CC=CC=C1
inchi:    InChI=1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2
inchiKey:    WRMNZCZEMHIOCP-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#8]-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

N-cyclopentylformamide: C(=O)NC1CCCC1

smiles_non_kekule:    O=CNC1CCCC1
smiles_kekule:    O=CNC1CCCC1
inchi:    InChI=1S/C6H11NO/c8-5-7-6-3-1-2-4-6/h5-6H,1-4H2,(H,7,8)
inchiKey:    WYLHQTSQMKMTGM-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]-[#6]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6](=[#8])-[#7]-[#6]1-[#6]-[#6]-[#6]-[#6]-1

indazole: c1ccc2[nH]ncc2c1

smiles_non_kekule:    c1ccc2[nH]ncc2c1
smiles_kekule:    C1=CC=C2NN=CC2=C1
inchi:    InChI=1S/C7H6N2/c1-2-4-7-6(3-1)5-8-9-7/h1-5H,(H,8,9)
inchiKey:    BAXOFTOLAUCFNW-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]2:[#7H]:[#7]:[#6]:[#6]:2:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]2:[#7H]:[#7]:[#6]:[#6]:2:[#6]:1

cyclopentanol: OC1CCCC1

smiles_non_kekule:    OC1CCCC1
smiles_kekule:    OC1CCCC1
inchi:    InChI=1S/C5H10O/c6-5-3-1-2-4-5/h5-6H,1-4H2
inchiKey:    XCIXKGXIYUWCLL-UHFFFAOYSA-N
smarts:    [#8]-[#6]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#8]-[#6]1-[#6]-[#6]-[#6]-[#6]-1

nicotinamide: NC(=O)c1cccnc1

smiles_non_kekule:    NC(=O)c1cccnc1
smiles_kekule:    NC(=O)C1=CC=CN=C1
inchi:    InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)
inchiKey:    DFPAKSUCGFBDDF-UHFFFAOYSA-N
smarts:    [#7]-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1
smarts_isomeric:    [#7]-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1

isopentane: CCC(C)C

smiles_non_kekule:    CCC(C)C
smiles_kekule:    CCC(C)C
inchi:    InChI=1S/C5H12/c1-4-5(2)3/h5H,4H2,1-3H3
inchiKey:    QWTDNUCVQCZILF-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6]-[#6](-[#6])-[#6]

hydrosulfonylethane: S(=O)(=O)CC

smiles_non_kekule:    CC[SH](=O)=O
smiles_kekule:    CC[SH](=O)=O
inchi:    InChI=1S/C2H6O2S/c1-2-5(3)4/h5H,2H2,1H3
inchiKey:    VCRTUEWZYXRBFN-UHFFFAOYSA-N
smarts:    [#16](=[#8])(=[#8])-[#6]-[#6]
smarts_isomeric:    [#16](=[#8])(=[#8])-[#6]-[#6]

tert-butyl carbamate: NC(=O)OC(C)(C)C

smiles_non_kekule:    CC(C)(C)OC(N)=O
smiles_kekule:    CC(C)(C)OC(N)=O
inchi:    InChI=1S/C5H11NO2/c1-5(2,3)8-4(6)7/h1-3H3,(H2,6,7)
inchiKey:    LFKDJXLFVYVEFG-UHFFFAOYSA-N
smarts:    [#7]-[#6](=[#8])-[#8]-[#6](-[#6])(-[#6])-[#6]
smarts_isomeric:    [#7]-[#6](=[#8])-[#8]-[#6](-[#6])(-[#6])-[#6]

(tetrahydrofuran-2-yl)methanol: OCC1CCCO1

smiles_non_kekule:    OCC1CCCO1
smiles_kekule:    OCC1CCCO1
inchi:    InChI=1S/C5H10O2/c6-4-5-2-1-3-7-5/h5-6H,1-4H2
inchiKey:    BSYVTEYKTMYBMK-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]1-[#6]-[#6]-[#6]-[#8]-1
smarts_isomeric:    [#8]-[#6]-[#6]1-[#6]-[#6]-[#6]-[#8]-1

N,N-dimethylacetamide: CC(=O)N(C)C

1-phenylpiperazine: N1CCN(c2ccccc2)CC1

smiles_non_kekule:    c1ccc(N2CCNCC2)cc1
smiles_kekule:    C1=CC=C(N2CCNCC2)C=C1
inchi:    InChI=1S/C10H14N2/c1-2-4-10(5-3-1)12-8-6-11-7-9-12/h1-5,11H,6-9H2
inchiKey:    YZTJYBJCZXZGCT-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#7](-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#7](-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1

2-methylpropan-1-ol: C(C)(C)CO

smiles_non_kekule:    CC(C)CO
smiles_kekule:    CC(C)CO
inchi:    InChI=1S/C4H10O/c1-4(2)3-5/h4-5H,3H2,1-2H3
inchiKey:    ZXEKIIBDNHEJCQ-UHFFFAOYSA-N
smarts:    [#6](-[#6])(-[#6])-[#6]-[#8]
smarts_isomeric:    [#6](-[#6])(-[#6])-[#6]-[#8]

N-methylethanamine: CCNC

smiles_non_kekule:    CCNC
smiles_kekule:    CCNC
inchi:    InChI=1S/C3H9N/c1-3-4-2/h4H,3H2,1-2H3
inchiKey:    LIWAQLJGPBVORC-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7]-[#6]
smarts_isomeric:    [#6]-[#6]-[#7]-[#6]

1,3-dichlorobenzene: c1ccc(Cl)cc1Cl

smiles_non_kekule:    Clc1cccc(Cl)c1
smiles_kekule:    ClC1=CC=CC(Cl)=C1
inchi:    InChI=1S/C6H4Cl2/c7-5-2-1-3-6(8)4-5/h1-4H
inchiKey:    ZPQOPVIELGIULI-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1-[#17]
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1-[#17]

tert-butyl formate: C(=O)OC(C)(C)C

smiles_non_kekule:    CC(C)(C)OC=O
smiles_kekule:    CC(C)(C)OC=O
inchi:    InChI=1S/C5H10O2/c1-5(2,3)7-4-6/h4H,1-3H3
inchiKey:    RUPAXCPQAAOIPB-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#8]-[#6](-[#6])(-[#6])-[#6]
smarts_isomeric:    [#6](=[#8])-[#8]-[#6](-[#6])(-[#6])-[#6]

thiophene-2-carbaldehyde: C(=O)c1cccs1

smiles_non_kekule:    O=Cc1cccs1
smiles_kekule:    O=CC1=CC=CS1
inchi:    InChI=1S/C5H4OS/c6-4-5-2-1-3-7-5/h1-4H
inchiKey:    CNUDBTRUORMMPA-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#16]:1
smarts_isomeric:    [#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#16]:1

1-methyl-1,4-diazepane: N1CCCN(C)CC1

smiles_non_kekule:    CN1CCCNCC1
smiles_kekule:    CN1CCCNCC1
inchi:    InChI=1S/C6H14N2/c1-8-5-2-3-7-4-6-8/h7H,2-6H2,1H3
inchiKey:    FXHRAKUEZPSMLJ-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#6]-[#7](-[#6])-[#6]-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#6]-[#7](-[#6])-[#6]-[#6]-1

N-phenylacetamide: c1ccc(NC(C)=O)cc1

smiles_non_kekule:    CC(=O)Nc1ccccc1
smiles_kekule:    CC(=O)NC1=CC=CC=C1
inchi:    InChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)
inchiKey:    FZERHIULMFGESH-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#7]-[#6](-[#6])=[#8]):[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#7]-[#6](-[#6])=[#8]):[#6]:[#6]:1

octane: CCCCCCCC

smiles_non_kekule:    CCCCCCCC
smiles_kekule:    CCCCCCCC
inchi:    InChI=1S/C8H18/c1-3-5-7-8-6-4-2/h3-8H2,1-2H3
inchiKey:    TVMXDCGIABBOFY-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]

1-methoxy-2-methylbenzene: Cc1ccccc1OC

smiles_non_kekule:    COc1ccccc1C
smiles_kekule:    COC1=CC=CC=C1C
inchi:    InChI=1S/C8H10O/c1-7-5-3-4-6-8(7)9-2/h3-6H,1-2H3
inchiKey:    DTFKRVXLBCAIOZ-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#8]-[#6]
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#8]-[#6]

1H-pyrrole-2,5-dione: N1C(=O)C=CC1=O

smiles_non_kekule:    O=C1C=CC(=O)N1
smiles_kekule:    O=C1C=CC(=O)N1
inchi:    InChI=1S/C4H3NO2/c6-3-1-2-4(7)5-3/h1-2H,(H,5,6,7)
inchiKey:    PEEHTFAAVSWFBL-UHFFFAOYSA-N
smarts:    [#7]1-[#6](=[#8])-[#6]=[#6]-[#6]-1=[#8]
smarts_isomeric:    [#7]1-[#6](=[#8])-[#6]=[#6]-[#6]-1=[#8]

sulfamic acid: OS(N)(=O)=O

smiles_non_kekule:    NS(=O)(=O)O
smiles_kekule:    NS(=O)(=O)O
inchi:    InChI=1S/H3NO3S/c1-5(2,3)4/h(H3,1,2,3,4)
inchiKey:    IIACRCGMVDHOTQ-UHFFFAOYSA-N
smarts:    [#8]-[#16](-[#7])(=[#8])=[#8]
smarts_isomeric:    [#8]-[#16](-[#7])(=[#8])=[#8]

2-methylisoindoline-1,3-dione: CN1C(=O)c2ccccc2C1=O

smiles_non_kekule:    CN1C(=O)c2ccccc2C1=O
smiles_kekule:    CN1C(=O)C2=CC=CC=C2C1=O
inchi:    InChI=1S/C9H7NO2/c1-10-8(11)6-4-2-3-5-7(6)9(10)12/h2-5H,1H3
inchiKey:    ZXLYYQUMYFHCLQ-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6](=[#8])-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2-[#6]-1=[#8]
smarts_isomeric:    [#6]-[#7]1-[#6](=[#8])-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2-[#6]-1=[#8]

(difluoromethyl)phosphonic acid: C(F)(F)P(=O)(O)O

smiles_non_kekule:    O=P(O)(O)C(F)F
smiles_kekule:    O=P(O)(O)C(F)F
inchi:    InChI=1S/CH3F2O3P/c2-1(3)7(4,5)6/h1H,(H2,4,5,6)
inchiKey:    NCEMUOYFYLEORV-UHFFFAOYSA-N
smarts:    [#6](-[#9])(-[#9])-[#15](=[#8])(-[#8])-[#8]
smarts_isomeric:    [#6](-[#9])(-[#9])-[#15](=[#8])(-[#8])-[#8]

pyrimidin-2-amine: c1ccnc(N)n1

smiles_non_kekule:    Nc1ncccn1
smiles_kekule:    NC1=NC=CC=N1
inchi:    InChI=1S/C4H5N3/c5-4-6-2-1-3-7-4/h1-3H,(H2,5,6,7)
inchiKey:    LJXQPZWIHJMPQQ-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#7]:[#6](-[#7]):[#7]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#7]:[#6](-[#7]):[#7]:1

1H-benzo[d]imidazole-5-carboxamide: c1nc2cc(C(N)=O)ccc2[nH]1

smiles_non_kekule:    NC(=O)c1ccc2[nH]cnc2c1
smiles_kekule:    NC(=O)C1=CC=C2NC=NC2=C1
inchi:    InChI=1S/C8H7N3O/c9-8(12)5-1-2-6-7(3-5)11-4-10-6/h1-4H,(H2,9,12)(H,10,11)
inchiKey:    FNLQDVXHDNFXIY-UHFFFAOYSA-N
smarts:    [#6]1:[#7]:[#6]2:[#6]:[#6](-[#6](-[#7])=[#8]):[#6]:[#6]:[#6]:2:[#7H]:1
smarts_isomeric:    [#6]1:[#7]:[#6]2:[#6]:[#6](-[#6](-[#7])=[#8]):[#6]:[#6]:[#6]:2:[#7H]:1

2-methylpropan-2-amine: NC(C)(C)C

smiles_non_kekule:    CC(C)(C)N
smiles_kekule:    CC(C)(C)N
inchi:    InChI=1S/C4H11N/c1-4(2,3)5/h5H2,1-3H3
inchiKey:    YBRBMKDOPFTVDT-UHFFFAOYSA-N
smarts:    [#7]-[#6](-[#6])(-[#6])-[#6]
smarts_isomeric:    [#7]-[#6](-[#6])(-[#6])-[#6]

N-(4-fluorophenyl)formamide: C(=O)Nc1ccc(F)cc1

smiles_non_kekule:    O=CNc1ccc(F)cc1
smiles_kekule:    O=CNC1=CC=C(F)C=C1
inchi:    InChI=1S/C7H6FNO/c8-6-1-3-7(4-2-6)9-5-10/h1-5H,(H,9,10)
inchiKey:    BUPDLPLGFRDHSJ-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]-[#6]1:[#6]:[#6]:[#6](-[#9]):[#6]:[#6]:1
smarts_isomeric:    [#6](=[#8])-[#7]-[#6]1:[#6]:[#6]:[#6](-[#9]):[#6]:[#6]:1

oxazole: c1cnco1

smiles_non_kekule:    c1cocn1
smiles_kekule:    C1=COC=N1
inchi:    InChI=1S/C3H3NO/c1-2-5-3-4-1/h1-3H
inchiKey:    ZCQWOFVYLHDMMC-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#7]:[#6]:[#8]:1
smarts_isomeric:    [#6]1:[#6]:[#7]:[#6]:[#8]:1

pyridin-3-ylmethanol: OCc1cccnc1

smiles_non_kekule:    OCc1cccnc1
smiles_kekule:    OCC1=CC=CN=C1
inchi:    InChI=1S/C6H7NO/c8-5-6-2-1-3-7-4-6/h1-4,8H,5H2
inchiKey:    MVQVNTPHUGQQHK-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1
smarts_isomeric:    [#8]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1

pyridin-3-ol: Oc1cccnc1

smiles_non_kekule:    Oc1cccnc1
smiles_kekule:    OC1=CC=CN=C1
inchi:    InChI=1S/C5H5NO/c7-5-2-1-3-6-4-5/h1-4,7H
inchiKey:    GRFNBEZIAWKNCO-UHFFFAOYSA-N
smarts:    [#8]-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1
smarts_isomeric:    [#8]-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1

picolinamide: NC(=O)c1ccccn1

smiles_non_kekule:    NC(=O)c1ccccn1
smiles_kekule:    NC(=O)C1=CC=CC=N1
inchi:    InChI=1S/C6H6N2O/c7-6(9)5-3-1-2-4-8-5/h1-4H,(H2,7,9)
inchiKey:    IBBMAWULFFBRKK-UHFFFAOYSA-N
smarts:    [#7]-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#7]:1
smarts_isomeric:    [#7]-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#7]:1

cyclopropylmethanol: OCC1CC1

smiles_non_kekule:    OCC1CC1
smiles_kekule:    OCC1CC1
inchi:    InChI=1S/C4H8O/c5-3-4-1-2-4/h4-5H,1-3H2
inchiKey:    GUDMZGLFZNLYEY-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]1-[#6]-[#6]-1
smarts_isomeric:    [#8]-[#6]-[#6]1-[#6]-[#6]-1

ethyl carbamate: NC(=O)OCC

smiles_non_kekule:    CCOC(N)=O
smiles_kekule:    CCOC(N)=O
inchi:    InChI=1S/C3H7NO2/c1-2-6-3(4)5/h2H2,1H3,(H2,4,5)
inchiKey:    JOYRKODLDBILNP-UHFFFAOYSA-N
smarts:    [#7]-[#6](=[#8])-[#8]-[#6]-[#6]
smarts_isomeric:    [#7]-[#6](=[#8])-[#8]-[#6]-[#6]

2-(diethylamino)ethan-1-ol: OCCN(CC)CC

smiles_non_kekule:    CCN(CC)CCO
smiles_kekule:    CCN(CC)CCO
inchi:    InChI=1S/C6H15NO/c1-3-7(4-2)5-6-8/h8H,3-6H2,1-2H3
inchiKey:    BFSVOASYOCHEOV-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]-[#7](-[#6]-[#6])-[#6]-[#6]
smarts_isomeric:    [#8]-[#6]-[#6]-[#7](-[#6]-[#6])-[#6]-[#6]

pyrocatechol: c1ccc(O)c(O)c1

smiles_non_kekule:    Oc1ccccc1O
smiles_kekule:    OC1=CC=CC=C1O
inchi:    InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H
inchiKey:    YCIMNLLNPGFGHC-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#8]):[#6](-[#8]):[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#8]):[#6](-[#8]):[#6]:1

acrylamide: NC(=O)C=C

smiles_non_kekule:    C=CC(N)=O
smiles_kekule:    C=CC(N)=O
inchi:    InChI=1S/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5)
inchiKey:    HRPVXLWXLXDGHG-UHFFFAOYSA-N
smarts:    [#7]-[#6](=[#8])-[#6]=[#6]
smarts_isomeric:    [#7]-[#6](=[#8])-[#6]=[#6]

azetidine: N1CCC1

smiles_non_kekule:    C1CNC1
smiles_kekule:    C1CNC1
inchi:    InChI=1S/C3H7N/c1-2-4-3-1/h4H,1-3H2
inchiKey:    HONIICLYMWZJFZ-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#6]-1

p-xylene: Cc1ccc(C)cc1

smiles_non_kekule:    Cc1ccc(C)cc1
smiles_kekule:    CC1=CC=C(C)C=C1
inchi:    InChI=1S/C8H10/c1-7-3-5-8(2)6-4-7/h3-6H,1-2H3
inchiKey:    URLKBWYHVLBVBO-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:1

1-methylpiperidin-4-ol: OC1CCN(C)CC1

smiles_non_kekule:    CN1CCC(O)CC1
smiles_kekule:    CN1CCC(O)CC1
inchi:    InChI=1S/C6H13NO/c1-7-4-2-6(8)3-5-7/h6,8H,2-5H2,1H3
inchiKey:    BAUWRHPMUVYFOD-UHFFFAOYSA-N
smarts:    [#8]-[#6]1-[#6]-[#6]-[#7](-[#6])-[#6]-[#6]-1
smarts_isomeric:    [#8]-[#6]1-[#6]-[#6]-[#7](-[#6])-[#6]-[#6]-1

4-hydrosulfonylmorpholine: S(=O)(=O)N1CCOCC1

smiles_non_kekule:    O=[SH](=O)N1CCOCC1
smiles_kekule:    O=[SH](=O)N1CCOCC1
inchi:    InChI=1S/C4H9NO3S/c6-9(7)5-1-3-8-4-2-5/h9H,1-4H2
inchiKey:    UJGSPQGOMONRFJ-UHFFFAOYSA-N
smarts:    [#16](=[#8])(=[#8])-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1
smarts_isomeric:    [#16](=[#8])(=[#8])-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1

4-methyl-1H-imidazole: Cc1c[nH]cn1

N-(pyridin-4-yl)formamide: C(=O)Nc1ccncc1

smiles_non_kekule:    O=CNc1ccncc1
smiles_kekule:    O=CNC1=CC=NC=C1
inchi:    InChI=1S/C6H6N2O/c9-5-8-6-1-3-7-4-2-6/h1-5H,(H,7,8,9)
inchiKey:    GSBXXONXMOZQSW-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]-[#6]1:[#6]:[#6]:[#7]:[#6]:[#6]:1
smarts_isomeric:    [#6](=[#8])-[#7]-[#6]1:[#6]:[#6]:[#7]:[#6]:[#6]:1

4-methoxyphenol: Oc1ccc(OC)cc1

smiles_non_kekule:    COc1ccc(O)cc1
smiles_kekule:    COC1=CC=C(O)C=C1
inchi:    InChI=1S/C7H8O2/c1-9-7-4-2-6(8)3-5-7/h2-5,8H,1H3
inchiKey:    NWVVVBRKAWDGAB-UHFFFAOYSA-N
smarts:    [#8]-[#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#8]-[#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6]:[#6]:1

fluoromethane: CF

smiles_non_kekule:    CF
smiles_kekule:    CF
inchi:    InChI=1S/CH3F/c1-2/h1H3
inchiKey:    NBVXSUQYWXRMNV-UHFFFAOYSA-N
smarts:    [#6]-[#9]
smarts_isomeric:    [#6]-[#9]

N-methylbenzamide: CNC(=O)c1ccccc1

smiles_non_kekule:    CNC(=O)c1ccccc1
smiles_kekule:    CNC(=O)C1=CC=CC=C1
inchi:    InChI=1S/C8H9NO/c1-9-8(10)7-5-3-2-4-6-7/h2-6H,1H3,(H,9,10)
inchiKey:    NCCHARWOCKOHIH-UHFFFAOYSA-N
smarts:    [#6]-[#7]-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#7]-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

pyridin-3-amine: Nc1cccnc1

smiles_non_kekule:    Nc1cccnc1
smiles_kekule:    NC1=CC=CN=C1
inchi:    InChI=1S/C5H6N2/c6-5-2-1-3-7-4-5/h1-4H,6H2
inchiKey:    CUYKNJBYIJFRCU-UHFFFAOYSA-N
smarts:    [#7]-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1
smarts_isomeric:    [#7]-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1

pyridin-4-ylmethanamine: NCc1ccncc1

smiles_non_kekule:    NCc1ccncc1
smiles_kekule:    NCC1=CC=NC=C1
inchi:    InChI=1S/C6H8N2/c7-5-6-1-3-8-4-2-6/h1-4H,5,7H2
inchiKey:    TXQWFIVRZNOPCK-UHFFFAOYSA-N
smarts:    [#7]-[#6]-[#6]1:[#6]:[#6]:[#7]:[#6]:[#6]:1
smarts_isomeric:    [#7]-[#6]-[#6]1:[#6]:[#6]:[#7]:[#6]:[#6]:1

imidazole: c1ncc[nH]1

smiles_non_kekule:    c1c[nH]cn1
smiles_kekule:    C1=CNC=N1
inchi:    InChI=1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)
inchiKey:    RAXXELZNTBOGNW-UHFFFAOYSA-N
smarts:    [#6]1:[#7]:[#6]:[#6]:[#7H]:1
smarts_isomeric:    [#6]1:[#7]:[#6]:[#6]:[#7H]:1

3-chlorophenol: Oc1cccc(Cl)c1

smiles_non_kekule:    Oc1cccc(Cl)c1
smiles_kekule:    OC1=CC=CC(Cl)=C1
inchi:    InChI=1S/C6H5ClO/c7-5-2-1-3-6(8)4-5/h1-4,8H
inchiKey:    HORNXRXVQWOLPJ-UHFFFAOYSA-N
smarts:    [#8]-[#6]1:[#6]:[#6]:[#6]:[#6](-[#17]):[#6]:1
smarts_isomeric:    [#8]-[#6]1:[#6]:[#6]:[#6]:[#6](-[#17]):[#6]:1

1-ethylurea: NC(=O)NCC

smiles_non_kekule:    CCNC(N)=O
smiles_kekule:    CCNC(N)=O
inchi:    InChI=1S/C3H8N2O/c1-2-5-3(4)6/h2H2,1H3,(H3,4,5,6)
inchiKey:    RYECOJGRJDOGPP-UHFFFAOYSA-N
smarts:    [#7]-[#6](=[#8])-[#7]-[#6]-[#6]
smarts_isomeric:    [#7]-[#6](=[#8])-[#7]-[#6]-[#6]

methyl benzoate: c1ccc(C(=O)OC)cc1

smiles_non_kekule:    COC(=O)c1ccccc1
smiles_kekule:    COC(=O)C1=CC=CC=C1
inchi:    InChI=1S/C8H8O2/c1-10-8(9)7-5-3-2-4-6-7/h2-6H,1H3
inchiKey:    QPJVMBTYPHYUOC-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#6](=[#8])-[#8]-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#6](=[#8])-[#8]-[#6]):[#6]:[#6]:1

(aminomethylene)bis(phosphonic acid): NC(P(=O)(O)O)P(=O)(O)O

smiles_non_kekule:    NC(P(=O)(O)O)P(=O)(O)O
smiles_kekule:    NC(P(=O)(O)O)P(=O)(O)O
inchi:    InChI=1S/CH7NO6P2/c2-1(9(3,4)5)10(6,7)8/h1H,2H2,(H2,3,4,5)(H2,6,7,8)
inchiKey:    FRCICXIVPRNPLM-UHFFFAOYSA-N
smarts:    [#7]-[#6](-[#15](=[#8])(-[#8])-[#8])-[#15](=[#8])(-[#8])-[#8]
smarts_isomeric:    [#7]-[#6](-[#15](=[#8])(-[#8])-[#8])-[#15](=[#8])(-[#8])-[#8]

pyridin-4-amine: Nc1ccncc1

smiles_non_kekule:    Nc1ccncc1
smiles_kekule:    NC1=CC=NC=C1
inchi:    InChI=1S/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7)
inchiKey:    NUKYPUAOHBNCPY-UHFFFAOYSA-N
smarts:    [#7]-[#6]1:[#6]:[#6]:[#7]:[#6]:[#6]:1
smarts_isomeric:    [#7]-[#6]1:[#6]:[#6]:[#7]:[#6]:[#6]:1

N-methyl-2-phenylcyclopropan-1-amine: CNC1CC1c1ccccc1

smiles_non_kekule:    CNC1CC1c1ccccc1
smiles_kekule:    CNC1CC1C1=CC=CC=C1
inchi:    InChI=1S/C10H13N/c1-11-10-7-9(10)8-5-3-2-4-6-8/h2-6,9-11H,7H2,1H3
inchiKey:    QJNGEXCJXPQCPA-UHFFFAOYSA-N
smarts:    [#6]-[#7]-[#6]1-[#6]-[#6]-1-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#7]-[#6]1-[#6]-[#6]-1-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

5-methoxy-3-methyl-1,3,4-oxadiazol-2(3H)-one: Cn1nc(OC)oc1=O

smiles_non_kekule:    COc1nn(C)c(=O)o1
smiles_kekule:    COC1=NN(C)C(=O)O1
inchi:    InChI=1S/C4H6N2O3/c1-6-4(7)9-3(5-6)8-2/h1-2H3
inchiKey:    VKPBSYCXLIMEIM-UHFFFAOYSA-N
smarts:    [#6]-[#7]1:[#7]:[#6](-[#8]-[#6]):[#8]:[#6]:1=[#8]
smarts_isomeric:    [#6]-[#7]1:[#7]:[#6](-[#8]-[#6]):[#8]:[#6]:1=[#8]

(methylsulfonyl)methane: CS(C)(=O)=O

smiles_non_kekule:    CS(C)(=O)=O
smiles_kekule:    CS(C)(=O)=O
inchi:    InChI=1S/C2H6O2S/c1-5(2,3)4/h1-2H3
inchiKey:    HHVIBTZHLRERCL-UHFFFAOYSA-N
smarts:    [#6]-[#16](-[#6])(=[#8])=[#8]
smarts_isomeric:    [#6]-[#16](-[#6])(=[#8])=[#8]

1-(piperidin-1-yl)ethan-1-one: C1CCN(C(C)=O)CC1

smiles_non_kekule:    CC(=O)N1CCCCC1
smiles_kekule:    CC(=O)N1CCCCC1
inchi:    InChI=1S/C7H13NO/c1-7(9)8-5-3-2-4-6-8/h2-6H2,1H3
inchiKey:    KDISMIMTGUMORD-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#7](-[#6](-[#6])=[#8])-[#6]-[#6]-1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#7](-[#6](-[#6])=[#8])-[#6]-[#6]-1

methyl acetate: CC(=O)OC

smiles_non_kekule:    COC(C)=O
smiles_kekule:    COC(C)=O
inchi:    InChI=1S/C3H6O2/c1-3(4)5-2/h1-2H3
inchiKey:    KXKVLQRXCPHEJC-UHFFFAOYSA-N
smarts:    [#6]-[#6](=[#8])-[#8]-[#6]
smarts_isomeric:    [#6]-[#6](=[#8])-[#8]-[#6]

4-chlorophenol: Oc1ccc(Cl)cc1

smiles_non_kekule:    Oc1ccc(Cl)cc1
smiles_kekule:    OC1=CC=C(Cl)C=C1
inchi:    InChI=1S/C6H5ClO/c7-5-1-3-6(8)4-2-5/h1-4,8H
inchiKey:    WXNZTHHGJRFXKQ-UHFFFAOYSA-N
smarts:    [#8]-[#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1
smarts_isomeric:    [#8]-[#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1

ethane-1,2-diamine: NCCN

smiles_non_kekule:    NCCN
smiles_kekule:    NCCN
inchi:    InChI=1S/C2H8N2/c3-1-2-4/h1-4H2
inchiKey:    PIICEJLVQHRZGT-UHFFFAOYSA-N
smarts:    [#7]-[#6]-[#6]-[#7]
smarts_isomeric:    [#7]-[#6]-[#6]-[#7]

4-methylpiperidine: N1CCC(C)CC1

smiles_non_kekule:    CC1CCNCC1
smiles_kekule:    CC1CCNCC1
inchi:    InChI=1S/C6H13N/c1-6-2-4-7-5-3-6/h6-7H,2-5H2,1H3
inchiKey:    UZOFELREXGAFOI-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#6](-[#6])-[#6]-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#6](-[#6])-[#6]-[#6]-1

benzyl formate: C(=O)OCc1ccccc1

smiles_non_kekule:    O=COCc1ccccc1
smiles_kekule:    O=COCC1=CC=CC=C1
inchi:    InChI=1S/C8H8O2/c9-7-10-6-8-4-2-1-3-5-8/h1-5,7H,6H2
inchiKey:    UYWQUFXKFGHYNT-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#8]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6](=[#8])-[#8]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

N,N-dimethylsulfonic amide: S(=O)(=O)N(C)C

smiles_non_kekule:    CN(C)[SH](=O)=O
smiles_kekule:    CN(C)[SH](=O)=O
inchi:    InChI=1S/C2H7NO2S/c1-3(2)6(4)5/h6H,1-2H3
inchiKey:    LVRCEUVOXCJYSV-UHFFFAOYSA-N
smarts:    [#16](=[#8])(=[#8])-[#7](-[#6])-[#6]
smarts_isomeric:    [#16](=[#8])(=[#8])-[#7](-[#6])-[#6]

4-methoxybenzaldehyde: C(=O)c1ccc(OC)cc1

smiles_non_kekule:    COc1ccc(C=O)cc1
smiles_kekule:    COC1=CC=C(C=O)C=C1
inchi:    InChI=1S/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3
inchiKey:    ZRSNZINYAWTAHE-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#6](=[#8])-[#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6]:[#6]:1

N-hydroxyacetamide: CC(=O)NO

smiles_non_kekule:    CC(=O)NO
smiles_kekule:    CC(=O)NO
inchi:    InChI=1S/C2H5NO2/c1-2(4)3-5/h5H,1H3,(H,3,4)
inchiKey:    RRUDCFGSUDOHDG-UHFFFAOYSA-N
smarts:    [#6]-[#6](=[#8])-[#7]-[#8]
smarts_isomeric:    [#6]-[#6](=[#8])-[#7]-[#8]

2-fluoroethan-1-ol: OCCF

smiles_non_kekule:    OCCF
smiles_kekule:    OCCF
inchi:    InChI=1S/C2H5FO/c3-1-2-4/h4H,1-2H2
inchiKey:    GGDYAKVUZMZKRV-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]-[#9]
smarts_isomeric:    [#8]-[#6]-[#6]-[#9]

2-aminobenzamide: Nc1ccccc1C(N)=O

smiles_non_kekule:    NC(=O)c1ccccc1N
smiles_kekule:    NC(=O)C1=CC=CC=C1N
inchi:    InChI=1S/C7H8N2O/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H2,9,10)
inchiKey:    PXBFMLJZNCDSMP-UHFFFAOYSA-N
smarts:    [#7]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6](-[#7])=[#8]
smarts_isomeric:    [#7]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6](-[#7])=[#8]

N-hydroxypropionamide: CCC(=O)NO

smiles_non_kekule:    CCC(=O)NO
smiles_kekule:    CCC(=O)NO
inchi:    InChI=1S/C3H7NO2/c1-2-3(5)4-6/h6H,2H2,1H3,(H,4,5)
inchiKey:    RSIPQHOWTCNEBI-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#7]-[#8]
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#7]-[#8]

2H-tetrazole: c1nn[nH]n1

smiles_non_kekule:    c1nn[nH]n1
smiles_kekule:    C1=NNN=N1
inchi:    InChI=1S/CH2N4/c1-2-4-5-3-1/h1H,(H,2,3,4,5)
inchiKey:    KJUGUADJHNHALS-UHFFFAOYSA-N
smarts:    [#6]1:[#7]:[#7]:[#7H]:[#7]:1
smarts_isomeric:    [#6]1:[#7]:[#7]:[#7H]:[#7]:1

prop-2-yn-1-ol: OCC#C

smiles_non_kekule:    C#CCO
smiles_kekule:    C#CCO
inchi:    InChI=1S/C3H4O/c1-2-3-4/h1,4H,3H2
inchiKey:    TVDSBUOJIPERQY-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]#[#6]
smarts_isomeric:    [#8]-[#6]-[#6]#[#6]

piperidin-4-ylmethanol: N1CCC(CO)CC1

smiles_non_kekule:    OCC1CCNCC1
smiles_kekule:    OCC1CCNCC1
inchi:    InChI=1S/C6H13NO/c8-5-6-1-3-7-4-2-6/h6-8H,1-5H2
inchiKey:    XBXHCBLBYQEYTI-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#6](-[#6]-[#8])-[#6]-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#6](-[#6]-[#8])-[#6]-[#6]-1

3-ethynylpyridine: C#Cc1cccnc1

smiles_non_kekule:    C#Cc1cccnc1
smiles_kekule:    C#CC1=CC=CN=C1
inchi:    InChI=1S/C7H5N/c1-2-7-4-3-5-8-6-7/h1,3-6H
inchiKey:    CLRPXACRDTXENY-UHFFFAOYSA-N
smarts:    [#6]#[#6]-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1
smarts_isomeric:    [#6]#[#6]-[#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1

4-chlorobenzaldehyde: C(=O)c1ccc(Cl)cc1

smiles_non_kekule:    O=Cc1ccc(Cl)cc1
smiles_kekule:    O=CC1=CC=C(Cl)C=C1
inchi:    InChI=1S/C7H5ClO/c8-7-3-1-6(5-9)2-4-7/h1-5H
inchiKey:    AVPYQKSLYISFPO-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1
smarts_isomeric:    [#6](=[#8])-[#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1

methylphosphonic acid: CP(=O)(O)O

smiles_non_kekule:    CP(=O)(O)O
smiles_kekule:    CP(=O)(O)O
inchi:    InChI=1S/CH5O3P/c1-5(2,3)4/h1H3,(H2,2,3,4)
inchiKey:    YACKEPLHDIMKIO-UHFFFAOYSA-N
smarts:    [#6]-[#15](=[#8])(-[#8])-[#8]
smarts_isomeric:    [#6]-[#15](=[#8])(-[#8])-[#8]

isobutyramide: NC(=O)C(C)C

smiles_non_kekule:    CC(C)C(N)=O
smiles_kekule:    CC(C)C(N)=O
inchi:    InChI=1S/C4H9NO/c1-3(2)4(5)6/h3H,1-2H3,(H2,5,6)
inchiKey:    WFKAJVHLWXSISD-UHFFFAOYSA-N
smarts:    [#7]-[#6](=[#8])-[#6](-[#6])-[#6]
smarts_isomeric:    [#7]-[#6](=[#8])-[#6](-[#6])-[#6]

cyclopropylmethanamine: NCC1CC1

smiles_non_kekule:    NCC1CC1
smiles_kekule:    NCC1CC1
inchi:    InChI=1S/C4H9N/c5-3-4-1-2-4/h4H,1-3,5H2
inchiKey:    IGSKHXTUVXSOMB-UHFFFAOYSA-N
smarts:    [#7]-[#6]-[#6]1-[#6]-[#6]-1
smarts_isomeric:    [#7]-[#6]-[#6]1-[#6]-[#6]-1

N,N-dimethylpyrrolidin-3-amine: N1CCC(N(C)C)C1

smiles_non_kekule:    CN(C)C1CCNC1
smiles_kekule:    CN(C)C1CCNC1
inchi:    InChI=1S/C6H14N2/c1-8(2)6-3-4-7-5-6/h6-7H,3-5H2,1-2H3
inchiKey:    AVAWMINJNRAQFS-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#6](-[#7](-[#6])-[#6])-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#6](-[#7](-[#6])-[#6])-[#6]-1

4,5-dihydrooxazol-2-amine: C1COC(N)=N1

smiles_non_kekule:    NC1=NCCO1
smiles_kekule:    NC1=NCCO1
inchi:    InChI=1S/C3H6N2O/c4-3-5-1-2-6-3/h1-2H2,(H2,4,5)
inchiKey:    YAXGBZDYGZBRBQ-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#8]-[#6](-[#7])=[#7]-1
smarts_isomeric:    [#6]1-[#6]-[#8]-[#6](-[#7])=[#7]-1

1,2,3,4-tetrahydroisoquinoline: N1CCc2ccccc2C1

smiles_non_kekule:    c1ccc2c(c1)CCNC2
smiles_kekule:    C1=CC=C2CNCCC2=C1
inchi:    InChI=1S/C9H11N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-4,10H,5-7H2
inchiKey:    UWYZHKAOTLEWKK-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2-[#6]-1

4-phenylmorpholine: c1ccc(N2CCOCC2)cc1

smiles_non_kekule:    c1ccc(N2CCOCC2)cc1
smiles_kekule:    C1=CC=C(N2CCOCC2)C=C1
inchi:    InChI=1S/C10H13NO/c1-2-4-10(5-3-1)11-6-8-12-9-7-11/h1-5H,6-9H2
inchiKey:    FHQRDEDZJIFJAL-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#7]2-[#6]-[#6]-[#8]-[#6]-[#6]-2):[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#7]2-[#6]-[#6]-[#8]-[#6]-[#6]-2):[#6]:[#6]:1

4,5-dihydro-1H-imidazole: C1=NCCN1

smiles_non_kekule:    C1=NCCN1
smiles_kekule:    C1=NCCN1
inchi:    InChI=1S/C3H6N2/c1-2-5-3-4-1/h3H,1-2H2,(H,4,5)
inchiKey:    MTNDZQHUAFNZQY-UHFFFAOYSA-N
smarts:    [#6]1=[#7]-[#6]-[#6]-[#7]-1
smarts_isomeric:    [#6]1=[#7]-[#6]-[#6]-[#7]-1

3-aminopropan-1-ol: NCCCO

smiles_non_kekule:    NCCCO
smiles_kekule:    NCCCO
inchi:    InChI=1S/C3H9NO/c4-2-1-3-5/h5H,1-4H2
inchiKey:    WUGQZFFCHPXWKQ-UHFFFAOYSA-N
smarts:    [#7]-[#6]-[#6]-[#6]-[#8]
smarts_isomeric:    [#7]-[#6]-[#6]-[#6]-[#8]

2,2,2-trifluoroacetaldehyde: C(=O)C(F)(F)F

smiles_non_kekule:    O=CC(F)(F)F
smiles_kekule:    O=CC(F)(F)F
inchi:    InChI=1S/C2HF3O/c3-2(4,5)1-6/h1H
inchiKey:    JVTSHOJDBRTPHD-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#6](-[#9])(-[#9])-[#9]
smarts_isomeric:    [#6](=[#8])-[#6](-[#9])(-[#9])-[#9]

trifluoromethanethiol: SC(F)(F)F

smiles_non_kekule:    FC(F)(F)S
smiles_kekule:    FC(F)(F)S
inchi:    InChI=1S/CHF3S/c2-1(3,4)5/h5H
inchiKey:    MFLLMKMFWIUACU-UHFFFAOYSA-N
smarts:    [#16]-[#6](-[#9])(-[#9])-[#9]
smarts_isomeric:    [#16]-[#6](-[#9])(-[#9])-[#9]

N-ethylacetamide: CCNC(C)=O

smiles_non_kekule:    CCNC(C)=O
smiles_kekule:    CCNC(C)=O
inchi:    InChI=1S/C4H9NO/c1-3-5-4(2)6/h3H2,1-2H3,(H,5,6)
inchiKey:    PMDCZENCAXMSOU-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7]-[#6](-[#6])=[#8]
smarts_isomeric:    [#6]-[#6]-[#7]-[#6](-[#6])=[#8]

N-methylaniline: N(C)c1ccccc1

smiles_non_kekule:    CNc1ccccc1
smiles_kekule:    CNC1=CC=CC=C1
inchi:    InChI=1S/C7H9N/c1-8-7-5-3-2-4-6-7/h2-6,8H,1H3
inchiKey:    AFBPFSWMIHJQDM-UHFFFAOYSA-N
smarts:    [#7](-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#7](-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

phenylmethanethiol: SCc1ccccc1

smiles_non_kekule:    SCc1ccccc1
smiles_kekule:    SCC1=CC=CC=C1
inchi:    InChI=1S/C7H8S/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2
inchiKey:    UENWRTRMUIOCKN-UHFFFAOYSA-N
smarts:    [#16]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#16]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

4-(pyrrolidin-1-yl)piperidine: N1CCC(N2CCCC2)CC1

smiles_non_kekule:    C1CCN(C2CCNCC2)C1
smiles_kekule:    C1CCN(C2CCNCC2)C1
inchi:    InChI=1S/C9H18N2/c1-2-8-11(7-1)9-3-5-10-6-4-9/h9-10H,1-8H2
inchiKey:    STWODXDTKGTVCJ-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#6](-[#7]2-[#6]-[#6]-[#6]-[#6]-2)-[#6]-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#6](-[#7]2-[#6]-[#6]-[#6]-[#6]-2)-[#6]-[#6]-1

4-(trifluoromethyl)pyrimidine: c1nccc(C(F)(F)F)n1

smiles_non_kekule:    FC(F)(F)c1ccncn1
smiles_kekule:    FC(F)(F)C1=NC=NC=C1
inchi:    InChI=1S/C5H3F3N2/c6-5(7,8)4-1-2-9-3-10-4/h1-3H
inchiKey:    BKDUWMJFLCNPKP-UHFFFAOYSA-N
smarts:    [#6]1:[#7]:[#6]:[#6]:[#6](-[#6](-[#9])(-[#9])-[#9]):[#7]:1
smarts_isomeric:    [#6]1:[#7]:[#6]:[#6]:[#6](-[#6](-[#9])(-[#9])-[#9]):[#7]:1

1-methoxy-3-methylbenzene: Cc1cccc(OC)c1

smiles_non_kekule:    COc1cccc(C)c1
smiles_kekule:    COC1=CC(C)=CC=C1
inchi:    InChI=1S/C8H10O/c1-7-4-3-5-8(6-7)9-2/h3-6H,1-2H3
inchiKey:    OSIGJGFTADMDOB-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6](-[#8]-[#6]):[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6](-[#8]-[#6]):[#6]:1

N-butylformamide: C(=O)NCCCC

smiles_non_kekule:    CCCCNC=O
smiles_kekule:    CCCCNC=O
inchi:    InChI=1S/C5H11NO/c1-2-3-4-6-5-7/h5H,2-4H2,1H3,(H,6,7)
inchiKey:    QQGNLKJAIVSNCO-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]-[#6]-[#6]-[#6]-[#6]
smarts_isomeric:    [#6](=[#8])-[#7]-[#6]-[#6]-[#6]-[#6]

2,2,2-trifluoroethan-1-ol: OCC(F)(F)F

smiles_non_kekule:    OCC(F)(F)F
smiles_kekule:    OCC(F)(F)F
inchi:    InChI=1S/C2H3F3O/c3-2(4,5)1-6/h6H,1H2
inchiKey:    RHQDFWAXVIIEBN-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6](-[#9])(-[#9])-[#9]
smarts_isomeric:    [#8]-[#6]-[#6](-[#9])(-[#9])-[#9]

p-toluidine: Nc1ccc(C)cc1

smiles_non_kekule:    Cc1ccc(N)cc1
smiles_kekule:    CC1=CC=C(N)C=C1
inchi:    InChI=1S/C7H9N/c1-6-2-4-7(8)5-3-6/h2-5H,8H2,1H3
inchiKey:    RZXMPPFPUUCRFN-UHFFFAOYSA-N
smarts:    [#7]-[#6]1:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#7]-[#6]1:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:1

1,3-dimethoxybenzene: c1cc(OC)cc(OC)c1

smiles_non_kekule:    COc1cccc(OC)c1
smiles_kekule:    COC1=CC(OC)=CC=C1
inchi:    InChI=1S/C8H10O2/c1-9-7-4-3-5-8(6-7)10-2/h3-6H,1-2H3
inchiKey:    DPZNOMCNRMUKPS-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6](-[#8]-[#6]):[#6]:[#6](-[#8]-[#6]):[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6](-[#8]-[#6]):[#6]:[#6](-[#8]-[#6]):[#6]:1

N,N-dimethyl-1-phenylmethanamine: CN(C)Cc1ccccc1

smiles_non_kekule:    CN(C)Cc1ccccc1
smiles_kekule:    CN(C)CC1=CC=CC=C1
inchi:    InChI=1S/C9H13N/c1-10(2)8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H3
inchiKey:    XXBDWLFCJWSEKW-UHFFFAOYSA-N
smarts:    [#6]-[#7](-[#6])-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#7](-[#6])-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

2-methylnaphthalene: Cc1ccc2ccccc2c1

smiles_non_kekule:    Cc1ccc2ccccc2c1
smiles_kekule:    CC1=CC=C2C=CC=CC2=C1
inchi:    InChI=1S/C11H10/c1-9-6-7-10-4-2-3-5-11(10)8-9/h2-8H,1H3
inchiKey:    QIMMUPPBPVKWKM-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#6]:1

tetrahydrofuran: C1CCCO1

smiles_non_kekule:    C1CCOC1
smiles_kekule:    C1CCOC1
inchi:    InChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2
inchiKey:    WYURNTSHIVDZCO-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#6]-[#8]-1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#6]-[#8]-1

acrylic acid: C=CC(=O)O

smiles_non_kekule:    C=CC(=O)O
smiles_kekule:    C=CC(=O)O
inchi:    InChI=1S/C3H4O2/c1-2-3(4)5/h2H,1H2,(H,4,5)
inchiKey:    NIXOWILDQLNWCW-UHFFFAOYSA-N
smarts:    [#6]=[#6]-[#6](=[#8])-[#8]
smarts_isomeric:    [#6]=[#6]-[#6](=[#8])-[#8]

2-(methylamino)ethan-1-ol: CNCCO

smiles_non_kekule:    CNCCO
smiles_kekule:    CNCCO
inchi:    InChI=1S/C3H9NO/c1-4-2-3-5/h4-5H,2-3H2,1H3
inchiKey:    OPKOKAMJFNKNAS-UHFFFAOYSA-N
smarts:    [#6]-[#7]-[#6]-[#6]-[#8]
smarts_isomeric:    [#6]-[#7]-[#6]-[#6]-[#8]

4-methylbenzaldehyde: C(=O)c1ccc(C)cc1

smiles_non_kekule:    Cc1ccc(C=O)cc1
smiles_kekule:    CC1=CC=C(C=O)C=C1
inchi:    InChI=1S/C8H8O/c1-7-2-4-8(6-9)5-3-7/h2-6H,1H3
inchiKey:    FXLOVSHXALFLKQ-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#6]1:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#6](=[#8])-[#6]1:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:1

3,4-dimethyl-1H-pyrazole-5-carboxylic acid: Cc1c(C)n[nH]c1C(=O)O

smiles_non_kekule:    Cc1n[nH]c(C(=O)O)c1C
smiles_kekule:    CC1=NNC(C(=O)O)=C1C
inchi:    InChI=1S/C6H8N2O2/c1-3-4(2)7-8-5(3)6(9)10/h1-2H3,(H,7,8)(H,9,10)
inchiKey:    URZZLPLGTZFNST-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6](-[#6]):[#7]:[#7H]:[#6]:1-[#6](=[#8])-[#8]
smarts_isomeric:    [#6]-[#6]1:[#6](-[#6]):[#7]:[#7H]:[#6]:1-[#6](=[#8])-[#8]

chloromethane: CCl

smiles_non_kekule:    CCl
smiles_kekule:    CCl
inchi:    InChI=1S/CH3Cl/c1-2/h1H3
inchiKey:    NEHMKBQYUWJMIP-UHFFFAOYSA-N
smarts:    [#6]-[#17]
smarts_isomeric:    [#6]-[#17]

butyramide: NC(=O)CCC

smiles_non_kekule:    CCCC(N)=O
smiles_kekule:    CCCC(N)=O
inchi:    InChI=1S/C4H9NO/c1-2-3-4(5)6/h2-3H2,1H3,(H2,5,6)
inchiKey:    DNSISZSEWVHGLH-UHFFFAOYSA-N
smarts:    [#7]-[#6](=[#8])-[#6]-[#6]-[#6]
smarts_isomeric:    [#7]-[#6](=[#8])-[#6]-[#6]-[#6]

1-chloro-4-hydrosulfonylbenzene: S(=O)(=O)c1ccc(Cl)cc1

smiles_non_kekule:    O=[SH](=O)c1ccc(Cl)cc1
smiles_kekule:    O=[SH](=O)C1=CC=C(Cl)C=C1
inchi:    InChI=1S/C6H5ClO2S/c7-5-1-3-6(4-2-5)10(8)9/h1-4,10H
inchiKey:    KYJLSJMYBCZTFZ-UHFFFAOYSA-N
smarts:    [#16](=[#8])(=[#8])-[#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1
smarts_isomeric:    [#16](=[#8])(=[#8])-[#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1

difluoromethane: C(F)F

smiles_non_kekule:    FCF
smiles_kekule:    FCF
inchi:    InChI=1S/CH2F2/c2-1-3/h1H2
inchiKey:    RWRIWBAIICGTTQ-UHFFFAOYSA-N
smarts:    [#6](-[#9])-[#9]
smarts_isomeric:    [#6](-[#9])-[#9]

3-(pyrrolidin-1-yl)propan-1-ol: OCCCN1CCCC1

smiles_non_kekule:    OCCCN1CCCC1
smiles_kekule:    OCCCN1CCCC1
inchi:    InChI=1S/C7H15NO/c9-7-3-6-8-4-1-2-5-8/h9H,1-7H2
inchiKey:    ZMJQROKRSPSLFH-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#8]-[#6]-[#6]-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-1

cyclopropylbenzene: C1CC1c1ccccc1

smiles_non_kekule:    c1ccc(C2CC2)cc1
smiles_kekule:    C1=CC=C(C2CC2)C=C1
inchi:    InChI=1S/C9H10/c1-2-4-8(5-3-1)9-6-7-9/h1-5,9H,6-7H2
inchiKey:    VFSFCYAQBIPUSL-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-1-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1-[#6]-[#6]-1-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

cumene: c1ccc(C(C)C)cc1

smiles_non_kekule:    CC(C)c1ccccc1
smiles_kekule:    CC(C)C1=CC=CC=C1
inchi:    InChI=1S/C9H12/c1-8(2)9-6-4-3-5-7-9/h3-8H,1-2H3
inchiKey:    RWGFKTVRMDUZSP-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#6](-[#6])-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#6](-[#6])-[#6]):[#6]:[#6]:1

2-methyltetrahydrofuran: CC1CCCO1

smiles_non_kekule:    CC1CCCO1
smiles_kekule:    CC1CCCO1
inchi:    InChI=1S/C5H10O/c1-5-3-2-4-6-5/h5H,2-4H2,1H3
inchiKey:    JWUJQDFVADABEY-UHFFFAOYSA-N
smarts:    [#6]-[#6]1-[#6]-[#6]-[#6]-[#8]-1
smarts_isomeric:    [#6]-[#6]1-[#6]-[#6]-[#6]-[#8]-1

N-methylpropan-2-amine: CNC(C)C

smiles_non_kekule:    CNC(C)C
smiles_kekule:    CNC(C)C
inchi:    InChI=1S/C4H11N/c1-4(2)5-3/h4-5H,1-3H3
inchiKey:    XHFGWHUWQXTGAT-UHFFFAOYSA-N
smarts:    [#6]-[#7]-[#6](-[#6])-[#6]
smarts_isomeric:    [#6]-[#7]-[#6](-[#6])-[#6]

alanine: CC(N)C(=O)O

smiles_non_kekule:    CC(N)C(=O)O
smiles_kekule:    CC(N)C(=O)O
inchi:    InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)
inchiKey:    QNAYBMKLOCPYGJ-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#7])-[#6](=[#8])-[#8]
smarts_isomeric:    [#6]-[#6](-[#7])-[#6](=[#8])-[#8]

1,2,3,6-tetrahydropyridine: C1=CCNCC1

smiles_non_kekule:    C1=CCNCC1
smiles_kekule:    C1=CCNCC1
inchi:    InChI=1S/C5H9N/c1-2-4-6-5-3-1/h1-2,6H,3-5H2
inchiKey:    FTAHXMZRJCZXDL-UHFFFAOYSA-N
smarts:    [#6]1=[#6]-[#6]-[#7]-[#6]-[#6]-1
smarts_isomeric:    [#6]1=[#6]-[#6]-[#7]-[#6]-[#6]-1

2-(trifluoromethyl)pyridine: c1ccc(C(F)(F)F)nc1

smiles_non_kekule:    FC(F)(F)c1ccccn1
smiles_kekule:    FC(F)(F)C1=CC=CC=N1
inchi:    InChI=1S/C6H4F3N/c7-6(8,9)5-3-1-2-4-10-5/h1-4H
inchiKey:    ATRQECRSCHYSNP-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#6](-[#9])(-[#9])-[#9]):[#7]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#6](-[#9])(-[#9])-[#9]):[#7]:[#6]:1

hydroquinone: Oc1ccc(O)cc1

smiles_non_kekule:    Oc1ccc(O)cc1
smiles_kekule:    OC1=CC=C(O)C=C1
inchi:    InChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H
inchiKey:    QIGBRXMKCJKVMJ-UHFFFAOYSA-N
smarts:    [#8]-[#6]1:[#6]:[#6]:[#6](-[#8]):[#6]:[#6]:1
smarts_isomeric:    [#8]-[#6]1:[#6]:[#6]:[#6](-[#8]):[#6]:[#6]:1

4-fluoroaniline: Nc1ccc(F)cc1

smiles_non_kekule:    Nc1ccc(F)cc1
smiles_kekule:    NC1=CC=C(F)C=C1
inchi:    InChI=1S/C6H6FN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2
inchiKey:    KRZCOLNOCZKSDF-UHFFFAOYSA-N
smarts:    [#7]-[#6]1:[#6]:[#6]:[#6](-[#9]):[#6]:[#6]:1
smarts_isomeric:    [#7]-[#6]1:[#6]:[#6]:[#6](-[#9]):[#6]:[#6]:1

1-fluoro-2-methoxybenzene: c1ccc(OC)c(F)c1

smiles_non_kekule:    COc1ccccc1F
smiles_kekule:    COC1=CC=CC=C1F
inchi:    InChI=1S/C7H7FO/c1-9-7-5-3-2-4-6(7)8/h2-5H,1H3
inchiKey:    JIXDOBAQOWOUPA-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6](-[#9]):[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6](-[#9]):[#6]:1

2-ethylidenehydrazine-1-carbothioamide: C(C)=NNC(N)=S

smiles_non_kekule:    CC=NNC(N)=S
smiles_kekule:    CC=NNC(N)=S
inchi:    InChI=1S/C3H7N3S/c1-2-5-6-3(4)7/h2H,1H3,(H3,4,6,7)
inchiKey:    OOPAKHKIEGNKDU-UHFFFAOYSA-N
smarts:    [#6](-[#6])=[#7]-[#7]-[#6](-[#7])=[#16]
smarts_isomeric:    [#6](-[#6])=[#7]-[#7]-[#6](-[#7])=[#16]

furan-2-carbaldehyde: C(=O)c1ccco1

smiles_non_kekule:    O=Cc1ccco1
smiles_kekule:    O=CC1=CC=CO1
inchi:    InChI=1S/C5H4O2/c6-4-5-2-1-3-7-5/h1-4H
inchiKey:    HYBBIBNJHNGZAN-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#8]:1
smarts_isomeric:    [#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#8]:1

butan-1-amine: NCCCC

smiles_non_kekule:    CCCCN
smiles_kekule:    CCCCN
inchi:    InChI=1S/C4H11N/c1-2-3-4-5/h2-5H2,1H3
inchiKey:    HQABUPZFAYXKJW-UHFFFAOYSA-N
smarts:    [#7]-[#6]-[#6]-[#6]-[#6]
smarts_isomeric:    [#7]-[#6]-[#6]-[#6]-[#6]

triaza-1,2-dien-2-ium: N=[N+]=N

smiles_non_kekule:    N=[N+]=N
smiles_kekule:    N=[N+]=N
inchi:    InChI=1S/H2N3/c1-3-2/h1-2H/q+1
inchiKey:    NZAJTENBEYCLTR-UHFFFAOYSA-N
smarts:    [#7]=[#7+]=[#7]
smarts_isomeric:    [#7]=[#7+]=[#7]

pyridin-2-ylmethanol: OCc1ccccn1

smiles_non_kekule:    OCc1ccccn1
smiles_kekule:    OCC1=CC=CC=N1
inchi:    InChI=1S/C6H7NO/c8-5-6-3-1-2-4-7-6/h1-4,8H,5H2
inchiKey:    SHNUBALDGXWUJI-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#7]:1
smarts_isomeric:    [#8]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#7]:1

resorcinol: c1cc(O)cc(O)c1

smiles_non_kekule:    Oc1cccc(O)c1
smiles_kekule:    OC1=CC(O)=CC=C1
inchi:    InChI=1S/C6H6O2/c7-5-2-1-3-6(8)4-5/h1-4,7-8H
inchiKey:    GHMLBKRAJCXXBS-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6](-[#8]):[#6]:[#6](-[#8]):[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6](-[#8]):[#6]:[#6](-[#8]):[#6]:1

piperidin-3-ol: N1CCCC(O)C1

smiles_non_kekule:    OC1CCCNC1
smiles_kekule:    OC1CCCNC1
inchi:    InChI=1S/C5H11NO/c7-5-2-1-3-6-4-5/h5-7H,1-4H2
inchiKey:    BIWOSRSKDCZIFM-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#6]-[#6](-[#8])-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#6]-[#6](-[#8])-[#6]-1

cyclopropanecarboxamide: NC(=O)C1CC1

smiles_non_kekule:    NC(=O)C1CC1
smiles_kekule:    NC(=O)C1CC1
inchi:    InChI=1S/C4H7NO/c5-4(6)3-1-2-3/h3H,1-2H2,(H2,5,6)
inchiKey:    AIMMVWOEOZMVMS-UHFFFAOYSA-N
smarts:    [#7]-[#6](=[#8])-[#6]1-[#6]-[#6]-1
smarts_isomeric:    [#7]-[#6](=[#8])-[#6]1-[#6]-[#6]-1

1-methyl-1H-1,2,4-triazole: Cn1cncn1

smiles_non_kekule:    Cn1cncn1
smiles_kekule:    CN1C=NC=N1
inchi:    InChI=1S/C3H5N3/c1-6-3-4-2-5-6/h2-3H,1H3
inchiKey:    MWZDIEIXRBWPLG-UHFFFAOYSA-N
smarts:    [#6]-[#7]1:[#6]:[#7]:[#6]:[#7]:1
smarts_isomeric:    [#6]-[#7]1:[#6]:[#7]:[#6]:[#7]:1

4-chlorobenzene-1,2-diol: Oc1ccc(Cl)cc1O

smiles_non_kekule:    Oc1ccc(Cl)cc1O
smiles_kekule:    OC1=CC=C(Cl)C=C1O
inchi:    InChI=1S/C6H5ClO2/c7-4-1-2-5(8)6(9)3-4/h1-3,8-9H
inchiKey:    WWOBYPKUYODHDG-UHFFFAOYSA-N
smarts:    [#8]-[#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1-[#8]
smarts_isomeric:    [#8]-[#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1-[#8]

N-methyl-1-phenylmethanamine: N(C)Cc1ccccc1

smiles_non_kekule:    CNCc1ccccc1
smiles_kekule:    CNCC1=CC=CC=C1
inchi:    InChI=1S/C8H11N/c1-9-7-8-5-3-2-4-6-8/h2-6,9H,7H2,1H3
inchiKey:    RIWRFSMVIUAEBX-UHFFFAOYSA-N
smarts:    [#7](-[#6])-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#7](-[#6])-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

pyrazin-2-amine: c1cnc(N)cn1

smiles_non_kekule:    Nc1cnccn1
smiles_kekule:    NC1=NC=CN=C1
inchi:    InChI=1S/C4H5N3/c5-4-3-6-1-2-7-4/h1-3H,(H2,5,7)
inchiKey:    XFTQRUTUGRCSGO-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#7]:[#6](-[#7]):[#6]:[#7]:1
smarts_isomeric:    [#6]1:[#6]:[#7]:[#6](-[#7]):[#6]:[#7]:1

thiophen-2-ylmethanamine: NCc1cccs1

smiles_non_kekule:    NCc1cccs1
smiles_kekule:    NCC1=CC=CS1
inchi:    InChI=1S/C5H7NS/c6-4-5-2-1-3-7-5/h1-3H,4,6H2
inchiKey:    FKKJJPMGAWGYPN-UHFFFAOYSA-N
smarts:    [#7]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#16]:1
smarts_isomeric:    [#7]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#16]:1

2-morpholinoethan-1-amine: NCCN1CCOCC1

smiles_non_kekule:    NCCN1CCOCC1
smiles_kekule:    NCCN1CCOCC1
inchi:    InChI=1S/C6H14N2O/c7-1-2-8-3-5-9-6-4-8/h1-7H2
inchiKey:    RWIVICVCHVMHMU-UHFFFAOYSA-N
smarts:    [#7]-[#6]-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1
smarts_isomeric:    [#7]-[#6]-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1

thiomorpholine 1,1-dioxide: N1CCS(=O)(=O)CC1

smiles_non_kekule:    O=S1(=O)CCNCC1
smiles_kekule:    O=S1(=O)CCNCC1
inchi:    InChI=1S/C4H9NO2S/c6-8(7)3-1-5-2-4-8/h5H,1-4H2
inchiKey:    NDOVLWQBFFJETK-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#16](=[#8])(=[#8])-[#6]-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#16](=[#8])(=[#8])-[#6]-[#6]-1

2-isopropoxypyridine: c1ccc(OC(C)C)nc1

smiles_non_kekule:    CC(C)Oc1ccccn1
smiles_kekule:    CC(C)OC1=CC=CC=N1
inchi:    InChI=1S/C8H11NO/c1-7(2)10-8-5-3-4-6-9-8/h3-7H,1-2H3
inchiKey:    IFZZDINNCWFGEO-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#8]-[#6](-[#6])-[#6]):[#7]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#8]-[#6](-[#6])-[#6]):[#7]:[#6]:1

pyridazine: c1ccnnc1

smiles_non_kekule:    c1ccnnc1
smiles_kekule:    C1=CC=NN=C1
inchi:    InChI=1S/C4H4N2/c1-2-4-6-5-3-1/h1-4H
inchiKey:    PBMFSQRYOILNGV-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#7]:[#7]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#7]:[#7]:[#6]:1

3-fluoropyridine: c1ccc(F)cn1

smiles_non_kekule:    Fc1cccnc1
smiles_kekule:    FC1=CC=CN=C1
inchi:    InChI=1S/C5H4FN/c6-5-2-1-3-7-4-5/h1-4H
inchiKey:    CELKOWQJPVJKIL-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#9]):[#6]:[#7]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#9]):[#6]:[#7]:1

isoquinoline: c1cncc2ccccc12

smiles_non_kekule:    c1ccc2cnccc2c1
smiles_kekule:    C1=CC=C2C=NC=CC2=C1
inchi:    InChI=1S/C9H7N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-7H
inchiKey:    AWJUIBRHMBBTKR-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#7]:[#6]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2
smarts_isomeric:    [#6]1:[#6]:[#7]:[#6]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2

4-chloroaniline: Nc1ccc(Cl)cc1

smiles_non_kekule:    Nc1ccc(Cl)cc1
smiles_kekule:    NC1=CC=C(Cl)C=C1
inchi:    InChI=1S/C6H6ClN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2
inchiKey:    QSNSCYSYFYORTR-UHFFFAOYSA-N
smarts:    [#7]-[#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1
smarts_isomeric:    [#7]-[#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1

pyrrolidin-2-one: N1CCCC1=O

smiles_non_kekule:    O=C1CCCN1
smiles_kekule:    O=C1CCCN1
inchi:    InChI=1S/C4H7NO/c6-4-2-1-3-5-4/h1-3H2,(H,5,6)
inchiKey:    HNJBEVLQSNELDL-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#6]-[#6]-1=[#8]
smarts_isomeric:    [#7]1-[#6]-[#6]-[#6]-[#6]-1=[#8]

5-methyloctahydropyrrolo[3,4-b]pyrrole: N1CCC2CN(C)CC21

smiles_non_kekule:    CN1CC2CCNC2C1
smiles_kekule:    CN1CC2CCNC2C1
inchi:    InChI=1S/C7H14N2/c1-9-4-6-2-3-8-7(6)5-9/h6-8H,2-5H2,1H3
inchiKey:    DLUDAUJQMXTXGQ-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#6]2-[#6]-[#7](-[#6])-[#6]-[#6]-1-2
smarts_isomeric:    [#7]1-[#6]-[#6]-[#6]2-[#6]-[#7](-[#6])-[#6]-[#6]-1-2

4-methoxybenzamide: NC(=O)c1ccc(OC)cc1

smiles_non_kekule:    COc1ccc(C(N)=O)cc1
smiles_kekule:    COC1=CC=C(C(N)=O)C=C1
inchi:    InChI=1S/C8H9NO2/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3,(H2,9,10)
inchiKey:    GUCPYIYFQVTFSI-UHFFFAOYSA-N
smarts:    [#7]-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#7]-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6]:[#6]:1

m-cresol: Oc1cccc(C)c1

smiles_non_kekule:    Cc1cccc(O)c1
smiles_kekule:    CC1=CC(O)=CC=C1
inchi:    InChI=1S/C7H8O/c1-6-3-2-4-7(8)5-6/h2-5,8H,1H3
inchiKey:    RLSSMJSEOOYNOY-UHFFFAOYSA-N
smarts:    [#8]-[#6]1:[#6]:[#6]:[#6]:[#6](-[#6]):[#6]:1
smarts_isomeric:    [#8]-[#6]1:[#6]:[#6]:[#6]:[#6](-[#6]):[#6]:1

4,4,5,5-tetramethyl-1,3,2-dioxaborolane: B1OC(C)(C)C(C)(C)O1

smiles_non_kekule:    CC1(C)OBOC1(C)C
smiles_kekule:    CC1(C)OBOC1(C)C
inchi:    InChI=1S/C6H13BO2/c1-5(2)6(3,4)9-7-8-5/h7H,1-4H3
inchiKey:    UCFSYHMCKWNKAH-UHFFFAOYSA-N
smarts:    [#5]1-[#8]-[#6](-[#6])(-[#6])-[#6](-[#6])(-[#6])-[#8]-1
smarts_isomeric:    [#5]1-[#8]-[#6](-[#6])(-[#6])-[#6](-[#6])(-[#6])-[#8]-1

N1,N1-dimethylethane-1,2-diamine: NCCN(C)C

smiles_non_kekule:    CN(C)CCN
smiles_kekule:    CN(C)CCN
inchi:    InChI=1S/C4H12N2/c1-6(2)4-3-5/h3-5H2,1-2H3
inchiKey:    DILRJUIACXKSQE-UHFFFAOYSA-N
smarts:    [#7]-[#6]-[#6]-[#7](-[#6])-[#6]
smarts_isomeric:    [#7]-[#6]-[#6]-[#7](-[#6])-[#6]

1-phenylthiourea: NC(=S)Nc1ccccc1

smiles_non_kekule:    NC(=S)Nc1ccccc1
smiles_kekule:    NC(=S)NC1=CC=CC=C1
inchi:    InChI=1S/C7H8N2S/c8-7(10)9-6-4-2-1-3-5-6/h1-5H,(H3,8,9,10)
inchiKey:    FULZLIGZKMKICU-UHFFFAOYSA-N
smarts:    [#7]-[#6](=[#16])-[#7]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#7]-[#6](=[#16])-[#7]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

1-methyl-4-(trifluoromethyl)benzene: Cc1ccc(C(F)(F)F)cc1

smiles_non_kekule:    Cc1ccc(C(F)(F)F)cc1
smiles_kekule:    CC1=CC=C(C(F)(F)F)C=C1
inchi:    InChI=1S/C8H7F3/c1-6-2-4-7(5-3-6)8(9,10)11/h2-5H,1H3
inchiKey:    LRLRAYMYEXQKID-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6](-[#6](-[#9])(-[#9])-[#9]):[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6](-[#6](-[#9])(-[#9])-[#9]):[#6]:[#6]:1

isopropoxybenzene: c1ccc(OC(C)C)cc1

smiles_non_kekule:    CC(C)Oc1ccccc1
smiles_kekule:    CC(C)OC1=CC=CC=C1
inchi:    InChI=1S/C9H12O/c1-8(2)10-9-6-4-3-5-7-9/h3-8H,1-2H3
inchiKey:    ZYNMJJNWXVKJJV-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#8]-[#6](-[#6])-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#8]-[#6](-[#6])-[#6]):[#6]:[#6]:1

4-methoxypiperidine: N1CCC(OC)CC1

smiles_non_kekule:    COC1CCNCC1
smiles_kekule:    COC1CCNCC1
inchi:    InChI=1S/C6H13NO/c1-8-6-2-4-7-5-3-6/h6-7H,2-5H2,1H3
inchiKey:    ZEYSHALLPAKUHG-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#6](-[#8]-[#6])-[#6]-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#6](-[#8]-[#6])-[#6]-[#6]-1

1,2-dichloro-4-methylbenzene: Cc1ccc(Cl)c(Cl)c1

smiles_non_kekule:    Cc1ccc(Cl)c(Cl)c1
smiles_kekule:    CC1=CC=C(Cl)C(Cl)=C1
inchi:    InChI=1S/C7H6Cl2/c1-5-2-3-6(8)7(9)4-5/h2-4H,1H3
inchiKey:    WYUIWKFIFOJVKW-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6](-[#17]):[#6](-[#17]):[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6](-[#17]):[#6](-[#17]):[#6]:1

1-(4-chlorophenyl)urea: NC(=O)Nc1ccc(Cl)cc1

smiles_non_kekule:    NC(=O)Nc1ccc(Cl)cc1
smiles_kekule:    NC(=O)NC1=CC=C(Cl)C=C1
inchi:    InChI=1S/C7H7ClN2O/c8-5-1-3-6(4-2-5)10-7(9)11/h1-4H,(H3,9,10,11)
inchiKey:    RECCURWJDVZHIH-UHFFFAOYSA-N
smarts:    [#7]-[#6](=[#8])-[#7]-[#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1
smarts_isomeric:    [#7]-[#6](=[#8])-[#7]-[#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1

thiazol-2-amine: Nc1nccs1

o-xylene: c1ccc(C)c(C)c1

smiles_non_kekule:    Cc1ccccc1C
smiles_kekule:    CC1=CC=CC=C1C
inchi:    InChI=1S/C8H10/c1-7-5-3-4-6-8(7)2/h3-6H,1-2H3
inchiKey:    CTQNGGLPUBDAKN-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](-[#6]):[#6](-[#6]):[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](-[#6]):[#6](-[#6]):[#6]:1

2-methyl-1,3,4-oxadiazole: c1nnc(C)o1

smiles_non_kekule:    Cc1nnco1
smiles_kekule:    CC1=NN=CO1
inchi:    InChI=1S/C3H4N2O/c1-3-5-4-2-6-3/h2H,1H3
inchiKey:    ZMSIFDIKIXVLDF-UHFFFAOYSA-N
smarts:    [#6]1:[#7]:[#7]:[#6](-[#6]):[#8]:1
smarts_isomeric:    [#6]1:[#7]:[#7]:[#6](-[#6]):[#8]:1

1-fluoro-3-methylbenzene: Cc1cccc(F)c1

smiles_non_kekule:    Cc1cccc(F)c1
smiles_kekule:    CC1=CC=CC(F)=C1
inchi:    InChI=1S/C7H7F/c1-6-3-2-4-7(8)5-6/h2-5H,1H3
inchiKey:    BTQZKHUEUDPRST-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6](-[#9]):[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6](-[#9]):[#6]:1

(methoxymethyl)benzene: COCc1ccccc1

smiles_non_kekule:    COCc1ccccc1
smiles_kekule:    COCC1=CC=CC=C1
inchi:    InChI=1S/C8H10O/c1-9-7-8-5-3-2-4-6-8/h2-6H,7H2,1H3
inchiKey:    GQKZBCPTCWJTAS-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#8]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

hydrazine: NN

smiles_non_kekule:    NN
smiles_kekule:    NN
inchi:    InChI=1S/H4N2/c1-2/h1-2H2
inchiKey:    OAKJQQAXSVQMHS-UHFFFAOYSA-N
smarts:    [#7]-[#7]
smarts_isomeric:    [#7]-[#7]

1-cyclohexylurea: NC(=O)NC1CCCCC1

smiles_non_kekule:    NC(=O)NC1CCCCC1
smiles_kekule:    NC(=O)NC1CCCCC1
inchi:    InChI=1S/C7H14N2O/c8-7(10)9-6-4-2-1-3-5-6/h6H,1-5H2,(H3,8,9,10)
inchiKey:    WUESWDIHTKHGQA-UHFFFAOYSA-N
smarts:    [#7]-[#6](=[#8])-[#7]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#7]-[#6](=[#8])-[#7]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

ethanethiol: SCC

smiles_non_kekule:    CCS
smiles_kekule:    CCS
inchi:    InChI=1S/C2H6S/c1-2-3/h3H,2H2,1H3
inchiKey:    DNJIEGIFACGWOD-UHFFFAOYSA-N
smarts:    [#16]-[#6]-[#6]
smarts_isomeric:    [#16]-[#6]-[#6]

N-hydroxypentanamide: CCCCC(=O)NO

smiles_non_kekule:    CCCCC(=O)NO
smiles_kekule:    CCCCC(=O)NO
inchi:    InChI=1S/C5H11NO2/c1-2-3-4-5(7)6-8/h8H,2-4H2,1H3,(H,6,7)
inchiKey:    ZMJLZDJLNRHSSQ-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6](=[#8])-[#7]-[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6](=[#8])-[#7]-[#8]

thiophene-2-carboxamide: NC(=O)c1cccs1

smiles_non_kekule:    NC(=O)c1cccs1
smiles_kekule:    NC(=O)C1=CC=CS1
inchi:    InChI=1S/C5H5NOS/c6-5(7)4-2-1-3-8-4/h1-3H,(H2,6,7)
inchiKey:    DENPQNAWGQXKCU-UHFFFAOYSA-N
smarts:    [#7]-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#16]:1
smarts_isomeric:    [#7]-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#16]:1

N-(cyclopropylmethyl)formamide: C(=O)NCC1CC1

smiles_non_kekule:    O=CNCC1CC1
smiles_kekule:    O=CNCC1CC1
inchi:    InChI=1S/C5H9NO/c7-4-6-3-5-1-2-5/h4-5H,1-3H2,(H,6,7)
inchiKey:    XABBWSLQKRPYMM-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]-[#6]-[#6]1-[#6]-[#6]-1
smarts_isomeric:    [#6](=[#8])-[#7]-[#6]-[#6]1-[#6]-[#6]-1

1-ethyl-2-methylpyrrolidine: CCN1CCCC1C

smiles_non_kekule:    CCN1CCCC1C
smiles_kekule:    CCN1CCCC1C
inchi:    InChI=1S/C7H15N/c1-3-8-6-4-5-7(8)2/h7H,3-6H2,1-2H3
inchiKey:    JKNXMPSMAZUQMJ-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-1-[#6]
smarts_isomeric:    [#6]-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-1-[#6]

pyridin-4-ylmethanol: OCc1ccncc1

smiles_non_kekule:    OCc1ccncc1
smiles_kekule:    OCC1=CC=NC=C1
inchi:    InChI=1S/C6H7NO/c8-5-6-1-3-7-4-2-6/h1-4,8H,5H2
inchiKey:    PTMBWNZJOQBTBK-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]1:[#6]:[#6]:[#7]:[#6]:[#6]:1
smarts_isomeric:    [#8]-[#6]-[#6]1:[#6]:[#6]:[#7]:[#6]:[#6]:1

triethylamine: CCN(CC)CC

4-hydroxy-2-oxobut-3-enoic acid: C(O)=CC(=O)C(=O)O

smiles_non_kekule:    O=C(O)C(=O)C=CO
smiles_kekule:    O=C(O)C(=O)C=CO
inchi:    InChI=1S/C4H4O4/c5-2-1-3(6)4(7)8/h1-2,5H,(H,7,8)
inchiKey:    AOXFNHQEJFNQDA-UHFFFAOYSA-N
smarts:    [#6](-[#8])=[#6]-[#6](=[#8])-[#6](=[#8])-[#8]
smarts_isomeric:    [#6](-[#8])=[#6]-[#6](=[#8])-[#6](=[#8])-[#8]

isonicotinaldehyde: C(=O)c1ccncc1

smiles_non_kekule:    O=Cc1ccncc1
smiles_kekule:    O=CC1=CC=NC=C1
inchi:    InChI=1S/C6H5NO/c8-5-6-1-3-7-4-2-6/h1-5H
inchiKey:    BGUWFUQJCDRPTL-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#6]1:[#6]:[#6]:[#7]:[#6]:[#6]:1
smarts_isomeric:    [#6](=[#8])-[#6]1:[#6]:[#6]:[#7]:[#6]:[#6]:1

1,1,1-trifluoroethane: CC(F)(F)F

smiles_non_kekule:    CC(F)(F)F
smiles_kekule:    CC(F)(F)F
inchi:    InChI=1S/C2H3F3/c1-2(3,4)5/h1H3
inchiKey:    UJPMYEOUBPIPHQ-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#9])(-[#9])-[#9]
smarts_isomeric:    [#6]-[#6](-[#9])(-[#9])-[#9]

isothiocyanic acid: N=C=S

smiles_non_kekule:    N=C=S
smiles_kekule:    N=C=S
inchi:    InChI=1S/CHNS/c2-1-3/h2H
inchiKey:    GRHBQAYDJPGGLF-UHFFFAOYSA-N
smarts:    [#7]=[#6]=[#16]
smarts_isomeric:    [#7]=[#6]=[#16]

phosphonic acid: P(=O)(O)O

smiles_non_kekule:    O=[PH](O)O
smiles_kekule:    O=[PH](O)O
inchi:    InChI=1S/H3O3P/c1-4(2)3/h4H,(H2,1,2,3)
inchiKey:    ABLZXFCXXLZCGV-UHFFFAOYSA-N
smarts:    [#15](=[#8])(-[#8])-[#8]
smarts_isomeric:    [#15](=[#8])(-[#8])-[#8]

2-hydroxy-4-oxobut-2-enoic acid: C(=O)C=C(O)C(=O)O

smiles_non_kekule:    O=CC=C(O)C(=O)O
smiles_kekule:    O=CC=C(O)C(=O)O
inchi:    InChI=1S/C4H4O4/c5-2-1-3(6)4(7)8/h1-2,6H,(H,7,8)
inchiKey:    TZTCZHBCXDJMMC-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#6]=[#6](-[#8])-[#6](=[#8])-[#8]
smarts_isomeric:    [#6](=[#8])-[#6]=[#6](-[#8])-[#6](=[#8])-[#8]

N,N-dimethylpiperidin-4-amine: CN(C)C1CCNCC1

smiles_non_kekule:    CN(C)C1CCNCC1
smiles_kekule:    CN(C)C1CCNCC1
inchi:    InChI=1S/C7H16N2/c1-9(2)7-3-5-8-6-4-7/h7-8H,3-6H2,1-2H3
inchiKey:    YFJAIURZMRJPDB-UHFFFAOYSA-N
smarts:    [#6]-[#7](-[#6])-[#6]1-[#6]-[#6]-[#7]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#7](-[#6])-[#6]1-[#6]-[#6]-[#7]-[#6]-[#6]-1

1-(pyridin-2-yl)piperazine: N1CCN(c2ccccn2)CC1

smiles_non_kekule:    c1ccc(N2CCNCC2)nc1
smiles_kekule:    C1=CC=C(N2CCNCC2)N=C1
inchi:    InChI=1S/C9H13N3/c1-2-4-11-9(3-1)12-7-5-10-6-8-12/h1-4,10H,5-8H2
inchiKey:    GZRKXKUVVPSREJ-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#7](-[#6]2:[#6]:[#6]:[#6]:[#6]:[#7]:2)-[#6]-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#7](-[#6]2:[#6]:[#6]:[#6]:[#6]:[#7]:2)-[#6]-[#6]-1

problem_type: 15/25 (loop 0/0)

[15:19:53] WARNING: Omitted undefined stereo

[15:19:53] WARNING: Omitted undefined stereo

[15:19:53] WARNING: Omitted undefined stereo

[15:19:53] WARNING: Omitted undefined stereo

[15:19:53] WARNING: Omitted undefined stereo

[15:19:53] WARNING: Omitted undefined stereo

[15:19:53] WARNING: Omitted undefined stereo

[15:19:53] WARNING: Proton(s) added/removed; Omitted undefined stereo

[15:19:53] WARNING: Omitted undefined stereo

Problem Template: _problem_essential_vitamins

Write structure of essential vitamins molecules.

Answer:

structure of essential vitamins molecules:

vitamin A: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CCO)C)C

vitamin C: C(C(C1C(=C(C(=O)O1)O)O)O)O

vitamin D: CC(C)CCCC(C)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C

vitamin E: CC1=C(C2=C(CCC(O2)(C)CCCC(C)CCCC(C)CCCC(C)C)C(=C1O)C)C

vitamin K: CC1=C(C(=O)C2=CC=CC=C2C1=O)CC=C(C)CCCC(C)CCCC(C)CCCC(C)C

thiamine: OCCC1=C(C)[N+](CC2=CN=C(C)N=C2N)=CS1

riboflavin: OC[C@H](O)[C@H](O)[C@H](O)CN(C(C=C1C)=C(C=C1C)N=C2C(N3)=O)C2=NC3=O

niacin: C1=CC(=CN=C1)C(=O)O

pantothenic acid: CC(C)(CO)C(C(=O)NCCC(=O)O)O

biotin: C1C2C(C(S1)CCCCC(=O)O)NC(=O)N2

b6: CC1=NC=C(C(=C1O)CO)CO

b12: CC1=CC2=C(C=C1C)N(C=N2)C3C(C(C(O3)CO)OP(=O)(O)OC(C)CNC(=O)CCC4(C(C5C6(C(C(C(=C(C7=NC(=CC8=NC(=C(C4=N5)C)C(C8(C)C)CCC(=O)N)C(C7(C)CC(=O)N)CCC(=O)N)C)[N-]6)CCC(=O)N)(C)CC(=O)N)C)CC(=O)N)C)O

folate: C1=CC(=CC=C1C(=O)NC(CCC(=O)O)C(=O)O)NCC2=CN=C3C(=N2)C(=O)NC(=N3)N

Solution:

structure of essential vitamins molecules:

vitamin A: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CCO)C)C

smiles_non_kekule:    CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CCO
smiles_kekule:    CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CCO
inchi:    InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3
inchiKey:    FPIPGXGPPPQFEQ-UHFFFAOYSA-N
smarts:    [#6]-[#6]1=[#6](-[#6](-[#6]-[#6]-[#6]-1)(-[#6])-[#6])-[#6]=[#6]-[#6](=[#6]-[#6]=[#6]-[#6](=[#6]-[#6]-[#8])-[#6])-[#6]
smarts_isomeric:    [#6]-[#6]1=[#6](-[#6](-[#6]-[#6]-[#6]-1)(-[#6])-[#6])-[#6]=[#6]-[#6](=[#6]-[#6]=[#6]-[#6](=[#6]-[#6]-[#8])-[#6])-[#6]

vitamin C: C(C(C1C(=C(C(=O)O1)O)O)O)O

smiles_non_kekule:    O=C1OC(C(O)CO)C(O)=C1O
smiles_kekule:    O=C1OC(C(O)CO)C(O)=C1O
inchi:    InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2
inchiKey:    CIWBSHSKHKDKBQ-UHFFFAOYSA-N
smarts:    [#6](-[#6](-[#6]1-[#6](=[#6](-[#6](=[#8])-[#8]-1)-[#8])-[#8])-[#8])-[#8]
smarts_isomeric:    [#6](-[#6](-[#6]1-[#6](=[#6](-[#6](=[#8])-[#8]-1)-[#8])-[#8])-[#8])-[#8]

vitamin D: CC(C)CCCC(C)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C

smiles_non_kekule:    C=C1CCC(O)CC1=CC=C1CCCC2(C)C1CCC2C(C)CCCC(C)C
smiles_kekule:    C=C1CCC(O)CC1=CC=C1CCCC2(C)C1CCC2C(C)CCCC(C)C
inchi:    InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3
inchiKey:    QYSXJUFSXHHAJI-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])-[#6]-[#6]-[#6]-[#6](-[#6])-[#6]1-[#6]-[#6]-[#6]2-[#6]-1(-[#6]-[#6]-[#6]-[#6]-2=[#6]-[#6]=[#6]1-[#6]-[#6](-[#6]-[#6]-[#6]-1=[#6])-[#8])-[#6]
smarts_isomeric:    [#6]-[#6](-[#6])-[#6]-[#6]-[#6]-[#6](-[#6])-[#6]1-[#6]-[#6]-[#6]2-[#6]-1(-[#6]-[#6]-[#6]-[#6]-2=[#6]-[#6]=[#6]1-[#6]-[#6](-[#6]-[#6]-[#6]-1=[#6])-[#8])-[#6]

vitamin E: CC1=C(C2=C(CCC(O2)(C)CCCC(C)CCCC(C)CCCC(C)C)C(=C1O)C)C

smiles_non_kekule:    Cc1c(C)c2c(c(C)c1O)CCC(C)(CCCC(C)CCCC(C)CCCC(C)C)O2
smiles_kekule:    CC1=C(C)C2=C(CCC(C)(CCCC(C)CCCC(C)CCCC(C)C)O2)C(C)=C1O
inchi:    InChI=1S/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3
inchiKey:    GVJHHUAWPYXKBD-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6](:[#6]2:[#6](-[#6]-[#6]-[#6](-[#8]-2)(-[#6])-[#6]-[#6]-[#6]-[#6](-[#6])-[#6]-[#6]-[#6]-[#6](-[#6])-[#6]-[#6]-[#6]-[#6](-[#6])-[#6]):[#6](:[#6]:1-[#8])-[#6])-[#6]
smarts_isomeric:    [#6]-[#6]1:[#6](:[#6]2:[#6](-[#6]-[#6]-[#6](-[#8]-2)(-[#6])-[#6]-[#6]-[#6]-[#6](-[#6])-[#6]-[#6]-[#6]-[#6](-[#6])-[#6]-[#6]-[#6]-[#6](-[#6])-[#6]):[#6](:[#6]:1-[#8])-[#6])-[#6]

vitamin K: CC1=C(C(=O)C2=CC=CC=C2C1=O)CC=C(C)CCCC(C)CCCC(C)CCCC(C)C

smiles_non_kekule:    CC(=CCC1=C(C)C(=O)c2ccccc2C1=O)CCCC(C)CCCC(C)CCCC(C)C
smiles_kekule:    CC(=CCC1=C(C)C(=O)C2=CC=CC=C2C1=O)CCCC(C)CCCC(C)CCCC(C)C
inchi:    InChI=1S/C31H46O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24H,9-17,21H2,1-6H3
inchiKey:    MBWXNTAXLNYFJB-UHFFFAOYSA-N
smarts:    [#6]-[#6]1=[#6](-[#6](=[#8])-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2-[#6]-1=[#8])-[#6]-[#6]=[#6](-[#6])-[#6]-[#6]-[#6]-[#6](-[#6])-[#6]-[#6]-[#6]-[#6](-[#6])-[#6]-[#6]-[#6]-[#6](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6]1=[#6](-[#6](=[#8])-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2-[#6]-1=[#8])-[#6]-[#6]=[#6](-[#6])-[#6]-[#6]-[#6]-[#6](-[#6])-[#6]-[#6]-[#6]-[#6](-[#6])-[#6]-[#6]-[#6]-[#6](-[#6])-[#6]

thiamine: OCCC1=C(C)[N+](CC2=CN=C(C)N=C2N)=CS1

smiles_non_kekule:    Cc1ncc(C[n+]2csc(CCO)c2C)c(N)n1
smiles_kekule:    CC1=NC=C(C[N+]2=CSC(CCO)=C2C)C(N)=N1
inchi:    InChI=1S/C12H17N4OS/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15)/q+1
inchiKey:    JZRWCGZRTZMZEH-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]-[#6]1:[#6](-[#6]):[#7+](-[#6]-[#6]2:[#6]:[#7]:[#6](-[#6]):[#7]:[#6]:2-[#7]):[#6]:[#16]:1
smarts_isomeric:    [#8]-[#6]-[#6]-[#6]1:[#6](-[#6]):[#7+](-[#6]-[#6]2:[#6]:[#7]:[#6](-[#6]):[#7]:[#6]:2-[#7]):[#6]:[#16]:1

riboflavin: OC[C@H](O)[C@H](O)[C@H](O)CN(C(C=C1C)=C(C=C1C)N=C2C(N3)=O)C2=NC3=O

smiles_non_kekule:    Cc1cc2nc3c(=O)[nH]c(=O)nc-3n(C[C@@H](O)[C@@H](O)[C@@H](O)CO)c2cc1C
smiles_kekule:    CC1=C(C)C=C2C(=C1)N=C1C(=NC(=O)NC1=O)N2C[C@@H](O)[C@@H](O)[C@@H](O)CO
inchi:    InChI=1S/C17H20N4O6/c1-7-3-9-10(4-8(7)2)21(5-11(23)14(25)12(24)6-22)15-13(18-9)16(26)20-17(27)19-15/h3-4,11-12,14,22-25H,5-6H2,1-2H3,(H,20,26,27)/t11-,12+,14-/m1/s1
inchiKey:    AUNGANRZJHBGPY-MBNYWOFBSA-N
smarts:    [#8]-[#6]-[#6H](-[#8])-[#6H](-[#8])-[#6H](-[#8])-[#6]-[#7]1:[#6]2:[#6]:[#6](-[#6]):[#6](:[#6]:[#6]:2:[#7]:[#6]2:[#6](:[#7H]:[#6](:[#7]:[#6]:1-2)=[#8])=[#8])-[#6]
smarts_isomeric:    [#8]-[#6]-[#6@H](-[#8])-[#6@H](-[#8])-[#6@H](-[#8])-[#6]-[#7]1:[#6]2:[#6]:[#6](-[#6]):[#6](:[#6]:[#6]:2:[#7]:[#6]2:[#6](:[#7H]:[#6](:[#7]:[#6]:1-2)=[#8])=[#8])-[#6]

niacin: C1=CC(=CN=C1)C(=O)O

smiles_non_kekule:    O=C(O)c1cccnc1
smiles_kekule:    O=C(O)C1=CN=CC=C1
inchi:    InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
inchiKey:    PVNIIMVLHYAWGP-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6](:[#6]:[#7]:[#6]:1)-[#6](=[#8])-[#8]
smarts_isomeric:    [#6]1:[#6]:[#6](:[#6]:[#7]:[#6]:1)-[#6](=[#8])-[#8]

pantothenic acid: CC(C)(CO)C(C(=O)NCCC(=O)O)O

smiles_non_kekule:    CC(C)(CO)C(O)C(=O)NCCC(=O)O
smiles_kekule:    CC(C)(CO)C(O)C(=O)NCCC(=O)O
inchi:    InChI=1S/C9H17NO5/c1-9(2,5-11)7(14)8(15)10-4-3-6(12)13/h7,11,14H,3-5H2,1-2H3,(H,10,15)(H,12,13)
inchiKey:    GHOKWGTUZJEAQD-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])(-[#6]-[#8])-[#6](-[#6](=[#8])-[#7]-[#6]-[#6]-[#6](=[#8])-[#8])-[#8]
smarts_isomeric:    [#6]-[#6](-[#6])(-[#6]-[#8])-[#6](-[#6](=[#8])-[#7]-[#6]-[#6]-[#6](=[#8])-[#8])-[#8]

biotin: C1C2C(C(S1)CCCCC(=O)O)NC(=O)N2

smiles_non_kekule:    O=C(O)CCCCC1SCC2NC(=O)NC21
smiles_kekule:    O=C(O)CCCCC1SCC2NC(=O)NC21
inchi:    InChI=1S/C10H16N2O3S/c13-8(14)4-2-1-3-7-9-6(5-16-7)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)
inchiKey:    YBJHBAHKTGYVGT-UHFFFAOYSA-N
smarts:    [#6]1-[#6]2-[#6](-[#6](-[#16]-1)-[#6]-[#6]-[#6]-[#6]-[#6](=[#8])-[#8])-[#7]-[#6](=[#8])-[#7]-2
smarts_isomeric:    [#6]1-[#6]2-[#6](-[#6](-[#16]-1)-[#6]-[#6]-[#6]-[#6]-[#6](=[#8])-[#8])-[#7]-[#6](=[#8])-[#7]-2

b6: CC1=NC=C(C(=C1O)CO)CO

smiles_non_kekule:    Cc1ncc(CO)c(CO)c1O
smiles_kekule:    CC1=NC=C(CO)C(CO)=C1O
inchi:    InChI=1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3
inchiKey:    LXNHXLLTXMVWPM-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#7]:[#6]:[#6](:[#6](:[#6]:1-[#8])-[#6]-[#8])-[#6]-[#8]
smarts_isomeric:    [#6]-[#6]1:[#7]:[#6]:[#6](:[#6](:[#6]:1-[#8])-[#6]-[#8])-[#6]-[#8]

b12: CC1=CC2=C(C=C1C)N(C=N2)C3C(C(C(O3)CO)OP(=O)(O)OC(C)CNC(=O)CCC4(C(C5C6(C(C(C(=C(C7=NC(=CC8=NC(=C(C4=N5)C)C(C8(C)C)CCC(=O)N)C(C7(C)CC(=O)N)CCC(=O)N)C)[N-]6)CCC(=O)N)(C)CC(=O)N)C)CC(=O)N)C)O

smiles_non_kekule:    CC1=C2N=C(C=C3N=C(C(C)=C4[N-]C(C)(C5N=C1C(C)(CCC(=O)NCC(C)OP(=O)(O)OC1C(CO)OC(n6cnc7cc(C)c(C)cc76)C1O)C5CC(N)=O)C(C)(CC(N)=O)C4CCC(N)=O)C(C)(CC(N)=O)C3CCC(N)=O)C(C)(C)C2CCC(N)=O
smiles_kekule:    CC1=C2N=C(C=C3N=C(C(C)=C4[N-]C(C)(C5N=C1C(C)(CCC(=O)NCC(C)OP(=O)(O)OC1C(CO)OC(N6C=NC7=C6C=C(C)C(C)=C7)C1O)C5CC(N)=O)C(C)(CC(N)=O)C4CCC(N)=O)C(C)(CC(N)=O)C3CCC(N)=O)C(C)(C)C2CCC(N)=O
inchi:    InChI=1S/C62H90N13O14P/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86)/p-1
inchiKey:    RHYVGCKRBKDRDX-UHFFFAOYSA-M
smarts:    [#6]-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1-[#6]):[#7](:[#6]:[#7]:2)-[#6]1-[#6](-[#6](-[#6](-[#8]-1)-[#6]-[#8])-[#8]-[#15](=[#8])(-[#8])-[#8]-[#6](-[#6])-[#6]-[#7]-[#6](=[#8])-[#6]-[#6]-[#6]1(-[#6](-[#6]2-[#6]3(-[#6](-[#6](-[#6](=[#6](-[#6]4=[#7]-[#6](=[#6]-[#6]5=[#7]-[#6](=[#6](-[#6]-1=[#7]-2)-[#6])-[#6](-[#6]-5(-[#6])-[#6])-[#6]-[#6]-[#6](=[#8])-[#7])-[#6](-[#6]-4(-[#6])-[#6]-[#6](=[#8])-[#7])-[#6]-[#6]-[#6](=[#8])-[#7])-[#6])-[#7-]-3)-[#6]-[#6]-[#6](=[#8])-[#7])(-[#6])-[#6]-[#6](=[#8])-[#7])-[#6])-[#6]-[#6](=[#8])-[#7])-[#6])-[#8]
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1-[#6]):[#7](:[#6]:[#7]:2)-[#6]1-[#6](-[#6](-[#6](-[#8]-1)-[#6]-[#8])-[#8]-[#15](=[#8])(-[#8])-[#8]-[#6](-[#6])-[#6]-[#7]-[#6](=[#8])-[#6]-[#6]-[#6]1(-[#6](-[#6]2-[#6]3(-[#6](-[#6](-[#6](=[#6](-[#6]4=[#7]-[#6](=[#6]-[#6]5=[#7]-[#6](=[#6](-[#6]-1=[#7]-2)-[#6])-[#6](-[#6]-5(-[#6])-[#6])-[#6]-[#6]-[#6](=[#8])-[#7])-[#6](-[#6]-4(-[#6])-[#6]-[#6](=[#8])-[#7])-[#6]-[#6]-[#6](=[#8])-[#7])-[#6])-[#7-]-3)-[#6]-[#6]-[#6](=[#8])-[#7])(-[#6])-[#6]-[#6](=[#8])-[#7])-[#6])-[#6]-[#6](=[#8])-[#7])-[#6])-[#8]

folate: C1=CC(=CC=C1C(=O)NC(CCC(=O)O)C(=O)O)NCC2=CN=C3C(=N2)C(=O)NC(=N3)N

smiles_non_kekule:    Nc1nc2ncc(CNc3ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc3)nc2c(=O)[nH]1
smiles_kekule:    NC1=NC2=NC=C(CNC3=CC=C(C(=O)NC(CCC(=O)O)C(=O)O)C=C3)N=C2C(=O)N1
inchi:    InChI=1S/C19H19N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,8,12,21H,5-7H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30)
inchiKey:    OVBPIULPVIDEAO-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1-[#6](=[#8])-[#7]-[#6](-[#6]-[#6]-[#6](=[#8])-[#8])-[#6](=[#8])-[#8])-[#7]-[#6]-[#6]1:[#6]:[#7]:[#6]2:[#6](:[#7]:1):[#6](=[#8]):[#7H]:[#6](:[#7]:2)-[#7]
smarts_isomeric:    [#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1-[#6](=[#8])-[#7]-[#6](-[#6]-[#6]-[#6](=[#8])-[#8])-[#6](=[#8])-[#8])-[#7]-[#6]-[#6]1:[#6]:[#7]:[#6]2:[#6](:[#7]:1):[#6](=[#8]):[#7H]:[#6](:[#7]:2)-[#7]

problem_type: 16/25 (loop 0/0)

[15:19:56] WARNING: Omitted undefined stereo

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(2)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Charges were rearranged; Accepted unusual valence(s): N(2)

[15:19:56] WARNING: Charges were rearranged

[15:19:56] WARNING: Accepted unusual valence(s): C(2)

[15:19:56] WARNING: Accepted unusual valence(s): O(1)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(2)

[15:19:56] WARNING: Accepted unusual valence(s): C(1)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): O(1)

[15:19:56] WARNING: Accepted unusual valence(s): O(1); Omitted undefined stereo

[15:19:56] WARNING: Accepted unusual valence(s): O(1)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3); Omitted undefined stereo

[15:19:56] WARNING: Accepted unusual valence(s): C(3); Omitted undefined stereo

[15:19:56] WARNING: Accepted unusual valence(s): C(2); Omitted undefined stereo

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): N(2)

[15:19:56] WARNING: Accepted unusual valence(s): O(1)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): N+1(2)

[15:19:56] WARNING: Accepted unusual valence(s): Si(3)

[15:19:56] WARNING: Accepted unusual valence(s): O(1)

[15:19:56] WARNING: Accepted unusual valence(s): S(3)

[15:19:56] WARNING: Accepted unusual valence(s): S(1)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): O(1)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(2)

[15:19:56] WARNING: Accepted unusual valence(s): S(1)

[15:19:56] WARNING: Accepted unusual valence(s): N(2)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(2)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): N(2)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): N(2)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): N(2)

[15:19:56] WARNING: Accepted unusual valence(s): C(3); N(2)

[15:19:56] WARNING: Accepted unusual valence(s): C(3); N(2)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): N(2)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): O(1)

[15:19:56] WARNING: Accepted unusual valence(s): N(2)

[15:19:56] WARNING: Accepted unusual valence(s): N(1)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): O(1)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(2)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): N(2)

[15:19:56] WARNING: Accepted unusual valence(s): N+1(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): N(1)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(2)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): O(1)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(2)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3); Omitted undefined stereo

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3); Omitted undefined stereo

[15:19:56] WARNING: Accepted unusual valence(s): S(1)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): O(1)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(2)

[15:19:56] WARNING: Accepted unusual valence(s): S(1)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Charges were rearranged; Accepted unusual valence(s): N(2)

[15:19:56] WARNING: Accepted unusual valence(s): N+1(3)

[15:19:56] WARNING: Accepted unusual valence(s): N(2)

[15:19:56] WARNING: Accepted unusual valence(s): N(2)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(2)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): O(1)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): P(2)

[15:19:56] WARNING: Accepted unusual valence(s): P(4)

[15:19:56] WARNING: Accepted unusual valence(s): P(4)

[15:19:56] WARNING: Accepted unusual valence(s): P(4)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Charges were rearranged; Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): N(2)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3); Omitted undefined stereo

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): O(1)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(2)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): Se(1)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): O(1)

[15:19:56] WARNING: Accepted unusual valence(s): Si(3)

[15:19:56] WARNING: Accepted unusual valence(s): Si(2)

[15:19:56] WARNING: Omitted undefined stereo

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3); Omitted undefined stereo

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): N(2)

[15:19:56] WARNING: Accepted unusual valence(s): S(5)

[15:19:56] WARNING: Accepted unusual valence(s): S(5)

[15:19:56] WARNING: Accepted unusual valence(s): S(1)

[15:19:56] WARNING: Accepted unusual valence(s): S(1)

[15:19:56] WARNING: Accepted unusual valence(s): S(5)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): S(1)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): N(2)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(1)

[15:19:56] WARNING: Accepted unusual valence(s): C(2)

[15:19:56] WARNING: Accepted unusual valence(s): S(5)

[15:19:56] WARNING: Accepted unusual valence(s): N(2)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

[15:19:56] WARNING: Accepted unusual valence(s): C(2)

[15:19:56] WARNING: Accepted unusual valence(s): N(2)

[15:19:56] WARNING: Accepted unusual valence(s): C(3)

Problem Template: _problem_iupac_blue_book_common_functional_groups

Write structure of iupac blue book common functional groups molecules.

Answer:

structure of iupac blue book common functional groups molecules:

acetamido: O=C(N)C

acetoacetyl: O=C(C)CC(=O)O

acetyl: C(C)=O

acryloyl: C=CC(C)=O

alanyl: N[CH](C)C(C)=O

beta-alanyl: NCCC(C)=O

allyl: [CH2]C=C

allylidene: [CH]C=C

amidino: NC=N

amino: N

amyl: [CH2]CCCC

anilino: NC1=CC=CC=C1

anisidino: NC1=CC=C(OC)C=C1

anthranoyl: NC1=CC=CC=C1[C](C)=O

arsino: [AsH3]

azelaoyl: O=CCCCCCCCC=O

azido: [N]=[N+]=[N-]

azo: C/N=N/C

azoxy: C/N=[N+]([O-])/C

benzal: [CH]C1=CC=CC=C1

benzamido: O=C(N)C1=CC=CC=C1

benzhydrol: OC(C1=CC=CC=C1)C2=CC=CC=C2

benzoxy: [O]CC1=CC=CC=C1

benzoyl: O=[C]C1=CC=CC=C1

benzyl: [CH2]C1=CC=CC=C1

benzylidene: [CH]C1=CC=CC=C1

benzylidyne: [C]C1=CC=CC=C1

biphenylyl: C1(C2=CC=CC=C2)=CC=CC=[C]1

biphenylene: C12=C3C=CC=CC3=C1C=CC=C2

butoxy: [O]CCCC

sec-butoxy: [O]C(C)CC

tert-butoxy: [O]C(C)(C)C

butyl: [CH2]CCC

sec-butyl: CC[CH]C

tert-butyl: C[C](C)C

butyryl: O=[C]CCC

caproyl: CCCCC[C]=O

capryl: CCCCCCCC

capryloyl: CCCCCCC[C]=O

carbamido: C(=O)(N)N

carbamoyl: N[C]=O

carbamyl: N[C]=O

carbazoyl: NN[C]=O

carbethoxy: O=[C]OCC

carbonyl: [CH]=O

carboxy: O=[C]O

cetyl: [CH2]CCCCCCCCCCCCCCC

chloroformyl: O=[C]Cl

cinnamoyl: O=[C]C=CC1=CC=CC=C1

cinnamyl: [CH2]C=CC1=CC=CC=C1

cinnamylidene: [CH]C=CC1=CC=CC=C1

cresyl: OC1=CC=C(C)C=C1

crotonoyl: C/C=C/[C]=O

crotyl: [CH2]/C=C/C

cyanamido: [NH]C#N

cyanato: [O]C#N

cyano: [C]#N

decanedioyl: O=[C]CCCCCCCC[C]=O

decanoyl: CCCCCCCCC[C]=O

diazo: [N+]=[N-]

diazoamino: N=NN

disilanyl: [SiH2][SiH3]

disiloxanyloxy: [O][SiH2]O[SiH3]

disulfinyl: O=[S]S=O

dithio: [S]S

enanthoyl: CCCCCC[C]=O

epoxy: [O]

ethenyl: [CH]=C

ethynyl: [C]#C

ethoxy: [O]CC

ethyl: [CH2]C

ethylene: C=C

ethylidene: [CH]C

ethylthio: [S]CC

formamido: O=C[NH]

formyl: [CH]=O

furmaroyl: O=CO

furfuryl: [CH2]C1=CC=CO1

furfurylidene: [CH]C1=CC=CO1

glutamoyl: N[C@@H](CC[C]=O)[C]=O

glutaryl: O=[C]CCC[C]=O

glycylamino: [NH]C(CN)=O

glycoloyl: OC[C]=O

glycyl: NC[C]=O

glyoxyoyl: O=[C]C=O

guanidino: [NH]C(N)=N

guanyl: N=[C]N

heptadecanoyl: CCCCCCCCCCCCCCCC[C]=O

heptanamido: CCCCCCC([NH])=O

heptanoyl: CCCCCC[C]=O.CCCCCCC([NH])=O

hexadecanoyl: CCCCCCCCCCCCCCC[C]=O.CCCCCC[C]=O.CCCCCCC([NH])=O

hexamethylene: CCCCCC

hexanedioyl: O=[C]CCCC[C]=O

hippuryl: [CH2]CNC(C1=CC=CC=C1)=O

hydrazino: N[NH]

hydrazo: NN

hydrocinnamoyl: O=[C]CCC1=CC=CC=C1

hydroperoxy: [O]O

hydroxyamino: [NH]O

imino: [NH]

iodoso: I=O

iodyl: O=I=O

isoamyl: [CH2]CC(C)C

isobutenyl: [CH]=C(C)C

isobutoxy: [O]CC(C)C

isobutyl: [CH2]C(C)C

isobutylidene: [CH]C(C)C

isobutyryl: O=[C]C(C)C

isocyanato: [N]=C=O

isocyano: [N+]#[C-]

isohexyl: [CH2]CCC(C)C

isoleucyl: N[C@@H]([C@@H](C)CC)[C]=O

isonitroso: [N]O

isopentyl: [CH2]CC(C)C

isopentylidene: [CH]CC(C)C

isopropenyl: C=[C]C

isopropoxy: [O]C(C)C

isopropyl: C[CH]C

isopropylidene: C[C]C

isothiocynato: N=C=S

isovaleryl: O=[C]CC(C)C

lactoyl: OC(C)[C]=O

lauroyl: CCCCCCCCCCC[C]=O

lauryl: [CH2]CCCCCCCCCCC

leucyl: N[C@@H](CC(C)C)[C]=O

levulinoyl: O=C(C)CC[C]=O

malonyl: O=[C]C[C]=O

mandeloyl: OC(C1=CC=CC=C1)[C]=O

mercapto: [SH]

mesityl: CC1=CC(C)=CC(C)=[C]1

methacryloyl: CC([C]=O)=C

methallyl: [CH2]C(C)=C

methionyl: N[C@@H](CCSC)[C]=O

methoxy: [O]C

methyl: [CH3]

methylene: [CH2]

methylthio: [S]C

myristoyl: CCCCCCCCCCCCC[C]=O

myristyl: [CH2]CCCCCCCCCCCCC

naphthyl: C12=CC=C[C]=C1C=CC=C2

naphthylene: C12=CC=CC=C1C=CC=C2

neopentyl: [CH2]C(C)(C)C

nitramino: [NH][N+]([O-])=O

nitro: O=[N+][O-]

nitrosamino: [NH]N=O

nitroso: [N]=O

nonanoyl: CCCCCCCC[C]=O

oleoyl: CCCCCCCC/C=C\CCCCCCC[C]=O

oxalyl: O=[C]C=O

oxo: [O]

palmitoyl: CCCCCCCCCCCCCCC[C]=O

pentamethylene: O=C1C(C=C)[C@@]2([H])SCCN12

pentyl: [CH2]CCCC

tert-pentyl: CC[C](C)C

phenacyl: [CH2]C(C1=CC=CC=C1)=O

phenacylidene: [CH]C(C1=CC=CC=C1)=O

phenethyl: [CH2]CC1=CC=CC=C1

phenoxy: [O]C1=CC=CC=C1

phenyl: [C]1=CC=CC=C1

phenylene: C1=C[C]=CC=[C]1

phosphino: [PH2]

phosphinyl: [PH2]=O

phospho: O=[P](O)O

phosphono: O=[P](O)O

phthaloyl: O=[C]C1=CC=CC=C1[C]=O

picryl: [O-][N+](C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=[C]1)=O

pimeloyl: O=[C]CCCCC[C]=O

piperidino: [N]1CCCCC1

pivaloyl: CC(C)(C)[C]=O

prenyl: [CH2]/C=C(C)\C

propargyl: [CH2]C#C

1-propenyl: [CH]=CC

2-propenyl: [CH2]C=C

propionyl: O=[C]CC

propoxy: [O]CCC

propyl: [CH2]CC

propylidene: [CH]CC

pyrryl: N1[C]=CC=C1

salicyloyl: OC1=CC=CC=C1[C]=O

selenyl: [SeH]

seryl: N[C@@H](CO)[C]=O

siloxy: [O][SiH3]

silyl: [SiH3]

silyene: [SiH2]

sorboyl: CC=CC=CC(O)=O

stearoyl: CCCCCCCCCCCCCCCCC[C]=O

stearyl: [CH2]CCCCCCCCCCCCCCCCC

styryl: [CH]=CC1=CC=CC=C1

suberoyl: O=[C]CCCCCC[C]=O

succinyl: O=[C]CC[C]=O

sulfamino: [NH]S(=O)(O)=O

sulfamoyl: O=[S](N)=O

sulfanilyl: O=[S](C1=CC=C(N)C=C1)=O

sulfeno: [S]O

sulfhydryl: [SH]

sulfinyl: S=O

sulfo: O=[S](O)=O

sulfonyl: O=S=O

terephthaloyl: O=[C]C1=CC=C([C]=O)C=C1

tetramethylene: CCCC

thienyl: [C]1=CC=CS1

thiocarbonyl: [CH]=S

thiocarboxy: S=[C]O

thiocyanato: [S]C#N

thionyl: S=O

threonyl: N[C@@H]([C@H](O)C)[C]=O

toluidino: [NH]C1=CC=C(C)C=C1

toluoyl: CC1=CC=C([C]=O)C=C1

tolyl: CC1=CC=[C]C=C1

alpha-tolyl: [C]C1=CC=CC=C1

tolylene: [CH]C1=CC=CC=C1

tosyl: O=[S](C1=CC=C(C)C=C1)=O

triazano: [NH]N[NH]

trimethylene: CCC

trityl: [C](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3

valeryl: O=[C]CCCC

valyl: N[C@@H](C(C)C)[C]=O

vinyl: [CH]=C

vinylidene: [C]=C

xylidino: [NH]C1=CC=C(C)C=C1C

xylyl: CC1=CC=[C]C(C)=C1

xylylene: NCC1=CC=CC(CN)=C1

Solution:

structure of iupac blue book common functional groups molecules:

acetamido: O=C(N)C

smiles_non_kekule:    CC(N)=O
smiles_kekule:    CC(N)=O
inchi:    InChI=1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4)
inchiKey:    DLFVBJFMPXGRIB-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#7])-[#6]
smarts_isomeric:    [#8]=[#6](-[#7])-[#6]

acetoacetyl: O=C(C)CC(=O)O

smiles_non_kekule:    CC(=O)CC(=O)O
smiles_kekule:    CC(=O)CC(=O)O
inchi:    InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)
inchiKey:    WDJHALXBUFZDSR-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6])-[#6]-[#6](=[#8])-[#8]
smarts_isomeric:    [#8]=[#6](-[#6])-[#6]-[#6](=[#8])-[#8]

acetyl: C(C)=O

acryloyl: C=CC(C)=O

smiles_non_kekule:    C=CC(C)=O
smiles_kekule:    C=CC(C)=O
inchi:    InChI=1S/C4H6O/c1-3-4(2)5/h3H,1H2,2H3
inchiKey:    FUSUHKVFWTUUBE-UHFFFAOYSA-N
smarts:    [#6]=[#6]-[#6](-[#6])=[#8]
smarts_isomeric:    [#6]=[#6]-[#6](-[#6])=[#8]

alanyl: N[CH](C)C(C)=O

smiles_non_kekule:    CC(=O)C(C)N
smiles_kekule:    CC(=O)C(C)N
inchi:    InChI=1S/C4H9NO/c1-3(5)4(2)6/h3H,5H2,1-2H3
inchiKey:    OLYWGXUJESDUAC-UHFFFAOYSA-N
smarts:    [#7]-[#6H](-[#6])-[#6](-[#6])=[#8]
smarts_isomeric:    [#7]-[#6H](-[#6])-[#6](-[#6])=[#8]

beta-alanyl: NCCC(C)=O

smiles_non_kekule:    CC(=O)CCN
smiles_kekule:    CC(=O)CCN
inchi:    InChI=1S/C4H9NO/c1-4(6)2-3-5/h2-3,5H2,1H3
inchiKey:    SUVYXKDAVYFUMG-UHFFFAOYSA-N
smarts:    [#7]-[#6]-[#6]-[#6](-[#6])=[#8]
smarts_isomeric:    [#7]-[#6]-[#6]-[#6](-[#6])=[#8]

allyl: [CH2]C=C

smiles_non_kekule:    [CH2]C=C
smiles_kekule:    [CH2]C=C
inchi:    InChI=1S/C3H5/c1-3-2/h3H,1-2H2
inchiKey:    RMRFFCXPLWYOOY-UHFFFAOYSA-N
smarts:    [#6H2]-[#6]=[#6]
smarts_isomeric:    [#6H2]-[#6]=[#6]

allylidene: [CH]C=C

smiles_non_kekule:    [CH]C=C
smiles_kekule:    [CH]C=C
inchi:    InChI=1S/C3H4/c1-3-2/h1,3H,2H2
inchiKey:    OQOPKWGTWCVGHN-UHFFFAOYSA-N
smarts:    [#6H]-[#6]=[#6]
smarts_isomeric:    [#6H]-[#6]=[#6]

amidino: NC=N

smiles_non_kekule:    N=CN
smiles_kekule:    N=CN
inchi:    InChI=1S/CH4N2/c2-1-3/h1H,(H3,2,3)
inchiKey:    PNKUSGQVOMIXLU-UHFFFAOYSA-N
smarts:    [#7]-[#6]=[#7]
smarts_isomeric:    [#7]-[#6]=[#7]

amino: N

smiles_non_kekule:    N
smiles_kekule:    N
inchi:    InChI=1S/H3N/h1H3
inchiKey:    QGZKDVFQNNGYKY-UHFFFAOYSA-N
smarts:    [#7]
smarts_isomeric:    [#7]

amyl: [CH2]CCCC

smiles_non_kekule:    [CH2]CCCC
smiles_kekule:    [CH2]CCCC
inchi:    InChI=1S/C5H11/c1-3-5-4-2/h1,3-5H2,2H3
inchiKey:    BFKVXNPJXXJUGQ-UHFFFAOYSA-N
smarts:    [#6H2]-[#6]-[#6]-[#6]-[#6]
smarts_isomeric:    [#6H2]-[#6]-[#6]-[#6]-[#6]

anilino: NC1=CC=CC=C1

anisidino: NC1=CC=C(OC)C=C1

anthranoyl: NC1=CC=CC=C1[C](C)=O

smiles_non_kekule:    CC(=O)c1ccccc1N
smiles_kekule:    CC(=O)C1=CC=CC=C1N
inchi:    InChI=1S/C8H9NO/c1-6(10)7-4-2-3-5-8(7)9/h2-5H,9H2,1H3
inchiKey:    GTDQGKWDWVUKTI-UHFFFAOYSA-N
smarts:    [#7]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6](-[#6])=[#8]
smarts_isomeric:    [#7]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6](-[#6])=[#8]

arsino: [AsH3]

smiles_non_kekule:    [AsH3]
smiles_kekule:    [AsH3]
inchi:    InChI=1S/AsH3/h1H3
inchiKey:    RBFQJDQYXXHULB-UHFFFAOYSA-N
smarts:    [AsH3]
smarts_isomeric:    [AsH3]

azelaoyl: O=CCCCCCCCC=O

smiles_non_kekule:    O=CCCCCCCCC=O
smiles_kekule:    O=CCCCCCCCC=O
inchi:    InChI=1S/C9H16O2/c10-8-6-4-2-1-3-5-7-9-11/h8-9H,1-7H2
inchiKey:    LEMKWEBKVMWZDU-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]
smarts_isomeric:    [#8]=[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]

azido: [N]=[N+]=[N-]

smiles_non_kekule:    [N]=[N+]=[N-]
smiles_kekule:    [N]=[N+]=[N-]
inchi:    InChI=1S/N3/c1-3-2
inchiKey:    DUAJIKVIRGATIW-UHFFFAOYSA-N
smarts:    [#7]=[#7+]=[#7-]
smarts_isomeric:    [#7]=[#7+]=[#7-]

azo: C/N=N/C

smiles_non_kekule:    C/N=N/C
smiles_kekule:    C/N=N/C
inchi:    InChI=1S/C2H6N2/c1-3-4-2/h1-2H3/b4-3+
inchiKey:    JCCAVOLDXDEODY-ONEGZZNKSA-N
smarts:    [#6]-[#7]=[#7]-[#6]
smarts_isomeric:    [#6]/[#7]=[#7]/[#6]

azoxy: C/N=[N+]([O-])/C

smiles_non_kekule:    C/N=[N+](/C)[O-]
smiles_kekule:    C/N=[N+](/C)[O-]
inchi:    InChI=1S/C2H6N2O/c1-3-4(2)5/h1-2H3/b4-3-
inchiKey:    DGAKHGXRMXWHBX-ARJAWSKDSA-N
smarts:    [#6]-[#7]=[#7+](-[#8-])-[#6]
smarts_isomeric:    [#6]/[#7]=[#7+](\[#8-])-[#6]

benzal: [CH]C1=CC=CC=C1

smiles_non_kekule:    [CH]c1ccccc1
smiles_kekule:    [CH]C1=CC=CC=C1
inchi:    InChI=1S/C7H6/c1-7-5-3-2-4-6-7/h1-6H
inchiKey:    YJLSVCJDMFHEHC-UHFFFAOYSA-N
smarts:    [#6H]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6H]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

benzamido: O=C(N)C1=CC=CC=C1

smiles_non_kekule:    NC(=O)c1ccccc1
smiles_kekule:    NC(=O)C1=CC=CC=C1
inchi:    InChI=1S/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9)
inchiKey:    KXDAEFPNCMNJSK-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#7])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#8]=[#6](-[#7])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

benzhydrol: OC(C1=CC=CC=C1)C2=CC=CC=C2

smiles_non_kekule:    OC(c1ccccc1)c1ccccc1
smiles_kekule:    OC(C1=CC=CC=C1)C1=CC=CC=C1
inchi:    InChI=1S/C13H12O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13-14H
inchiKey:    QILSFLSDHQAZET-UHFFFAOYSA-N
smarts:    [#8]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#8]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

benzoxy: [O]CC1=CC=CC=C1

smiles_non_kekule:    [O]Cc1ccccc1
smiles_kekule:    [O]CC1=CC=CC=C1
inchi:    InChI=1S/C7H7O/c8-6-7-4-2-1-3-5-7/h1-5H,6H2
inchiKey:    SMDGVPQREIZILS-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#8]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

benzoyl: O=[C]C1=CC=CC=C1

smiles_non_kekule:    O=[C]c1ccccc1
smiles_kekule:    O=[C]C1=CC=CC=C1
inchi:    InChI=1S/C7H5O/c8-6-7-4-2-1-3-5-7/h1-5H
inchiKey:    LEVJVKGPFAQPOI-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#8]=[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

benzyl: [CH2]C1=CC=CC=C1

smiles_non_kekule:    [CH2]c1ccccc1
smiles_kekule:    [CH2]C1=CC=CC=C1
inchi:    InChI=1S/C7H7/c1-7-5-3-2-4-6-7/h2-6H,1H2
inchiKey:    SLRMQYXOBQWXCR-UHFFFAOYSA-N
smarts:    [#6H2]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6H2]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

benzylidene: [CH]C1=CC=CC=C1

benzylidyne: [C]C1=CC=CC=C1

smiles_non_kekule:    [C]c1ccccc1
smiles_kekule:    [C]C1=CC=CC=C1
inchi:    InChI=1S/C7H5/c1-7-5-3-2-4-6-7/h2-6H
inchiKey:    BWDKGSMUZMQRCK-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

biphenylyl: C1(C2=CC=CC=C2)=CC=CC=[C]1

smiles_non_kekule:    [c]1ccccc1-c1ccccc1
smiles_kekule:    [C]1=CC=CC=C1C1=CC=CC=C1
inchi:    InChI=1S/C12H9/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1-9H
inchiKey:    PIGVXRKGKGOZME-UHFFFAOYSA-N
smarts:    [#6]1(-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2):[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1(-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2):[#6]:[#6]:[#6]:[#6]:[#6]:1

biphenylene: C12=C3C=CC=CC3=C1C=CC=C2

smiles_non_kekule:    c1ccc2c(c1)=c1ccccc1=2
smiles_kekule:    C1=CC2=C3C=CC=CC3=C2C=C1
inchi:    InChI=1S/C12H8/c1-2-6-10-9(5-1)11-7-3-4-8-12(10)11/h1-8H
inchiKey:    IFVTZJHWGZSXFD-UHFFFAOYSA-N
smarts:    [#6]12=[#6]3:[#6]:[#6]:[#6]:[#6]:[#6]:3=[#6]:1:[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#6]12=[#6]3:[#6]:[#6]:[#6]:[#6]:[#6]:3=[#6]:1:[#6]:[#6]:[#6]:[#6]:2

butoxy: [O]CCCC

smiles_non_kekule:    CCCC[O]
smiles_kekule:    CCCC[O]
inchi:    InChI=1S/C4H9O/c1-2-3-4-5/h2-4H2,1H3
inchiKey:    QOOQLKSEGVNYLA-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]-[#6]-[#6]
smarts_isomeric:    [#8]-[#6]-[#6]-[#6]-[#6]

sec-butoxy: [O]C(C)CC

smiles_non_kekule:    CCC(C)[O]
smiles_kekule:    CCC(C)[O]
inchi:    InChI=1S/C4H9O/c1-3-4(2)5/h4H,3H2,1-2H3
inchiKey:    HFQYJCVJLPOROO-UHFFFAOYSA-N
smarts:    [#8]-[#6](-[#6])-[#6]-[#6]
smarts_isomeric:    [#8]-[#6](-[#6])-[#6]-[#6]

tert-butoxy: [O]C(C)(C)C

smiles_non_kekule:    CC(C)(C)[O]
smiles_kekule:    CC(C)(C)[O]
inchi:    InChI=1S/C4H9O/c1-4(2,3)5/h1-3H3
inchiKey:    ZLRFPQPVXRIBCQ-UHFFFAOYSA-N
smarts:    [#8]-[#6](-[#6])(-[#6])-[#6]
smarts_isomeric:    [#8]-[#6](-[#6])(-[#6])-[#6]

butyl: [CH2]CCC

smiles_non_kekule:    [CH2]CCC
smiles_kekule:    [CH2]CCC
inchi:    InChI=1S/C4H9/c1-3-4-2/h1,3-4H2,2H3
inchiKey:    WPWHSFAFEBZWBB-UHFFFAOYSA-N
smarts:    [#6H2]-[#6]-[#6]-[#6]
smarts_isomeric:    [#6H2]-[#6]-[#6]-[#6]

sec-butyl: CC[CH]C

smiles_non_kekule:    C[CH]CC
smiles_kekule:    C[CH]CC
inchi:    InChI=1S/C4H9/c1-3-4-2/h3H,4H2,1-2H3
inchiKey:    ULOIAOPTGWSNHU-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6H]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6H]-[#6]

tert-butyl: C[C](C)C

smiles_non_kekule:    C[C](C)C
smiles_kekule:    C[C](C)C
inchi:    InChI=1S/C4H9/c1-4(2)3/h1-3H3
inchiKey:    IIVWHGMLFGNMOW-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6](-[#6])-[#6]

butyryl: O=[C]CCC

smiles_non_kekule:    CCC[C]=O
smiles_kekule:    CCC[C]=O
inchi:    InChI=1S/C4H7O/c1-2-3-4-5/h2-3H2,1H3
inchiKey:    PCDHSSHKDZYLLI-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#6]-[#6]-[#6]
smarts_isomeric:    [#8]=[#6]-[#6]-[#6]-[#6]

caproyl: CCCCC[C]=O

smiles_non_kekule:    CCCCC[C]=O
smiles_kekule:    CCCCC[C]=O
inchi:    InChI=1S/C6H11O/c1-2-3-4-5-6-7/h2-5H2,1H3
inchiKey:    MOMDHKVDJYHNRF-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]

capryl: CCCCCCCC

capryloyl: CCCCCCC[C]=O

smiles_non_kekule:    CCCCCCC[C]=O
smiles_kekule:    CCCCCCC[C]=O
inchi:    InChI=1S/C8H15O/c1-2-3-4-5-6-7-8-9/h2-7H2,1H3
inchiKey:    CPYJUVWVXLWTPP-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]

carbamido: C(=O)(N)N

smiles_non_kekule:    NC(N)=O
smiles_kekule:    NC(N)=O
inchi:    InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4)
inchiKey:    XSQUKJJJFZCRTK-UHFFFAOYSA-N
smarts:    [#6](=[#8])(-[#7])-[#7]
smarts_isomeric:    [#6](=[#8])(-[#7])-[#7]

carbamoyl: N[C]=O

smiles_non_kekule:    N[C]=O
smiles_kekule:    N[C]=O
inchi:    InChI=1S/CH2NO/c2-1-3/h(H2,2,3)
inchiKey:    KKFDJZZADQONDE-UHFFFAOYSA-N
smarts:    [#7]-[#6]=[#8]
smarts_isomeric:    [#7]-[#6]=[#8]

carbamyl: N[C]=O

carbazoyl: NN[C]=O

smiles_non_kekule:    NN[C]=O
smiles_kekule:    NN[C]=O
inchi:    InChI=1S/CH3N2O/c2-3-1-4/h2H2,(H,3,4)
inchiKey:    ODKLAPPRSKDKFQ-UHFFFAOYSA-N
smarts:    [#7]-[#7]-[#6]=[#8]
smarts_isomeric:    [#7]-[#7]-[#6]=[#8]

carbethoxy: O=[C]OCC

smiles_non_kekule:    CCO[C]=O
smiles_kekule:    CCO[C]=O
inchi:    InChI=1S/C3H5O2/c1-2-5-3-4/h2H2,1H3
inchiKey:    CHFVGNWUBCAWOL-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#8]-[#6]-[#6]
smarts_isomeric:    [#8]=[#6]-[#8]-[#6]-[#6]

carbonyl: [CH]=O

smiles_non_kekule:    [CH]=O
smiles_kekule:    [CH]=O
inchi:    InChI=1S/CHO/c1-2/h1H
inchiKey:    CFHIDWOYWUOIHU-UHFFFAOYSA-N
smarts:    [#6H]=[#8]
smarts_isomeric:    [#6H]=[#8]

carboxy: O=[C]O

smiles_non_kekule:    O=[C]O
smiles_kekule:    O=[C]O
inchi:    InChI=1S/CHO2/c2-1-3/h(H,2,3)
inchiKey:    ORTFAQDWJHRMNX-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#8]
smarts_isomeric:    [#8]=[#6]-[#8]

cetyl: [CH2]CCCCCCCCCCCCCCC

smiles_non_kekule:    [CH2]CCCCCCCCCCCCCCC
smiles_kekule:    [CH2]CCCCCCCCCCCCCCC
inchi:    InChI=1S/C16H33/c1-3-5-7-9-11-13-15-16-14-12-10-8-6-4-2/h1,3-16H2,2H3
inchiKey:    VHOGADCBMMJONL-UHFFFAOYSA-N
smarts:    [#6H2]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]
smarts_isomeric:    [#6H2]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]

chloroformyl: O=[C]Cl

smiles_non_kekule:    O=[C]Cl
smiles_kekule:    O=[C]Cl
inchi:    InChI=1S/CClO/c2-1-3
inchiKey:    DDKMFOUTRRODRE-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#17]
smarts_isomeric:    [#8]=[#6]-[#17]

cinnamoyl: O=[C]C=CC1=CC=CC=C1

smiles_non_kekule:    O=[C]C=Cc1ccccc1
smiles_kekule:    O=[C]C=CC1=CC=CC=C1
inchi:    InChI=1S/C9H7O/c10-8-4-7-9-5-2-1-3-6-9/h1-7H
inchiKey:    AJSWOFGOXSEBNS-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#6]=[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#8]=[#6]-[#6]=[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

cinnamyl: [CH2]C=CC1=CC=CC=C1

smiles_non_kekule:    [CH2]C=Cc1ccccc1
smiles_kekule:    [CH2]C=CC1=CC=CC=C1
inchi:    InChI=1S/C9H9/c1-2-6-9-7-4-3-5-8-9/h2-8H,1H2
inchiKey:    ICTGSQARZKHWET-UHFFFAOYSA-N
smarts:    [#6H2]-[#6]=[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6H2]-[#6]=[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

cinnamylidene: [CH]C=CC1=CC=CC=C1

smiles_non_kekule:    [CH]C=Cc1ccccc1
smiles_kekule:    [CH]C=CC1=CC=CC=C1
inchi:    InChI=1S/C9H8/c1-2-6-9-7-4-3-5-8-9/h1-8H
inchiKey:    DVRHENDBDQJBOA-UHFFFAOYSA-N
smarts:    [#6H]-[#6]=[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6H]-[#6]=[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

cresyl: OC1=CC=C(C)C=C1

smiles_non_kekule:    Cc1ccc(O)cc1
smiles_kekule:    CC1=CC=C(O)C=C1
inchi:    InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3
inchiKey:    IWDCLRJOBJJRNH-UHFFFAOYSA-N
smarts:    [#8]-[#6]1:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#8]-[#6]1:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:1

crotonoyl: C/C=C/[C]=O

smiles_non_kekule:    C/C=C/[C]=O
smiles_kekule:    C/C=C/[C]=O
inchi:    InChI=1S/C4H5O/c1-2-3-4-5/h2-3H,1H3/b3-2+
inchiKey:    RDUWVWJVALYSPI-NSCUHMNNSA-N
smarts:    [#6]-[#6]=[#6]-[#6]=[#8]
smarts_isomeric:    [#6]/[#6]=[#6]/[#6]=[#8]

crotyl: [CH2]/C=C/C

smiles_non_kekule:    [CH2]/C=C/C
smiles_kekule:    [CH2]/C=C/C
inchi:    InChI=1S/C4H7/c1-3-4-2/h3-4H,1H2,2H3/b4-3+
inchiKey:    CRPTXKKKIGGDBX-ONEGZZNKSA-N
smarts:    [#6H2]-[#6]=[#6]-[#6]
smarts_isomeric:    [#6H2]/[#6]=[#6]/[#6]

cyanamido: [NH]C#N

smiles_non_kekule:    N#C[NH]
smiles_kekule:    N#C[NH]
inchi:    InChI=1S/CHN2/c2-1-3/h2H
inchiKey:    RCDKZYGELCBJTH-UHFFFAOYSA-N
smarts:    [#7H]-[#6]#[#7]
smarts_isomeric:    [#7H]-[#6]#[#7]

cyanato: [O]C#N

smiles_non_kekule:    N#C[O]
smiles_kekule:    N#C[O]
inchi:    InChI=1S/CNO/c2-1-3
inchiKey:    HKKDKUMUWRTAIA-UHFFFAOYSA-N
smarts:    [#8]-[#6]#[#7]
smarts_isomeric:    [#8]-[#6]#[#7]

cyano: [C]#N

smiles_non_kekule:    [C]#N
smiles_kekule:    [C]#N
inchi:    InChI=1S/CN/c1-2
inchiKey:    JEVCWSUVFOYBFI-UHFFFAOYSA-N
smarts:    [#6]#[#7]
smarts_isomeric:    [#6]#[#7]

decanedioyl: O=[C]CCCCCCCC[C]=O

smiles_non_kekule:    O=[C]CCCCCCCC[C]=O
smiles_kekule:    O=[C]CCCCCCCC[C]=O
inchi:    InChI=1S/C10H16O2/c11-9-7-5-3-1-2-4-6-8-10-12/h1-8H2
inchiKey:    WLGBFZSBQQAXRJ-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]
smarts_isomeric:    [#8]=[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]

decanoyl: CCCCCCCCC[C]=O

smiles_non_kekule:    CCCCCCCCC[C]=O
smiles_kekule:    CCCCCCCCC[C]=O
inchi:    InChI=1S/C10H19O/c1-2-3-4-5-6-7-8-9-10-11/h2-9H2,1H3
inchiKey:    WLDBKDYSWDAYMZ-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]

diazo: [N+]=[N-]

smiles_non_kekule:    [N+]=[N-]
smiles_kekule:    [N+]=[N-]
inchi:    InChI=1S/N2/c1-2
inchiKey:    IJGRMHOSHXDMSA-UHFFFAOYSA-N
smarts:    [#7+]=[#7-]
smarts_isomeric:    [#7+]=[#7-]

diazoamino: N=NN

smiles_non_kekule:    N=NN
smiles_kekule:    N=NN
inchi:    InChI=1S/H3N3/c1-3-2/h(H3,1,2)
inchiKey:    AYNNSCRYTDRFCP-UHFFFAOYSA-N
smarts:    [#7]=[#7]-[#7]
smarts_isomeric:    [#7]=[#7]-[#7]

disilanyl: [SiH2][SiH3]

smiles_non_kekule:    [SiH2][SiH3]
smiles_kekule:    [SiH2][SiH3]
inchi:    InChI=1S/H5Si2/c1-2/h1H2,2H3
inchiKey:    PDULIKUVYCXPGX-UHFFFAOYSA-N
smarts:    [SiH2]-[SiH3]
smarts_isomeric:    [SiH2]-[SiH3]

disiloxanyloxy: [O][SiH2]O[SiH3]

smiles_non_kekule:    [O][SiH2]O[SiH3]
smiles_kekule:    [O][SiH2]O[SiH3]
inchi:    InChI=1S/H5O2Si2/c1-4-2-3/h4H2,3H3
inchiKey:    KKNGGIDYVYYXPP-UHFFFAOYSA-N
smarts:    [#8]-[SiH2]-[#8]-[SiH3]
smarts_isomeric:    [#8]-[SiH2]-[#8]-[SiH3]

disulfinyl: O=[S]S=O

smiles_non_kekule:    O=[S][SH]=O
smiles_kekule:    O=[S][SH]=O
inchi:    InChI=1S/O2S2/c1-3-4-2
inchiKey:    AXYLJRYHRATPSG-UHFFFAOYSA-N
smarts:    [#8]=[#16]-[#16]=[#8]
smarts_isomeric:    [#8]=[#16]-[#16]=[#8]

dithio: [S]S

smiles_non_kekule:    [S]S
smiles_kekule:    [S]S
inchi:    InChI=1S/HS2/c1-2/h1H
inchiKey:    PYPQFOINVKFSJD-UHFFFAOYSA-N
smarts:    [#16]-[#16]
smarts_isomeric:    [#16]-[#16]

enanthoyl: CCCCCC[C]=O

smiles_non_kekule:    CCCCCC[C]=O
smiles_kekule:    CCCCCC[C]=O
inchi:    InChI=1S/C7H13O/c1-2-3-4-5-6-7-8/h2-6H2,1H3
inchiKey:    FZCFGTYSKJLRRR-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]

epoxy: [O]

smiles_non_kekule:    [O]
smiles_kekule:    [O]
inchi:    InChI=1S/O
inchiKey:    QVGXLLKOCUKJST-UHFFFAOYSA-N
smarts:    [#8]
smarts_isomeric:    [#8]

ethenyl: [CH]=C

smiles_non_kekule:    [CH]=C
smiles_kekule:    [CH]=C
inchi:    InChI=1S/C2H3/c1-2/h1H,2H2
inchiKey:    ORGHESHFQPYLAO-UHFFFAOYSA-N
smarts:    [#6H]=[#6]
smarts_isomeric:    [#6H]=[#6]

ethynyl: [C]#C

smiles_non_kekule:    [C]#C
smiles_kekule:    [C]#C
inchi:    InChI=1S/C2H/c1-2/h1H
inchiKey:    XEHVFKKSDRMODV-UHFFFAOYSA-N
smarts:    [#6]#[#6]
smarts_isomeric:    [#6]#[#6]

ethoxy: [O]CC

smiles_non_kekule:    CC[O]
smiles_kekule:    CC[O]
inchi:    InChI=1S/C2H5O/c1-2-3/h2H2,1H3
inchiKey:    VOLGAXAGEUPBDM-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]
smarts_isomeric:    [#8]-[#6]-[#6]

ethyl: [CH2]C

smiles_non_kekule:    [CH2]C
smiles_kekule:    [CH2]C
inchi:    InChI=1S/C2H5/c1-2/h1H2,2H3
inchiKey:    QUPDWYMUPZLYJZ-UHFFFAOYSA-N
smarts:    [#6H2]-[#6]
smarts_isomeric:    [#6H2]-[#6]

ethylene: C=C

smiles_non_kekule:    C=C
smiles_kekule:    C=C
inchi:    InChI=1S/C2H4/c1-2/h1-2H2
inchiKey:    VGGSQFUCUMXWEO-UHFFFAOYSA-N
smarts:    [#6]=[#6]
smarts_isomeric:    [#6]=[#6]

ethylidene: [CH]C

ethylthio: [S]CC

smiles_non_kekule:    CC[S]
smiles_kekule:    CC[S]
inchi:    InChI=1S/C2H5S/c1-2-3/h2H2,1H3
inchiKey:    WYRSGXAIHNMKOL-UHFFFAOYSA-N
smarts:    [#16]-[#6]-[#6]
smarts_isomeric:    [#16]-[#6]-[#6]

formamido: O=C[NH]

smiles_non_kekule:    [NH]C=O
smiles_kekule:    [NH]C=O
inchi:    InChI=1S/CH2NO/c2-1-3/h1-2H
inchiKey:    RUFOWFPQNWYPAD-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#7H]
smarts_isomeric:    [#8]=[#6]-[#7H]

formyl: [CH]=O

furmaroyl: O=CO

smiles_non_kekule:    O=CO
smiles_kekule:    O=CO
inchi:    InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3)
inchiKey:    BDAGIHXWWSANSR-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#8]
smarts_isomeric:    [#8]=[#6]-[#8]

furfuryl: [CH2]C1=CC=CO1

smiles_non_kekule:    [CH2]c1ccco1
smiles_kekule:    [CH2]C1=CC=CO1
inchi:    InChI=1S/C5H5O/c1-5-3-2-4-6-5/h2-4H,1H2
inchiKey:    IPEWNTLWCRYSRY-UHFFFAOYSA-N
smarts:    [#6H2]-[#6]1:[#6]:[#6]:[#6]:[#8]:1
smarts_isomeric:    [#6H2]-[#6]1:[#6]:[#6]:[#6]:[#8]:1

furfurylidene: [CH]C1=CC=CO1

smiles_non_kekule:    [CH]c1ccco1
smiles_kekule:    [CH]C1=CC=CO1
inchi:    InChI=1S/C5H4O/c1-5-3-2-4-6-5/h1-4H
inchiKey:    CXKHDEVHFAULNO-UHFFFAOYSA-N
smarts:    [#6H]-[#6]1:[#6]:[#6]:[#6]:[#8]:1
smarts_isomeric:    [#6H]-[#6]1:[#6]:[#6]:[#6]:[#8]:1

glutamoyl: N[C@@H](CC[C]=O)[C]=O

smiles_non_kekule:    N[C@H]([C]=O)CC[C]=O
smiles_kekule:    N[C@H]([C]=O)CC[C]=O
inchi:    InChI=1S/C5H7NO2/c6-5(4-8)2-1-3-7/h5H,1-2,6H2/t5-/m0/s1
inchiKey:    FHMQITZHWGAHIW-YFKPBYRVSA-N
smarts:    [#7]-[#6H](-[#6]-[#6]-[#6]=[#8])-[#6]=[#8]
smarts_isomeric:    [#7]-[#6@@H](-[#6]-[#6]-[#6]=[#8])-[#6]=[#8]

glutaryl: O=[C]CCC[C]=O

smiles_non_kekule:    O=[C]CCC[C]=O
smiles_kekule:    O=[C]CCC[C]=O
inchi:    InChI=1S/C5H6O2/c6-4-2-1-3-5-7/h1-3H2
inchiKey:    LFMZGLJNFRZVBS-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#6]-[#6]-[#6]-[#6]=[#8]
smarts_isomeric:    [#8]=[#6]-[#6]-[#6]-[#6]-[#6]=[#8]

glycylamino: [NH]C(CN)=O

smiles_non_kekule:    [NH]C(=O)CN
smiles_kekule:    [NH]C(=O)CN
inchi:    InChI=1S/C2H5N2O/c3-1-2(4)5/h4H,1,3H2
inchiKey:    KNGHGFVNHHXTGR-UHFFFAOYSA-N
smarts:    [#7H]-[#6](-[#6]-[#7])=[#8]
smarts_isomeric:    [#7H]-[#6](-[#6]-[#7])=[#8]

glycoloyl: OC[C]=O

smiles_non_kekule:    O=[C]CO
smiles_kekule:    O=[C]CO
inchi:    InChI=1S/C2H3O2/c3-1-2-4/h3H,1H2
inchiKey:    JSBBMMHTNIUVTC-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]=[#8]
smarts_isomeric:    [#8]-[#6]-[#6]=[#8]

glycyl: NC[C]=O

smiles_non_kekule:    NC[C]=O
smiles_kekule:    NC[C]=O
inchi:    InChI=1S/C2H4NO/c3-1-2-4/h1,3H2
inchiKey:    ANXOZVKTXWJGOY-UHFFFAOYSA-N
smarts:    [#7]-[#6]-[#6]=[#8]
smarts_isomeric:    [#7]-[#6]-[#6]=[#8]

glyoxyoyl: O=[C]C=O

smiles_non_kekule:    O=[C]C=O
smiles_kekule:    O=[C]C=O
inchi:    InChI=1S/C2HO2/c3-1-2-4/h1H
inchiKey:    IKFPMWBBLSRQRA-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#6]=[#8]
smarts_isomeric:    [#8]=[#6]-[#6]=[#8]

guanidino: [NH]C(N)=N

smiles_non_kekule:    [NH]C(=N)N
smiles_kekule:    [NH]C(=N)N
inchi:    InChI=1S/CH4N3/c2-1(3)4/h2H,(H3,3,4)
inchiKey:    DJJILYWKVKCPMZ-UHFFFAOYSA-N
smarts:    [#7H]-[#6](-[#7])=[#7]
smarts_isomeric:    [#7H]-[#6](-[#7])=[#7]

guanyl: N=[C]N

smiles_non_kekule:    N=[C]N
smiles_kekule:    N=[C]N
inchi:    InChI=1S/CH3N2/c2-1-3/h(H3,2,3)
inchiKey:    ULJJYIGVIAGSIT-UHFFFAOYSA-N
smarts:    [#7]=[#6]-[#7]
smarts_isomeric:    [#7]=[#6]-[#7]

heptadecanoyl: CCCCCCCCCCCCCCCC[C]=O

smiles_non_kekule:    CCCCCCCCCCCCCCCC[C]=O
smiles_kekule:    CCCCCCCCCCCCCCCC[C]=O
inchi:    InChI=1S/C17H33O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18/h2-16H2,1H3
inchiKey:    QKZVRNPGICFIEB-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]

heptanamido: CCCCCCC([NH])=O

smiles_non_kekule:    CCCCCCC([NH])=O
smiles_kekule:    CCCCCCC([NH])=O
inchi:    InChI=1S/C7H14NO/c1-2-3-4-5-6-7(8)9/h8H,2-6H2,1H3
inchiKey:    OKQVWEWJRVMMDN-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6](-[#7H])=[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6](-[#7H])=[#8]

heptanoyl: CCCCCC[C]=O.CCCCCCC([NH])=O

smiles_non_kekule:    CCCCCCC([NH])=O.CCCCCC[C]=O
smiles_kekule:    CCCCCCC([NH])=O.CCCCCC[C]=O
inchi:    InChI=1S/C7H14NO.C7H13O/c1-2-3-4-5-6-7(8)9;1-2-3-4-5-6-7-8/h8H,2-6H2,1H3;2-6H2,1H3
inchiKey:    IRFFVXOOYKSKJX-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8].[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6](-[#7H])=[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8].[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6](-[#7H])=[#8]

hexadecanoyl: CCCCCCCCCCCCCCC[C]=O.CCCCCC[C]=O.CCCCCCC([NH])=O

smiles_non_kekule:    CCCCCCC([NH])=O.CCCCCCCCCCCCCCC[C]=O.CCCCCC[C]=O
smiles_kekule:    CCCCCCC([NH])=O.CCCCCCCCCCCCCCC[C]=O.CCCCCC[C]=O
inchi:    InChI=1S/C16H31O.C7H14NO.C7H13O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17;1-2-3-4-5-6-7(8)9;1-2-3-4-5-6-7-8/h2-15H2,1H3;8H,2-6H2,1H3;2-6H2,1H3
inchiKey:    GJNAZOMLCMQSGK-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8].[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8].[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6](-[#7H])=[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8].[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8].[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6](-[#7H])=[#8]

hexamethylene: CCCCCC

hexanedioyl: O=[C]CCCC[C]=O

smiles_non_kekule:    O=[C]CCCC[C]=O
smiles_kekule:    O=[C]CCCC[C]=O
inchi:    InChI=1S/C6H8O2/c7-5-3-1-2-4-6-8/h1-4H2
inchiKey:    XCHUVXKTSGTHFU-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]
smarts_isomeric:    [#8]=[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]

hippuryl: [CH2]CNC(C1=CC=CC=C1)=O

smiles_non_kekule:    [CH2]CNC(=O)c1ccccc1
smiles_kekule:    [CH2]CNC(=O)C1=CC=CC=C1
inchi:    InChI=1S/C9H10NO/c1-2-10-9(11)8-6-4-3-5-7-8/h3-7H,1-2H2,(H,10,11)
inchiKey:    FONLMWMORIACNQ-UHFFFAOYSA-N
smarts:    [#6H2]-[#6]-[#7]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)=[#8]
smarts_isomeric:    [#6H2]-[#6]-[#7]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)=[#8]

hydrazino: N[NH]

smiles_non_kekule:    [NH]N
smiles_kekule:    [NH]N
inchi:    InChI=1S/H3N2/c1-2/h1H,2H2
inchiKey:    LURQBQNWDYASPJ-UHFFFAOYSA-N
smarts:    [#7]-[#7H]
smarts_isomeric:    [#7]-[#7H]

hydrazo: NN

smiles_non_kekule:    NN
smiles_kekule:    NN
inchi:    InChI=1S/H4N2/c1-2/h1-2H2
inchiKey:    OAKJQQAXSVQMHS-UHFFFAOYSA-N
smarts:    [#7]-[#7]
smarts_isomeric:    [#7]-[#7]

hydrocinnamoyl: O=[C]CCC1=CC=CC=C1

smiles_non_kekule:    O=[C]CCc1ccccc1
smiles_kekule:    O=[C]CCC1=CC=CC=C1
inchi:    InChI=1S/C9H9O/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7H2
inchiKey:    OOHPFUUSZUFJHA-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#8]=[#6]-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

hydroperoxy: [O]O

smiles_non_kekule:    [O]O
smiles_kekule:    [O]O
inchi:    InChI=1S/HO2/c1-2/h1H
inchiKey:    OUUQCZGPVNCOIJ-UHFFFAOYSA-N
smarts:    [#8]-[#8]
smarts_isomeric:    [#8]-[#8]

hydroxyamino: [NH]O

smiles_non_kekule:    [NH]O
smiles_kekule:    [NH]O
inchi:    InChI=1S/H2NO/c1-2/h1-2H
inchiKey:    MMZRZHBDYRHGII-UHFFFAOYSA-N
smarts:    [#7H]-[#8]
smarts_isomeric:    [#7H]-[#8]

imino: [NH]

smiles_non_kekule:    [NH]
smiles_kekule:    [NH]
inchi:    InChI=1S/HN/h1H
inchiKey:    PDCKRJPYJMCOFO-UHFFFAOYSA-N
smarts:    [#7H]
smarts_isomeric:    [#7H]

iodoso: I=O

smiles_non_kekule:    O=[IH]
smiles_kekule:    O=[IH]
inchi:    InChI=1S/HIO/c1-2/h1H
inchiKey:    OTNDGZFPFXAOBG-UHFFFAOYSA-N
smarts:    [#53]=[#8]
smarts_isomeric:    [#53]=[#8]

iodyl: O=I=O

smiles_non_kekule:    O=[IH]=O
smiles_kekule:    O=[IH]=O
inchi:    InChI=1S/HIO2/c2-1-3/h1H
inchiKey:    TXXYMOXOCONMDN-UHFFFAOYSA-N
smarts:    [#8]=[#53]=[#8]
smarts_isomeric:    [#8]=[#53]=[#8]

isoamyl: [CH2]CC(C)C

smiles_non_kekule:    [CH2]CC(C)C
smiles_kekule:    [CH2]CC(C)C
inchi:    InChI=1S/C5H11/c1-4-5(2)3/h5H,1,4H2,2-3H3
inchiKey:    TXFXGCPVIYCUIT-UHFFFAOYSA-N
smarts:    [#6H2]-[#6]-[#6](-[#6])-[#6]
smarts_isomeric:    [#6H2]-[#6]-[#6](-[#6])-[#6]

isobutenyl: [CH]=C(C)C

smiles_non_kekule:    [CH]=C(C)C
smiles_kekule:    [CH]=C(C)C
inchi:    InChI=1S/C4H7/c1-4(2)3/h1H,2-3H3
inchiKey:    ZVYGPDVHHRTJCD-UHFFFAOYSA-N
smarts:    [#6H]=[#6](-[#6])-[#6]
smarts_isomeric:    [#6H]=[#6](-[#6])-[#6]

isobutoxy: [O]CC(C)C

smiles_non_kekule:    CC(C)C[O]
smiles_kekule:    CC(C)C[O]
inchi:    InChI=1S/C4H9O/c1-4(2)3-5/h4H,3H2,1-2H3
inchiKey:    PBRXKNKPUMMYPO-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6](-[#6])-[#6]
smarts_isomeric:    [#8]-[#6]-[#6](-[#6])-[#6]

isobutyl: [CH2]C(C)C

smiles_non_kekule:    [CH2]C(C)C
smiles_kekule:    [CH2]C(C)C
inchi:    InChI=1S/C4H9/c1-4(2)3/h4H,1H2,2-3H3
inchiKey:    KTOQRRDVVIDEAA-UHFFFAOYSA-N
smarts:    [#6H2]-[#6](-[#6])-[#6]
smarts_isomeric:    [#6H2]-[#6](-[#6])-[#6]

isobutylidene: [CH]C(C)C

smiles_non_kekule:    [CH]C(C)C
smiles_kekule:    [CH]C(C)C
inchi:    InChI=1S/C4H8/c1-4(2)3/h1,4H,2-3H3
inchiKey:    KESNYEOEHYIICS-UHFFFAOYSA-N
smarts:    [#6H]-[#6](-[#6])-[#6]
smarts_isomeric:    [#6H]-[#6](-[#6])-[#6]

isobutyryl: O=[C]C(C)C

smiles_non_kekule:    CC(C)[C]=O
smiles_kekule:    CC(C)[C]=O
inchi:    InChI=1S/C4H7O/c1-4(2)3-5/h4H,1-2H3
inchiKey:    RYDOQJPDRXMRRP-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#6](-[#6])-[#6]
smarts_isomeric:    [#8]=[#6]-[#6](-[#6])-[#6]

isocyanato: [N]=C=O

smiles_non_kekule:    [N]=C=O
smiles_kekule:    [N]=C=O
inchi:    InChI=1S/CNO/c2-1-3
inchiKey:    HKKDKUMUWRTAIA-UHFFFAOYSA-N
smarts:    [#7]=[#6]=[#8]
smarts_isomeric:    [#7]=[#6]=[#8]

isocyano: [N+]#[C-]

smiles_non_kekule:    [C-]#[N+]
smiles_kekule:    [C-]#[N+]
inchi:    InChI=1S/CN/c1-2
inchiKey:    JEVCWSUVFOYBFI-UHFFFAOYSA-N
smarts:    [#7+]#[#6-]
smarts_isomeric:    [#7+]#[#6-]

isohexyl: [CH2]CCC(C)C

smiles_non_kekule:    [CH2]CCC(C)C
smiles_kekule:    [CH2]CCC(C)C
inchi:    InChI=1S/C6H13/c1-4-5-6(2)3/h6H,1,4-5H2,2-3H3
inchiKey:    CCIHKGBEUNXZHW-UHFFFAOYSA-N
smarts:    [#6H2]-[#6]-[#6]-[#6](-[#6])-[#6]
smarts_isomeric:    [#6H2]-[#6]-[#6]-[#6](-[#6])-[#6]

isoleucyl: N[C@@H]([C@@H](C)CC)[C]=O

smiles_non_kekule:    CC[C@H](C)[C@H](N)[C]=O
smiles_kekule:    CC[C@H](C)[C@H](N)[C]=O
inchi:    InChI=1S/C6H12NO/c1-3-5(2)6(7)4-8/h5-6H,3,7H2,1-2H3/t5-,6+/m0/s1
inchiKey:    OPNBLVIHGHEVRZ-NTSWFWBYSA-N
smarts:    [#7]-[#6H](-[#6H](-[#6])-[#6]-[#6])-[#6]=[#8]
smarts_isomeric:    [#7]-[#6@@H](-[#6@@H](-[#6])-[#6]-[#6])-[#6]=[#8]

isonitroso: [N]O

smiles_non_kekule:    [N]O
smiles_kekule:    [N]O
inchi:    InChI=1S/HNO/c1-2/h2H
inchiKey:    JSGZKHJWRITPII-UHFFFAOYSA-N
smarts:    [#7]-[#8]
smarts_isomeric:    [#7]-[#8]

isopentyl: [CH2]CC(C)C

isopentylidene: [CH]CC(C)C

smiles_non_kekule:    [CH]CC(C)C
smiles_kekule:    [CH]CC(C)C
inchi:    InChI=1S/C5H10/c1-4-5(2)3/h1,5H,4H2,2-3H3
inchiKey:    YUEFPCVWKIOPNA-UHFFFAOYSA-N
smarts:    [#6H]-[#6]-[#6](-[#6])-[#6]
smarts_isomeric:    [#6H]-[#6]-[#6](-[#6])-[#6]

isopropenyl: C=[C]C

smiles_non_kekule:    C=[C]C
smiles_kekule:    C=[C]C
inchi:    InChI=1S/C3H5/c1-3-2/h1H2,2H3
inchiKey:    NMTZQIYQFZGXQT-UHFFFAOYSA-N
smarts:    [#6]=[#6]-[#6]
smarts_isomeric:    [#6]=[#6]-[#6]

isopropoxy: [O]C(C)C

smiles_non_kekule:    CC(C)[O]
smiles_kekule:    CC(C)[O]
inchi:    InChI=1S/C3H7O/c1-3(2)4/h3H,1-2H3
inchiKey:    ZOAMZFNAPHWBEN-UHFFFAOYSA-N
smarts:    [#8]-[#6](-[#6])-[#6]
smarts_isomeric:    [#8]-[#6](-[#6])-[#6]

isopropyl: C[CH]C

smiles_non_kekule:    C[CH]C
smiles_kekule:    C[CH]C
inchi:    InChI=1S/C3H7/c1-3-2/h3H,1-2H3
inchiKey:    HNUALPPJLMYHDK-UHFFFAOYSA-N
smarts:    [#6]-[#6H]-[#6]
smarts_isomeric:    [#6]-[#6H]-[#6]

isopropylidene: C[C]C

smiles_non_kekule:    C[C]C
smiles_kekule:    C[C]C
inchi:    InChI=1S/C3H6/c1-3-2/h1-2H3
inchiKey:    IPZJQDSFZGZEOY-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]

isothiocynato: N=C=S

isovaleryl: O=[C]CC(C)C

smiles_non_kekule:    CC(C)C[C]=O
smiles_kekule:    CC(C)C[C]=O
inchi:    InChI=1S/C5H9O/c1-5(2)3-4-6/h5H,3H2,1-2H3
inchiKey:    NHKWWADFZCTJFK-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#6]-[#6](-[#6])-[#6]
smarts_isomeric:    [#8]=[#6]-[#6]-[#6](-[#6])-[#6]

lactoyl: OC(C)[C]=O

smiles_non_kekule:    CC(O)[C]=O
smiles_kekule:    CC(O)[C]=O
inchi:    InChI=1S/C3H5O2/c1-3(5)2-4/h3,5H,1H3
inchiKey:    JWSLLAZAEOGIPU-UHFFFAOYSA-N
smarts:    [#8]-[#6](-[#6])-[#6]=[#8]
smarts_isomeric:    [#8]-[#6](-[#6])-[#6]=[#8]

lauroyl: CCCCCCCCCCC[C]=O

smiles_non_kekule:    CCCCCCCCCCC[C]=O
smiles_kekule:    CCCCCCCCCCC[C]=O
inchi:    InChI=1S/C12H23O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h2-11H2,1H3
inchiKey:    AOKILAMWAXXPKC-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]

lauryl: [CH2]CCCCCCCCCCC

smiles_non_kekule:    [CH2]CCCCCCCCCCC
smiles_kekule:    [CH2]CCCCCCCCCCC
inchi:    InChI=1S/C12H25/c1-3-5-7-9-11-12-10-8-6-4-2/h1,3-12H2,2H3
inchiKey:    GDNCXORZAMVMIW-UHFFFAOYSA-N
smarts:    [#6H2]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]
smarts_isomeric:    [#6H2]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]

leucyl: N[C@@H](CC(C)C)[C]=O

smiles_non_kekule:    CC(C)C[C@H](N)[C]=O
smiles_kekule:    CC(C)C[C@H](N)[C]=O
inchi:    InChI=1S/C6H12NO/c1-5(2)3-6(7)4-8/h5-6H,3,7H2,1-2H3/t6-/m0/s1
inchiKey:    PNLOVMFGPRECRH-LURJTMIESA-N
smarts:    [#7]-[#6H](-[#6]-[#6](-[#6])-[#6])-[#6]=[#8]
smarts_isomeric:    [#7]-[#6@@H](-[#6]-[#6](-[#6])-[#6])-[#6]=[#8]

levulinoyl: O=C(C)CC[C]=O

smiles_non_kekule:    CC(=O)CC[C]=O
smiles_kekule:    CC(=O)CC[C]=O
inchi:    InChI=1S/C5H7O2/c1-5(7)3-2-4-6/h2-3H2,1H3
inchiKey:    UNBAEPCAFYIQNM-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6])-[#6]-[#6]-[#6]=[#8]
smarts_isomeric:    [#8]=[#6](-[#6])-[#6]-[#6]-[#6]=[#8]

malonyl: O=[C]C[C]=O

smiles_non_kekule:    O=[C]C[C]=O
smiles_kekule:    O=[C]C[C]=O
inchi:    InChI=1S/C3H2O2/c4-2-1-3-5/h1H2
inchiKey:    BFMGUPVTDJTZRI-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#6]-[#6]=[#8]
smarts_isomeric:    [#8]=[#6]-[#6]-[#6]=[#8]

mandeloyl: OC(C1=CC=CC=C1)[C]=O

smiles_non_kekule:    O=[C]C(O)c1ccccc1
smiles_kekule:    O=[C]C(O)C1=CC=CC=C1
inchi:    InChI=1S/C8H7O2/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H
inchiKey:    GJYRKILHYZIGEE-UHFFFAOYSA-N
smarts:    [#8]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]=[#8]
smarts_isomeric:    [#8]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]=[#8]

mercapto: [SH]

smiles_non_kekule:    [SH]
smiles_kekule:    [SH]
inchi:    InChI=1S/HS/h1H
inchiKey:    PXQLVRUNWNTZOS-UHFFFAOYSA-N
smarts:    [#16H]
smarts_isomeric:    [#16H]

mesityl: CC1=CC(C)=CC(C)=[C]1

smiles_non_kekule:    Cc1[c]c(C)cc(C)c1
smiles_kekule:    CC1=CC(C)=CC(C)=[C]1
inchi:    InChI=1S/C9H11/c1-7-4-8(2)6-9(3)5-7/h4-5H,1-3H3
inchiKey:    ZLHNEKNMRTVOBZ-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6](-[#6]):[#6]:[#6](-[#6]):[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6](-[#6]):[#6]:[#6](-[#6]):[#6]:1

methacryloyl: CC([C]=O)=C

smiles_non_kekule:    C=C(C)[C]=O
smiles_kekule:    C=C(C)[C]=O
inchi:    InChI=1S/C4H5O/c1-4(2)3-5/h1H2,2H3
inchiKey:    KHZBQMMGVPWWAU-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]=[#8])=[#6]
smarts_isomeric:    [#6]-[#6](-[#6]=[#8])=[#6]

methallyl: [CH2]C(C)=C

smiles_non_kekule:    [CH2]C(=C)C
smiles_kekule:    [CH2]C(=C)C
inchi:    InChI=1S/C4H7/c1-4(2)3/h1-2H2,3H3
inchiKey:    LJXPWUAAAAXJBX-UHFFFAOYSA-N
smarts:    [#6H2]-[#6](-[#6])=[#6]
smarts_isomeric:    [#6H2]-[#6](-[#6])=[#6]

methionyl: N[C@@H](CCSC)[C]=O

smiles_non_kekule:    CSCC[C@H](N)[C]=O
smiles_kekule:    CSCC[C@H](N)[C]=O
inchi:    InChI=1S/C5H10NOS/c1-8-3-2-5(6)4-7/h5H,2-3,6H2,1H3/t5-/m0/s1
inchiKey:    VGOFWGKOJFECER-YFKPBYRVSA-N
smarts:    [#7]-[#6H](-[#6]-[#6]-[#16]-[#6])-[#6]=[#8]
smarts_isomeric:    [#7]-[#6@@H](-[#6]-[#6]-[#16]-[#6])-[#6]=[#8]

methoxy: [O]C

smiles_non_kekule:    C[O]
smiles_kekule:    C[O]
inchi:    InChI=1S/CH3O/c1-2/h1H3
inchiKey:    GRVDJDISBSALJP-UHFFFAOYSA-N
smarts:    [#8]-[#6]
smarts_isomeric:    [#8]-[#6]

methyl: [CH3]

smiles_non_kekule:    [CH3]
smiles_kekule:    [CH3]
inchi:    InChI=1S/CH3/h1H3
inchiKey:    WCYWZMWISLQXQU-UHFFFAOYSA-N
smarts:    [#6H3]
smarts_isomeric:    [#6H3]

methylene: [CH2]

smiles_non_kekule:    [CH2]
smiles_kekule:    [CH2]
inchi:    InChI=1S/CH2/h1H2
inchiKey:    HZVOZRGWRWCICA-UHFFFAOYSA-N
smarts:    [#6H2]
smarts_isomeric:    [#6H2]

methylthio: [S]C

smiles_non_kekule:    C[S]
smiles_kekule:    C[S]
inchi:    InChI=1S/CH3S/c1-2/h1H3
inchiKey:    QSLPNSWXUQHVLP-UHFFFAOYSA-N
smarts:    [#16]-[#6]
smarts_isomeric:    [#16]-[#6]

myristoyl: CCCCCCCCCCCCC[C]=O

smiles_non_kekule:    CCCCCCCCCCCCC[C]=O
smiles_kekule:    CCCCCCCCCCCCC[C]=O
inchi:    InChI=1S/C14H27O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15/h2-13H2,1H3
inchiKey:    RLSSKEPLTFVCGD-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]

myristyl: [CH2]CCCCCCCCCCCCC

smiles_non_kekule:    [CH2]CCCCCCCCCCCCC
smiles_kekule:    [CH2]CCCCCCCCCCCCC
inchi:    InChI=1S/C14H29/c1-3-5-7-9-11-13-14-12-10-8-6-4-2/h1,3-14H2,2H3
inchiKey:    GHYJHZQFXONUDK-UHFFFAOYSA-N
smarts:    [#6H2]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]
smarts_isomeric:    [#6H2]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]

naphthyl: C12=CC=C[C]=C1C=CC=C2

smiles_non_kekule:    [c]1cccc2ccccc12
smiles_kekule:    [C]1=C2C=CC=CC2=CC=C1
inchi:    InChI=1S/C10H7/c1-2-6-10-8-4-3-7-9(10)5-1/h1-7H
inchiKey:    ZHZZWIQPCAMTIM-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#6]:[#6]:2

naphthylene: C12=CC=CC=C1C=CC=C2

smiles_non_kekule:    c1ccc2ccccc2c1
smiles_kekule:    C1=CC=C2C=CC=CC2=C1
inchi:    InChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
inchiKey:    UFWIBTONFRDIAS-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#6]:[#6]:2

neopentyl: [CH2]C(C)(C)C

smiles_non_kekule:    [CH2]C(C)(C)C
smiles_kekule:    [CH2]C(C)(C)C
inchi:    InChI=1S/C5H11/c1-5(2,3)4/h1H2,2-4H3
inchiKey:    GJWHXWMUGWZNTO-UHFFFAOYSA-N
smarts:    [#6H2]-[#6](-[#6])(-[#6])-[#6]
smarts_isomeric:    [#6H2]-[#6](-[#6])(-[#6])-[#6]

nitramino: [NH][N+]([O-])=O

smiles_non_kekule:    [NH][N+](=O)[O-]
smiles_kekule:    [NH][N+](=O)[O-]
inchi:    InChI=1S/HN2O2/c1-2(3)4/h1H
inchiKey:    GUFHGRQQQGOQBJ-UHFFFAOYSA-N
smarts:    [#7H]-[#7+](-[#8-])=[#8]
smarts_isomeric:    [#7H]-[#7+](-[#8-])=[#8]

nitro: O=[N+][O-]

smiles_non_kekule:    O=[N+][O-]
smiles_kekule:    O=[N+][O-]
inchi:    InChI=1S/NO2/c2-1-3
inchiKey:    JCXJVPUVTGWSNB-UHFFFAOYSA-N
smarts:    [#8]=[#7+]-[#8-]
smarts_isomeric:    [#8]=[#7+]-[#8-]

nitrosamino: [NH]N=O

smiles_non_kekule:    [NH]N=O
smiles_kekule:    [NH]N=O
inchi:    InChI=1S/HN2O/c1-2-3/h1H
inchiKey:    GCSMFBHRGGAVQC-UHFFFAOYSA-N
smarts:    [#7H]-[#7]=[#8]
smarts_isomeric:    [#7H]-[#7]=[#8]

nitroso: [N]=O

smiles_non_kekule:    [N]=O
smiles_kekule:    [N]=O
inchi:    InChI=1S/NO/c1-2
inchiKey:    MWUXSHHQAYIFBG-UHFFFAOYSA-N
smarts:    [#7]=[#8]
smarts_isomeric:    [#7]=[#8]

nonanoyl: CCCCCCCC[C]=O

smiles_non_kekule:    CCCCCCCC[C]=O
smiles_kekule:    CCCCCCCC[C]=O
inchi:    InChI=1S/C9H17O/c1-2-3-4-5-6-7-8-9-10/h2-8H2,1H3
inchiKey:    PJMKKSGLJJBQMY-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]

oleoyl: CCCCCCCC/C=C\CCCCCCC[C]=O

smiles_non_kekule:    CCCCCCCC/C=C\CCCCCCC[C]=O
smiles_kekule:    CCCCCCCC/C=C\CCCCCCC[C]=O
inchi:    InChI=1S/C18H33O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h9-10H,2-8,11-17H2,1H3/b10-9-
inchiKey:    WEKFVWJGTAVCKQ-KTKRTIGZSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]/[#6]=[#6]\[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]

oxalyl: O=[C]C=O

oxo: [O]

smiles_non_kekule:    [O]
smiles_kekule:    [O]
inchi:    InChI=1S/O
inchiKey:    QVGXLLKOCUKJST-UHFFFAOYSA-N
smarts:    [#8]
smarts_isomeric:    [#8]

palmitoyl: CCCCCCCCCCCCCCC[C]=O

smiles_non_kekule:    CCCCCCCCCCCCCCC[C]=O
smiles_kekule:    CCCCCCCCCCCCCCC[C]=O
inchi:    InChI=1S/C16H31O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h2-15H2,1H3
inchiKey:    VUWGOFIOIABGTR-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]

pentamethylene: O=C1C(C=C)[C@@]2([H])SCCN12

smiles_non_kekule:    C=CC1C(=O)N2CCS[C@H]12
smiles_kekule:    C=CC1C(=O)N2CCS[C@H]12
inchi:    InChI=1S/C7H9NOS/c1-2-5-6(9)8-3-4-10-7(5)8/h2,5,7H,1,3-4H2/t5?,7-/m1/s1
inchiKey:    BIPUXDRCJZDTQP-NQPNHJOESA-N
smarts:    [#8]=[#6]1-[#6](-[#6]=[#6])-[#6H]2-[#16]-[#6]-[#6]-[#7]-1-2
smarts_isomeric:    [#8]=[#6]1-[#6](-[#6]=[#6])-[#6@H]2-[#16]-[#6]-[#6]-[#7]-1-2

pentyl: [CH2]CCCC

tert-pentyl: CC[C](C)C

smiles_non_kekule:    CC[C](C)C
smiles_kekule:    CC[C](C)C
inchi:    InChI=1S/C5H11/c1-4-5(2)3/h4H2,1-3H3
inchiKey:    CGERYHYIVJQVLJ-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6]-[#6](-[#6])-[#6]

phenacyl: [CH2]C(C1=CC=CC=C1)=O

smiles_non_kekule:    [CH2]C(=O)c1ccccc1
smiles_kekule:    [CH2]C(=O)C1=CC=CC=C1
inchi:    InChI=1S/C8H7O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H2
inchiKey:    XAKBSHICSHRJCL-UHFFFAOYSA-N
smarts:    [#6H2]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)=[#8]
smarts_isomeric:    [#6H2]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)=[#8]

phenacylidene: [CH]C(C1=CC=CC=C1)=O

smiles_non_kekule:    [CH]C(=O)c1ccccc1
smiles_kekule:    [CH]C(=O)C1=CC=CC=C1
inchi:    InChI=1S/C8H6O/c1-7(9)8-5-3-2-4-6-8/h1-6H
inchiKey:    FBHFGBXBLVLGAJ-UHFFFAOYSA-N
smarts:    [#6H]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)=[#8]
smarts_isomeric:    [#6H]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)=[#8]

phenethyl: [CH2]CC1=CC=CC=C1

smiles_non_kekule:    [CH2]Cc1ccccc1
smiles_kekule:    [CH2]CC1=CC=CC=C1
inchi:    InChI=1S/C8H9/c1-2-8-6-4-3-5-7-8/h3-7H,1-2H2
inchiKey:    KRTGJZMJJVEKRX-UHFFFAOYSA-N
smarts:    [#6H2]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6H2]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

phenoxy: [O]C1=CC=CC=C1

smiles_non_kekule:    [O]c1ccccc1
smiles_kekule:    [O]C1=CC=CC=C1
inchi:    InChI=1S/C6H5O/c7-6-4-2-1-3-5-6/h1-5H
inchiKey:    KHUXNRRPPZOJPT-UHFFFAOYSA-N
smarts:    [#8]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#8]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

phenyl: [C]1=CC=CC=C1

smiles_non_kekule:    [c]1ccccc1
smiles_kekule:    [C]1=CC=CC=C1
inchi:    InChI=1S/C6H5/c1-2-4-6-5-3-1/h1-5H
inchiKey:    CIUQDSCDWFSTQR-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

phenylene: C1=C[C]=CC=[C]1

smiles_non_kekule:    [c]1cc[c]cc1
smiles_kekule:    [C]1=CC=[C]C=C1
inchi:    InChI=1S/C6H4/c1-2-4-6-5-3-1/h1-2,5-6H
inchiKey:    AIESRBVWAFETPR-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

phosphino: [PH2]

smiles_non_kekule:    [PH2]
smiles_kekule:    [PH2]
inchi:    InChI=1S/H2P/h1H2
inchiKey:    FVZVCSNXTFCBQU-UHFFFAOYSA-N
smarts:    [#15H2]
smarts_isomeric:    [#15H2]

phosphinyl: [PH2]=O

smiles_non_kekule:    O=[PH2]
smiles_kekule:    O=[PH2]
inchi:    InChI=1S/H2OP/c1-2/h2H2
inchiKey:    NRXKEONAFOCNGW-UHFFFAOYSA-N
smarts:    [#15H2]=[#8]
smarts_isomeric:    [#15H2]=[#8]

phospho: O=[P](O)O

smiles_non_kekule:    O=[P](O)O
smiles_kekule:    O=[P](O)O
inchi:    InChI=1S/H2O3P/c1-4(2)3/h(H2,1,2,3)
inchiKey:    NJRWNWYFPOFDFN-UHFFFAOYSA-N
smarts:    [#8]=[#15](-[#8])-[#8]
smarts_isomeric:    [#8]=[#15](-[#8])-[#8]

phosphono: O=[P](O)O

phthaloyl: O=[C]C1=CC=CC=C1[C]=O

smiles_non_kekule:    O=[C]c1ccccc1[C]=O
smiles_kekule:    O=[C]C1=CC=CC=C1[C]=O
inchi:    InChI=1S/C8H4O2/c9-5-7-3-1-2-4-8(7)6-10/h1-4H
inchiKey:    SUZCNPIZPHBIRX-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]=[#8]
smarts_isomeric:    [#8]=[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]=[#8]

picryl: [O-][N+](C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=[C]1)=O

smiles_non_kekule:    O=[N+]([O-])c1[c]c([N+](=O)[O-])cc([N+](=O)[O-])c1
smiles_kekule:    O=[N+]([O-])C1=[C]C([N+](=O)[O-])=CC([N+](=O)[O-])=C1
inchi:    InChI=1S/C6H2N3O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-2H
inchiKey:    YFFCAMVNLCYBKQ-UHFFFAOYSA-N
smarts:    [#8-]-[#7+](-[#6]1:[#6]:[#6](-[#7+](-[#8-])=[#8]):[#6]:[#6](-[#7+](-[#8-])=[#8]):[#6]:1)=[#8]
smarts_isomeric:    [#8-]-[#7+](-[#6]1:[#6]:[#6](-[#7+](-[#8-])=[#8]):[#6]:[#6](-[#7+](-[#8-])=[#8]):[#6]:1)=[#8]

pimeloyl: O=[C]CCCCC[C]=O

smiles_non_kekule:    O=[C]CCCCC[C]=O
smiles_kekule:    O=[C]CCCCC[C]=O
inchi:    InChI=1S/C7H10O2/c8-6-4-2-1-3-5-7-9/h1-5H2
inchiKey:    VMNQDIWLTPYTOY-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]
smarts_isomeric:    [#8]=[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]

piperidino: [N]1CCCCC1

smiles_non_kekule:    C1CC[N]CC1
smiles_kekule:    C1CC[N]CC1
inchi:    InChI=1S/C5H10N/c1-2-4-6-5-3-1/h1-5H2
inchiKey:    KZKRRZFCAYOXQE-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

pivaloyl: CC(C)(C)[C]=O

smiles_non_kekule:    CC(C)(C)[C]=O
smiles_kekule:    CC(C)(C)[C]=O
inchi:    InChI=1S/C5H9O/c1-5(2,3)4-6/h1-3H3
inchiKey:    YQTCQNIPQMJNTI-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])(-[#6])-[#6]=[#8]
smarts_isomeric:    [#6]-[#6](-[#6])(-[#6])-[#6]=[#8]

prenyl: [CH2]/C=C(C)\C

smiles_non_kekule:    [CH2]C=C(C)C
smiles_kekule:    [CH2]C=C(C)C
inchi:    InChI=1S/C5H9/c1-4-5(2)3/h4H,1H2,2-3H3
inchiKey:    ICPOKTZORRQGLK-UHFFFAOYSA-N
smarts:    [#6H2]-[#6]=[#6](-[#6])-[#6]
smarts_isomeric:    [#6H2]-[#6]=[#6](-[#6])-[#6]

propargyl: [CH2]C#C

smiles_non_kekule:    C#C[CH2]
smiles_kekule:    C#C[CH2]
inchi:    InChI=1S/C3H3/c1-3-2/h1H,2H2
inchiKey:    DITHIFQMPPCBCU-UHFFFAOYSA-N
smarts:    [#6H2]-[#6]#[#6]
smarts_isomeric:    [#6H2]-[#6]#[#6]

1-propenyl: [CH]=CC

smiles_non_kekule:    [CH]=CC
smiles_kekule:    [CH]=CC
inchi:    InChI=1S/C3H5/c1-3-2/h1,3H,2H3
inchiKey:    ZLRGTQBGRLOXCT-UHFFFAOYSA-N
smarts:    [#6H]=[#6]-[#6]
smarts_isomeric:    [#6H]=[#6]-[#6]

2-propenyl: [CH2]C=C

propionyl: O=[C]CC

smiles_non_kekule:    CC[C]=O
smiles_kekule:    CC[C]=O
inchi:    InChI=1S/C3H5O/c1-2-3-4/h2H2,1H3
inchiKey:    UFUASNAHBMBJIX-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#6]-[#6]
smarts_isomeric:    [#8]=[#6]-[#6]-[#6]

propoxy: [O]CCC

smiles_non_kekule:    CCC[O]
smiles_kekule:    CCC[O]
inchi:    InChI=1S/C3H7O/c1-2-3-4/h2-3H2,1H3
inchiKey:    JAVBBFXUGDCHLZ-UHFFFAOYSA-N
smarts:    [#8]-[#6]-[#6]-[#6]
smarts_isomeric:    [#8]-[#6]-[#6]-[#6]

propyl: [CH2]CC

smiles_non_kekule:    [CH2]CC
smiles_kekule:    [CH2]CC
inchi:    InChI=1S/C3H7/c1-3-2/h1,3H2,2H3
inchiKey:    OCBFFGCSTGGPSQ-UHFFFAOYSA-N
smarts:    [#6H2]-[#6]-[#6]
smarts_isomeric:    [#6H2]-[#6]-[#6]

propylidene: [CH]CC

smiles_non_kekule:    [CH]CC
smiles_kekule:    [CH]CC
inchi:    InChI=1S/C3H6/c1-3-2/h1H,3H2,2H3
inchiKey:    OSFBJERFMQCEQY-UHFFFAOYSA-N
smarts:    [#6H]-[#6]-[#6]
smarts_isomeric:    [#6H]-[#6]-[#6]

pyrryl: N1[C]=CC=C1

smiles_non_kekule:    [c]1ccc[nH]1
smiles_kekule:    [C]1=CC=CN1
inchi:    InChI=1S/C4H4N/c1-2-4-5-3-1/h1-3,5H
inchiKey:    HPVLTCVIGICMSV-UHFFFAOYSA-N
smarts:    [#7H]1:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#7H]1:[#6]:[#6]:[#6]:[#6]:1

salicyloyl: OC1=CC=CC=C1[C]=O

smiles_non_kekule:    O=[C]c1ccccc1O
smiles_kekule:    O=[C]C1=CC=CC=C1O
inchi:    InChI=1S/C7H5O2/c8-5-6-3-1-2-4-7(6)9/h1-4,9H
inchiKey:    XFFRMKRRNBORDM-UHFFFAOYSA-N
smarts:    [#8]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]=[#8]
smarts_isomeric:    [#8]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]=[#8]

selenyl: [SeH]

smiles_non_kekule:    [SeH]
smiles_kekule:    [SeH]
inchi:    InChI=1S/HSe/h1H
inchiKey:    VUGWMQXJZSOYNI-UHFFFAOYSA-N
smarts:    [SeH]
smarts_isomeric:    [SeH]

seryl: N[C@@H](CO)[C]=O

smiles_non_kekule:    N[C@H]([C]=O)CO
smiles_kekule:    N[C@H]([C]=O)CO
inchi:    InChI=1S/C3H6NO2/c4-3(1-5)2-6/h3,5H,1,4H2/t3-/m0/s1
inchiKey:    JHOHPIVAXRTWDZ-VKHMYHEASA-N
smarts:    [#7]-[#6H](-[#6]-[#8])-[#6]=[#8]
smarts_isomeric:    [#7]-[#6@@H](-[#6]-[#8])-[#6]=[#8]

siloxy: [O][SiH3]

smiles_non_kekule:    [O][SiH3]
smiles_kekule:    [O][SiH3]
inchi:    InChI=1S/H3OSi/c1-2/h2H3
inchiKey:    UXMAWJKSGBRJKV-UHFFFAOYSA-N
smarts:    [#8]-[SiH3]
smarts_isomeric:    [#8]-[SiH3]

silyl: [SiH3]

smiles_non_kekule:    [SiH3]
smiles_kekule:    [SiH3]
inchi:    InChI=1S/H3Si/h1H3
inchiKey:    OLRJXMHANKMLTD-UHFFFAOYSA-N
smarts:    [SiH3]
smarts_isomeric:    [SiH3]

silyene: [SiH2]

smiles_non_kekule:    [SiH2]
smiles_kekule:    [SiH2]
inchi:    InChI=1S/H2Si/h1H2
inchiKey:    XMIJDTGORVPYLW-UHFFFAOYSA-N
smarts:    [SiH2]
smarts_isomeric:    [SiH2]

sorboyl: CC=CC=CC(O)=O

smiles_non_kekule:    CC=CC=CC(=O)O
smiles_kekule:    CC=CC=CC(=O)O
inchi:    InChI=1S/C6H8O2/c1-2-3-4-5-6(7)8/h2-5H,1H3,(H,7,8)
inchiKey:    WSWCOQWTEOXDQX-UHFFFAOYSA-N
smarts:    [#6]-[#6]=[#6]-[#6]=[#6]-[#6](-[#8])=[#8]
smarts_isomeric:    [#6]-[#6]=[#6]-[#6]=[#6]-[#6](-[#8])=[#8]

stearoyl: CCCCCCCCCCCCCCCCC[C]=O

smiles_non_kekule:    CCCCCCCCCCCCCCCCC[C]=O
smiles_kekule:    CCCCCCCCCCCCCCCCC[C]=O
inchi:    InChI=1S/C18H35O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h2-17H2,1H3
inchiKey:    GCVXGRDQZGQPOB-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]

stearyl: [CH2]CCCCCCCCCCCCCCCCC

smiles_non_kekule:    [CH2]CCCCCCCCCCCCCCCCC
smiles_kekule:    [CH2]CCCCCCCCCCCCCCCCC
inchi:    InChI=1S/C18H37/c1-3-5-7-9-11-13-15-17-18-16-14-12-10-8-6-4-2/h1,3-18H2,2H3
inchiKey:    MDLWEBWGXACWGE-UHFFFAOYSA-N
smarts:    [#6H2]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]
smarts_isomeric:    [#6H2]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]

styryl: [CH]=CC1=CC=CC=C1

smiles_non_kekule:    [CH]=Cc1ccccc1
smiles_kekule:    [CH]=CC1=CC=CC=C1
inchi:    InChI=1S/C8H7/c1-2-8-6-4-3-5-7-8/h1-7H
inchiKey:    XXZXPSKZWQWGKG-UHFFFAOYSA-N
smarts:    [#6H]=[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6H]=[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

suberoyl: O=[C]CCCCCC[C]=O

smiles_non_kekule:    O=[C]CCCCCC[C]=O
smiles_kekule:    O=[C]CCCCCC[C]=O
inchi:    InChI=1S/C8H12O2/c9-7-5-3-1-2-4-6-8-10/h1-6H2
inchiKey:    HRCIPQFPQWPNSL-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]
smarts_isomeric:    [#8]=[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]=[#8]

succinyl: O=[C]CC[C]=O

smiles_non_kekule:    O=[C]CC[C]=O
smiles_kekule:    O=[C]CC[C]=O
inchi:    InChI=1S/C4H4O2/c5-3-1-2-4-6/h1-2H2
inchiKey:    NOSOEJSZWOKISI-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#6]-[#6]-[#6]=[#8]
smarts_isomeric:    [#8]=[#6]-[#6]-[#6]-[#6]=[#8]

sulfamino: [NH]S(=O)(O)=O

smiles_non_kekule:    [NH]S(=O)(=O)O
smiles_kekule:    [NH]S(=O)(=O)O
inchi:    InChI=1S/H2NO3S/c1-5(2,3)4/h1H,(H,2,3,4)
inchiKey:    ITWDDPVXHOXFOB-UHFFFAOYSA-N
smarts:    [#7H]-[#16](=[#8])(-[#8])=[#8]
smarts_isomeric:    [#7H]-[#16](=[#8])(-[#8])=[#8]

sulfamoyl: O=[S](N)=O

smiles_non_kekule:    N[S](=O)=O
smiles_kekule:    N[S](=O)=O
inchi:    InChI=1S/H2NO2S/c1-4(2)3/h(H2,1,2,3)
inchiKey:    RZTIGQMEMMYINC-UHFFFAOYSA-N
smarts:    [#8]=[#16](-[#7])=[#8]
smarts_isomeric:    [#8]=[#16](-[#7])=[#8]

sulfanilyl: O=[S](C1=CC=C(N)C=C1)=O

smiles_non_kekule:    Nc1ccc([S](=O)=O)cc1
smiles_kekule:    NC1=CC=C([S](=O)=O)C=C1
inchi:    InChI=1S/C6H6NO2S/c7-5-1-3-6(4-2-5)10(8)9/h1-4H,7H2
inchiKey:    FWCWCIZNSHDOGX-UHFFFAOYSA-N
smarts:    [#8]=[#16](-[#6]1:[#6]:[#6]:[#6](-[#7]):[#6]:[#6]:1)=[#8]
smarts_isomeric:    [#8]=[#16](-[#6]1:[#6]:[#6]:[#6](-[#7]):[#6]:[#6]:1)=[#8]

sulfeno: [S]O

smiles_non_kekule:    O[S]
smiles_kekule:    O[S]
inchi:    InChI=1S/HOS/c1-2/h1H
inchiKey:    ZXYFGZNMDRNOGQ-UHFFFAOYSA-N
smarts:    [#16]-[#8]
smarts_isomeric:    [#16]-[#8]

sulfhydryl: [SH]

smiles_non_kekule:    [SH]
smiles_kekule:    [SH]
inchi:    InChI=1S/HS/h1H
inchiKey:    PXQLVRUNWNTZOS-UHFFFAOYSA-N
smarts:    [#16H]
smarts_isomeric:    [#16H]

sulfinyl: S=O

smiles_non_kekule:    O=S
smiles_kekule:    O=S
inchi:    InChI=1S/OS/c1-2
inchiKey:    XTQHKBHJIVJGKJ-UHFFFAOYSA-N
smarts:    [#16]=[#8]
smarts_isomeric:    [#16]=[#8]

sulfo: O=[S](O)=O

smiles_non_kekule:    O=[S](=O)O
smiles_kekule:    O=[S](=O)O
inchi:    InChI=1S/HO3S/c1-4(2)3/h(H,1,2,3)
inchiKey:    IYLJUMIQCMKJHF-UHFFFAOYSA-N
smarts:    [#8]=[#16](-[#8])=[#8]
smarts_isomeric:    [#8]=[#16](-[#8])=[#8]

sulfonyl: O=S=O

smiles_non_kekule:    O=S=O
smiles_kekule:    O=S=O
inchi:    InChI=1S/O2S/c1-3-2
inchiKey:    RAHZWNYVWXNFOC-UHFFFAOYSA-N
smarts:    [#8]=[#16]=[#8]
smarts_isomeric:    [#8]=[#16]=[#8]

terephthaloyl: O=[C]C1=CC=C([C]=O)C=C1

smiles_non_kekule:    O=[C]c1ccc([C]=O)cc1
smiles_kekule:    O=[C]C1=CC=C([C]=O)C=C1
inchi:    InChI=1S/C8H4O2/c9-5-7-1-2-8(6-10)4-3-7/h1-4H
inchiKey:    GZDTWTRECSTKAA-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#6]1:[#6]:[#6]:[#6](-[#6]=[#8]):[#6]:[#6]:1
smarts_isomeric:    [#8]=[#6]-[#6]1:[#6]:[#6]:[#6](-[#6]=[#8]):[#6]:[#6]:1

tetramethylene: CCCC

thienyl: [C]1=CC=CS1

smiles_non_kekule:    [c]1cccs1
smiles_kekule:    [C]1=CC=CS1
inchi:    InChI=1S/C4H3S/c1-2-4-5-3-1/h1-3H
inchiKey:    AYLIEDQYYJIGDP-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]:[#16]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]:[#16]:1

thiocarbonyl: [CH]=S

smiles_non_kekule:    [CH]=S
smiles_kekule:    [CH]=S
inchi:    InChI=1S/CHS/c1-2/h1H
inchiKey:    RIFHJAODNHLCBH-UHFFFAOYSA-N
smarts:    [#6H]=[#16]
smarts_isomeric:    [#6H]=[#16]

thiocarboxy: S=[C]O

smiles_non_kekule:    O[C]=S
smiles_kekule:    O[C]=S
inchi:    InChI=1S/CHOS/c2-1-3/h(H,2,3)
inchiKey:    JHBZTUAPQNXDSK-UHFFFAOYSA-N
smarts:    [#16]=[#6]-[#8]
smarts_isomeric:    [#16]=[#6]-[#8]

thiocyanato: [S]C#N

smiles_non_kekule:    N#C[S]
smiles_kekule:    N#C[S]
inchi:    InChI=1S/CNS/c2-1-3
inchiKey:    NYAZXHASVIWIRJ-UHFFFAOYSA-N
smarts:    [#16]-[#6]#[#7]
smarts_isomeric:    [#16]-[#6]#[#7]

thionyl: S=O

smiles_non_kekule:    O=S
smiles_kekule:    O=S
inchi:    InChI=1S/OS/c1-2
inchiKey:    XTQHKBHJIVJGKJ-UHFFFAOYSA-N
smarts:    [#16]=[#8]
smarts_isomeric:    [#16]=[#8]

threonyl: N[C@@H]([C@H](O)C)[C]=O

smiles_non_kekule:    C[C@@H](O)[C@H](N)[C]=O
smiles_kekule:    C[C@@H](O)[C@H](N)[C]=O
inchi:    InChI=1S/C4H8NO2/c1-3(7)4(5)2-6/h3-4,7H,5H2,1H3/t3-,4-/m1/s1
inchiKey:    LBNOHMKSMASMIG-QWWZWVQMSA-N
smarts:    [#7]-[#6H](-[#6H](-[#8])-[#6])-[#6]=[#8]
smarts_isomeric:    [#7]-[#6@@H](-[#6@H](-[#8])-[#6])-[#6]=[#8]

toluidino: [NH]C1=CC=C(C)C=C1

smiles_non_kekule:    Cc1ccc([NH])cc1
smiles_kekule:    CC1=CC=C([NH])C=C1
inchi:    InChI=1S/C7H8N/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3
inchiKey:    XANOUUABLVQSEY-UHFFFAOYSA-N
smarts:    [#7H]-[#6]1:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#7H]-[#6]1:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:1

toluoyl: CC1=CC=C([C]=O)C=C1

smiles_non_kekule:    Cc1ccc([C]=O)cc1
smiles_kekule:    CC1=CC=C([C]=O)C=C1
inchi:    InChI=1S/C8H7O/c1-7-2-4-8(6-9)5-3-7/h2-5H,1H3
inchiKey:    GLEZJVLBKVYSTF-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6](-[#6]=[#8]):[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6](-[#6]=[#8]):[#6]:[#6]:1

tolyl: CC1=CC=[C]C=C1

smiles_non_kekule:    Cc1cc[c]cc1
smiles_kekule:    CC1=CC=[C]C=C1
inchi:    InChI=1S/C7H7/c1-7-5-3-2-4-6-7/h3-6H,1H3
inchiKey:    HCBPHBQMSDVIPZ-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

alpha-tolyl: [C]C1=CC=CC=C1

tolylene: [CH]C1=CC=CC=C1

tosyl: O=[S](C1=CC=C(C)C=C1)=O

smiles_non_kekule:    Cc1ccc([S](=O)=O)cc1
smiles_kekule:    CC1=CC=C([S](=O)=O)C=C1
inchi:    InChI=1S/C7H7O2S/c1-6-2-4-7(5-3-6)10(8)9/h2-5H,1H3
inchiKey:    OHJXSEODCOULCR-UHFFFAOYSA-N
smarts:    [#8]=[#16](-[#6]1:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:1)=[#8]
smarts_isomeric:    [#8]=[#16](-[#6]1:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:1)=[#8]

triazano: [NH]N[NH]

smiles_non_kekule:    [NH]N[NH]
smiles_kekule:    [NH]N[NH]
inchi:    InChI=1S/H3N3/c1-3-2/h1-3H
inchiKey:    VAIXWGCPJZFGGP-UHFFFAOYSA-N
smarts:    [#7H]-[#7]-[#7H]
smarts_isomeric:    [#7H]-[#7]-[#7H]

trimethylene: CCC

trityl: [C](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3

smiles_non_kekule:    c1ccc([C](c2ccccc2)c2ccccc2)cc1
smiles_kekule:    C1=CC=C([C](C2=CC=CC=C2)C2=CC=CC=C2)C=C1
inchi:    InChI=1S/C19H15/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
inchiKey:    OHSJPLSEQNCRLW-UHFFFAOYSA-N
smarts:    [#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

valeryl: O=[C]CCCC

smiles_non_kekule:    CCCC[C]=O
smiles_kekule:    CCCC[C]=O
inchi:    InChI=1S/C5H9O/c1-2-3-4-5-6/h2-4H2,1H3
inchiKey:    IXAXVYMFIJYCSG-UHFFFAOYSA-N
smarts:    [#8]=[#6]-[#6]-[#6]-[#6]-[#6]
smarts_isomeric:    [#8]=[#6]-[#6]-[#6]-[#6]-[#6]

valyl: N[C@@H](C(C)C)[C]=O

smiles_non_kekule:    CC(C)[C@H](N)[C]=O
smiles_kekule:    CC(C)[C@H](N)[C]=O
inchi:    InChI=1S/C5H10NO/c1-4(2)5(6)3-7/h4-5H,6H2,1-2H3/t5-/m1/s1
inchiKey:    AZMKLWDRMGVETL-RXMQYKEDSA-N
smarts:    [#7]-[#6H](-[#6](-[#6])-[#6])-[#6]=[#8]
smarts_isomeric:    [#7]-[#6@@H](-[#6](-[#6])-[#6])-[#6]=[#8]

vinyl: [CH]=C

vinylidene: [C]=C

smiles_non_kekule:    [C]=C
smiles_kekule:    [C]=C
inchi:    InChI=1S/C2H2/c1-2/h1H2
inchiKey:    SNVLJLYUUXKWOJ-UHFFFAOYSA-N
smarts:    [#6]=[#6]
smarts_isomeric:    [#6]=[#6]

xylidino: [NH]C1=CC=C(C)C=C1C

smiles_non_kekule:    Cc1ccc([NH])c(C)c1
smiles_kekule:    CC1=CC=C([NH])C(C)=C1
inchi:    InChI=1S/C8H10N/c1-6-3-4-8(9)7(2)5-6/h3-5,9H,1-2H3
inchiKey:    RTRRUBOJVHELPD-UHFFFAOYSA-N
smarts:    [#7H]-[#6]1:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:1-[#6]
smarts_isomeric:    [#7H]-[#6]1:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:1-[#6]

xylyl: CC1=CC=[C]C(C)=C1

smiles_non_kekule:    Cc1[c]ccc(C)c1
smiles_kekule:    CC1=CC(C)=CC=[C]1
inchi:    InChI=1S/C8H9/c1-7-4-3-5-8(2)6-7/h3-4,6H,1-2H3
inchiKey:    KCVDYBUYBYTWQA-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6](-[#6]):[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6](-[#6]):[#6]:1

xylylene: NCC1=CC=CC(CN)=C1

smiles_non_kekule:    NCc1cccc(CN)c1
smiles_kekule:    NCC1=CC=CC(CN)=C1
inchi:    InChI=1S/C8H12N2/c9-5-7-2-1-3-8(4-7)6-10/h1-4H,5-6,9-10H2
inchiKey:    FDLQZKYLHJJBHD-UHFFFAOYSA-N
smarts:    [#7]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6](-[#6]-[#7]):[#6]:1
smarts_isomeric:    [#7]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6](-[#6]-[#7]):[#6]:1

problem_type: 17/25 (loop 0/0)

[15:20:57] ERROR: Unsupported in this mode element '*'

[15:20:57] Invalid InChI prefix in generating InChI Key
[15:20:57] WARNING: Charges were rearranged

[15:20:57] SMILES Parse Error: syntax error while parsing: C&1&1&1&1
[15:20:57] SMILES Parse Error: Failed parsing SMILES 'C&1&1&1&1' for input: 'C&1&1&1&1'
[15:20:57] WARNING: Charges were rearranged

[15:20:57] WARNING: Proton(s) added/removed

[15:20:57] SMILES Parse Error: syntax error while parsing: C&1&1&1
[15:20:57] SMILES Parse Error: Failed parsing SMILES 'C&1&1&1' for input: 'C&1&1&1'
[15:20:57] WARNING: Proton(s) added/removed

[15:20:57] WARNING: Accepted unusual valence(s): N+1(3)

[15:20:57] WARNING: Charges were rearranged

[15:20:57] WARNING: Omitted undefined stereo

[15:20:57] SMILES Parse Error: syntax error while parsing: c1ccccc1C&1&1
[15:20:57] SMILES Parse Error: Failed parsing SMILES 'c1ccccc1C&1&1' for input: 'c1ccccc1C&1&1'

Problem Template: _problem_open_smiles_functional_groups

[15:20:57] Explicit valence for atom # 1 N, 4, is greater than permitted

Write structure of open smiles functional groups molecules.

Answer:

structure of open smiles functional groups molecules:

1,1,1-trifluoroethane: CC(F)(F)F

1,1'-biphenyl: C1(C2=CC=CC=C2)=CC=CC=C1

1H-indene: C1(CC=C2)=C2C=CC=C1

1H-pyrrole: [NH]1CCCC1

2-butyne: CC#CC

2-ethyl-1-butanol: CCC(CC)CO

2-methylpenta-2,3-diene: CC=C=C(C)C

(E)-1,2-dimethyldiazene: C/N=N/C

N,N-dimethylacetamide: CC(N(C)C)=O

N-methylpropan-2-imine: C/C(C)=N/C

(Z)-N,N,N'-trimethylacetimidamide: C/C(N(C)C)=N/C

acetic anydride: CC(=O)OC(=O)C

acyl bromide: C(=O)Br

acyl chloride: C(=O)Cl

acyl fluoride: C(=O)F

acyl iodide: C(=O)I

aldehyde: CC=O

amide: C(=O)N

amino: *N

anthracene: C12=CC=CC=C1C=C3C(C=CC=C3)=C2

azide: C([N-][N+]#N)

benzene: C1=CC=CC=C1

benzene thiol: C1=CC=C(C=C1)S

bicyclohexyl: C1CCCCC1C1CCCCC1

bromine: Br

but-1-ene: CCC=C

but-1-yne: CCC#C

carbon dioxide: O=C=O

carboxylic acid: C(=O)O

chlorine: Cl

chloromethyl methyl ether: COCCl

cyclobutadiene: C1=CC=C1

cyclobutane: C1CCC1

cycloheptane: C1CCCCCC1

cyclohexane: C1CCCCC1

cyclohexa-1,3-diene: C1=CCCC=C1

cyclohexa-1,4-diene: C1=CCC=CC1

cyclohexene: C=1CCCCC=1

cyclopentane: C1CCCC1

cyclopenta-1,3-diene: C1=CCC=C1

cyclopropane: C1CC1

cyclopropene: C1=CC1

deuteroethane: [2H][CH2]C

dimethyl ether: COC

diethyl ether: CCOCC

diisopropyl ether: CC(C)OC(C)C

diazomethane: C=[N+]=[N-]

diammonium thiosulfate: [NH4+].[NH4+].[O-]S(=O)(=O)[S-]

enamine: N

ethane: CC

ethanethiol: CCS

ethanol: CCO

ethene: C=C

ether: COC

ester: C(=O)OC

fluorine: F

formaldehyde: C=O

furan: C1OC=CC=1

hydrogen cyanide: C#N

hydroxide: [OH-]

hydroxyl amine: NO

indane: C1=CC=CC(CCC2)=C12

ketone: CC(=O)C

methane: C

methanethiol: CS

methyl acetate: CC(OC)=O

methyl pyrrole: CN1CCCC1

methyl tert-butyl ether: CC(C)(C)OC

naphthalene: C12=CC=CC=C1C=CC=C2

nitro: [N+](=O)[O-]

nitromethane: C[N+]([O-])=O

pentalene: C12=CC=CC1=CC=C2

perhydroisoquinoline: N1CC2CCCC2CC1

phenol: OC1CCCCC1

phenyl: C=1(C=CC=CC1)

primary alcohol: O

primary amine: N

propan-2-one: CC(C)=O

propanol: CCC=O

prop-1-ene: CC=C

prop-1-yne: CC#C

pyridine: N1CCCCC1

secondary amine: NC

spiro[5.5]undecane: C12(CCCCC1)CCCCC2

sulfoxide: S(=O)(=O)

tetramethylammonium: C[N+](C)(C)C

thiol: S

thiosulfate: OS(=O)(=S)O

trimethylamine: CN(C)C

triphenylene: C1(C=CC=C2)=C2C(C=CC=C3)=C3C4=C1C=CC=C4

Solution:

structure of open smiles functional groups molecules:

1,1,1-trifluoroethane: CC(F)(F)F

1,1'-biphenyl: C1(C2=CC=CC=C2)=CC=CC=C1

smiles_non_kekule:    c1ccc(-c2ccccc2)cc1
smiles_kekule:    C1=CC=C(C2=CC=CC=C2)C=C1
inchi:    InChI=1S/C12H10/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1-10H
inchiKey:    ZUOUZKKEUPVFJK-UHFFFAOYSA-N
smarts:    [#6]1(-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2):[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1(-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2):[#6]:[#6]:[#6]:[#6]:[#6]:1

1H-indene: C1(CC=C2)=C2C=CC=C1

smiles_non_kekule:    C1=Cc2ccccc2C1
smiles_kekule:    C1=CC2=C(C=CC=C2)C1
inchi:    InChI=1S/C9H8/c1-2-5-9-7-3-6-8(9)4-1/h1-6H,7H2
inchiKey:    YBYIRNPNPLQARY-UHFFFAOYSA-N
smarts:    [#6]12-[#6]-[#6]=[#6]-[#6]:1:[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#6]12-[#6]-[#6]=[#6]-[#6]:1:[#6]:[#6]:[#6]:[#6]:2

1H-pyrrole: [NH]1CCCC1

smiles_non_kekule:    C1CCNC1
smiles_kekule:    C1CCNC1
inchi:    InChI=1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2
inchiKey:    RWRDLPDLKQPQOW-UHFFFAOYSA-N
smarts:    [#7H]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#7H]1-[#6]-[#6]-[#6]-[#6]-1

2-butyne: CC#CC

smiles_non_kekule:    CC#CC
smiles_kekule:    CC#CC
inchi:    InChI=1S/C4H6/c1-3-4-2/h1-2H3
inchiKey:    XNMQEEKYCVKGBD-UHFFFAOYSA-N
smarts:    [#6]-[#6]#[#6]-[#6]
smarts_isomeric:    [#6]-[#6]#[#6]-[#6]

2-ethyl-1-butanol: CCC(CC)CO

smiles_non_kekule:    CCC(CC)CO
smiles_kekule:    CCC(CC)CO
inchi:    InChI=1S/C6H14O/c1-3-6(4-2)5-7/h6-7H,3-5H2,1-2H3
inchiKey:    TZYRSLHNPKPEFV-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](-[#6]-[#6])-[#6]-[#8]
smarts_isomeric:    [#6]-[#6]-[#6](-[#6]-[#6])-[#6]-[#8]

2-methylpenta-2,3-diene: CC=C=C(C)C

smiles_non_kekule:    CC=C=C(C)C
smiles_kekule:    CC=C=C(C)C
inchi:    InChI=1S/C6H10/c1-4-5-6(2)3/h4H,1-3H3
inchiKey:    JWMDOGMKTRMFDS-UHFFFAOYSA-N
smarts:    [#6]-[#6]=[#6]=[#6](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6]=[#6]=[#6](-[#6])-[#6]

(E)-1,2-dimethyldiazene: C/N=N/C

N,N-dimethylacetamide: CC(N(C)C)=O

smiles_non_kekule:    CC(=O)N(C)C
smiles_kekule:    CC(=O)N(C)C
inchi:    InChI=1S/C4H9NO/c1-4(6)5(2)3/h1-3H3
inchiKey:    FXHOOIRPVKKKFG-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#7](-[#6])-[#6])=[#8]
smarts_isomeric:    [#6]-[#6](-[#7](-[#6])-[#6])=[#8]

N-methylpropan-2-imine: C/C(C)=N/C

smiles_non_kekule:    CN=C(C)C
smiles_kekule:    CN=C(C)C
inchi:    InChI=1S/C4H9N/c1-4(2)5-3/h1-3H3
inchiKey:    GPASKFIFXOCRNP-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])=[#7]-[#6]
smarts_isomeric:    [#6]-[#6](-[#6])=[#7]-[#6]

(Z)-N,N,N'-trimethylacetimidamide: C/C(N(C)C)=N/C

smiles_non_kekule:    C/N=C(/C)N(C)C
smiles_kekule:    C/N=C(/C)N(C)C
inchi:    InChI=1S/C5H12N2/c1-5(6-2)7(3)4/h1-4H3/b6-5-
inchiKey:    UCBFBQXXPWLTSZ-WAYWQWQTSA-N
smarts:    [#6]-[#6](-[#7](-[#6])-[#6])=[#7]-[#6]
smarts_isomeric:    [#6]/[#6](-[#7](-[#6])-[#6])=[#7]/[#6]

acetic anydride: CC(=O)OC(=O)C

smiles_non_kekule:    CC(=O)OC(C)=O
smiles_kekule:    CC(=O)OC(C)=O
inchi:    InChI=1S/C4H6O3/c1-3(5)7-4(2)6/h1-2H3
inchiKey:    WFDIJRYMOXRFFG-UHFFFAOYSA-N
smarts:    [#6]-[#6](=[#8])-[#8]-[#6](=[#8])-[#6]
smarts_isomeric:    [#6]-[#6](=[#8])-[#8]-[#6](=[#8])-[#6]

acyl bromide: C(=O)Br

smiles_non_kekule:    O=CBr
smiles_kekule:    O=CBr
inchi:    InChI=1S/CHBrO/c2-1-3/h1H
inchiKey:    AIFARXRIYKCEEV-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#35]
smarts_isomeric:    [#6](=[#8])-[#35]

acyl chloride: C(=O)Cl

smiles_non_kekule:    O=CCl
smiles_kekule:    O=CCl
inchi:    InChI=1S/CHClO/c2-1-3/h1H
inchiKey:    GFAUNYMRSKVDJL-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#17]
smarts_isomeric:    [#6](=[#8])-[#17]

acyl fluoride: C(=O)F

smiles_non_kekule:    O=CF
smiles_kekule:    O=CF
inchi:    InChI=1S/CHFO/c2-1-3/h1H
inchiKey:    NHGVZTMBVDFPHJ-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#9]
smarts_isomeric:    [#6](=[#8])-[#9]

acyl iodide: C(=O)I

smiles_non_kekule:    O=CI
smiles_kekule:    O=CI
inchi:    InChI=1S/CHIO/c2-1-3/h1H
inchiKey:    KWOITLGQRDFDFP-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#53]
smarts_isomeric:    [#6](=[#8])-[#53]

aldehyde: CC=O

amide: C(=O)N

smiles_non_kekule:    NC=O
smiles_kekule:    NC=O
inchi:    InChI=1S/CH3NO/c2-1-3/h1H,(H2,2,3)
inchiKey:    ZHNUHDYFZUAESO-UHFFFAOYSA-N
smarts:    [#6](=[#8])-[#7]
smarts_isomeric:    [#6](=[#8])-[#7]

amino: *N

smiles_non_kekule:    *N
smiles_kekule:    *N
inchi:
inchiKey:
smarts:    [#0]-[#7]
smarts_isomeric:    [#0]-[#7]

anthracene: C12=CC=CC=C1C=C3C(C=CC=C3)=C2

smiles_non_kekule:    c1ccc2cc3ccccc3cc2c1
smiles_kekule:    C1=CC=C2C=C3C=CC=CC3=CC2=C1
inchi:    InChI=1S/C14H10/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1/h1-10H
inchiKey:    MWPLVEDNUUSJAV-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]1:[#6](:[#6]:[#6]:[#6]:[#6]:1):[#6]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]1:[#6](:[#6]:[#6]:[#6]:[#6]:1):[#6]:2

azide: C([N-][N+]#N)

smiles_non_kekule:    C[N-][N+]#N
smiles_kekule:    C[N-][N+]#N
inchi:    InChI=1S/CH3N3/c1-3-4-2/h1H3
inchiKey:    PBTHJVDBCFJQGG-UHFFFAOYSA-N
smarts:    [#6]-[#7-]-[#7+]#[#7]
smarts_isomeric:    [#6]-[#7-]-[#7+]#[#7]

benzene: C1=CC=CC=C1

benzene thiol: C1=CC=C(C=C1)S

smiles_non_kekule:    Sc1ccccc1
smiles_kekule:    SC1=CC=CC=C1
inchi:    InChI=1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H
inchiKey:    RMVRSNDYEFQCLF-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#16]
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#16]

bicyclohexyl: C1CCCCC1C1CCCCC1

smiles_non_kekule:    C1CCC(C2CCCCC2)CC1
smiles_kekule:    C1CCC(C2CCCCC2)CC1
inchi:    InChI=1S/C12H22/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h11-12H,1-10H2
inchiKey:    WVIIMZNLDWSIRH-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

bromine: Br

smiles_non_kekule:    Br
smiles_kekule:    Br
inchi:    InChI=1S/BrH/h1H
inchiKey:    CPELXLSAUQHCOX-UHFFFAOYSA-N
smarts:    [#35]
smarts_isomeric:    [#35]

but-1-ene: CCC=C

smiles_non_kekule:    C=CCC
smiles_kekule:    C=CCC
inchi:    InChI=1S/C4H8/c1-3-4-2/h3H,1,4H2,2H3
inchiKey:    VXNZUUAINFGPBY-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]=[#6]
smarts_isomeric:    [#6]-[#6]-[#6]=[#6]

but-1-yne: CCC#C

smiles_non_kekule:    C#CCC
smiles_kekule:    C#CCC
inchi:    InChI=1S/C4H6/c1-3-4-2/h1H,4H2,2H3
inchiKey:    KDKYADYSIPSCCQ-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]#[#6]
smarts_isomeric:    [#6]-[#6]-[#6]#[#6]

carbon dioxide: O=C=O

smiles_non_kekule:    O=C=O
smiles_kekule:    O=C=O
inchi:    InChI=1S/CO2/c2-1-3
inchiKey:    CURLTUGMZLYLDI-UHFFFAOYSA-N
smarts:    [#8]=[#6]=[#8]
smarts_isomeric:    [#8]=[#6]=[#8]

carboxylic acid: C(=O)O

chlorine: Cl

smiles_non_kekule:    Cl
smiles_kekule:    Cl
inchi:    InChI=1S/ClH/h1H
inchiKey:    VEXZGXHMUGYJMC-UHFFFAOYSA-N
smarts:    [#17]
smarts_isomeric:    [#17]

chloromethyl methyl ether: COCCl

smiles_non_kekule:    COCCl
smiles_kekule:    COCCl
inchi:    InChI=1S/C2H5ClO/c1-4-2-3/h2H2,1H3
inchiKey:    XJUZRXYOEPSWMB-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]-[#17]
smarts_isomeric:    [#6]-[#8]-[#6]-[#17]

cyclobutadiene: C1=CC=C1

smiles_non_kekule:    C1=CC=C1
smiles_kekule:    C1=CC=C1
inchi:    InChI=1S/C4H4/c1-2-4-3-1/h1-4H
inchiKey:    HWEQKSVYKBUIIK-UHFFFAOYSA-N
smarts:    [#6]1=[#6]-[#6]=[#6]-1
smarts_isomeric:    [#6]1=[#6]-[#6]=[#6]-1

cyclobutane: C1CCC1

cycloheptane: C1CCCCCC1

smiles_non_kekule:    C1CCCCCC1
smiles_kekule:    C1CCCCCC1
inchi:    InChI=1S/C7H14/c1-2-4-6-7-5-3-1/h1-7H2
inchiKey:    DMEGYFMYUHOHGS-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-1

cyclohexane: C1CCCCC1

cyclohexa-1,3-diene: C1=CCCC=C1

smiles_non_kekule:    C1=CCCC=C1
smiles_kekule:    C1=CCCC=C1
inchi:    InChI=1S/C6H8/c1-2-4-6-5-3-1/h1-4H,5-6H2
inchiKey:    MGNZXYYWBUKAII-UHFFFAOYSA-N
smarts:    [#6]1=[#6]-[#6]-[#6]-[#6]=[#6]-1
smarts_isomeric:    [#6]1=[#6]-[#6]-[#6]-[#6]=[#6]-1

cyclohexa-1,4-diene: C1=CCC=CC1

smiles_non_kekule:    C1=CCC=CC1
smiles_kekule:    C1=CCC=CC1
inchi:    InChI=1S/C6H8/c1-2-4-6-5-3-1/h1-2,5-6H,3-4H2
inchiKey:    UVJHQYIOXKWHFD-UHFFFAOYSA-N
smarts:    [#6]1=[#6]-[#6]-[#6]=[#6]-[#6]-1
smarts_isomeric:    [#6]1=[#6]-[#6]-[#6]=[#6]-[#6]-1

cyclohexene: C=1CCCCC=1

smiles_non_kekule:    C1=CCCCC1
smiles_kekule:    C1=CCCCC1
inchi:    InChI=1S/C6H10/c1-2-4-6-5-3-1/h1-2H,3-6H2
inchiKey:    HGCIXCUEYOPUTN-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#6]-[#6]-[#6]=1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#6]-[#6]-[#6]=1

cyclopentane: C1CCCC1

cyclopenta-1,3-diene: C1=CCC=C1

smiles_non_kekule:    C1=CCC=C1
smiles_kekule:    C1=CCC=C1
inchi:    InChI=1S/C5H6/c1-2-4-5-3-1/h1-4H,5H2
inchiKey:    ZSWFCLXCOIISFI-UHFFFAOYSA-N
smarts:    [#6]1=[#6]-[#6]-[#6]=[#6]-1
smarts_isomeric:    [#6]1=[#6]-[#6]-[#6]=[#6]-1

cyclopropane: C1CC1

cyclopropene: C1=CC1

smiles_non_kekule:    C1=CC1
smiles_kekule:    C1=CC1
inchi:    InChI=1S/C3H4/c1-2-3-1/h1-2H,3H2
inchiKey:    OOXWYYGXTJLWHA-UHFFFAOYSA-N
smarts:    [#6]1=[#6]-[#6]-1
smarts_isomeric:    [#6]1=[#6]-[#6]-1

deuteroethane: [2H][CH2]C

smiles_non_kekule:    [2H]CC
smiles_kekule:    [2H]CC
inchi:    InChI=1S/C2H6/c1-2/h1-2H3/i1D
inchiKey:    OTMSDBZUPAUEDD-MICDWDOJSA-N
smarts:    [2H]-[#6H2]-[#6]
smarts_isomeric:    [2H]-[#6H2]-[#6]

dimethyl ether: COC

diethyl ether: CCOCC

diisopropyl ether: CC(C)OC(C)C

smiles_non_kekule:    CC(C)OC(C)C
smiles_kekule:    CC(C)OC(C)C
inchi:    InChI=1S/C6H14O/c1-5(2)7-6(3)4/h5-6H,1-4H3
inchiKey:    ZAFNJMIOTHYJRJ-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])-[#8]-[#6](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6](-[#6])-[#8]-[#6](-[#6])-[#6]

diazomethane: C=[N+]=[N-]

smiles_non_kekule:    C=[N+]=[N-]
smiles_kekule:    C=[N+]=[N-]
inchi:    InChI=1S/CH2N2/c1-3-2/h1H2
inchiKey:    YXHKONLOYHBTNS-UHFFFAOYSA-N
smarts:    [#6]=[#7+]=[#7-]
smarts_isomeric:    [#6]=[#7+]=[#7-]

diammonium thiosulfate: [NH4+].[NH4+].[O-]S(=O)(=O)[S-]

smiles_non_kekule:    O=S(=O)([O-])[S-].[NH4+].[NH4+]
smiles_kekule:    O=S(=O)([O-])[S-].[NH4+].[NH4+]
inchi:    InChI=1S/2H3N.H2O3S2/c;;1-5(2,3)4/h2*1H3;(H2,1,2,3,4)
inchiKey:    XYXNTHIYBIDHGM-UHFFFAOYSA-N
smarts:    [#7H4+].[#7H4+].[#8-]-[#16](=[#8])(=[#8])-[#16-]
smarts_isomeric:    [#7H4+].[#7H4+].[#8-]-[#16](=[#8])(=[#8])-[#16-]

enamine: N

smiles_non_kekule:    N
smiles_kekule:    N
inchi:    InChI=1S/H3N/h1H3
inchiKey:    QGZKDVFQNNGYKY-UHFFFAOYSA-N
smarts:    [#7]
smarts_isomeric:    [#7]

ethane: CC

smiles_non_kekule:    CC
smiles_kekule:    CC
inchi:    InChI=1S/C2H6/c1-2/h1-2H3
inchiKey:    OTMSDBZUPAUEDD-UHFFFAOYSA-N
smarts:    [#6]-[#6]
smarts_isomeric:    [#6]-[#6]

ethanethiol: CCS

smiles_non_kekule:    CCS
smiles_kekule:    CCS
inchi:    InChI=1S/C2H6S/c1-2-3/h3H,2H2,1H3
inchiKey:    DNJIEGIFACGWOD-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#16]
smarts_isomeric:    [#6]-[#6]-[#16]

ethanol: CCO

ethene: C=C

smiles_non_kekule:    C=C
smiles_kekule:    C=C
inchi:    InChI=1S/C2H4/c1-2/h1-2H2
inchiKey:    VGGSQFUCUMXWEO-UHFFFAOYSA-N
smarts:    [#6]=[#6]
smarts_isomeric:    [#6]=[#6]

ether: COC

ester: C(=O)OC

fluorine: F

smiles_non_kekule:    F
smiles_kekule:    F
inchi:    InChI=1S/FH/h1H
inchiKey:    KRHYYFGTRYWZRS-UHFFFAOYSA-N
smarts:    [#9]
smarts_isomeric:    [#9]

formaldehyde: C=O

smiles_non_kekule:    C=O
smiles_kekule:    C=O
inchi:    InChI=1S/CH2O/c1-2/h1H2
inchiKey:    WSFSSNUMVMOOMR-UHFFFAOYSA-N
smarts:    [#6]=[#8]
smarts_isomeric:    [#6]=[#8]

furan: C1OC=CC=1

smiles_non_kekule:    c1ccoc1
smiles_kekule:    C1=COC=C1
inchi:    InChI=1S/C4H4O/c1-2-4-5-3-1/h1-4H
inchiKey:    YLQBMQCUIZJEEH-UHFFFAOYSA-N
smarts:    [#6]1:[#8]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#8]:[#6]:[#6]:[#6]:1

hydrogen cyanide: C#N

smiles_non_kekule:    C#N
smiles_kekule:    C#N
inchi:    InChI=1S/CHN/c1-2/h1H
inchiKey:    LELOWRISYMNNSU-UHFFFAOYSA-N
smarts:    [#6]#[#7]
smarts_isomeric:    [#6]#[#7]

hydroxide: [OH-]

smiles_non_kekule:    [OH-]
smiles_kekule:    [OH-]
inchi:    InChI=1S/H2O/h1H2/p-1
inchiKey:    XLYOFNOQVPJJNP-UHFFFAOYSA-M
smarts:    [#8H-]
smarts_isomeric:    [#8H-]

hydroxyl amine: NO

smiles_non_kekule:    NO
smiles_kekule:    NO
inchi:    InChI=1S/H3NO/c1-2/h2H,1H2
inchiKey:    AVXURJPOCDRRFD-UHFFFAOYSA-N
smarts:    [#7]-[#8]
smarts_isomeric:    [#7]-[#8]

indane: C1=CC=CC(CCC2)=C12

smiles_non_kekule:    c1ccc2c(c1)CCC2
smiles_kekule:    C1=CC2=C(C=C1)CCC2
inchi:    InChI=1S/C9H10/c1-2-5-9-7-3-6-8(9)4-1/h1-2,4-5H,3,6-7H2
inchiKey:    PQNFLJBBNBOBRQ-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]:[#6]2-[#6]-[#6]-[#6]-[#6]:1:2
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]:[#6]2-[#6]-[#6]-[#6]-[#6]:1:2

ketone: CC(=O)C

methane: C

smiles_non_kekule:    C
smiles_kekule:    C
inchi:    InChI=1S/CH4/h1H4
inchiKey:    VNWKTOKETHGBQD-UHFFFAOYSA-N
smarts:    [#6]
smarts_isomeric:    [#6]

methanethiol: CS

methyl acetate: CC(OC)=O

methyl pyrrole: CN1CCCC1

methyl tert-butyl ether: CC(C)(C)OC

naphthalene: C12=CC=CC=C1C=CC=C2

smiles_non_kekule:    c1ccc2ccccc2c1
smiles_kekule:    C1=CC=C2C=CC=CC2=C1
inchi:    InChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
inchiKey:    UFWIBTONFRDIAS-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#6]:[#6]:2

nitro: [N+](=O)[O-]

nitromethane: C[N+]([O-])=O

smiles_non_kekule:    C[N+](=O)[O-]
smiles_kekule:    C[N+](=O)[O-]
inchi:    InChI=1S/CH3NO2/c1-2(3)4/h1H3
inchiKey:    LYGJENNIWJXYER-UHFFFAOYSA-N
smarts:    [#6]-[#7+](-[#8-])=[#8]
smarts_isomeric:    [#6]-[#7+](-[#8-])=[#8]

pentalene: C12=CC=CC1=CC=C2

smiles_non_kekule:    C1=CC2=CC=CC2=C1
smiles_kekule:    C1=CC2=CC=CC2=C1
inchi:    InChI=1S/C8H6/c1-3-7-5-2-6-8(7)4-1/h1-6H
inchiKey:    GUVXZFRDPCKWEM-UHFFFAOYSA-N
smarts:    [#6]12=[#6]-[#6]=[#6]-[#6]-1=[#6]-[#6]=[#6]-2
smarts_isomeric:    [#6]12=[#6]-[#6]=[#6]-[#6]-1=[#6]-[#6]=[#6]-2

perhydroisoquinoline: N1CC2CCCC2CC1

smiles_non_kekule:    C1CC2CCNCC2C1
smiles_kekule:    C1CC2CCNCC2C1
inchi:    InChI=1S/C8H15N/c1-2-7-4-5-9-6-8(7)3-1/h7-9H,1-6H2
inchiKey:    KPXSPHQLZBMRLW-UHFFFAOYSA-N
smarts:    [#7]1-[#6]-[#6]2-[#6]-[#6]-[#6]-[#6]-2-[#6]-[#6]-1
smarts_isomeric:    [#7]1-[#6]-[#6]2-[#6]-[#6]-[#6]-[#6]-2-[#6]-[#6]-1

phenol: OC1CCCCC1

smiles_non_kekule:    OC1CCCCC1
smiles_kekule:    OC1CCCCC1
inchi:    InChI=1S/C6H12O/c7-6-4-2-1-3-5-6/h6-7H,1-5H2
inchiKey:    HPXRVTGHNJAIIH-UHFFFAOYSA-N
smarts:    [#8]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#8]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

phenyl: C=1(C=CC=CC1)

primary alcohol: O

smiles_non_kekule:    O
smiles_kekule:    O
inchi:    InChI=1S/H2O/h1H2
inchiKey:    XLYOFNOQVPJJNP-UHFFFAOYSA-N
smarts:    [#8]
smarts_isomeric:    [#8]

primary amine: N

smiles_non_kekule:    N
smiles_kekule:    N
inchi:    InChI=1S/H3N/h1H3
inchiKey:    QGZKDVFQNNGYKY-UHFFFAOYSA-N
smarts:    [#7]
smarts_isomeric:    [#7]

propan-2-one: CC(C)=O

smiles_non_kekule:    CC(C)=O
smiles_kekule:    CC(C)=O
inchi:    InChI=1S/C3H6O/c1-3(2)4/h1-2H3
inchiKey:    CSCPPACGZOOCGX-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])=[#8]
smarts_isomeric:    [#6]-[#6](-[#6])=[#8]

propanol: CCC=O

smiles_non_kekule:    CCC=O
smiles_kekule:    CCC=O
inchi:    InChI=1S/C3H6O/c1-2-3-4/h3H,2H2,1H3
inchiKey:    NBBJYMSMWIIQGU-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]=[#8]
smarts_isomeric:    [#6]-[#6]-[#6]=[#8]

prop-1-ene: CC=C

prop-1-yne: CC#C

pyridine: N1CCCCC1

secondary amine: NC

smiles_non_kekule:    CN
smiles_kekule:    CN
inchi:    InChI=1S/CH5N/c1-2/h2H2,1H3
inchiKey:    BAVYZALUXZFZLV-UHFFFAOYSA-N
smarts:    [#7]-[#6]
smarts_isomeric:    [#7]-[#6]

spiro[5.5]undecane: C12(CCCCC1)CCCCC2

smiles_non_kekule:    C1CCC2(CC1)CCCCC2
smiles_kekule:    C1CCC2(CC1)CCCCC2
inchi:    InChI=1S/C11H20/c1-3-7-11(8-4-1)9-5-2-6-10-11/h1-10H2
inchiKey:    NECLQTPQJZSWOE-UHFFFAOYSA-N
smarts:    [#6]12(-[#6]-[#6]-[#6]-[#6]-[#6]-1)-[#6]-[#6]-[#6]-[#6]-[#6]-2
smarts_isomeric:    [#6]12(-[#6]-[#6]-[#6]-[#6]-[#6]-1)-[#6]-[#6]-[#6]-[#6]-[#6]-2

sulfoxide: S(=O)(=O)

smiles_non_kekule:    O=S=O
smiles_kekule:    O=S=O
inchi:    InChI=1S/O2S/c1-3-2
inchiKey:    RAHZWNYVWXNFOC-UHFFFAOYSA-N
smarts:    [#16](=[#8])=[#8]
smarts_isomeric:    [#16](=[#8])=[#8]

tetramethylammonium: C[N+](C)(C)C

smiles_non_kekule:    C[N+](C)(C)C
smiles_kekule:    C[N+](C)(C)C
inchi:    InChI=1S/C4H12N/c1-5(2,3)4/h1-4H3/q+1
inchiKey:    QEMXHQIAXOOASZ-UHFFFAOYSA-N
smarts:    [#6]-[#7+](-[#6])(-[#6])-[#6]
smarts_isomeric:    [#6]-[#7+](-[#6])(-[#6])-[#6]

thiol: S

smiles_non_kekule:    S
smiles_kekule:    S
inchi:    InChI=1S/H2S/h1H2
inchiKey:    RWSOTUBLDIXVET-UHFFFAOYSA-N
smarts:    [#16]
smarts_isomeric:    [#16]

thiosulfate: OS(=O)(=S)O

smiles_non_kekule:    O=S(O)(O)=S
smiles_kekule:    O=S(O)(O)=S
inchi:    InChI=1S/H2O3S2/c1-5(2,3)4/h(H2,1,2,3,4)
inchiKey:    DHCDFWKWKRSZHF-UHFFFAOYSA-N
smarts:    [#8]-[#16](=[#8])(=[#16])-[#8]
smarts_isomeric:    [#8]-[#16](=[#8])(=[#16])-[#8]

trimethylamine: CN(C)C

triphenylene: C1(C=CC=C2)=C2C(C=CC=C3)=C3C4=C1C=CC=C4

smiles_non_kekule:    c1ccc2c(c1)c1ccccc1c1ccccc21
smiles_kekule:    C1=CC=C2C(=C1)C1=CC=CC=C1C1=C2C=CC=C1
inchi:    InChI=1S/C18H12/c1-2-8-14-13(7-1)15-9-3-4-11-17(15)18-12-6-5-10-16(14)18/h1-12H
inchiKey:    SLGBZMMZGDRARJ-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]1:[#6]:2:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]1:[#6]:2:[#6]:[#6]:[#6]:[#6]:1

problem_type: 18/25 (loop 0/0)

[15:21:17] WARNING: Omitted undefined stereo

[15:21:17] WARNING: Omitted undefined stereo

[15:21:17] WARNING: Metal was disconnected; Proton(s) added/removed

[15:21:17] WARNING: Omitted undefined stereo

[15:21:17] WARNING: Omitted undefined stereo

[15:21:17] WARNING: Omitted undefined stereo

Problem Template: _problem_polyfluoroalkyl_substances

Write structure of polyfluoroalkyl substances molecules.

Answer:

structure of polyfluoroalkyl substances molecules:

perfluorohexanoic acid: C(=O)(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)O

perfluoroheptanoic acid: C(=O)(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O

perfluorononanoic acid: C(=O)(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O

perfluorodecanoic acid: C(=O)(C(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O

perfluorobutanesulfonic acid: C(C(C(F)(F)S(=O)(=O)O)(F)F)(C(F)(F)F)(F)F

perfluorohexanesulfonic acid: C(C(C(C(F)(F)S(=O)(=O)O)(F)F)(F)F)(C(C(F)(F)F)(F)F)(F)F

perfluoroundecanoic acid: C(=O)(C(C(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O

2-(N-ethyl-perfluorooctane sulfanamido) acetic acid: CCN(CC(=O)O)S(=O)(=O)C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F

2-(N-Methyl-perfluorooctane sulfanamido) acetic acid: CN(CC(=O)O)S(=O)(=O)C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F

hexafluoropropylene Oxide Dimer Acid: C1(C(O1)(F)F)(C(F)(F)F)F

perfluorotetradecanoic acid: C(=O)(C(C(C(C(C(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O

perfluorotridecanoic acid: C(=O)(C(C(C(C(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O

4,8-dioxa-3H-perfluorononanoic: C(C(C(=O)O)(F)F)(OC(C(C(OC(F)(F)F)(F)F)(F)F)(F)F)F

6:2 chlorinated polyfluorinated ether sulfonic acid: FC(Cl)(C(F)(C(F)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)(S(=O)(O[K])=O)F)F)F

perfluorobutanoic acid: FC(F)(C(F)(C(O)=O)F)C(F)(F)F

perfluoro-n-pentanoic acid: C(=O)(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)O

nafion byproduct 2: C(C(F)(F)F)(OC(C(C(F)(F)F)(OC(C(F)(F)S(=O)(=O)O)(F)F)F)(F)F)F

perfluoro-3,5,7,9-tetraoxadecanoic acid: C(=O)(C(OC(OC(OC(OC(F)(F)F)(F)F)(F)F)(F)F)(F)F)O

perfluoro-3,5,7,9,11-pentaoxadodecanoic acid: C(=O)(C(OC(OC(OC(OC(OC(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O

2,2,3,3-tetrafluoro-3-((1,1,1,2,3,3-hexafluoro-3-(1,2,2,2-tetrafluoroethoxy)propan-2-yl)oxy)propanoic acid: C(=O)(C(C(F)(F)F)(OC(C(OC(C(C(F)(F)F)(F)F)(F)F)(F)F)(C(F)(F)F)F)F)O

h,1h,2h,2h-perfluorooctanesulfonic acid: C(C(C(C(C(F)(F)S(=O)(=O)O)(F)F)(F)F)(F)F)(C(C(C(F)(F)F)(F)F)(F)F)(F)F

2-(perfluorooctyl)ethane-1-sulfonic acid: C(CS(=O)(=O)O)C(C(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F

perfluoropentanesulfonic acid: C(C(C(F)(F)F)(F)F)(C(C(F)(F)S(=O)(=O)O)(F)F)(F)F

perfluoroheptanesulfonic acid: C(C(C(C(F)(F)F)(F)F)(F)F)(C(C(C(F)(F)S(=O)(=O)O)(F)F)(F)F)(F)F

perfluorononanesulfonic acid: C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(C(C(C(C(F)(F)S(=O)(=O)O)(F)F)(F)F)(F)F)(F)F

perfluorodecanesulfonic acid: C(C(C(C(C(C(F)(F)S(=O)(=O)O)(F)F)(F)F)(F)F)(F)F)(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F

hexafluoropropylene oxide trimer acid: C(=O)(C(C(F)(F)F)(OC(C(C(F)(F)F)(OC(C(C(F)(F)F)(F)F)(F)F)F)(F)F)F)F

Solution:

structure of polyfluoroalkyl substances molecules:

perfluorohexanoic acid: C(=O)(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)O

smiles_non_kekule:    O=C(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
smiles_kekule:    O=C(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
inchi:    InChI=1S/C6HF11O2/c7-2(8,1(18)19)3(9,10)4(11,12)5(13,14)6(15,16)17/h(H,18,19)
inchiKey:    PXUULQAPEKKVAH-UHFFFAOYSA-N
smarts:    [#6](=[#8])(-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#8]
smarts_isomeric:    [#6](=[#8])(-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#8]

perfluoroheptanoic acid: C(=O)(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O

smiles_non_kekule:    O=C(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
smiles_kekule:    O=C(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
inchi:    InChI=1S/C7HF13O2/c8-2(9,1(21)22)3(10,11)4(12,13)5(14,15)6(16,17)7(18,19)20/h(H,21,22)
inchiKey:    ZWBAMYVPMDSJGQ-UHFFFAOYSA-N
smarts:    [#6](=[#8])(-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#8]
smarts_isomeric:    [#6](=[#8])(-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#8]

perfluorononanoic acid: C(=O)(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O

smiles_non_kekule:    O=C(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
smiles_kekule:    O=C(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
inchi:    InChI=1S/C9HF17O2/c10-2(11,1(27)28)3(12,13)4(14,15)5(16,17)6(18,19)7(20,21)8(22,23)9(24,25)26/h(H,27,28)
inchiKey:    UZUFPBIDKMEQEQ-UHFFFAOYSA-N
smarts:    [#6](=[#8])(-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#8]
smarts_isomeric:    [#6](=[#8])(-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#8]

perfluorodecanoic acid: C(=O)(C(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O

smiles_non_kekule:    O=C(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
smiles_kekule:    O=C(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
inchi:    InChI=1S/C10HF19O2/c11-2(12,1(30)31)3(13,14)4(15,16)5(17,18)6(19,20)7(21,22)8(23,24)9(25,26)10(27,28)29/h(H,30,31)
inchiKey:    PCIUEQPBYFRTEM-UHFFFAOYSA-N
smarts:    [#6](=[#8])(-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#8]
smarts_isomeric:    [#6](=[#8])(-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#8]

perfluorobutanesulfonic acid: C(C(C(F)(F)S(=O)(=O)O)(F)F)(C(F)(F)F)(F)F

smiles_non_kekule:    O=S(=O)(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
smiles_kekule:    O=S(=O)(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
inchi:    InChI=1S/C4HF9O3S/c5-1(6,3(9,10)11)2(7,8)4(12,13)17(14,15)16/h(H,14,15,16)
inchiKey:    JGTNAGYHADQMCM-UHFFFAOYSA-N
smarts:    [#6](-[#6](-[#6](-[#9])(-[#9])-[#16](=[#8])(=[#8])-[#8])(-[#9])-[#9])(-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9]
smarts_isomeric:    [#6](-[#6](-[#6](-[#9])(-[#9])-[#16](=[#8])(=[#8])-[#8])(-[#9])-[#9])(-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9]

perfluorohexanesulfonic acid: C(C(C(C(F)(F)S(=O)(=O)O)(F)F)(F)F)(C(C(F)(F)F)(F)F)(F)F

smiles_non_kekule:    O=S(=O)(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
smiles_kekule:    O=S(=O)(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
inchi:    InChI=1S/C6HF13O3S/c7-1(8,3(11,12)5(15,16)17)2(9,10)4(13,14)6(18,19)23(20,21)22/h(H,20,21,22)
inchiKey:    QZHDEAJFRJCDMF-UHFFFAOYSA-N
smarts:    [#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#16](=[#8])(=[#8])-[#8])(-[#9])-[#9])(-[#9])-[#9])(-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9]
smarts_isomeric:    [#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#16](=[#8])(=[#8])-[#8])(-[#9])-[#9])(-[#9])-[#9])(-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9]

perfluoroundecanoic acid: C(=O)(C(C(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O

smiles_non_kekule:    O=C(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
smiles_kekule:    O=C(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
inchi:    InChI=1S/C11HF21O2/c12-2(13,1(33)34)3(14,15)4(16,17)5(18,19)6(20,21)7(22,23)8(24,25)9(26,27)10(28,29)11(30,31)32/h(H,33,34)
inchiKey:    SIDINRCMMRKXGQ-UHFFFAOYSA-N
smarts:    [#6](=[#8])(-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#8]
smarts_isomeric:    [#6](=[#8])(-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#8]

2-(N-ethyl-perfluorooctane sulfanamido) acetic acid: CCN(CC(=O)O)S(=O)(=O)C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F

smiles_non_kekule:    CCN(CC(=O)O)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
smiles_kekule:    CCN(CC(=O)O)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
inchi:    InChI=1S/C12H8F17NO4S/c1-2-30(3-4(31)32)35(33,34)12(28,29)10(23,24)8(19,20)6(15,16)5(13,14)7(17,18)9(21,22)11(25,26)27/h2-3H2,1H3,(H,31,32)
inchiKey:    CKRXVVGETMYFIO-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7](-[#6]-[#6](=[#8])-[#8])-[#16](=[#8])(=[#8])-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9]
smarts_isomeric:    [#6]-[#6]-[#7](-[#6]-[#6](=[#8])-[#8])-[#16](=[#8])(=[#8])-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9]

2-(N-Methyl-perfluorooctane sulfanamido) acetic acid: CN(CC(=O)O)S(=O)(=O)C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F

smiles_non_kekule:    CN(CC(=O)O)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
smiles_kekule:    CN(CC(=O)O)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
inchi:    InChI=1S/C11H6F17NO4S/c1-29(2-3(30)31)34(32,33)11(27,28)9(22,23)7(18,19)5(14,15)4(12,13)6(16,17)8(20,21)10(24,25)26/h2H2,1H3,(H,30,31)
inchiKey:    QNDHIRFIMVNHBN-UHFFFAOYSA-N
smarts:    [#6]-[#7](-[#6]-[#6](=[#8])-[#8])-[#16](=[#8])(=[#8])-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9]
smarts_isomeric:    [#6]-[#7](-[#6]-[#6](=[#8])-[#8])-[#16](=[#8])(=[#8])-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9]

hexafluoropropylene Oxide Dimer Acid: C1(C(O1)(F)F)(C(F)(F)F)F

smiles_non_kekule:    FC(F)(F)C1(F)OC1(F)F
smiles_kekule:    FC(F)(F)C1(F)OC1(F)F
inchi:    InChI=1S/C3F6O/c4-1(2(5,6)7)3(8,9)10-1
inchiKey:    PGFXOWRDDHCDTE-UHFFFAOYSA-N
smarts:    [#6]1(-[#6](-[#8]-1)(-[#9])-[#9])(-[#6](-[#9])(-[#9])-[#9])-[#9]
smarts_isomeric:    [#6]1(-[#6](-[#8]-1)(-[#9])-[#9])(-[#6](-[#9])(-[#9])-[#9])-[#9]

perfluorotetradecanoic acid: C(=O)(C(C(C(C(C(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O

smiles_non_kekule:    O=C(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
smiles_kekule:    O=C(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
inchi:    InChI=1S/C14HF27O2/c15-2(16,1(42)43)3(17,18)4(19,20)5(21,22)6(23,24)7(25,26)8(27,28)9(29,30)10(31,32)11(33,34)12(35,36)13(37,38)14(39,40)41/h(H,42,43)
inchiKey:    RUDINRUXCKIXAJ-UHFFFAOYSA-N
smarts:    [#6](=[#8])(-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#8]
smarts_isomeric:    [#6](=[#8])(-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#8]

perfluorotridecanoic acid: C(=O)(C(C(C(C(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O

smiles_non_kekule:    O=C(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
smiles_kekule:    O=C(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
inchi:    InChI=1S/C13HF25O2/c14-2(15,1(39)40)3(16,17)4(18,19)5(20,21)6(22,23)7(24,25)8(26,27)9(28,29)10(30,31)11(32,33)12(34,35)13(36,37)38/h(H,39,40)
inchiKey:    LVDGGZAZAYHXEY-UHFFFAOYSA-N
smarts:    [#6](=[#8])(-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#8]
smarts_isomeric:    [#6](=[#8])(-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#8]

4,8-dioxa-3H-perfluorononanoic: C(C(C(=O)O)(F)F)(OC(C(C(OC(F)(F)F)(F)F)(F)F)(F)F)F

smiles_non_kekule:    O=C(O)C(F)(F)C(F)OC(F)(F)C(F)(F)C(F)(F)OC(F)(F)F
smiles_kekule:    O=C(O)C(F)(F)C(F)OC(F)(F)C(F)(F)C(F)(F)OC(F)(F)F
inchi:    InChI=1S/C7H2F12O4/c8-1(3(9,10)2(20)21)22-5(13,14)4(11,12)6(15,16)23-7(17,18)19/h1H,(H,20,21)
inchiKey:    AFDRCEOKCOUICI-UHFFFAOYSA-N
smarts:    [#6](-[#6](-[#6](=[#8])-[#8])(-[#9])-[#9])(-[#8]-[#6](-[#6](-[#6](-[#8]-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#9]
smarts_isomeric:    [#6](-[#6](-[#6](=[#8])-[#8])(-[#9])-[#9])(-[#8]-[#6](-[#6](-[#6](-[#8]-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#9]

6:2 chlorinated polyfluorinated ether sulfonic acid: FC(Cl)(C(F)(C(F)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)(S(=O)(O[K])=O)F)F)F

smiles_non_kekule:    O=S(=O)(O[K])C(F)(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)Cl
smiles_kekule:    O=S(=O)(O[K])C(F)(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)Cl
inchi:    InChI=1S/C7HClF14O4S.K/c8-4(15,16)2(11,12)1(9,10)3(13,14)5(17,18)26-6(19,20)7(21,22)27(23,24)25;/h(H,23,24,25);/q;+1/p-1
inchiKey:    SMHFNNYEYMKSJU-UHFFFAOYSA-M
smarts:    [#9]-[#6](-[#17])(-[#6](-[#9])(-[#6](-[#9])(-[#9])-[#6](-[#9])(-[#9])-[#6](-[#9])(-[#9])-[#8]-[#6](-[#9])(-[#9])-[#6](-[#9])(-[#16](=[#8])(-[#8]-[K])=[#8])-[#9])-[#9])-[#9]
smarts_isomeric:    [#9]-[#6](-[#17])(-[#6](-[#9])(-[#6](-[#9])(-[#9])-[#6](-[#9])(-[#9])-[#6](-[#9])(-[#9])-[#8]-[#6](-[#9])(-[#9])-[#6](-[#9])(-[#16](=[#8])(-[#8]-[K])=[#8])-[#9])-[#9])-[#9]

perfluorobutanoic acid: FC(F)(C(F)(C(O)=O)F)C(F)(F)F

smiles_non_kekule:    O=C(O)C(F)(F)C(F)(F)C(F)(F)F
smiles_kekule:    O=C(O)C(F)(F)C(F)(F)C(F)(F)F
inchi:    InChI=1S/C4HF7O2/c5-2(6,1(12)13)3(7,8)4(9,10)11/h(H,12,13)
inchiKey:    YPJUNDFVDDCYIH-UHFFFAOYSA-N
smarts:    [#9]-[#6](-[#9])(-[#6](-[#9])(-[#6](-[#8])=[#8])-[#9])-[#6](-[#9])(-[#9])-[#9]
smarts_isomeric:    [#9]-[#6](-[#9])(-[#6](-[#9])(-[#6](-[#8])=[#8])-[#9])-[#6](-[#9])(-[#9])-[#9]

perfluoro-n-pentanoic acid: C(=O)(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)O

smiles_non_kekule:    O=C(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
smiles_kekule:    O=C(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
inchi:    InChI=1S/C5HF9O2/c6-2(7,1(15)16)3(8,9)4(10,11)5(12,13)14/h(H,15,16)
inchiKey:    CXZGQIAOTKWCDB-UHFFFAOYSA-N
smarts:    [#6](=[#8])(-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#8]
smarts_isomeric:    [#6](=[#8])(-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#8]

nafion byproduct 2: C(C(F)(F)F)(OC(C(C(F)(F)F)(OC(C(F)(F)S(=O)(=O)O)(F)F)F)(F)F)F

smiles_non_kekule:    O=S(=O)(O)C(F)(F)C(F)(F)OC(F)(C(F)(F)F)C(F)(F)OC(F)C(F)(F)F
smiles_kekule:    O=S(=O)(O)C(F)(F)C(F)(F)OC(F)(C(F)(F)F)C(F)(F)OC(F)C(F)(F)F
inchi:    InChI=1S/C7H2F14O5S/c8-1(2(9,10)11)25-5(16,17)3(12,4(13,14)15)26-6(18,19)7(20,21)27(22,23)24/h1H,(H,22,23,24)
inchiKey:    KOHJZTAURQTUHH-UHFFFAOYSA-N
smarts:    [#6](-[#6](-[#9])(-[#9])-[#9])(-[#8]-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#8]-[#6](-[#6](-[#9])(-[#9])-[#16](=[#8])(=[#8])-[#8])(-[#9])-[#9])-[#9])(-[#9])-[#9])-[#9]
smarts_isomeric:    [#6](-[#6](-[#9])(-[#9])-[#9])(-[#8]-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#8]-[#6](-[#6](-[#9])(-[#9])-[#16](=[#8])(=[#8])-[#8])(-[#9])-[#9])-[#9])(-[#9])-[#9])-[#9]

perfluoro-3,5,7,9-tetraoxadecanoic acid: C(=O)(C(OC(OC(OC(OC(F)(F)F)(F)F)(F)F)(F)F)(F)F)O

smiles_non_kekule:    O=C(O)C(F)(F)OC(F)(F)OC(F)(F)OC(F)(F)OC(F)(F)F
smiles_kekule:    O=C(O)C(F)(F)OC(F)(F)OC(F)(F)OC(F)(F)OC(F)(F)F
inchi:    InChI=1S/C6HF11O6/c7-2(8,1(18)19)20-4(12,13)22-6(16,17)23-5(14,15)21-3(9,10)11/h(H,18,19)
inchiKey:    RVMKCACFKFAJPS-UHFFFAOYSA-N
smarts:    [#6](=[#8])(-[#6](-[#8]-[#6](-[#8]-[#6](-[#8]-[#6](-[#8]-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#8]
smarts_isomeric:    [#6](=[#8])(-[#6](-[#8]-[#6](-[#8]-[#6](-[#8]-[#6](-[#8]-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#8]

perfluoro-3,5,7,9,11-pentaoxadodecanoic acid: C(=O)(C(OC(OC(OC(OC(OC(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O

smiles_non_kekule:    O=C(O)C(F)(F)OC(F)(F)OC(F)(F)OC(F)(F)OC(F)(F)OC(F)(F)F
smiles_kekule:    O=C(O)C(F)(F)OC(F)(F)OC(F)(F)OC(F)(F)OC(F)(F)OC(F)(F)F
inchi:    InChI=1S/C7HF13O7/c8-2(9,1(21)22)23-4(13,14)25-6(17,18)27-7(19,20)26-5(15,16)24-3(10,11)12/h(H,21,22)
inchiKey:    FVHYBZSZYQKTPP-UHFFFAOYSA-N
smarts:    [#6](=[#8])(-[#6](-[#8]-[#6](-[#8]-[#6](-[#8]-[#6](-[#8]-[#6](-[#8]-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#8]
smarts_isomeric:    [#6](=[#8])(-[#6](-[#8]-[#6](-[#8]-[#6](-[#8]-[#6](-[#8]-[#6](-[#8]-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#8]

2,2,3,3-tetrafluoro-3-((1,1,1,2,3,3-hexafluoro-3-(1,2,2,2-tetrafluoroethoxy)propan-2-yl)oxy)propanoic acid: C(=O)(C(C(F)(F)F)(OC(C(OC(C(C(F)(F)F)(F)F)(F)F)(F)F)(C(F)(F)F)F)F)O

smiles_non_kekule:    O=C(O)C(F)(OC(F)(C(F)(F)F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F
smiles_kekule:    O=C(O)C(F)(OC(F)(C(F)(F)F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F
inchi:    InChI=1S/C9HF17O4/c10-2(1(27)28,5(14,15)16)29-4(13,7(20,21)22)9(25,26)30-8(23,24)3(11,12)6(17,18)19/h(H,27,28)
inchiKey:    WJCPJLIVJBLSDS-UHFFFAOYSA-N
smarts:    [#6](=[#8])(-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#8]-[#6](-[#6](-[#8]-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#6](-[#9])(-[#9])-[#9])-[#9])-[#9])-[#8]
smarts_isomeric:    [#6](=[#8])(-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#8]-[#6](-[#6](-[#8]-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#6](-[#9])(-[#9])-[#9])-[#9])-[#9])-[#8]

h,1h,2h,2h-perfluorooctanesulfonic acid: C(C(C(C(C(F)(F)S(=O)(=O)O)(F)F)(F)F)(F)F)(C(C(C(F)(F)F)(F)F)(F)F)(F)F

smiles_non_kekule:    O=S(=O)(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
smiles_kekule:    O=S(=O)(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
inchi:    InChI=1S/C8HF17O3S/c9-1(10,3(13,14)5(17,18)7(21,22)23)2(11,12)4(15,16)6(19,20)8(24,25)29(26,27)28/h(H,26,27,28)
inchiKey:    YFSUTJLHUFNCNZ-UHFFFAOYSA-N
smarts:    [#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#16](=[#8])(=[#8])-[#8])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9]
smarts_isomeric:    [#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#16](=[#8])(=[#8])-[#8])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9]

2-(perfluorooctyl)ethane-1-sulfonic acid: C(CS(=O)(=O)O)C(C(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F

smiles_non_kekule:    O=S(=O)(O)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
smiles_kekule:    O=S(=O)(O)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
inchi:    InChI=1S/C12H5F21O3S/c13-3(14,1-2-37(34,35)36)4(15,16)5(17,18)6(19,20)7(21,22)8(23,24)9(25,26)10(27,28)11(29,30)12(31,32)33/h1-2H2,(H,34,35,36)
inchiKey:    AJMAYLFJZQYRHN-UHFFFAOYSA-N
smarts:    [#6](-[#6]-[#16](=[#8])(=[#8])-[#8])-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9]
smarts_isomeric:    [#6](-[#6]-[#16](=[#8])(=[#8])-[#8])-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9]

perfluoropentanesulfonic acid: C(C(C(F)(F)F)(F)F)(C(C(F)(F)S(=O)(=O)O)(F)F)(F)F

smiles_non_kekule:    O=S(=O)(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
smiles_kekule:    O=S(=O)(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
inchi:    InChI=1S/C5HF11O3S/c6-1(7,2(8,9)4(12,13)14)3(10,11)5(15,16)20(17,18)19/h(H,17,18,19)
inchiKey:    ACEKLXZRZOWKRY-UHFFFAOYSA-N
smarts:    [#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#6](-[#6](-[#9])(-[#9])-[#16](=[#8])(=[#8])-[#8])(-[#9])-[#9])(-[#9])-[#9]
smarts_isomeric:    [#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#6](-[#6](-[#9])(-[#9])-[#16](=[#8])(=[#8])-[#8])(-[#9])-[#9])(-[#9])-[#9]

perfluoroheptanesulfonic acid: C(C(C(C(F)(F)F)(F)F)(F)F)(C(C(C(F)(F)S(=O)(=O)O)(F)F)(F)F)(F)F

smiles_non_kekule:    O=S(=O)(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
smiles_kekule:    O=S(=O)(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
inchi:    InChI=1S/C7HF15O3S/c8-1(9,2(10,11)4(14,15)6(18,19)20)3(12,13)5(16,17)7(21,22)26(23,24)25/h(H,23,24,25)
inchiKey:    OYGQVDSRYXATEL-UHFFFAOYSA-N
smarts:    [#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#6](-[#6](-[#6](-[#9])(-[#9])-[#16](=[#8])(=[#8])-[#8])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9]
smarts_isomeric:    [#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#6](-[#6](-[#6](-[#9])(-[#9])-[#16](=[#8])(=[#8])-[#8])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9]

perfluorononanesulfonic acid: C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(C(C(C(C(F)(F)S(=O)(=O)O)(F)F)(F)F)(F)F)(F)F

smiles_non_kekule:    O=S(=O)(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
smiles_kekule:    O=S(=O)(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
inchi:    InChI=1S/C9HF19O3S/c10-1(11,2(12,13)4(16,17)6(20,21)8(24,25)26)3(14,15)5(18,19)7(22,23)9(27,28)32(29,30)31/h(H,29,30,31)
inchiKey:    MNEXVZFQQPKDHC-UHFFFAOYSA-N
smarts:    [#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#16](=[#8])(=[#8])-[#8])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9]
smarts_isomeric:    [#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#16](=[#8])(=[#8])-[#8])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9]

perfluorodecanesulfonic acid: C(C(C(C(C(C(F)(F)S(=O)(=O)O)(F)F)(F)F)(F)F)(F)F)(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F

smiles_non_kekule:    O=S(=O)(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
smiles_kekule:    O=S(=O)(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
inchi:    InChI=1S/C10HF21O3S/c11-1(12,3(15,16)5(19,20)7(23,24)9(27,28)29)2(13,14)4(17,18)6(21,22)8(25,26)10(30,31)35(32,33)34/h(H,32,33,34)
inchiKey:    HYWZIAVPBSTISZ-UHFFFAOYSA-N
smarts:    [#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#16](=[#8])(=[#8])-[#8])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9]
smarts_isomeric:    [#6](-[#6](-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#16](=[#8])(=[#8])-[#8])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#6](-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9]

hexafluoropropylene oxide trimer acid: C(=O)(C(C(F)(F)F)(OC(C(C(F)(F)F)(OC(C(C(F)(F)F)(F)F)(F)F)F)(F)F)F)F

smiles_non_kekule:    O=C(F)C(F)(OC(F)(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F)C(F)(F)F
smiles_kekule:    O=C(F)C(F)(OC(F)(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F)C(F)(F)F
inchi:    InChI=1S/C9F18O3/c10-1(28)2(11,5(15,16)17)29-9(26,27)4(14,7(21,22)23)30-8(24,25)3(12,13)6(18,19)20
inchiKey:    YSIGVPOSKQLNTO-UHFFFAOYSA-N
smarts:    [#6](=[#8])(-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#8]-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#8]-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#9])(-[#9])-[#9])-[#9])-[#9]
smarts_isomeric:    [#6](=[#8])(-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#8]-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#8]-[#6](-[#6](-[#6](-[#9])(-[#9])-[#9])(-[#9])-[#9])(-[#9])-[#9])-[#9])(-[#9])-[#9])-[#9])-[#9]

problem_type: 19/25 (loop 0/0)

Problem Template: _problem_privileged_scaffolds_for_kinase_inhibitors

[15:21:24] WARNING: Omitted undefined stereo

Write structure of privileged scaffolds for kinase inhibitors molecules.

Answer:

structure of privileged scaffolds for kinase inhibitors molecules:

indole: C12=CC=CC=C1C=CN2

quinoline: C12=CC=CC=C1C=CC=N2

phenylpiperazine: C1(N2CCNCC2)=CC=CC=C1

biphenyl: C1(C2=CC=CC=C2)=CC=CC=C1

benzimidazole: C12=CC=CC=C1NC=N2

quinazoline: C12=CC=CC=C1C=NC=N2

purine: C12=NC=NC=C1NC=N2

indoline: C12=CC=CC=C1CCN2

isoquinoline: C12=CC=CC=C1C=NC=C2

benzylpiperidine: N1(CC2=CC=CC=C2)CCCCC1

aminopyridazine: NC1=CC=CN=N1

4-phenylpiperidine: C1(C2CCNCC2)=CC=CC=C1

chromone: O=C1C=COC2=CC=CC=C21

4-hydroxyquinazoline: O=C1NC=NC2=CC=CC=C21

benzothiophene: C12=CC=CC=C1SC=C2

benzofuran: C12=CC=CC=C1OC=C2

quinoxaline: C12=CC=CC=C1N=CC=N2

benzo[d]oxazole: C12=CC=CC=C1OC=N2

1,2,3,4-tetrahydroisoquinoline: C12=CC=CC=C1CCNC2

thiazolidine-2,4-dione: O=C(N1)SCC1=O

1,2,3,4-tetrahydroquinoline: C12=CC=CC=C1CCCN2

2H-chromen-2-one: O=C1OC2=CC=CC=C2C=C1

1-(piperidin-4-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one: O=C1N(C2CCNCC2)C3=CC=CC=C3N1

5H-dibenzo[b,e][1,4]diazepine: C1(C=CC=C2)=C2NC(C=CC=C3)=C3C=N1

3,4-dihydropyrimidin-2(1H)-one: O=C1NC=CCN1

3,4-dihydropyrimidine-2(1H)-thione: S=C1NC=CCN1

6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol: OCC1OC(O)C(O)C(O)C1O

1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one: O=C(NC1)C2(CCNCC2)N1C3=CC=CC=C3

1,4-dihydropyridine: C1=CNC=CC1

2-(tetrazol-5-yl)biphenyl: C1(C2=CC=CC=C2C3=NN=NN3)=CC=CC=C1

Solution:

structure of privileged scaffolds for kinase inhibitors molecules:

indole: C12=CC=CC=C1C=CN2

quinoline: C12=CC=CC=C1C=CC=N2

smiles_non_kekule:    c1ccc2ncccc2c1
smiles_kekule:    C1=CC=C2N=CC=CC2=C1
inchi:    InChI=1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H
inchiKey:    SMWDFEZZVXVKRB-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#6]:[#7]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#6]:[#7]:2

phenylpiperazine: C1(N2CCNCC2)=CC=CC=C1

biphenyl: C1(C2=CC=CC=C2)=CC=CC=C1

smiles_non_kekule:    c1ccc(-c2ccccc2)cc1
smiles_kekule:    C1=CC=C(C2=CC=CC=C2)C=C1
inchi:    InChI=1S/C12H10/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1-10H
inchiKey:    ZUOUZKKEUPVFJK-UHFFFAOYSA-N
smarts:    [#6]1(-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2):[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1(-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2):[#6]:[#6]:[#6]:[#6]:[#6]:1

benzimidazole: C12=CC=CC=C1NC=N2

quinazoline: C12=CC=CC=C1C=NC=N2

smiles_non_kekule:    c1ccc2ncncc2c1
smiles_kekule:    C1=CC=C2N=CN=CC2=C1
inchi:    InChI=1S/C8H6N2/c1-2-4-8-7(3-1)5-9-6-10-8/h1-6H
inchiKey:    JWVCLYRUEFBMGU-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#7]:[#6]:[#7]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#7]:[#6]:[#7]:2

purine: C12=NC=NC=C1NC=N2

indoline: C12=CC=CC=C1CCN2

smiles_non_kekule:    c1ccc2c(c1)CCN2
smiles_kekule:    C1=CC=C2NCCC2=C1
inchi:    InChI=1S/C8H9N/c1-2-4-8-7(3-1)5-6-9-8/h1-4,9H,5-6H2
inchiKey:    LPAGFVYQRIESJQ-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6]-[#7]-2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6]-[#7]-2

isoquinoline: C12=CC=CC=C1C=NC=C2

smiles_non_kekule:    c1ccc2cnccc2c1
smiles_kekule:    C1=CC=C2C=NC=CC2=C1
inchi:    InChI=1S/C9H7N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-7H
inchiKey:    AWJUIBRHMBBTKR-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#7]:[#6]:[#6]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#7]:[#6]:[#6]:2

benzylpiperidine: N1(CC2=CC=CC=C2)CCCCC1

aminopyridazine: NC1=CC=CN=N1

smiles_non_kekule:    Nc1cccnn1
smiles_kekule:    NC1=CC=CN=N1
inchi:    InChI=1S/C4H5N3/c5-4-2-1-3-6-7-4/h1-3H,(H2,5,7)
inchiKey:    LETVJWLLIMJADE-UHFFFAOYSA-N
smarts:    [#7]-[#6]1:[#6]:[#6]:[#6]:[#7]:[#7]:1
smarts_isomeric:    [#7]-[#6]1:[#6]:[#6]:[#6]:[#7]:[#7]:1

4-phenylpiperidine: C1(C2CCNCC2)=CC=CC=C1

chromone: O=C1C=COC2=CC=CC=C21

smiles_non_kekule:    O=c1ccoc2ccccc12
smiles_kekule:    O=C1C=COC2=CC=CC=C12
inchi:    InChI=1S/C9H6O2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6H
inchiKey:    OTAFHZMPRISVEM-UHFFFAOYSA-N
smarts:    [#8]=[#6]1:[#6]:[#6]:[#8]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2
smarts_isomeric:    [#8]=[#6]1:[#6]:[#6]:[#8]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2

4-hydroxyquinazoline: O=C1NC=NC2=CC=CC=C21

smiles_non_kekule:    O=c1[nH]cnc2ccccc12
smiles_kekule:    O=C1NC=NC2=CC=CC=C12
inchi:    InChI=1S/C8H6N2O/c11-8-6-3-1-2-4-7(6)9-5-10-8/h1-5H,(H,9,10,11)
inchiKey:    QMNUDYFKZYBWQX-UHFFFAOYSA-N
smarts:    [#8]=[#6]1:[#7H]:[#6]:[#7]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2
smarts_isomeric:    [#8]=[#6]1:[#7H]:[#6]:[#7]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2

benzothiophene: C12=CC=CC=C1SC=C2

smiles_non_kekule:    c1ccc2sccc2c1
smiles_kekule:    C1=CC=C2SC=CC2=C1
inchi:    InChI=1S/C8H6S/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
inchiKey:    FCEHBMOGCRZNNI-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#16]:[#6]:[#6]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#16]:[#6]:[#6]:2

benzofuran: C12=CC=CC=C1OC=C2

smiles_non_kekule:    c1ccc2occc2c1
smiles_kekule:    C1=CC=C2OC=CC2=C1
inchi:    InChI=1S/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
inchiKey:    IANQTJSKSUMEQM-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#8]:[#6]:[#6]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#8]:[#6]:[#6]:2

quinoxaline: C12=CC=CC=C1N=CC=N2

benzo[d]oxazole: C12=CC=CC=C1OC=N2

1,2,3,4-tetrahydroisoquinoline: C12=CC=CC=C1CCNC2

smiles_non_kekule:    c1ccc2c(c1)CCNC2
smiles_kekule:    C1=CC=C2CNCCC2=C1
inchi:    InChI=1S/C9H11N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-4,10H,5-7H2
inchiKey:    UWYZHKAOTLEWKK-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6]-[#7]-[#6]-2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6]-[#7]-[#6]-2

thiazolidine-2,4-dione: O=C(N1)SCC1=O

smiles_non_kekule:    O=C1CSC(=O)N1
smiles_kekule:    O=C1CSC(=O)N1
inchi:    InChI=1S/C3H3NO2S/c5-2-1-7-3(6)4-2/h1H2,(H,4,5,6)
inchiKey:    ZOBPZXTWZATXDG-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#7]-[#6](-[#6]-[#16]-1)=[#8]
smarts_isomeric:    [#8]=[#6]1-[#7]-[#6](-[#6]-[#16]-1)=[#8]

1,2,3,4-tetrahydroquinoline: C12=CC=CC=C1CCCN2

smiles_non_kekule:    c1ccc2c(c1)CCCN2
smiles_kekule:    C1=CC=C2NCCCC2=C1
inchi:    InChI=1S/C9H11N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-2,4,6,10H,3,5,7H2
inchiKey:    LBUJPTNKIBCYBY-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6]-[#6]-[#7]-2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6]-[#6]-[#7]-2

2H-chromen-2-one: O=C1OC2=CC=CC=C2C=C1

smiles_non_kekule:    O=c1ccc2ccccc2o1
smiles_kekule:    O=C1C=CC2=CC=CC=C2O1
inchi:    InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
inchiKey:    ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
smarts:    [#8]=[#6]1:[#8]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#6]:[#6]:1
smarts_isomeric:    [#8]=[#6]1:[#8]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#6]:[#6]:1

1-(piperidin-4-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one: O=C1N(C2CCNCC2)C3=CC=CC=C3N1

5H-dibenzo[b,e][1,4]diazepine: C1(C=CC=C2)=C2NC(C=CC=C3)=C3C=N1

smiles_non_kekule:    C1=Nc2ccccc2Nc2ccccc21
smiles_kekule:    C1=NC2=CC=CC=C2NC2=C1C=CC=C2
inchi:    InChI=1S/C13H10N2/c1-2-6-11-10(5-1)9-14-12-7-3-4-8-13(12)15-11/h1-9,15H
inchiKey:    BLOPFAKSIQBSIG-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#7]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]=[#7]-2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#7]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]=[#7]-2

3,4-dihydropyrimidin-2(1H)-one: O=C1NC=CCN1

smiles_non_kekule:    O=C1NC=CCN1
smiles_kekule:    O=C1NC=CCN1
inchi:    InChI=1S/C4H6N2O/c7-4-5-2-1-3-6-4/h1-2H,3H2,(H2,5,6,7)
inchiKey:    QGKGASXQTBQINX-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#7]-[#6]=[#6]-[#6]-[#7]-1
smarts_isomeric:    [#8]=[#6]1-[#7]-[#6]=[#6]-[#6]-[#7]-1

3,4-dihydropyrimidine-2(1H)-thione: S=C1NC=CCN1

smiles_non_kekule:    S=C1NC=CCN1
smiles_kekule:    S=C1NC=CCN1
inchi:    InChI=1S/C4H6N2S/c7-4-5-2-1-3-6-4/h1-2H,3H2,(H2,5,6,7)
inchiKey:    MBOCEPWYDNXEKN-UHFFFAOYSA-N
smarts:    [#16]=[#6]1-[#7]-[#6]=[#6]-[#6]-[#7]-1
smarts_isomeric:    [#16]=[#6]1-[#7]-[#6]=[#6]-[#6]-[#7]-1

6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol: OCC1OC(O)C(O)C(O)C1O

1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one: O=C(NC1)C2(CCNCC2)N1C3=CC=CC=C3

1,4-dihydropyridine: C1=CNC=CC1

smiles_non_kekule:    C1=CNC=CC1
smiles_kekule:    C1=CNC=CC1
inchi:    InChI=1S/C5H7N/c1-2-4-6-5-3-1/h2-6H,1H2
inchiKey:    YNGDWRXWKFWCJY-UHFFFAOYSA-N
smarts:    [#6]1=[#6]-[#7]-[#6]=[#6]-[#6]-1
smarts_isomeric:    [#6]1=[#6]-[#7]-[#6]=[#6]-[#6]-1

2-(tetrazol-5-yl)biphenyl: C1(C2=CC=CC=C2C3=NN=NN3)=CC=CC=C1

smiles_non_kekule:    c1ccc(-c2ccccc2-c2nnn[nH]2)cc1
smiles_kekule:    C1=CC=C(C2=CC=CC=C2C2=NN=NN2)C=C1
inchi:    InChI=1S/C13H10N4/c1-2-6-10(7-3-1)11-8-4-5-9-12(11)13-14-16-17-15-13/h1-9H,(H,14,15,16,17)
inchiKey:    HLAYLOOJBAJIRU-UHFFFAOYSA-N
smarts:    [#6]1(-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2-[#6]2:[#7]:[#7]:[#7]:[#7H]:2):[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1(-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2-[#6]2:[#7]:[#7]:[#7]:[#7H]:2):[#6]:[#6]:[#6]:[#6]:[#6]:1

problem_type: 20/25 (loop 0/0)

[15:21:30] WARNING: Accepted unusual valence(s): N(2)

[15:21:30] WARNING: Omitted undefined stereo

[15:21:30] WARNING: Omitted undefined stereo

Problem Template: _problem_rings_in_drugs

Write structure of rings in drugs molecules.

Answer:

structure of rings in drugs molecules:

benzene: C1=CC=CC=C1

pyridine: C1=CC=CN=C1

piperidine: N1CCCCC1

piperazine: N1CCNCC1

cyclohexane: C1CCCCC1

oxane: O1CCCCC1

imidazole: C1=NC=CN1

pyrrolidine: C1CCNC1

(R)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one: O=C1C[C@@H]2N1C=CCS2

cyclopropane: C1CC1

tetrahydrofuran: C1CCOC1

thiazole: C1=NC=CS1

indole: C12=CC=CC=C1C=CN2

diazine: C1=NC=CC=N1

(R)-4-thia-1-azabicyclo[3.2.0]heptan-7-one: O=C1N2CCS[C@@H]2C1

6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one: O=C1C=CC(C2C[C@H](CCC3)C3CC2)C(CCC)=C1

tetrazole: N1=NN=C[N]1

cyclopentane: C1CCCC1

thiophenyl: C1=CC=CS1

naphthalene: C12=CC=CC=C1C=CC=C2

1H-benzo[d]imidazole: C12=CC=CC=C1N=CN2

quinoline: C12=CC=CC=C1C=CC=N2

1H-purine: C12=CNC=NC1=NC=N2

1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one: O=C1CCC([C@@H]2C[C@H](CCC3)C3CC2)C(CCC)=C1

furan: C1=CC=CO1

1H-1,2,4-Triazole: N1=CN=CN1

10H-Phenothiazine: C12=CC=CC=C1NC3=C(C=CC=C3)S2

quinazoline: C12=CC=CC=C1C=NC=N2

morpholine: C1CNCCO1

pyrimidin-2(1H)-one: O=C1N=CC=CN1

quinolin-4(1H)-one: O=C1C2=C(C=CC=C2)NC=C1

(9S,14R)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one: O=C1C=CC([C@H]2CCC3[C@@H](CCC3)C2)C(CCC)=C1

isoxazole: C1=CC=NO1

imidazoline: C1=NCCN1

1,4-dihydropyridine: C1=CCC=CN1

pyrimidine-2,4(1H,3H)-dione: O=C(N1)NC=CC1=O

3,4-dihydro-2H-benzo[e][1,4]diazepin-2-one: O=C1N=C2C=CC=CC2=CNC1

cyclohexene: C1=CCCCC1

pyrrolidin-2-one: O=C1NCCC1

imidazolidine-2,4-dione: O=C(CN1)NC1=O

1,2,3,4-tetrahydroisoquinoline: C1(C=CC=C2)=C2CCNC1

3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide: O=S1(NCNC2=C1C=CC=C2)=O

7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene: CCCC1=CC=CC=C1[C@@H]2C[C@H](CCC3)C3CC2

1H-pyrazole: N1=CC=CN1

quinuclidine: C1(CC2)CCN2CC1

epoxide: C1CO1

pyrazine: C1=CN=CC=N1

oxazolidinone: O=C1OCCN1

tetrahydronaphthalene: C1(C=CC=C2)=C2CCCC1

adamantane: C1(CC(C2)C3)CC2CC3C1

1,8-naphthyridin-4(1H)-one: O=C(C=CN1)C2=C1N=CC=C2

3,7-dihydro-1H-purine-2,6-dione: O=C(C(NC=N1)=C1N2)NC2=O

hexadecahydro-1H-cyclopenta[a]phenanthrene: CCC[C@H]1CCCCC1[C@@H]2C[C@H](CCC3)C3CC2

7,8,9,10-tetrahydrotetracene-5,12-dione: O=C(C(C=C(CCCC1)C1=C2)=C2C3=O)C4=C3C=CC=C4

cyclobutane: C1CCC1

1,2-dihydro-3H-1,2,4-triazol-3-one: O=C1NNC=N1

1,3,4-thiadiazole: C1=NN=CS1

azepane: C1NCCCCC1

8-azabicyclo[3.2.1]octane: C12CCCC(CC2)N1

piperidine-2,6-dione: O=C(N1)CCCC1=O

2,3-dihydro-1H-indene: O=C(N1)CCCC1=O

benzo[d]isoxazole: C12=CC=CC=C1C=NO2

1,9-dihydro-6H-purin-6-one: O=C1C2=C(NC=N2)N=CN1

9H-fluorene: C12=CC=CC=C1C3=C(C=CC=C3)C2

10,11-dihydro-5H-dibenzo[b,f]azepine: C12=CC=CC=C1CCC3=C(C=CC=C3)N2

(6aR,10aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline: C12=CC=CC3=C1C(C[C@@H]4[C@@H]2CCCN4)=CN3

1H-pyrrole: C1=CC=CN1

1,3-dioxolane: O1CCOC1

(1R,5S)-3-azabicyclo[3.1.0]hexane: [C@@H]1(C2)[C@H]2CNC1

cyclopentanone: O=C1CCCC1

pyrrolidine-2,5-dione: O=C(N1)CCC1=O

pyrazolidine: O=C(NN1)CC1=O

(R)-1-azabicyclo[3.2.0]hept-2-en-7-one: O=C1N2C=CC[C@@H]2C1

thiazolidine-2,4-dione: O=C(CS1)NC1=O

benzofuran: C12=CC=CC=C1C=CO2

1H-indazole: C12=CC=CC=C1C=NN2

indolin-2-one: O=C1NC2=CC=CC=C2C1

benzo[b]thiophene: C12=CC=CC=C1C=CS2

(R)-1,2,3,7,8,8a-hexahydronaphthalene: C12=CCCC[C@@H]1CCC=C2

4,5,6,7-tetrahydrothieno[3,2-c]pyridine: C1(C=CS2)=C2CCNC1

4H-chromen-4-one: O=C(C=CO1)C2=C1C=CC=C2

3,4-dihydroquino-2(1H)-one: O=C(CC1)NC2=C1C=CC=C2

napthalene-1,4-dione: O=C(C=CC1=O)C2=C1C=CC=C2

2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide: O=S(C1=C2C=CC=C1)(NC=N2)=O

4H-benzo[f][1,2,4]triazolo[4,3-a][1,4]diazepine: C1(N2C(CN=C3)=NN=C2)=C3C=CC=C1

9H-thioxanthene: C12=CC=CC=C1CC3=C(C=CC=C3)S2

(5aR,8aR)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one: O=C(OC1)[C@H]2[C@H]1CC3=CC4=C(C=C3C2)OCO4

(3a1S,5aS,10bS)-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole: C12=CC=CC=C1[C@@]34[C@H](CCC5[C@@H]3N(CC=C5)CC4)N2

(4aR,5aR)-4a,5a,6,12a-tetrahydrotetracene-1,11(4H,5H)-dione: O=C1C2=CC3[C@H](CC=CC3=O)C[C@@H]2CC4=CC=CC=C41

1H-1,2,3-triazole: N1=NC=CN1

azetidin-2-one: O=C1NCC1

oxetan-2-one: O=C1OCC1

Solution:

structure of rings in drugs molecules:

benzene: C1=CC=CC=C1

pyridine: C1=CC=CN=C1

smiles_non_kekule:    c1ccncc1
smiles_kekule:    C1=CC=NC=C1
inchi:    InChI=1S/C5H5N/c1-2-4-6-5-3-1/h1-5H
inchiKey:    JUJWROOIHBZHMG-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]:[#7]:[#6]:1

piperidine: N1CCCCC1

piperazine: N1CCNCC1

cyclohexane: C1CCCCC1

oxane: O1CCCCC1

smiles_non_kekule:    C1CCOCC1
smiles_kekule:    C1CCOCC1
inchi:    InChI=1S/C5H10O/c1-2-4-6-5-3-1/h1-5H2
inchiKey:    DHXVGJBLRPWPCS-UHFFFAOYSA-N
smarts:    [#8]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#8]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

imidazole: C1=NC=CN1

smiles_non_kekule:    c1c[nH]cn1
smiles_kekule:    C1=CNC=N1
inchi:    InChI=1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)
inchiKey:    RAXXELZNTBOGNW-UHFFFAOYSA-N
smarts:    [#6]1:[#7]:[#6]:[#6]:[#7H]:1
smarts_isomeric:    [#6]1:[#7]:[#6]:[#6]:[#7H]:1

pyrrolidine: C1CCNC1

smiles_non_kekule:    C1CCNC1
smiles_kekule:    C1CCNC1
inchi:    InChI=1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2
inchiKey:    RWRDLPDLKQPQOW-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#7]-[#6]-1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#7]-[#6]-1

(R)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one: O=C1C[C@@H]2N1C=CCS2

smiles_non_kekule:    O=C1C[C@H]2SCC=CN12
smiles_kekule:    O=C1C[C@H]2SCC=CN12
inchi:    InChI=1S/C6H7NOS/c8-5-4-6-7(5)2-1-3-9-6/h1-2,6H,3-4H2/t6-/m1/s1
inchiKey:    FZEVMBJWXHDLDB-ZCFIWIBFSA-N
smarts:    [#8]=[#6]1-[#6]-[#6H]2-[#7]-1-[#6]=[#6]-[#6]-[#16]-2
smarts_isomeric:    [#8]=[#6]1-[#6]-[#6@@H]2-[#7]-1-[#6]=[#6]-[#6]-[#16]-2

cyclopropane: C1CC1

tetrahydrofuran: C1CCOC1

thiazole: C1=NC=CS1

indole: C12=CC=CC=C1C=CN2

diazine: C1=NC=CC=N1

smiles_non_kekule:    c1cncnc1
smiles_kekule:    C1=CN=CN=C1
inchi:    InChI=1S/C4H4N2/c1-2-5-4-6-3-1/h1-4H
inchiKey:    CZPWVGJYEJSRLH-UHFFFAOYSA-N
smarts:    [#6]1:[#7]:[#6]:[#6]:[#6]:[#7]:1
smarts_isomeric:    [#6]1:[#7]:[#6]:[#6]:[#6]:[#7]:1

(R)-4-thia-1-azabicyclo[3.2.0]heptan-7-one: O=C1N2CCS[C@@H]2C1

smiles_non_kekule:    O=C1C[C@H]2SCCN12
smiles_kekule:    O=C1C[C@H]2SCCN12
inchi:    InChI=1S/C5H7NOS/c7-4-3-5-6(4)1-2-8-5/h5H,1-3H2/t5-/m1/s1
inchiKey:    WSHJJCPTKWSMRR-RXMQYKEDSA-N
smarts:    [#8]=[#6]1-[#7]2-[#6]-[#6]-[#16]-[#6H]-2-[#6]-1
smarts_isomeric:    [#8]=[#6]1-[#7]2-[#6]-[#6]-[#16]-[#6@@H]-2-[#6]-1

6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one: O=C1C=CC(C2C[C@H](CCC3)C3CC2)C(CCC)=C1

smiles_non_kekule:    CCCC1=CC(=O)C=CC1C1CCC2CCC[C@H]2C1
smiles_kekule:    CCCC1=CC(=O)C=CC1C1CCC2CCC[C@H]2C1
inchi:    InChI=1S/C18H26O/c1-2-4-15-12-17(19)9-10-18(15)16-8-7-13-5-3-6-14(13)11-16/h9-10,12-14,16,18H,2-8,11H2,1H3/t13?,14-,16?,18?/m0/s1
inchiKey:    ICLIUBWHCFTNIQ-FMUUVHIJSA-N
smarts:    [#8]=[#6]1-[#6]=[#6]-[#6](-[#6]2-[#6]-[#6H]3-[#6]-[#6]-[#6]-[#6]-3-[#6]-[#6]-2)-[#6](-[#6]-[#6]-[#6])=[#6]-1
smarts_isomeric:    [#8]=[#6]1-[#6]=[#6]-[#6](-[#6]2-[#6]-[#6@@H]3-[#6]-[#6]-[#6]-[#6]-3-[#6]-[#6]-2)-[#6](-[#6]-[#6]-[#6])=[#6]-1

tetrazole: N1=NN=C[N]1

smiles_non_kekule:    C1=NN=N[N]1
smiles_kekule:    C1=NN=N[N]1
inchi:    InChI=1S/CHN4/c1-2-4-5-3-1/h1H
inchiKey:    GIQAUVQROAMBGV-UHFFFAOYSA-N
smarts:    [#7]1=[#7]-[#7]=[#6]-[#7]-1
smarts_isomeric:    [#7]1=[#7]-[#7]=[#6]-[#7]-1

cyclopentane: C1CCCC1

thiophenyl: C1=CC=CS1

naphthalene: C12=CC=CC=C1C=CC=C2

smiles_non_kekule:    c1ccc2ccccc2c1
smiles_kekule:    C1=CC=C2C=CC=CC2=C1
inchi:    InChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
inchiKey:    UFWIBTONFRDIAS-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#6]:[#6]:2

1H-benzo[d]imidazole: C12=CC=CC=C1N=CN2

smiles_non_kekule:    c1ccc2[nH]cnc2c1
smiles_kekule:    C1=CC=C2NC=NC2=C1
inchi:    InChI=1S/C7H6N2/c1-2-4-7-6(3-1)8-5-9-7/h1-5H,(H,8,9)
inchiKey:    HYZJCKYKOHLVJF-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#7]:[#6]:[#7H]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#7]:[#6]:[#7H]:2

quinoline: C12=CC=CC=C1C=CC=N2

smiles_non_kekule:    c1ccc2ncccc2c1
smiles_kekule:    C1=CC=C2N=CC=CC2=C1
inchi:    InChI=1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H
inchiKey:    SMWDFEZZVXVKRB-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#6]:[#7]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#6]:[#6]:[#7]:2

1H-purine: C12=CNC=NC1=NC=N2

smiles_non_kekule:    c1nc2c[nH]cnc-2n1
smiles_kekule:    C1=NC2=CNC=NC2=N1
inchi:    InChI=1S/C5H4N4/c1-4-5(8-2-6-1)9-3-7-4/h1-3H,(H,6,7,8,9)
inchiKey:    KDCGOANMDULRCW-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#7H]:[#6]:[#7]:[#6]-1:[#7]:[#6]:[#7]:2
smarts_isomeric:    [#6]12:[#6]:[#7H]:[#6]:[#7]:[#6]-1:[#7]:[#6]:[#7]:2

1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one: O=C1CCC([C@@H]2C[C@H](CCC3)C3CC2)C(CCC)=C1

smiles_non_kekule:    CCCC1=CC(=O)CCC1[C@H]1CCC2CCC[C@H]2C1
smiles_kekule:    CCCC1=CC(=O)CCC1[C@H]1CCC2CCC[C@H]2C1
inchi:    InChI=1S/C18H28O/c1-2-4-15-12-17(19)9-10-18(15)16-8-7-13-5-3-6-14(13)11-16/h12-14,16,18H,2-11H2,1H3/t13?,14-,16-,18?/m0/s1
inchiKey:    MRGLZXGXTZZPIP-NOAVELHRSA-N
smarts:    [#8]=[#6]1-[#6]-[#6]-[#6](-[#6H]2-[#6]-[#6H]3-[#6]-[#6]-[#6]-[#6]-3-[#6]-[#6]-2)-[#6](-[#6]-[#6]-[#6])=[#6]-1
smarts_isomeric:    [#8]=[#6]1-[#6]-[#6]-[#6](-[#6@@H]2-[#6]-[#6@@H]3-[#6]-[#6]-[#6]-[#6]-3-[#6]-[#6]-2)-[#6](-[#6]-[#6]-[#6])=[#6]-1

furan: C1=CC=CO1

1H-1,2,4-Triazole: N1=CN=CN1

smiles_non_kekule:    c1nc[nH]n1
smiles_kekule:    C1=NNC=N1
inchi:    InChI=1S/C2H3N3/c1-3-2-5-4-1/h1-2H,(H,3,4,5)
inchiKey:    NSPMIYGKQJPBQR-UHFFFAOYSA-N
smarts:    [#7]1:[#6]:[#7]:[#6]:[#7H]:1
smarts_isomeric:    [#7]1:[#6]:[#7]:[#6]:[#7H]:1

10H-Phenothiazine: C12=CC=CC=C1NC3=C(C=CC=C3)S2

smiles_non_kekule:    c1ccc2c(c1)Nc1ccccc1S2
smiles_kekule:    C1=CC=C2SC3=C(C=CC=C3)NC2=C1
inchi:    InChI=1S/C12H9NS/c1-3-7-11-9(5-1)13-10-6-2-4-8-12(10)14-11/h1-8,13H
inchiKey:    WJFKNYWRSNBZNX-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#7]-[#6]1:[#6](:[#6]:[#6]:[#6]:[#6]:1)-[#16]-2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#7]-[#6]1:[#6](:[#6]:[#6]:[#6]:[#6]:1)-[#16]-2

quinazoline: C12=CC=CC=C1C=NC=N2

morpholine: C1CNCCO1

smiles_non_kekule:    C1COCCN1
smiles_kekule:    C1COCCN1
inchi:    InChI=1S/C4H9NO/c1-3-6-4-2-5-1/h5H,1-4H2
inchiKey:    YNAVUWVOSKDBBP-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#7]-[#6]-[#6]-[#8]-1
smarts_isomeric:    [#6]1-[#6]-[#7]-[#6]-[#6]-[#8]-1

pyrimidin-2(1H)-one: O=C1N=CC=CN1

smiles_non_kekule:    O=c1nccc[nH]1
smiles_kekule:    O=C1N=CC=CN1
inchi:    InChI=1S/C4H4N2O/c7-4-5-2-1-3-6-4/h1-3H,(H,5,6,7)
inchiKey:    VTGOHKSTWXHQJK-UHFFFAOYSA-N
smarts:    [#8]=[#6]1:[#7]:[#6]:[#6]:[#6]:[#7H]:1
smarts_isomeric:    [#8]=[#6]1:[#7]:[#6]:[#6]:[#6]:[#7H]:1

quinolin-4(1H)-one: O=C1C2=C(C=CC=C2)NC=C1

smiles_non_kekule:    O=c1cc[nH]c2ccccc12
smiles_kekule:    O=C1C=CNC2=C1C=CC=C2
inchi:    InChI=1S/C9H7NO/c11-9-5-6-10-8-4-2-1-3-7(8)9/h1-6H,(H,10,11)
inchiKey:    PMZDQRJGMBOQBF-UHFFFAOYSA-N
smarts:    [#8]=[#6]1:[#6]2:[#6](:[#6]:[#6]:[#6]:[#6]:2):[#7H]:[#6]:[#6]:1
smarts_isomeric:    [#8]=[#6]1:[#6]2:[#6](:[#6]:[#6]:[#6]:[#6]:2):[#7H]:[#6]:[#6]:1

(9S,14R)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one: O=C1C=CC([C@H]2CCC3[C@@H](CCC3)C2)C(CCC)=C1

smiles_non_kekule:    CCCC1=CC(=O)C=CC1[C@H]1CCC2CCC[C@H]2C1
smiles_kekule:    CCCC1=CC(=O)C=CC1[C@H]1CCC2CCC[C@H]2C1
inchi:    InChI=1S/C18H26O/c1-2-4-15-12-17(19)9-10-18(15)16-8-7-13-5-3-6-14(13)11-16/h9-10,12-14,16,18H,2-8,11H2,1H3/t13?,14-,16-,18?/m0/s1
inchiKey:    ICLIUBWHCFTNIQ-NOAVELHRSA-N
smarts:    [#8]=[#6]1-[#6]=[#6]-[#6](-[#6H]2-[#6]-[#6]-[#6]3-[#6H](-[#6]-[#6]-[#6]-3)-[#6]-2)-[#6](-[#6]-[#6]-[#6])=[#6]-1
smarts_isomeric:    [#8]=[#6]1-[#6]=[#6]-[#6](-[#6@H]2-[#6]-[#6]-[#6]3-[#6@@H](-[#6]-[#6]-[#6]-3)-[#6]-2)-[#6](-[#6]-[#6]-[#6])=[#6]-1

isoxazole: C1=CC=NO1

imidazoline: C1=NCCN1

1,4-dihydropyridine: C1=CCC=CN1

smiles_non_kekule:    C1=CNC=CC1
smiles_kekule:    C1=CNC=CC1
inchi:    InChI=1S/C5H7N/c1-2-4-6-5-3-1/h2-6H,1H2
inchiKey:    YNGDWRXWKFWCJY-UHFFFAOYSA-N
smarts:    [#6]1=[#6]-[#6]-[#6]=[#6]-[#7]-1
smarts_isomeric:    [#6]1=[#6]-[#6]-[#6]=[#6]-[#7]-1

pyrimidine-2,4(1H,3H)-dione: O=C(N1)NC=CC1=O

smiles_non_kekule:    O=c1cc[nH]c(=O)[nH]1
smiles_kekule:    O=C1C=CNC(=O)N1
inchi:    InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
inchiKey:    ISAKRJDGNUQOIC-UHFFFAOYSA-N
smarts:    [#8]=[#6]1:[#7H]:[#6](:[#6]:[#6]:[#7H]:1)=[#8]
smarts_isomeric:    [#8]=[#6]1:[#7H]:[#6](:[#6]:[#6]:[#7H]:1)=[#8]

3,4-dihydro-2H-benzo[e][1,4]diazepin-2-one: O=C1N=C2C=CC=CC2=CNC1

smiles_non_kekule:    O=C1CNC=c2ccccc2=N1
smiles_kekule:    O=C1CNC=C2C=CC=CC2=N1
inchi:    InChI=1S/C9H8N2O/c12-9-6-10-5-7-3-1-2-4-8(7)11-9/h1-5,10H,6H2
inchiKey:    CXQVJKKXCGVEBS-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#7]=[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2=[#6]-[#7]-[#6]-1
smarts_isomeric:    [#8]=[#6]1-[#7]=[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2=[#6]-[#7]-[#6]-1

cyclohexene: C1=CCCCC1

smiles_non_kekule:    C1=CCCCC1
smiles_kekule:    C1=CCCCC1
inchi:    InChI=1S/C6H10/c1-2-4-6-5-3-1/h1-2H,3-6H2
inchiKey:    HGCIXCUEYOPUTN-UHFFFAOYSA-N
smarts:    [#6]1=[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]1=[#6]-[#6]-[#6]-[#6]-[#6]-1

pyrrolidin-2-one: O=C1NCCC1

smiles_non_kekule:    O=C1CCCN1
smiles_kekule:    O=C1CCCN1
inchi:    InChI=1S/C4H7NO/c6-4-2-1-3-5-4/h1-3H2,(H,5,6)
inchiKey:    HNJBEVLQSNELDL-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#7]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#8]=[#6]1-[#7]-[#6]-[#6]-[#6]-1

imidazolidine-2,4-dione: O=C(CN1)NC1=O

smiles_non_kekule:    O=C1CNC(=O)N1
smiles_kekule:    O=C1CNC(=O)N1
inchi:    InChI=1S/C3H4N2O2/c6-2-1-4-3(7)5-2/h1H2,(H2,4,5,6,7)
inchiKey:    WJRBRSLFGCUECM-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#6]-[#7]-[#6](-[#7]-1)=[#8]
smarts_isomeric:    [#8]=[#6]1-[#6]-[#7]-[#6](-[#7]-1)=[#8]

1,2,3,4-tetrahydroisoquinoline: C1(C=CC=C2)=C2CCNC1

smiles_non_kekule:    c1ccc2c(c1)CCNC2
smiles_kekule:    C1=CC=C2CNCCC2=C1
inchi:    InChI=1S/C9H11N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-4,10H,5-7H2
inchiKey:    UWYZHKAOTLEWKK-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6]-[#7]-[#6]-2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6]-[#7]-[#6]-2

3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide: O=S1(NCNC2=C1C=CC=C2)=O

smiles_non_kekule:    O=S1(=O)NCNc2ccccc21
smiles_kekule:    O=S1(=O)NCNC2=C1C=CC=C2
inchi:    InChI=1S/C7H8N2O2S/c10-12(11)7-4-2-1-3-6(7)8-5-9-12/h1-4,8-9H,5H2
inchiKey:    OKXYPUDKVYVJDI-UHFFFAOYSA-N
smarts:    [#8]=[#16]1(-[#7]-[#6]-[#7]-[#6]2:[#6]-1:[#6]:[#6]:[#6]:[#6]:2)=[#8]
smarts_isomeric:    [#8]=[#16]1(-[#7]-[#6]-[#7]-[#6]2:[#6]-1:[#6]:[#6]:[#6]:[#6]:2)=[#8]

7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene: CCCC1=CC=CC=C1[C@@H]2C[C@H](CCC3)C3CC2

smiles_non_kekule:    CCCc1ccccc1[C@H]1CCC2CCC[C@H]2C1
smiles_kekule:    CCCC1=CC=CC=C1[C@H]1CCC2CCC[C@H]2C1
inchi:    InChI=1S/C18H26/c1-2-6-15-7-3-4-10-18(15)17-12-11-14-8-5-9-16(14)13-17/h3-4,7,10,14,16-17H,2,5-6,8-9,11-13H2,1H3/t14?,16-,17-/m0/s1
inchiKey:    NTMHWPCYRJTPRQ-HGVHAKBWSA-N
smarts:    [#6]-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6H]1-[#6]-[#6H]2-[#6]-[#6]-[#6]-[#6]-2-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6@@H]1-[#6]-[#6@@H]2-[#6]-[#6]-[#6]-[#6]-2-[#6]-[#6]-1

1H-pyrazole: N1=CC=CN1

smiles_non_kekule:    c1cn[nH]c1
smiles_kekule:    C1=CNN=C1
inchi:    InChI=1S/C3H4N2/c1-2-4-5-3-1/h1-3H,(H,4,5)
inchiKey:    WTKZEGDFNFYCGP-UHFFFAOYSA-N
smarts:    [#7]1:[#6]:[#6]:[#6]:[#7H]:1
smarts_isomeric:    [#7]1:[#6]:[#6]:[#6]:[#7H]:1

quinuclidine: C1(CC2)CCN2CC1

smiles_non_kekule:    C1CN2CCC1CC2
smiles_kekule:    C1CN2CCC1CC2
inchi:    InChI=1S/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2
inchiKey:    SBYHFKPVCBCYGV-UHFFFAOYSA-N
smarts:    [#6]12-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-2
smarts_isomeric:    [#6]12-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-2

epoxide: C1CO1

pyrazine: C1=CN=CC=N1

oxazolidinone: O=C1OCCN1

smiles_non_kekule:    O=C1NCCO1
smiles_kekule:    O=C1NCCO1
inchi:    InChI=1S/C3H5NO2/c5-3-4-1-2-6-3/h1-2H2,(H,4,5)
inchiKey:    IZXIZTKNFFYFOF-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#8]-[#6]-[#6]-[#7]-1
smarts_isomeric:    [#8]=[#6]1-[#8]-[#6]-[#6]-[#7]-1

tetrahydronaphthalene: C1(C=CC=C2)=C2CCCC1

smiles_non_kekule:    c1ccc2c(c1)CCCC2
smiles_kekule:    C1=CC=C2CCCCC2=C1
inchi:    InChI=1S/C10H12/c1-2-6-10-8-4-3-7-9(10)5-1/h1-2,5-6H,3-4,7-8H2
inchiKey:    CXWXQJXEFPUFDZ-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6]-[#6]-[#6]-2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6]-[#6]-[#6]-2

adamantane: C1(CC(C2)C3)CC2CC3C1

smiles_non_kekule:    C1C2CC3CC1CC(C2)C3
smiles_kekule:    C1C2CC3CC1CC(C2)C3
inchi:    InChI=1S/C10H16/c1-7-2-9-4-8(1)5-10(3-7)6-9/h7-10H,1-6H2
inchiKey:    ORILYTVJVMAKLC-UHFFFAOYSA-N
smarts:    [#6]12-[#6]-[#6]3-[#6]-[#6](-[#6]-1)-[#6]-[#6](-[#6]-3)-[#6]-2
smarts_isomeric:    [#6]12-[#6]-[#6]3-[#6]-[#6](-[#6]-1)-[#6]-[#6](-[#6]-3)-[#6]-2

1,8-naphthyridin-4(1H)-one: O=C(C=CN1)C2=C1N=CC=C2

smiles_non_kekule:    O=c1cc[nH]c2ncccc12
smiles_kekule:    O=C1C=CNC2=C1C=CC=N2
inchi:    InChI=1S/C8H6N2O/c11-7-3-5-10-8-6(7)2-1-4-9-8/h1-5H,(H,9,10,11)
inchiKey:    NQUIRWXTTAMWIU-UHFFFAOYSA-N
smarts:    [#8]=[#6]1:[#6]:[#6]:[#7H]:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#7]:2
smarts_isomeric:    [#8]=[#6]1:[#6]:[#6]:[#7H]:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#7]:2

3,7-dihydro-1H-purine-2,6-dione: O=C(C(NC=N1)=C1N2)NC2=O

smiles_non_kekule:    O=c1[nH]c(=O)c2[nH]cnc2[nH]1
smiles_kekule:    O=C1NC(=O)C2=C(N=CN2)N1
inchi:    InChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)
inchiKey:    LRFVTYWOQMYALW-UHFFFAOYSA-N
smarts:    [#8]=[#6]1:[#6]2:[#7H]:[#6]:[#7]:[#6]:2:[#7H]:[#6](:[#7H]:1)=[#8]
smarts_isomeric:    [#8]=[#6]1:[#6]2:[#7H]:[#6]:[#7]:[#6]:2:[#7H]:[#6](:[#7H]:1)=[#8]

hexadecahydro-1H-cyclopenta[a]phenanthrene: CCC[C@H]1CCCCC1[C@@H]2C[C@H](CCC3)C3CC2

smiles_non_kekule:    CCC[C@H]1CCCCC1[C@H]1CCC2CCC[C@H]2C1
smiles_kekule:    CCC[C@H]1CCCCC1[C@H]1CCC2CCC[C@H]2C1
inchi:    InChI=1S/C18H32/c1-2-6-15-7-3-4-10-18(15)17-12-11-14-8-5-9-16(14)13-17/h14-18H,2-13H2,1H3/t14?,15-,16-,17-,18?/m0/s1
inchiKey:    VAXZFHBFXBHSQV-WHRQZHCMSA-N
smarts:    [#6]-[#6]-[#6]-[#6H]1-[#6]-[#6]-[#6]-[#6]-[#6]-1-[#6H]1-[#6]-[#6H]2-[#6]-[#6]-[#6]-[#6]-2-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6]-[#6]-[#6@H]1-[#6]-[#6]-[#6]-[#6]-[#6]-1-[#6@@H]1-[#6]-[#6@@H]2-[#6]-[#6]-[#6]-[#6]-2-[#6]-[#6]-1

7,8,9,10-tetrahydrotetracene-5,12-dione: O=C(C(C=C(CCCC1)C1=C2)=C2C3=O)C4=C3C=CC=C4

smiles_non_kekule:    O=C1c2ccccc2C(=O)c2cc3c(cc21)CCCC3
smiles_kekule:    O=C1C2=C(C=CC=C2)C(=O)C2=C1C=C1CCCCC1=C2
inchi:    InChI=1S/C18H14O2/c19-17-13-7-3-4-8-14(13)18(20)16-10-12-6-2-1-5-11(12)9-15(16)17/h3-4,7-10H,1-2,5-6H2
inchiKey:    XFOHBSLKSOSFBE-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#6]2:[#6]:[#6]3-[#6]-[#6]-[#6]-[#6]-[#6]:3:[#6]:[#6]:2-[#6](=[#8])-[#6]2:[#6]-1:[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#8]=[#6]1-[#6]2:[#6]:[#6]3-[#6]-[#6]-[#6]-[#6]-[#6]:3:[#6]:[#6]:2-[#6](=[#8])-[#6]2:[#6]-1:[#6]:[#6]:[#6]:[#6]:2

cyclobutane: C1CCC1

1,2-dihydro-3H-1,2,4-triazol-3-one: O=C1NNC=N1

smiles_non_kekule:    O=c1nc[nH][nH]1
smiles_kekule:    O=C1N=CNN1
inchi:    InChI=1S/C2H3N3O/c6-2-3-1-4-5-2/h1H,(H2,3,4,5,6)
inchiKey:    LZTSCEYDCZBRCJ-UHFFFAOYSA-N
smarts:    [#8]=[#6]1:[#7H]:[#7H]:[#6]:[#7]:1
smarts_isomeric:    [#8]=[#6]1:[#7H]:[#7H]:[#6]:[#7]:1

1,3,4-thiadiazole: C1=NN=CS1

smiles_non_kekule:    c1nncs1
smiles_kekule:    C1=NN=CS1
inchi:    InChI=1S/C2H2N2S/c1-3-4-2-5-1/h1-2H
inchiKey:    MBIZXFATKUQOOA-UHFFFAOYSA-N
smarts:    [#6]1:[#7]:[#7]:[#6]:[#16]:1
smarts_isomeric:    [#6]1:[#7]:[#7]:[#6]:[#16]:1

azepane: C1NCCCCC1

smiles_non_kekule:    C1CCCNCC1
smiles_kekule:    C1CCCNCC1
inchi:    InChI=1S/C6H13N/c1-2-4-6-7-5-3-1/h7H,1-6H2
inchiKey:    ZSIQJIWKELUFRJ-UHFFFAOYSA-N
smarts:    [#6]1-[#7]-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]1-[#7]-[#6]-[#6]-[#6]-[#6]-[#6]-1

8-azabicyclo[3.2.1]octane: C12CCCC(CC2)N1

smiles_non_kekule:    C1CC2CCC(C1)N2
smiles_kekule:    C1CC2CCC(C1)N2
inchi:    InChI=1S/C7H13N/c1-2-6-4-5-7(3-1)8-6/h6-8H,1-5H2
inchiKey:    DGGKXQQCVPAUEA-UHFFFAOYSA-N
smarts:    [#6]12-[#6]-[#6]-[#6]-[#6](-[#6]-[#6]-1)-[#7]-2
smarts_isomeric:    [#6]12-[#6]-[#6]-[#6]-[#6](-[#6]-[#6]-1)-[#7]-2

piperidine-2,6-dione: O=C(N1)CCCC1=O

smiles_non_kekule:    O=C1CCCC(=O)N1
smiles_kekule:    O=C1CCCC(=O)N1
inchi:    InChI=1S/C5H7NO2/c7-4-2-1-3-5(8)6-4/h1-3H2,(H,6,7,8)
inchiKey:    KNCYXPMJDCCGSJ-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#7]-[#6](-[#6]-[#6]-[#6]-1)=[#8]
smarts_isomeric:    [#8]=[#6]1-[#7]-[#6](-[#6]-[#6]-[#6]-1)=[#8]

2,3-dihydro-1H-indene: O=C(N1)CCCC1=O

benzo[d]isoxazole: C12=CC=CC=C1C=NO2

smiles_non_kekule:    c1ccc2oncc2c1
smiles_kekule:    C1=CC=C2ON=CC2=C1
inchi:    InChI=1S/C7H5NO/c1-2-4-7-6(3-1)5-8-9-7/h1-5H
inchiKey:    KTZQTRPPVKQPFO-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#7]:[#8]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#7]:[#8]:2

1,9-dihydro-6H-purin-6-one: O=C1C2=C(NC=N2)N=CN1

smiles_non_kekule:    O=c1[nH]cnc2[nH]cnc12
smiles_kekule:    O=C1NC=NC2=C1N=CN2
inchi:    InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
inchiKey:    FDGQSTZJBFJUBT-UHFFFAOYSA-N
smarts:    [#8]=[#6]1:[#6]2:[#6](:[#7H]:[#6]:[#7]:2):[#7]:[#6]:[#7H]:1
smarts_isomeric:    [#8]=[#6]1:[#6]2:[#6](:[#7H]:[#6]:[#7]:2):[#7]:[#6]:[#7H]:1

9H-fluorene: C12=CC=CC=C1C3=C(C=CC=C3)C2

smiles_non_kekule:    c1ccc2c(c1)Cc1ccccc1-2
smiles_kekule:    C1=CC=C2C(=C1)CC1=C2C=CC=C1
inchi:    InChI=1S/C13H10/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)12/h1-8H,9H2
inchiKey:    NIHNNTQXNPWCJQ-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]1:[#6](:[#6]:[#6]:[#6]:[#6]:1)-[#6]-2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]1:[#6](:[#6]:[#6]:[#6]:[#6]:1)-[#6]-2

10,11-dihydro-5H-dibenzo[b,f]azepine: C12=CC=CC=C1CCC3=C(C=CC=C3)N2

smiles_non_kekule:    c1ccc2c(c1)CCc1ccccc1N2
smiles_kekule:    C1=CC=C2NC3=C(C=CC=C3)CCC2=C1
inchi:    InChI=1S/C14H13N/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)15-13/h1-8,15H,9-10H2
inchiKey:    ZSMRRZONCYIFNB-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6]-[#6]1:[#6](:[#6]:[#6]:[#6]:[#6]:1)-[#7]-2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6]-[#6]1:[#6](:[#6]:[#6]:[#6]:[#6]:1)-[#7]-2

(6aR,10aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline: C12=CC=CC3=C1C(C[C@@H]4[C@@H]2CCCN4)=CN3

smiles_non_kekule:    c1cc2c3c(c[nH]c3c1)C[C@H]1NCCC[C@H]21
smiles_kekule:    C1=CC2=C3C(=CN2)C[C@H]2NCCC[C@@H]2C3=C1
inchi:    InChI=1S/C14H16N2/c1-3-11-10-4-2-6-15-13(10)7-9-8-16-12(5-1)14(9)11/h1,3,5,8,10,13,15-16H,2,4,6-7H2/t10-,13-/m1/s1
inchiKey:    RHGUXDUPXYFCTE-ZWNOBZJWSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]3:[#6]:1:[#6](-[#6]-[#6H]1-[#6H]-2-[#6]-[#6]-[#6]-[#7]-1):[#6]:[#7H]:3
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]3:[#6]:1:[#6](-[#6]-[#6@@H]1-[#6@@H]-2-[#6]-[#6]-[#6]-[#7]-1):[#6]:[#7H]:3

1H-pyrrole: C1=CC=CN1

smiles_non_kekule:    c1cc[nH]c1
smiles_kekule:    C1=CNC=C1
inchi:    InChI=1S/C4H5N/c1-2-4-5-3-1/h1-5H
inchiKey:    KAESVJOAVNADME-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]:[#7H]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]:[#7H]:1

1,3-dioxolane: O1CCOC1

smiles_non_kekule:    C1COCO1
smiles_kekule:    C1COCO1
inchi:    InChI=1S/C3H6O2/c1-2-5-3-4-1/h1-3H2
inchiKey:    WNXJIVFYUVYPPR-UHFFFAOYSA-N
smarts:    [#8]1-[#6]-[#6]-[#8]-[#6]-1
smarts_isomeric:    [#8]1-[#6]-[#6]-[#8]-[#6]-1

(1R,5S)-3-azabicyclo[3.1.0]hexane: [C@@H]1(C2)[C@H]2CNC1

smiles_non_kekule:    C1NC[C@@H]2C[C@H]12
smiles_kekule:    C1NC[C@@H]2C[C@H]12
inchi:    InChI=1S/C5H9N/c1-4-2-6-3-5(1)4/h4-6H,1-3H2/t4-,5+
inchiKey:    HGWUUOXXAIISDB-SYDPRGILSA-N
smarts:    [#6]1-[#6H]2-[#6H]-1-[#6]-[#7]-[#6]-2
smarts_isomeric:    [#6]1-[#6@@H]2-[#6@H]-1-[#6]-[#7]-[#6]-2

cyclopentanone: O=C1CCCC1

smiles_non_kekule:    O=C1CCCC1
smiles_kekule:    O=C1CCCC1
inchi:    InChI=1S/C5H8O/c6-5-3-1-2-4-5/h1-4H2
inchiKey:    BGTOWKSIORTVQH-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#8]=[#6]1-[#6]-[#6]-[#6]-[#6]-1

pyrrolidine-2,5-dione: O=C(N1)CCC1=O

smiles_non_kekule:    O=C1CCC(=O)N1
smiles_kekule:    O=C1CCC(=O)N1
inchi:    InChI=1S/C4H5NO2/c6-3-1-2-4(7)5-3/h1-2H2,(H,5,6,7)
inchiKey:    KZNICNPSHKQLFF-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#7]-[#6](-[#6]-[#6]-1)=[#8]
smarts_isomeric:    [#8]=[#6]1-[#7]-[#6](-[#6]-[#6]-1)=[#8]

pyrazolidine: O=C(NN1)CC1=O

smiles_non_kekule:    O=C1CC(=O)NN1
smiles_kekule:    O=C1CC(=O)NN1
inchi:    InChI=1S/C3H4N2O2/c6-2-1-3(7)5-4-2/h1H2,(H,4,6)(H,5,7)
inchiKey:    DNTVKOMHCDKATN-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#7]-[#7]-[#6](-[#6]-1)=[#8]
smarts_isomeric:    [#8]=[#6]1-[#7]-[#7]-[#6](-[#6]-1)=[#8]

(R)-1-azabicyclo[3.2.0]hept-2-en-7-one: O=C1N2C=CC[C@@H]2C1

smiles_non_kekule:    O=C1C[C@H]2CC=CN12
smiles_kekule:    O=C1C[C@H]2CC=CN12
inchi:    InChI=1S/C6H7NO/c8-6-4-5-2-1-3-7(5)6/h1,3,5H,2,4H2/t5-/m1/s1
inchiKey:    YZBQHRLRFGPBSL-RXMQYKEDSA-N
smarts:    [#8]=[#6]1-[#7]2-[#6]=[#6]-[#6]-[#6H]-2-[#6]-1
smarts_isomeric:    [#8]=[#6]1-[#7]2-[#6]=[#6]-[#6]-[#6@@H]-2-[#6]-1

thiazolidine-2,4-dione: O=C(CS1)NC1=O

smiles_non_kekule:    O=C1CSC(=O)N1
smiles_kekule:    O=C1CSC(=O)N1
inchi:    InChI=1S/C3H3NO2S/c5-2-1-7-3(6)4-2/h1H2,(H,4,5,6)
inchiKey:    ZOBPZXTWZATXDG-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#6]-[#16]-[#6](-[#7]-1)=[#8]
smarts_isomeric:    [#8]=[#6]1-[#6]-[#16]-[#6](-[#7]-1)=[#8]

benzofuran: C12=CC=CC=C1C=CO2

1H-indazole: C12=CC=CC=C1C=NN2

smiles_non_kekule:    c1ccc2[nH]ncc2c1
smiles_kekule:    C1=CC=C2NN=CC2=C1
inchi:    InChI=1S/C7H6N2/c1-2-4-7-6(3-1)5-8-9-7/h1-5H,(H,8,9)
inchiKey:    BAXOFTOLAUCFNW-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#7]:[#7H]:2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#6]:[#7]:[#7H]:2

indolin-2-one: O=C1NC2=CC=CC=C2C1

smiles_non_kekule:    O=C1Cc2ccccc2N1
smiles_kekule:    O=C1CC2=CC=CC=C2N1
inchi:    InChI=1S/C8H7NO/c10-8-5-6-3-1-2-4-7(6)9-8/h1-4H,5H2,(H,9,10)
inchiKey:    JYGFTBXVXVMTGB-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#7]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2-[#6]-1
smarts_isomeric:    [#8]=[#6]1-[#7]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2-[#6]-1

benzo[b]thiophene: C12=CC=CC=C1C=CS2

(R)-1,2,3,7,8,8a-hexahydronaphthalene: C12=CCCC[C@@H]1CCC=C2

smiles_non_kekule:    C1=CC2=CCCC[C@@H]2CC1
smiles_kekule:    C1=CC2=CCCC[C@@H]2CC1
inchi:    InChI=1S/C10H14/c1-2-6-10-8-4-3-7-9(10)5-1/h1,5,7,10H,2-4,6,8H2/t10-/m0/s1
inchiKey:    ZGYZCSRPTRJWLK-JTQLQIEISA-N
smarts:    [#6]12=[#6]-[#6]-[#6]-[#6]-[#6H]-1-[#6]-[#6]-[#6]=[#6]-2
smarts_isomeric:    [#6]12=[#6]-[#6]-[#6]-[#6]-[#6@@H]-1-[#6]-[#6]-[#6]=[#6]-2

4,5,6,7-tetrahydrothieno[3,2-c]pyridine: C1(C=CS2)=C2CCNC1

smiles_non_kekule:    c1cc2c(s1)CCNC2
smiles_kekule:    C1=CC2=C(CCNC2)S1
inchi:    InChI=1S/C7H9NS/c1-3-8-5-6-2-4-9-7(1)6/h2,4,8H,1,3,5H2
inchiKey:    OGUWOLDNYOTRBO-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#16]:[#6]:1-[#6]-[#6]-[#7]-[#6]-2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#16]:[#6]:1-[#6]-[#6]-[#7]-[#6]-2

4H-chromen-4-one: O=C(C=CO1)C2=C1C=CC=C2

3,4-dihydroquino-2(1H)-one: O=C(CC1)NC2=C1C=CC=C2

smiles_non_kekule:    O=C1CCc2ccccc2N1
smiles_kekule:    O=C1CCC2=C(C=CC=C2)N1
inchi:    InChI=1S/C9H9NO/c11-9-6-5-7-3-1-2-4-8(7)10-9/h1-4H,5-6H2,(H,10,11)
inchiKey:    TZOYXRMEFDYWDQ-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#6]-[#6]-[#6]2:[#6](-[#7]-1):[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#8]=[#6]1-[#6]-[#6]-[#6]2:[#6](-[#7]-1):[#6]:[#6]:[#6]:[#6]:2

napthalene-1,4-dione: O=C(C=CC1=O)C2=C1C=CC=C2

smiles_non_kekule:    O=C1C=CC(=O)c2ccccc21
smiles_kekule:    O=C1C=CC(=O)C2=C1C=CC=C2
inchi:    InChI=1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H
inchiKey:    FRASJONUBLZVQX-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#6]=[#6]-[#6](=[#8])-[#6]2:[#6]-1:[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#8]=[#6]1-[#6]=[#6]-[#6](=[#8])-[#6]2:[#6]-1:[#6]:[#6]:[#6]:[#6]:2

2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide: O=S(C1=C2C=CC=C1)(NC=N2)=O

smiles_non_kekule:    O=S1(=O)NC=Nc2ccccc21
smiles_kekule:    O=S1(=O)NC=NC2=C1C=CC=C2
inchi:    InChI=1S/C7H6N2O2S/c10-12(11)7-4-2-1-3-6(7)8-5-9-12/h1-5H,(H,8,9)
inchiKey:    BBNGVMNBBLPZIR-UHFFFAOYSA-N
smarts:    [#8]=[#16]1(-[#6]2:[#6](:[#6]:[#6]:[#6]:[#6]:2)-[#7]=[#6]-[#7]-1)=[#8]
smarts_isomeric:    [#8]=[#16]1(-[#6]2:[#6](:[#6]:[#6]:[#6]:[#6]:2)-[#7]=[#6]-[#7]-1)=[#8]

4H-benzo[f][1,2,4]triazolo[4,3-a][1,4]diazepine: C1(N2C(CN=C3)=NN=C2)=C3C=CC=C1

smiles_non_kekule:    C1=NCc2nncn2-c2ccccc21
smiles_kekule:    C1=NCC2=NN=CN2C2=C1C=CC=C2
inchi:    InChI=1S/C10H8N4/c1-2-4-9-8(3-1)5-11-6-10-13-12-7-14(9)10/h1-5,7H,6H2
inchiKey:    LKRNZLYYWVHIFZ-UHFFFAOYSA-N
smarts:    [#6]12-[#7]3:[#6](-[#6]-[#7]=[#6]-[#6]:1:[#6]:[#6]:[#6]:[#6]:2):[#7]:[#7]:[#6]:3
smarts_isomeric:    [#6]12-[#7]3:[#6](-[#6]-[#7]=[#6]-[#6]:1:[#6]:[#6]:[#6]:[#6]:2):[#7]:[#7]:[#6]:3

9H-thioxanthene: C12=CC=CC=C1CC3=C(C=CC=C3)S2

smiles_non_kekule:    c1ccc2c(c1)Cc1ccccc1S2
smiles_kekule:    C1=CC=C2SC3=C(C=CC=C3)CC2=C1
inchi:    InChI=1S/C13H10S/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-8H,9H2
inchiKey:    PQJUJGAVDBINPI-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6]1:[#6](:[#6]:[#6]:[#6]:[#6]:1)-[#16]-2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6]1:[#6](:[#6]:[#6]:[#6]:[#6]:1)-[#16]-2

(5aR,8aR)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one: O=C(OC1)[C@H]2[C@H]1CC3=CC4=C(C=C3C2)OCO4

smiles_non_kekule:    O=C1OC[C@@H]2Cc3cc4c(cc3C[C@@H]12)OCO4
smiles_kekule:    O=C1OC[C@@H]2CC3=CC4=C(C=C3C[C@@H]12)OCO4
inchi:    InChI=1S/C13H12O4/c14-13-10-2-8-4-12-11(16-6-17-12)3-7(8)1-9(10)5-15-13/h3-4,9-10H,1-2,5-6H2/t9-,10+/m0/s1
inchiKey:    KDAVTDIQCUOJNV-VHSXEESVSA-N
smarts:    [#8]=[#6]1-[#8]-[#6]-[#6H]2-[#6H]-1-[#6]-[#6]1:[#6](-[#6]-2):[#6]:[#6]2:[#6](:[#6]:1)-[#8]-[#6]-[#8]-2
smarts_isomeric:    [#8]=[#6]1-[#8]-[#6]-[#6@H]2-[#6@H]-1-[#6]-[#6]1:[#6](-[#6]-2):[#6]:[#6]2:[#6](:[#6]:1)-[#8]-[#6]-[#8]-2

(3a1S,5aS,10bS)-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole: C12=CC=CC=C1[C@@]34[C@H](CCC5[C@@H]3N(CC=C5)CC4)N2

smiles_non_kekule:    C1=CC2CC[C@@H]3Nc4ccccc4[C@@]34CCN(C1)[C@@H]24
smiles_kekule:    C1=CC2CC[C@@H]3NC4=CC=CC=C4[C@@]34CCN(C1)[C@@H]24
inchi:    InChI=1S/C17H20N2/c1-2-6-14-13(5-1)17-9-11-19-10-3-4-12(16(17)19)7-8-15(17)18-14/h1-6,12,15-16,18H,7-11H2/t12?,15-,16-,17-/m0/s1
inchiKey:    CHFSMDACATVRBM-CPWCDSSXSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]13-[#6H](-[#6]-[#6]-[#6]4-[#6H]-1-[#7](-[#6]-[#6]=[#6]-4)-[#6]-[#6]-3)-[#7]-2
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6@@]13-[#6@H](-[#6]-[#6]-[#6]4-[#6@@H]-1-[#7](-[#6]-[#6]=[#6]-4)-[#6]-[#6]-3)-[#7]-2

(4aR,5aR)-4a,5a,6,12a-tetrahydrotetracene-1,11(4H,5H)-dione: O=C1C2=CC3[C@H](CC=CC3=O)C[C@@H]2CC4=CC=CC=C41

smiles_non_kekule:    O=C1C2=CC3C(=O)C=CC[C@@H]3C[C@@H]2Cc2ccccc21
smiles_kekule:    O=C1C2=CC3C(=O)C=CC[C@@H]3C[C@@H]2CC2=CC=CC=C12
inchi:    InChI=1S/C18H16O2/c19-17-7-3-5-12-9-13-8-11-4-1-2-6-14(11)18(20)16(13)10-15(12)17/h1-4,6-7,10,12-13,15H,5,8-9H2/t12-,13+,15?/m1/s1
inchiKey:    KRZVXWRCQRFOLN-NEJHNUGDSA-N
smarts:    [#8]=[#6]1-[#6]2=[#6]-[#6]3-[#6H](-[#6]-[#6]=[#6]-[#6]-3=[#8])-[#6]-[#6H]-2-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2-1
smarts_isomeric:    [#8]=[#6]1-[#6]2=[#6]-[#6]3-[#6@H](-[#6]-[#6]=[#6]-[#6]-3=[#8])-[#6]-[#6@@H]-2-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2-1

1H-1,2,3-triazole: N1=NC=CN1

smiles_non_kekule:    c1c[nH]nn1
smiles_kekule:    C1=CNN=N1
inchi:    InChI=1S/C2H3N3/c1-2-4-5-3-1/h1-2H,(H,3,4,5)
inchiKey:    QWENRTYMTSOGBR-UHFFFAOYSA-N
smarts:    [#7]1:[#7]:[#6]:[#6]:[#7H]:1
smarts_isomeric:    [#7]1:[#7]:[#6]:[#6]:[#7H]:1

azetidin-2-one: O=C1NCC1

smiles_non_kekule:    O=C1CCN1
smiles_kekule:    O=C1CCN1
inchi:    InChI=1S/C3H5NO/c5-3-1-2-4-3/h1-2H2,(H,4,5)
inchiKey:    MNFORVFSTILPAW-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#7]-[#6]-[#6]-1
smarts_isomeric:    [#8]=[#6]1-[#7]-[#6]-[#6]-1

oxetan-2-one: O=C1OCC1

smiles_non_kekule:    O=C1CCO1
smiles_kekule:    O=C1CCO1
inchi:    InChI=1S/C3H4O2/c4-3-1-2-5-3/h1-2H2
inchiKey:    VEZXCJBBBCKRPI-UHFFFAOYSA-N
smarts:    [#8]=[#6]1-[#8]-[#6]-[#6]-1
smarts_isomeric:    [#8]=[#6]1-[#8]-[#6]-[#6]-1

problem_type: 21/25 (loop 0/0)

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Charges were rearranged

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Omitted undefined stereo

[15:21:52] WARNING: Charges were rearranged

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Charges were rearranged

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo; Proton(s) added/removed

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Proton(s) added/removed; Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:53] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Charges were rearranged

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

[15:21:54] WARNING: Omitted undefined stereo

Problem Template: _problem_schedule_one

Write structure of schedule one molecules.

Answer:

structure of schedule one molecules:

acetyl-alpha-methylfentanyl: CC(CC1=CC=CC=C1)N2CCC(CC2)N(C3=CC=CC=C3)C(=O)C

acetylmethadol: CCC(C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)OC(=O)C

acetylfentanyl: CC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3

acrylfentanyl: C=CC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3

ah-7921: ClC1=CC=C(C(NCC2(CCCCC2)N(C)C)=O)C=C1Cl

allylprodine: CCC(=O)OC1(CCN(CC1CC=C)C)C2=CC=CC=C2

alphaacetylmethadol: CCC(C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)OC(=O)C

alphameprodine: CCC1CN(CCC1(C2=CC=CC=C2)OC(=O)CC)C

alphamethadol: CCC(C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)O

alpha-methylfentanyl: O=C(N(c1ccccc1)C3CCN(C(Cc2ccccc2)C)CC3)CC

alpha-methylthiofentanyl: CCC(=O)N(C1CCN(CC1)C(C)CC2=CC=CS2)C3=CC=CC=C3

benzethidine: CCOC(=O)C1(CCN(CC1)CCOCC2=CC=CC=C2)C3=CC=CC=C3

betacetylmethadol: CCC(C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)OC(=O)C

beta-hydroxyfentanyl: CCC(=O)N(C1CCN(CC1)CC(C2=CC=CC=C2)O)C3=CC=CC=C3

beta-hydroxy-3-methylfentanyl: CCC(=O)N(C1CCN(CC1C)CC(C2=CC=CC=C2)O)C3=CC=CC=C3

beta-hydroxythiofentanyl: CCC(=O)N(C1CCN(CC1)CC(C2=CC=CS2)O)C3=CC=CC=C3

betameprodine: CCC1CN(CCC1(C2=CC=CC=C2)OC(=O)CC)C

betamethadol: CCC(C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)O

beta-methylfentanyl: CCC(=O)N(C1CCN(CC1)CC(C)C2=CC=CC=C2)C3=CC=CC=C3

beta′-phenylfentanyl: O=C(CCC1=CC=CC=C1)N(C2CCN(CCC3=CC=CC=C3)CC2)C4=CC=CC=C4

betaprodine: CCC(=O)OC1(CCN(CC1C)C)C2=CC=CC=C2

butyrylfentanyl: CCCC(=O)N(C2CCN(CCc1ccccc1)CC2)c3ccccc3

clonitazene: CCN(CC)CCN1C2=C(C=C(C=C2)[N+](=O)[O-])N=C1CC3=CC=C(C=C3)Cl

crotonylfentanyl: CC=CC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3

cyclopentylfentanyl: C1CCC(C1)C(=O)N(C2CCN(CC2)CCC3=CC=CC=C3)C4=CC=CC=C4

cyclopropylfentanyl: C1CC1C(=O)N(C2CCN(CC2)CCC3=CC=CC=C3)C4=CC=CC=C4

dextromoramide: CC(CN1CCOCC1)C(C2=CC=CC=C2)(C3=CC=CC=C3)C(=O)N4CCCC4

diampromide: CCC(=O)N(CC(C)N(C)CCC1=CC=CC=C1)C2=CC=CC=C2

diethylthiambutene: CCN(CC)C(C)C=C(C1=CC=CS1)C2=CC=CS2

difenoxin: C1CN(CCC1(C2=CC=CC=C2)C(=O)O)CCC(C#N)(C3=CC=CC=C3)C4=CC=CC=C4

dimenoxadol: CCOC(C1=CC=CC=C1)(C2=CC=CC=C2)C(=O)OCCN(C)C

dimepheptanol: CCC(C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)O

dimethylthiambutene: CC(C=C(C1=CC=CS1)C2=CC=CS2)N(C)C

dioxaphetylbutyrate: CCOC(=O)C(CCN1CCOCC1)(c1ccccc1)c1ccccc1

dipipanone: CCC(=O)C(CC(C)N1CCCCC1)(C2=CC=CC=C2)C3=CC=CC=C3

ethylmethylthiambutene: CCN(C)C(C)C=C(C1=CC=CS1)C2=CC=CS2

etonitazene: CCN(CC)CCN1C2=C(C=C(C=C2)[N+](=O)[O-])N=C1CC3=CC=C(C=C3)OCC

etoxeridine: CCOC(=O)C1(CCN(CC1)CCOCCO)C2=CC=CC=C2

fentanylcarbamate: O=C(N(C1=CC=CC=C1)C2CCN(CCC3=CC=CC=C3)CC2)OCC

4-fluoroisobutyrylfentanyl: CC(C)C(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=C(C=C3)F

2′-fluoroortho-fluorofentanyl: O=C(CC)N(C1CCN(CCC2=CC=CC=C2F)CC1)C3=C(F)C=CC=C3

furanylfentanyl: C1CN(CCC1N(C2=CC=CC=C2)C(=O)C3=CC=CO3)CCC4=CC=CC=C4

furethidine: CCOC(=O)C1(CCN(CC1)CCOCC2CCCO2)C3=CC=CC=C3

hydroxypethidine: CCOC(=O)C1(CCN(CC1)C)C2=CC(=CC=C2)O

isobutyrylfentanyl: CC(C)C(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3

isotonitazene: CCN(CC)CCN1C(CC2=CC=C(OC(C)C)C=C2)=NC3=CC([N+]([O-])=O)=CC=C31

ketobemidone: CCC(=O)C1(CCN(CC1)C)C2=CC(=CC=C2)O

levomoramide: C[C@@H](CN1CCOCC1)C(c1ccccc1)(c1ccccc1)C(=O)N1CCCC1

levophenacylmorphan: C1CCC23CCN(C(C2C1)CC4=C3C=C(C=C4)O)CC(=O)C5=CC=CC=C5

methoxyacetylfentanyl: c3ccccc3N(C(=O)COC)C1CCN(CC1)CCc2ccccc2

4′-methylacetylfentanyl: CC(N(C1CCN(CCC2=CC=C(C)C=C2)CC1)C3=CC=CC=C3)=O

3-methylfentanyl: CCC(=O)N(C1CCN(CC1C)CCC2=CC=CC=C2)C3=CC=CC=C3

3-methylthiofentanyl: CCC(=O)N(C1CCN(CC1C)CCC2=CC=CS2)C3=CC=CC=C3

morpheridine: CCOC(=O)C1(CCN(CC1)CCN2CCOCC2)C3=CC=CC=C3

mppp: O=C(CC3=CC=CC=C3)N(C(C2=CC=CC=C2)CN1CCCC1)C

mt-45: c3ccccc3CC(c2ccccc2)N(CC1)CCN1C4CCCCC4

noracymethadol: CCC(C(CC(C)NC)(C1=CC=CC=C1)C2=CC=CC=C2)OC(=O)C

norlevorphanol: C1CCC23CCNC(C2C1)CC4=C3C=C(C=C4)O

normethadone: CCC(=O)C(CCN(C)C)(C1=CC=CC=C1)C2=CC=CC=C2

norpipanone: CCC(=O)C(CCN1CCCCC1)(C2=CC=CC=C2)C3=CC=CC=C3

ocfentanil: COCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3F

ortho-fluoroacrylfentanyl: O=C(N(C1=CC=CC=C1F)C2CCN(CCC3=CC=CC=C3)CC2)C=C

ortho-fluorobutyrylfentanyl: CCCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=C(C=C3)F

ortho-fluorofentanyl: CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3F

ortho-fluoroisobutyrylfentanyl: CC(C)C(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C3=C(F)C=CC=C3

ortho-methylacetylfentanyl: CC(N(C1CCN(CCC2=CC=CC=C2)CC1)C3=C(C)C=CC=C3)=O

ortho-methylmethoxyacetylfentanyl: O=C(COC)N(C1CCN(CCC2=CC=CC=C2)CC1)C3=C(C)C=CC=C3

para-chloroisobutyrylfentanyl: O=C(C(C)C)N(C1CCN(CCC2=CC=CC=C2)CC1)C3=CC=C(Cl)C=C3

para-fluorobutyrylfentanyl: C1C(CCN(C1)CCc1ccccc1)N(c1ccc(cc1)F)C(=O)CCC

para-fluorofentanyl: CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=C(C=C3)F

para-fluorofuranylfentanyl: O=C(C1=CC=CO1)N(C2CCN(CCC3=CC=CC=C3)CC2)C4=CC=C(F)C=C4

para-methoxybutyrylfentanyl: O=C(CCC)N(C1CCN(CCC2=CC=CC=C2)CC1)C3=CC=C(OC)C=C3

para-methylfentanyl: O=C(CC)N(C1CCN(CCC2=CC=CC=C2)CC1)C3=CC=C(C)C=C3

pepap: O=C(C)OC1(CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3

phenadoxone: CCC(=O)C(CC(C)N1CCOCC1)(C2=CC=CC=C2)C3=CC=CC=C3

phenampromide: CCC(=O)N(C1=CC=CC=C1)C(C)CN2CCCCC2

phenomorphan: C1CCC23CCN(C(C2C1)CC4=C3C=C(C=C4)O)CCC5=CC=CC=C5

phenoperidine: CCOC(=O)C1(CCN(CC1)CCC(C2=CC=CC=C2)O)C3=CC=CC=C3

phenylfentanyl: O=C(C1=CC=CC=C1)N(C2CCN(CCC3=CC=CC=C3)CC2)C4=CC=CC=C4

piritramide: C1CCN(CC1)C2(CCN(CC2)CCC(C#N)(C3=CC=CC=C3)C4=CC=CC=C4)C(=O)N

proheptazine: CCC(=O)OC1(CCCN(CC1C)C)C2=CC=CC=C2

properidine: CC(C)OC(=O)C1(CCN(CC1)C)C2=CC=CC=C2

propiram: CCC(=O)N(C1=CC=CC=N1)C(C)CN2CCCCC2

racemoramide: CC(CN1CCOCC1)C(C2=CC=CC=C2)(C3=CC=CC=C3)C(=O)N4CCCC4

tetrahydrofuranylfentanyl: C1CC(OC1)C(=O)N(C2CCN(CC2)CCC3=CC=CC=C3)C4=CC=CC=C4

thiofentanyl: CCC(=O)N(C1CCN(CC1)CCC2=CC=CS2)C3=CC=CC=C3

thiofuranylfentanyl: O=C(N(C1CCN(CCC2=CC=CC=C2)CC1)C3=CC=CC=C3)C4=CC=CS4

tilidine: CCOC(=O)C1(CCC=CC1N(C)C)C2=CC=CC=C2

trimeperidine: CCC(=O)OC1(CC(N(CC1C)C)C)C2=CC=CC=C2

pinky: CN(C)C1CCCCC1N(C)C(=O)C2=CC(=C(C=C2)Cl)Cl

valerylfentanyl: CCCCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3

acetorphine: CCCC(C)(C1CC23C=CC1(C4C25CCN(C3CC6=C5C(=C(C=C6)OC(=O)C)O4)C)OC)O

acetyldihydrocodeine: CC(=O)OC1CCC2C3CC4=C5C2(C1OC5=C(C=C4)OC)CCN3C

benzylmorphine: CN1CCC23C4C1CC5=C2C(=C(C=C5)OCC6=CC=CC=C6)OC3C(C=C4)O

codeinemethylbromide: C[N+]1(CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)O)C.[Br-]

codeine-n-oxide: C[N+]1(CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)O)[O-]

cyprenorphine: CC(C)(C1CC23C=CC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)O

desomorphine: CN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3CCC4

dihydromorphine: CN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(CC4)O

drotebanol: CN1CCC23CC(CCC2(C1CC4=C3C(=C(C=C4)OC)OC)O)O

etorphine: CCCC(C)(C1CC23C=CC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)C)OC)O

heroin: CC(=O)OC1C=CC2C3CC4=C5C2(C1OC5=C(C=C4)OC(=O)C)CCN3C

hydromorphinol: CN1CCC23C4C(CCC2(C1CC5=C3C(=C(C=C5)O)O4)O)O

methyldesorphine: CC1=CCC2C3CC4=C5C2(C1OC5=C(C=C4)O)CCN3C

methyldihydromorphine: CC1(CCC2C3CC4=C5C2(C1OC5=C(C=C4)O)CCN3C)O

morphinemethylbromide: C[N+]1(CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(C=C4)O)C.[Br-]

morphinemethylsulfonate: CN1CCC23C4C1CC5=C2C(=C(C=C5)OS(=O)(=O)C)OC3C(C=C4)O

morphine-n-oxide: C[N+]1(CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(C=C4)O)[O-]

myrophine: CCCCCCCCCCCCCC(=O)OC1C=CC2C3CC4=C5C2(C1OC5=C(C=C4)OCC6=CC=CC=C6)CCN3C

nicocodeine: CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)OC(=O)C6=CN=CC=C6

nicomorphine: CN1CCC23C4C1CC5=C2C(=C(C=C5)OC(=O)C6=CN=CC=C6)OC3C(C=C4)OC(=O)C7=CN=CC=C7

normorphine: C1CNC2CC3=C4C15C2C=CC(C5OC4=C(C=C3)O)O

pholcodine: CN1CCC23C4C1CC5=C2C(=C(C=C5)OCCN6CCOCC6)OC3C(C=C4)O

thebacon: CC(=O)OC1=CCC2C3CC4=C5C2(C1OC5=C(C=C4)OC)CCN3C

alpha-ethyltryptamine: CCC(CC1=CNC2=CC=CC=C21)N

4-bromo-2,5-dimethoxy-amphetamine: CC(CC1=CC(=C(C=C1OC)Br)OC)N

4-bromo-2,5-dimethoxyphenethylamine: COC1=CC(=C(C=C1CCN)OC)Br

2,5-dimethoxyamphetamine: CC(CC1=C(C=CC(=C1)OC)OC)N

2,5-dimethoxy-4-ethylamphet-amine: CCC1=CC(=C(C=C1OC)CC(C)N)OC

2,5-dimethoxy-4-(n)-propylthiophenethylamine: CCCSC1=C(C=C(C(=C1)OC)CCN)OC

4-methoxyamphetamine: CC(CC1=CC=C(C=C1)OC)N

5-methoxy-3,4-methylenedioxy-amphetamine: CC(CC1=CC2=C(C(=C1)OC)OCO2)N

4-methyl-2,5-dimethoxy-amphetamine: CC(CC1=CC(=C(C=C1OC)SC)OC)N

3,4-methylenedioxyamphetamine: CC(CC1=CC2=C(C=C1)OCO2)N

3,4-methylenedioxymethamphetamine: CC(CC1=CC2=C(C=C1)OCO2)NC

3,4-methylenedioxy-n-ethylamphetamine: CCNC(C)CC1=CC2=C(C=C1)OCO2

n-hydroxy-3,4-methylenedioxyamphetamine: CC(CC1=CC2=C(C=C1)OCO2)NO

3,4,5-trimethoxyamphetamine: CC(CC1=CC(=C(C(=C1)OC)OC)OC)N

5-methoxy-n,n-dimethyltryptamine: CN(C)CCC1=CNC2=C1C=C(C=C2)OC

alpha-methyltryptamine: CC(CC1=CNC2=CC=CC=C21)N

bufotenine: CN(C)CCC1=CNC2=C1C=C(C=C2)O

diethyltryptamine: CCN(CC)CCC1=CNC2=CC=CC=C21

dimethyltryptamine: CN(C)CCC1=CNC2=CC=CC=C21

5-methoxy-n,n-diisopropyltryptamine: CC(C)N(CCC1=CNC2=C1C=C(C=C2)OC)C(C)C

ibogaine: CCC1CC2CC3C1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC

lysergicaciddiethylamide: CCN(CC)C(=O)C1CN(C2CC3=CNC4=CC=CC(=C34)C2=C1)C

marihuana: CCCCCC1=CC(=C2C3C=C(CCC3C(OC2=C1)(C)C)C)O

mescaline: COC1=CC(=CC(=C1OC)OC)CCN

parahexyl: CCCCCCC1=CC(=C2C3=C(CCC(C3)C)C(OC2=C1)(C)C)O

peyote: COC1=CC(=CC(=C1OC)OC)CCN

n-ethyl-3-piperidylbenzilate: O=C(OC1CCCN(CC)C1)C(O)(c2ccccc2)c3ccccc3

n-methyl-3-piperidylbenzilate: CN1CCCC(C1)OC(=O)C(C2=CC=CC=C2)(C3=CC=CC=C3)O

psilocybin: CN(C)CCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O

psilocyn: CN(C)CCC1=CNC2=C1C(=CC=C2)O

tetrahydrocannabinols: CCCCCC1=CC(=C2C3C=C(CCC3C(OC2=C1)(C)C)C)O

n-ethyl-1-phenylcyclohexylamine: ClC(Cl)=C(Cl)Cl

pyrrolidine-phencyclidine: c1ccccc1C3(N2CCCC2)CCCCC3

thiophene-phencyclidine: C1CCC(CC1)(C2=CC=CS2)N3CCCCC3

1-[1-(2-thienyl)cyclohexyl]pyrrolidine: C1CCC(CC1)(C2=CC=CS2)N3CCCC3

mephedrone: CC1=CC=C(C=C1)C(=O)C(C)NC

mdpv: CCCC(C(=O)C1=CC2=C(C=C1)OCO2)N3CCCC3

2c-e: COc1cc(CC)c(cc1CCN)OC

2c-d: O(c1cc(c(OC)cc1CCN)C)C

2c-c: COc1cc(CCN)c(cc1Cl)OC

2c-i: Ic1cc(OC)c(cc1OC)CCN

2c-t-2: CCSc1cc(OC)c(cc1OC)CCN

2c-t-4: CC(C)Sc1cc(OC)c(cc1OC)CCN

2c-h: O(c1ccc(OC)cc1CCN)C

2c-n: [O-][N+](=O)c1cc(OC)c(cc1OC)CCN

2c-p: COC1=C(CCN)C=C(OC)C(CCC)=C1

methylone: CC(C(=O)C1=CC2=C(C=C1)OCO2)NC

ur-144: CCCCCN1C=C(C2=CC=CC=C21)C(=O)C3C(C3(C)C)(C)C

5-fluoro-ur-144: FCCCCCN1C=C(C(C2C(C)(C)C2(C)C)=O)C3=C1C=CC=C3

apinaca: C3C4CC2CC3CC(C4)(C2)NC(=O)c(nn1CCCCC)c5c1cccc5

quinolin-8-yl 5-fluoro-1-pentylindole-3-carboxylate: CCCCCN1C=C(C2=C1C=CC(=C2)F)C(=O)OC3=CC=CC4=C3N=CC=C4

quinolin-8-yl1-(5-fluoropentyl)-1h-indole-3-carboxylate: C1=CC=C2C(=C1)C(=CN2CCCCCF)C(=O)OC3=CC=CC4=C3N=CC=C4

n-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1h-indazole-3-carboxamide: CC(C)C(C(=O)N)NC(=O)C1=NN(C2=CC=CC=C21)CC3=CC=C(C=C3)F

n-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-pentyl-1h-indazole-3-carboxamide: O=C(C1=NN(CCCCC)C2=C1C=CC=C2)NC(C(C)(C)C)C(N)=O

2c-i-nbome: COC1=CC=CC=C1CNCCC2=CC(=C(C=C2OC)I)OC

2c-c-nbome: COc2ccccc2CNCCc(cc1OC)c(OC)cc1Cl

2c-b-nbome: COC1=CC=CC=C1CNCCC2=CC(=C(C=C2OC)Br)OC

4-mec: CCNC(C)C(=O)C1=CC=C(C=C1)C

4-meppp: CC1=CC=C(C=C1)C(=O)C(C)N2CCCC2

alpha-pvp: CCCC(C(C1=CC=CC=C1)=O)N2CCCC2

butylone: CCC(C(=O)C1=CC2=C(C=C1)OCO2)NC

pentedrone: CCCC(C(=O)C1=CC=CC=C1)NC

pentylone: CCCC(C(=O)C1=CC2=C(C=C1)OCO2)NC

flephedrone: CC(C(=O)C1=CC=C(C=C1)F)NC

3-fmc: FC1=CC=CC(=C1)C(C(C)NC)=O

naphyrone: CCCC(C(C1=CC2=C(C=C1)C=CC=C2)=O)N3CCCC3

alpha-pbp: C2CCCN2C(CC)C(=O)c1ccccc1

ab-chminaca: CC(C)C(C(=O)N)NC(=O)C1=NN(C2=CC=CC=C21)CC3CCCCC3

ab-pinaca: CCCCCN1C2=CC=CC=C2C(=N1)C(=O)NC(C(C)C)C(=O)N

thj-2201: O=C(C1=CC=CC2=C1C=CC=C2)C3=NN(CCCCCF)C4=C3C=CC=C4

mab-chminaca: O=C(NC(C(N)=O)C(C)(C)C)C1=NN(CC2CCCCC2)C3=C1C=CC=C3

5f-mdmb-pinaca: COC(=O)C(NC(=O)c1nn(CCCCCF)c2ccccc12)C(C)(C)C

5f-amb: CC(C)C(C(=O)OC)NC(=O)C1=NN(C2=CC=CC=C21)CCCCCF

5f-apinaca: O=C(C1=NN(C2=C1C=CC=C2)CCCCCF)NC34CC5CC(C4)CC(C5)C3

adb-fubinaca: CC(C)(C)C(C(=O)N)NC(=O)C1=NN(C2=CC=CC=C21)CC3=CC=C(C=C3)F

mdmb-chmica: COC(=O)[C@@H](NC(=O)c1cn(CC2CCCCC2)c3ccccc13)C(C)(C)C

mdmb-fubinaca: CC(C)(C)C(C(=O)OC)NC(=O)C1=NN(C2=CC=CC=C21)CC3=CC=C(C=C3)F

mmb-fubinaca: FC(C=C1)=CC=C1CN2N=C(C(N[C@H](C(OC)=O)C(C)C)=O)C3=CC=CC=C32

ethylone: CCNC(C)C(=O)C1=CC2=C(C=C1)OCO2

nm2201: FCCCCCN1C=C(C(OC2=C(C=CC=C3)C3=CC=C2)=O)C4=CC=CC=C41

5f-ab-pinaca: CC(C)C(C(=O)N)NC(=O)C1=NN(C2=CC=CC=C21)CCCCCF

4-cn-cumyl-butinaca: O=C(NC(C)(C)C1=CC=CC=C1)C2=NN(CCCCC#N)C3=C2C=CC=C3

mmb-chmica: CC(C)C(C(=O)OC)NC(=O)C1=CN(C2=CC=CC=C21)CC3CCCCC3

5f-cumyl-p7aica: CC(C)(C1=CC=CC=C1)NC(=O)C2=CN(C3=C2C=CC=N3)CCCCCF

n-ethylpentylone: CCCC(C(=O)C1=CC2=C(C=C1)OCO2)NCC

4f-mdmb-binaca: O=C(N[C@H](C(OC)=O)C(C)(C)C)C1=NN(CCCCF)C2=C1C=CC=C2

para-methoxymethamphetamine: CC(CC1=CC=C(C=C1)OC)NC

gamma-hydroxybutyricacid: C(CC(=O)O)CO

mecloqualone: CC1=NC2=CC=CC=C2C(=O)N1C3=CC=CC=C3Cl

methaqualone: CC1=CC=CC=C1N2C(=NC3=CC=CC=C3C2=O)C

aminorex: C1C(OC(=N1)N)C2=CC=CC=C2

n-benzylpiperazine: C1CN(CCN1)CC2=CC=CC=C2

cathinone: CC(C(=O)C1=CC=CC=C1)N

4,4′-dimethylaminorex: CC(N=C(N)O1)C1C2=CC=C(C)C=C2

fenethylline: CC(CC1=CC=CC=C1)NCCN2C=NC3=C2C(=O)N(C(=O)N3C)C

methcathinone: CC(C(=O)C1=CC=CC=C1)NC

(±)cis-4-methylaminorex: CC1C(OC(=N1)N)C2=CC=CC=C2

n-ethylamphetamine: CC(NCC)CC1=CC=CC=C1

n,n-dimethylamphetamine: CC(CC1=CC=CC=C1)N(C)C

cp-47,479: CCCCCCC(C)(C)c1ccc(c(c1)O)[C@H]2CCC[C@H](C2)O

cannabicyclohexanol: CCCCCCCC(C)(C)C1=CC(=C(C=C1)C2CCCC(C2)O)O

jwh-018: CCCCCN1C=C(C(C2=CC=CC3=CC=CC=C32)=O)C4=CC=CC=C41

jwh-073: CCCCN1C=C(C2=CC=CC=C21)C(=O)C3=CC=CC4=CC=CC=C43

jwh-019: c3cccc2c3cccc2C(=O)c1cn(CCCCCC)c4c1cccc4

jwh-200: O=C(C1=CC=CC2=C1C=CC=C2)C3=CN(C4=C3C=CC=C4)CCN5CCOCC5

jwh-250: COc2ccccc2CC(=O)c(c3ccccc13)cn1CCCCC

jwh-081: CCCCCn3c1ccccc1c(c3)C(=O)c4c2ccccc2c(OC)cc4

jwh-122: CCCCCn1cc(c2c1cccc2)C(=O)c3ccc(c4c3cccc4)C

jwh-398: c14ccccc1n(CCCCC)cc4C(=O)c(cc3)c2ccccc2c3Cl

am-2201: O=C(C1=CN(CCCCCF)C2=C1C=CC=C2)C3=CC=CC4=C3C=CC=C4

am-694: Ic2ccccc2C(=O)c1cn(CCCCCF)c3ccccc13

rcs-4: CCCCCn1cc(c2c1cccc2)C(=O)c3ccc(cc3)OC

rcs-8: COc1ccccc1CC(=O)c2cn(c3c2cccc3)CCC4CCCCC4

jwh-203: Clc2ccccc2CC(=O)c1cn(CCCCC)c3ccccc13

5f-edmb-pinaca: CC(C)(C)C(NC(C1=NN(CCCCCF)C2=C1C=CC=C2)=O)C(OCC)=O

5f-mdmb-pica: O=C(N[C@H](C(OC)=O)C(C)(C)C)C1=CN(CCCCCF)C2=C1C=CC=C2

fub-apinaca: C1C2CC3CC1CC(C2)(C3)NC(=O)C4=NN(C5=CC=CC=C54)CC6=CC=C(C=C6)F

5f-cumyl-pinaca: CC(C)(C1=CC=CC=C1)NC(=O)C2=NN(C3=CC=CC=C32)CCCCCF

fub-144: Fc1ccc(cc1)Cn1cc(c2c1cccc2)C(=O)C1C(C1(C)C)(C)C

2-(ethylamino)-1-phenylhexan-1-one: CCCCC(C(=O)C1=CC=CC=C1)NCC

alpha-pyrrolidinohexiophenone: C1(=CC=CC=C1)C(C(CCCC)N2CCCC2)=O

4-meap: CC1=CC=C(C(C(CCC)NCC)=O)C=C1

4′-methyl-alpha-pyrrolidinohexanophenone: CC1=CC=C(C(C(CCCC)N2CCCC2)=O)C=C1

1-phenyl-2-(pyrrolidin-1-yl)heptan-1-one: CCCCCC(C(=O)C1=CC=CC=C1)N2CCCC2

4′-chloro-alpha-pvp: CCCC(C(=O)C1=CC=C(C=C1)Cl)N2CCCC2

brorphine: CC(C1=CC=C(Br)C=C1)N2CCC(N3C(NC4=C3C=CC=C4)=O)CC2

Solution:

structure of schedule one molecules:

acetyl-alpha-methylfentanyl: CC(CC1=CC=CC=C1)N2CCC(CC2)N(C3=CC=CC=C3)C(=O)C

smiles_non_kekule:    CC(=O)N(c1ccccc1)C1CCN(C(C)Cc2ccccc2)CC1
smiles_kekule:    CC(=O)N(C1=CC=CC=C1)C1CCN(C(C)CC2=CC=CC=C2)CC1
inchi:    InChI=1S/C22H28N2O/c1-18(17-20-9-5-3-6-10-20)23-15-13-22(14-16-23)24(19(2)25)21-11-7-4-8-12-21/h3-12,18,22H,13-17H2,1-2H3
inchiKey:    OKTLVZBUKMRPLL-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](=[#8])-[#6]
smarts_isomeric:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](=[#8])-[#6]

acetylmethadol: CCC(C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)OC(=O)C

smiles_non_kekule:    CCC(OC(C)=O)C(CC(C)N(C)C)(c1ccccc1)c1ccccc1
smiles_kekule:    CCC(OC(C)=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1
inchi:    InChI=1S/C23H31NO2/c1-6-22(26-19(3)25)23(17-18(2)24(4)5,20-13-9-7-10-14-20)21-15-11-8-12-16-21/h7-16,18,22H,6,17H2,1-5H3
inchiKey:    XBMIVRRWGCYBTQ-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](-[#6](-[#6]-[#6](-[#6])-[#7](-[#6])-[#6])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8]-[#6](=[#8])-[#6]
smarts_isomeric:    [#6]-[#6]-[#6](-[#6](-[#6]-[#6](-[#6])-[#7](-[#6])-[#6])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8]-[#6](=[#8])-[#6]

acetylfentanyl: CC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3

smiles_non_kekule:    CC(=O)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    CC(=O)N(C1=CC=CC=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C21H26N2O/c1-18(24)23(20-10-6-3-7-11-20)21-13-16-22(17-14-21)15-12-19-8-4-2-5-9-19/h2-11,21H,12-17H2,1H3
inchiKey:    FYIUUQUPOKIKNI-UHFFFAOYSA-N
smarts:    [#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

acrylfentanyl: C=CC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3

smiles_non_kekule:    C=CC(=O)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    C=CC(=O)N(C1=CC=CC=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C22H26N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h2-12,21H,1,13-18H2
inchiKey:    RFQNLMWUIJJEQF-UHFFFAOYSA-N
smarts:    [#6]=[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]=[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

ah-7921: ClC1=CC=C(C(NCC2(CCCCC2)N(C)C)=O)C=C1Cl

smiles_non_kekule:    CN(C)C1(CNC(=O)c2ccc(Cl)c(Cl)c2)CCCCC1
smiles_kekule:    CN(C)C1(CNC(=O)C2=CC=C(Cl)C(Cl)=C2)CCCCC1
inchi:    InChI=1S/C16H22Cl2N2O/c1-20(2)16(8-4-3-5-9-16)11-19-15(21)12-6-7-13(17)14(18)10-12/h6-7,10H,3-5,8-9,11H2,1-2H3,(H,19,21)
inchiKey:    JMZROFPPEXCTST-UHFFFAOYSA-N
smarts:    [#17]-[#6]1:[#6]:[#6]:[#6](-[#6](-[#7]-[#6]-[#6]2(-[#6]-[#6]-[#6]-[#6]-[#6]-2)-[#7](-[#6])-[#6])=[#8]):[#6]:[#6]:1-[#17]
smarts_isomeric:    [#17]-[#6]1:[#6]:[#6]:[#6](-[#6](-[#7]-[#6]-[#6]2(-[#6]-[#6]-[#6]-[#6]-[#6]-2)-[#7](-[#6])-[#6])=[#8]):[#6]:[#6]:1-[#17]

allylprodine: CCC(=O)OC1(CCN(CC1CC=C)C)C2=CC=CC=C2

smiles_non_kekule:    C=CCC1CN(C)CCC1(OC(=O)CC)c1ccccc1
smiles_kekule:    C=CCC1CN(C)CCC1(OC(=O)CC)C1=CC=CC=C1
inchi:    InChI=1S/C18H25NO2/c1-4-9-16-14-19(3)13-12-18(16,21-17(20)5-2)15-10-7-6-8-11-15/h4,6-8,10-11,16H,1,5,9,12-14H2,2-3H3
inchiKey:    KGYFOSCXVAXULR-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#8]-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1-[#6]-[#6]=[#6])-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#8]-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1-[#6]-[#6]=[#6])-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

alphaacetylmethadol: CCC(C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)OC(=O)C

alphameprodine: CCC1CN(CCC1(C2=CC=CC=C2)OC(=O)CC)C

smiles_non_kekule:    CCC(=O)OC1(c2ccccc2)CCN(C)CC1CC
smiles_kekule:    CCC(=O)OC1(C2=CC=CC=C2)CCN(C)CC1CC
inchi:    InChI=1S/C17H25NO2/c1-4-14-13-18(3)12-11-17(14,20-16(19)5-2)15-9-7-6-8-10-15/h6-10,14H,4-5,11-13H2,1-3H3
inchiKey:    ODEGQXRCQDVXSJ-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]1-[#6]-[#7](-[#6]-[#6]-[#6]-1(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8]-[#6](=[#8])-[#6]-[#6])-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]1-[#6]-[#7](-[#6]-[#6]-[#6]-1(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8]-[#6](=[#8])-[#6]-[#6])-[#6]

alphamethadol: CCC(C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)O

smiles_non_kekule:    CCC(O)C(CC(C)N(C)C)(c1ccccc1)c1ccccc1
smiles_kekule:    CCC(O)C(CC(C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1
inchi:    InChI=1S/C21H29NO/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17,20,23H,5,16H2,1-4H3
inchiKey:    QIRAYNIFEOXSPW-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](-[#6](-[#6]-[#6](-[#6])-[#7](-[#6])-[#6])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8]
smarts_isomeric:    [#6]-[#6]-[#6](-[#6](-[#6]-[#6](-[#6])-[#7](-[#6])-[#6])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8]

alpha-methylfentanyl: O=C(N(c1ccccc1)C3CCN(C(Cc2ccccc2)C)CC3)CC

smiles_non_kekule:    CCC(=O)N(c1ccccc1)C1CCN(C(C)Cc2ccccc2)CC1
smiles_kekule:    CCC(=O)N(C1=CC=CC=C1)C1CCN(C(C)CC2=CC=CC=C2)CC1
inchi:    InChI=1S/C23H30N2O/c1-3-23(26)25(21-12-8-5-9-13-21)22-14-16-24(17-15-22)19(2)18-20-10-6-4-7-11-20/h4-13,19,22H,3,14-18H2,1-2H3
inchiKey:    NGTVDHYUFBKWID-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1-[#6]-[#6]-[#7](-[#6](-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6])-[#6]-[#6]-1)-[#6]-[#6]
smarts_isomeric:    [#8]=[#6](-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1-[#6]-[#6]-[#7](-[#6](-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6])-[#6]-[#6]-1)-[#6]-[#6]

alpha-methylthiofentanyl: CCC(=O)N(C1CCN(CC1)C(C)CC2=CC=CS2)C3=CC=CC=C3

smiles_non_kekule:    CCC(=O)N(c1ccccc1)C1CCN(C(C)Cc2cccs2)CC1
smiles_kekule:    CCC(=O)N(C1=CC=CC=C1)C1CCN(C(C)CC2=CC=CS2)CC1
inchi:    InChI=1S/C21H28N2OS/c1-3-21(24)23(18-8-5-4-6-9-18)19-11-13-22(14-12-19)17(2)16-20-10-7-15-25-20/h4-10,15,17,19H,3,11-14,16H2,1-2H3
inchiKey:    YPOXDUYRRSUFFG-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6](-[#6])-[#6]-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6](-[#6])-[#6]-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

benzethidine: CCOC(=O)C1(CCN(CC1)CCOCC2=CC=CC=C2)C3=CC=CC=C3

smiles_non_kekule:    CCOC(=O)C1(c2ccccc2)CCN(CCOCc2ccccc2)CC1
smiles_kekule:    CCOC(=O)C1(C2=CC=CC=C2)CCN(CCOCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C23H29NO3/c1-2-27-22(25)23(21-11-7-4-8-12-21)13-15-24(16-14-23)17-18-26-19-20-9-5-3-6-10-20/h3-12H,2,13-19H2,1H3
inchiKey:    UVTBZAWTRVBTMK-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#8]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#8]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

betacetylmethadol: CCC(C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)OC(=O)C

beta-hydroxyfentanyl: CCC(=O)N(C1CCN(CC1)CC(C2=CC=CC=C2)O)C3=CC=CC=C3

smiles_non_kekule:    CCC(=O)N(c1ccccc1)C1CCN(CC(O)c2ccccc2)CC1
smiles_kekule:    CCC(=O)N(C1=CC=CC=C1)C1CCN(CC(O)C2=CC=CC=C2)CC1
inchi:    InChI=1S/C22H28N2O2/c1-2-22(26)24(19-11-7-4-8-12-19)20-13-15-23(16-14-20)17-21(25)18-9-5-3-6-10-18/h3-12,20-21,25H,2,13-17H2,1H3
inchiKey:    JEFVHLMGRUJLET-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

beta-hydroxy-3-methylfentanyl: CCC(=O)N(C1CCN(CC1C)CC(C2=CC=CC=C2)O)C3=CC=CC=C3

smiles_non_kekule:    CCC(=O)N(c1ccccc1)C1CCN(CC(O)c2ccccc2)CC1C
smiles_kekule:    CCC(=O)N(C1=CC=CC=C1)C1CCN(CC(O)C2=CC=CC=C2)CC1C
inchi:    InChI=1S/C23H30N2O2/c1-3-23(27)25(20-12-8-5-9-13-20)21-14-15-24(16-18(21)2)17-22(26)19-10-6-4-7-11-19/h4-13,18,21-22,26H,3,14-17H2,1-2H3
inchiKey:    FRPRNNRJTCONEC-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1-[#6])-[#6]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1-[#6])-[#6]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

beta-hydroxythiofentanyl: CCC(=O)N(C1CCN(CC1)CC(C2=CC=CS2)O)C3=CC=CC=C3

smiles_non_kekule:    CCC(=O)N(c1ccccc1)C1CCN(CC(O)c2cccs2)CC1
smiles_kekule:    CCC(=O)N(C1=CC=CC=C1)C1CCN(CC(O)C2=CC=CS2)CC1
inchi:    InChI=1S/C20H26N2O2S/c1-2-20(24)22(16-7-4-3-5-8-16)17-10-12-21(13-11-17)15-18(23)19-9-6-14-25-19/h3-9,14,17-18,23H,2,10-13,15H2,1H3
inchiKey:    GLAAETOTOUGGSB-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

betameprodine: CCC1CN(CCC1(C2=CC=CC=C2)OC(=O)CC)C

betamethadol: CCC(C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)O

beta-methylfentanyl: CCC(=O)N(C1CCN(CC1)CC(C)C2=CC=CC=C2)C3=CC=CC=C3

smiles_non_kekule:    CCC(=O)N(c1ccccc1)C1CCN(CC(C)c2ccccc2)CC1
smiles_kekule:    CCC(=O)N(C1=CC=CC=C1)C1CCN(CC(C)C2=CC=CC=C2)CC1
inchi:    InChI=1S/C23H30N2O/c1-3-23(26)25(21-12-8-5-9-13-21)22-14-16-24(17-15-22)18-19(2)20-10-6-4-7-11-20/h4-13,19,22H,3,14-18H2,1-2H3
inchiKey:    UXIGUKSHASXDNI-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6](-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6](-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

beta′-phenylfentanyl: O=C(CCC1=CC=CC=C1)N(C2CCN(CCC3=CC=CC=C3)CC2)C4=CC=CC=C4

smiles_non_kekule:    O=C(CCc1ccccc1)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    O=C(CCC1=CC=CC=C1)N(C1=CC=CC=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C28H32N2O/c31-28(17-16-24-10-4-1-5-11-24)30(26-14-8-3-9-15-26)27-19-22-29(23-20-27)21-18-25-12-6-2-7-13-25/h1-15,27H,16-23H2
inchiKey:    DIRAGWDYMRIDIO-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#8]=[#6](-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

betaprodine: CCC(=O)OC1(CCN(CC1C)C)C2=CC=CC=C2

smiles_non_kekule:    CCC(=O)OC1(c2ccccc2)CCN(C)CC1C
smiles_kekule:    CCC(=O)OC1(C2=CC=CC=C2)CCN(C)CC1C
inchi:    InChI=1S/C16H23NO2/c1-4-15(18)19-16(14-8-6-5-7-9-14)10-11-17(3)12-13(16)2/h5-9,13H,4,10-12H2,1-3H3
inchiKey:    UVAZQQHAVMNMHE-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#8]-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1-[#6])-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#8]-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1-[#6])-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

butyrylfentanyl: CCCC(=O)N(C2CCN(CCc1ccccc1)CC2)c3ccccc3

smiles_non_kekule:    CCCC(=O)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    CCCC(=O)N(C1=CC=CC=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C23H30N2O/c1-2-9-23(26)25(21-12-7-4-8-13-21)22-15-18-24(19-16-22)17-14-20-10-5-3-6-11-20/h3-8,10-13,22H,2,9,14-19H2,1H3
inchiKey:    QQOMYEQLWQJRKK-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

clonitazene: CCN(CC)CCN1C2=C(C=C(C=C2)[N+](=O)[O-])N=C1CC3=CC=C(C=C3)Cl

smiles_non_kekule:    CCN(CC)CCn1c(Cc2ccc(Cl)cc2)nc2cc([N+](=O)[O-])ccc21
smiles_kekule:    CCN(CC)CCN1C(CC2=CC=C(Cl)C=C2)=NC2=C1C=CC([N+](=O)[O-])=C2
inchi:    InChI=1S/C20H23ClN4O2/c1-3-23(4-2)11-12-24-19-10-9-17(25(26)27)14-18(19)22-20(24)13-15-5-7-16(21)8-6-15/h5-10,14H,3-4,11-13H2,1-2H3
inchiKey:    GPZLDQAEBHTMPG-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7](-[#6]-[#6])-[#6]-[#6]-[#7]1:[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#7+](=[#8])-[#8-]):[#7]:[#6]:1-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#17]
smarts_isomeric:    [#6]-[#6]-[#7](-[#6]-[#6])-[#6]-[#6]-[#7]1:[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#7+](=[#8])-[#8-]):[#7]:[#6]:1-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#17]

crotonylfentanyl: CC=CC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3

smiles_non_kekule:    CC=CC(=O)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    CC=CC(=O)N(C1=CC=CC=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C23H28N2O/c1-2-9-23(26)25(21-12-7-4-8-13-21)22-15-18-24(19-16-22)17-14-20-10-5-3-6-11-20/h2-13,22H,14-19H2,1H3
inchiKey:    VDYXGPCGBKLRDA-UHFFFAOYSA-N
smarts:    [#6]-[#6]=[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]=[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

cyclopentylfentanyl: C1CCC(C1)C(=O)N(C2CCN(CC2)CCC3=CC=CC=C3)C4=CC=CC=C4

smiles_non_kekule:    O=C(C1CCCC1)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    O=C(C1CCCC1)N(C1=CC=CC=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C25H32N2O/c28-25(22-11-7-8-12-22)27(23-13-5-2-6-14-23)24-16-19-26(20-17-24)18-15-21-9-3-1-4-10-21/h1-6,9-10,13-14,22,24H,7-8,11-12,15-20H2
inchiKey:    PEASFKSPITUZGT-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#6](-[#6]-1)-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#6](-[#6]-1)-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

cyclopropylfentanyl: C1CC1C(=O)N(C2CCN(CC2)CCC3=CC=CC=C3)C4=CC=CC=C4

smiles_non_kekule:    O=C(C1CC1)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    O=C(C1CC1)N(C1=CC=CC=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C23H28N2O/c26-23(20-11-12-20)25(21-9-5-2-6-10-21)22-14-17-24(18-15-22)16-13-19-7-3-1-4-8-19/h1-10,20,22H,11-18H2
inchiKey:    OIQSKDSKROTEMN-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-1-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1-[#6]-[#6]-1-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

dextromoramide: CC(CN1CCOCC1)C(C2=CC=CC=C2)(C3=CC=CC=C3)C(=O)N4CCCC4

smiles_non_kekule:    CC(CN1CCOCC1)C(C(=O)N1CCCC1)(c1ccccc1)c1ccccc1
smiles_kekule:    CC(CN1CCOCC1)C(C(=O)N1CCCC1)(C1=CC=CC=C1)C1=CC=CC=C1
inchi:    InChI=1S/C25H32N2O2/c1-21(20-26-16-18-29-19-17-26)25(22-10-4-2-5-11-22,23-12-6-3-7-13-23)24(28)27-14-8-9-15-27/h2-7,10-13,21H,8-9,14-20H2,1H3
inchiKey:    INUNXTSAACVKJS-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1)-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](=[#8])-[#7]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6](-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1)-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](=[#8])-[#7]1-[#6]-[#6]-[#6]-[#6]-1

diampromide: CCC(=O)N(CC(C)N(C)CCC1=CC=CC=C1)C2=CC=CC=C2

smiles_non_kekule:    CCC(=O)N(CC(C)N(C)CCc1ccccc1)c1ccccc1
smiles_kekule:    CCC(=O)N(CC(C)N(C)CCC1=CC=CC=C1)C1=CC=CC=C1
inchi:    InChI=1S/C21H28N2O/c1-4-21(24)23(20-13-9-6-10-14-20)17-18(2)22(3)16-15-19-11-7-5-8-12-19/h5-14,18H,4,15-17H2,1-3H3
inchiKey:    RXTHKWVSXOIHJS-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]-[#6](-[#6])-[#7](-[#6])-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]-[#6](-[#6])-[#7](-[#6])-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

diethylthiambutene: CCN(CC)C(C)C=C(C1=CC=CS1)C2=CC=CS2

smiles_non_kekule:    CCN(CC)C(C)C=C(c1cccs1)c1cccs1
smiles_kekule:    CCN(CC)C(C)C=C(C1=CC=CS1)C1=CC=CS1
inchi:    InChI=1S/C16H21NS2/c1-4-17(5-2)13(3)12-14(15-8-6-10-18-15)16-9-7-11-19-16/h6-13H,4-5H2,1-3H3
inchiKey:    CBYWMRHUUVRIAF-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7](-[#6]-[#6])-[#6](-[#6])-[#6]=[#6](-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#6]1:[#6]:[#6]:[#6]:[#16]:1
smarts_isomeric:    [#6]-[#6]-[#7](-[#6]-[#6])-[#6](-[#6])-[#6]=[#6](-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#6]1:[#6]:[#6]:[#6]:[#16]:1

difenoxin: C1CN(CCC1(C2=CC=CC=C2)C(=O)O)CCC(C#N)(C3=CC=CC=C3)C4=CC=CC=C4

smiles_non_kekule:    N#CC(CCN1CCC(C(=O)O)(c2ccccc2)CC1)(c1ccccc1)c1ccccc1
smiles_kekule:    N#CC(CCN1CCC(C(=O)O)(C2=CC=CC=C2)CC1)(C1=CC=CC=C1)C1=CC=CC=C1
inchi:    InChI=1S/C28H28N2O2/c29-22-28(24-12-6-2-7-13-24,25-14-8-3-9-15-25)18-21-30-19-16-27(17-20-30,26(31)32)23-10-4-1-5-11-23/h1-15H,16-21H2,(H,31,32)
inchiKey:    UFIVBRCCIRTJTN-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#7](-[#6]-[#6]-[#6]-1(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](=[#8])-[#8])-[#6]-[#6]-[#6](-[#6]#[#7])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1-[#6]-[#7](-[#6]-[#6]-[#6]-1(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](=[#8])-[#8])-[#6]-[#6]-[#6](-[#6]#[#7])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

dimenoxadol: CCOC(C1=CC=CC=C1)(C2=CC=CC=C2)C(=O)OCCN(C)C

smiles_non_kekule:    CCOC(C(=O)OCCN(C)C)(c1ccccc1)c1ccccc1
smiles_kekule:    CCOC(C(=O)OCCN(C)C)(C1=CC=CC=C1)C1=CC=CC=C1
inchi:    InChI=1S/C20H25NO3/c1-4-24-20(17-11-7-5-8-12-17,18-13-9-6-10-14-18)19(22)23-16-15-21(2)3/h5-14H,4,15-16H2,1-3H3
inchiKey:    RHUWRJWFHUKVED-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](=[#8])-[#8]-[#6]-[#6]-[#7](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6]-[#8]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](=[#8])-[#8]-[#6]-[#6]-[#7](-[#6])-[#6]

dimepheptanol: CCC(C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)O

dimethylthiambutene: CC(C=C(C1=CC=CS1)C2=CC=CS2)N(C)C

smiles_non_kekule:    CC(C=C(c1cccs1)c1cccs1)N(C)C
smiles_kekule:    CC(C=C(C1=CC=CS1)C1=CC=CS1)N(C)C
inchi:    InChI=1S/C14H17NS2/c1-11(15(2)3)10-12(13-6-4-8-16-13)14-7-5-9-17-14/h4-11H,1-3H3
inchiKey:    CANBGVXYBPOLRR-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]=[#6](-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#7](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6](-[#6]=[#6](-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#7](-[#6])-[#6]

dioxaphetylbutyrate: CCOC(=O)C(CCN1CCOCC1)(c1ccccc1)c1ccccc1

smiles_non_kekule:    CCOC(=O)C(CCN1CCOCC1)(c1ccccc1)c1ccccc1
smiles_kekule:    CCOC(=O)C(CCN1CCOCC1)(C1=CC=CC=C1)C1=CC=CC=C1
inchi:    InChI=1S/C22H27NO3/c1-2-26-21(24)22(19-9-5-3-6-10-19,20-11-7-4-8-12-20)13-14-23-15-17-25-18-16-23/h3-12H,2,13-18H2,1H3
inchiKey:    LQGIXNQCOXNCRP-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6](-[#6]-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6](-[#6]-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

dipipanone: CCC(=O)C(CC(C)N1CCCCC1)(C2=CC=CC=C2)C3=CC=CC=C3

smiles_non_kekule:    CCC(=O)C(CC(C)N1CCCCC1)(c1ccccc1)c1ccccc1
smiles_kekule:    CCC(=O)C(CC(C)N1CCCCC1)(C1=CC=CC=C1)C1=CC=CC=C1
inchi:    InChI=1S/C24H31NO/c1-3-23(26)24(21-13-7-4-8-14-21,22-15-9-5-10-16-22)19-20(2)25-17-11-6-12-18-25/h4-5,7-10,13-16,20H,3,6,11-12,17-19H2,1-2H3
inchiKey:    SVDHSZFEQYXRDC-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#6](-[#6]-[#6](-[#6])-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#6](-[#6]-[#6](-[#6])-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

ethylmethylthiambutene: CCN(C)C(C)C=C(C1=CC=CS1)C2=CC=CS2

smiles_non_kekule:    CCN(C)C(C)C=C(c1cccs1)c1cccs1
smiles_kekule:    CCN(C)C(C)C=C(C1=CC=CS1)C1=CC=CS1
inchi:    InChI=1S/C15H19NS2/c1-4-16(3)12(2)11-13(14-7-5-9-17-14)15-8-6-10-18-15/h5-12H,4H2,1-3H3
inchiKey:    MORSAEFGQPDBKM-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7](-[#6])-[#6](-[#6])-[#6]=[#6](-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#6]1:[#6]:[#6]:[#6]:[#16]:1
smarts_isomeric:    [#6]-[#6]-[#7](-[#6])-[#6](-[#6])-[#6]=[#6](-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#6]1:[#6]:[#6]:[#6]:[#16]:1

etonitazene: CCN(CC)CCN1C2=C(C=C(C=C2)[N+](=O)[O-])N=C1CC3=CC=C(C=C3)OCC

smiles_non_kekule:    CCOc1ccc(Cc2nc3cc([N+](=O)[O-])ccc3n2CCN(CC)CC)cc1
smiles_kekule:    CCOC1=CC=C(CC2=NC3=C(C=CC([N+](=O)[O-])=C3)N2CCN(CC)CC)C=C1
inchi:    InChI=1S/C22H28N4O3/c1-4-24(5-2)13-14-25-21-12-9-18(26(27)28)16-20(21)23-22(25)15-17-7-10-19(11-8-17)29-6-3/h7-12,16H,4-6,13-15H2,1-3H3
inchiKey:    PXDBZSCGSQSKST-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7](-[#6]-[#6])-[#6]-[#6]-[#7]1:[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#7+](=[#8])-[#8-]):[#7]:[#6]:1-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#6]
smarts_isomeric:    [#6]-[#6]-[#7](-[#6]-[#6])-[#6]-[#6]-[#7]1:[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#7+](=[#8])-[#8-]):[#7]:[#6]:1-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#6]

etoxeridine: CCOC(=O)C1(CCN(CC1)CCOCCO)C2=CC=CC=C2

smiles_non_kekule:    CCOC(=O)C1(c2ccccc2)CCN(CCOCCO)CC1
smiles_kekule:    CCOC(=O)C1(C2=CC=CC=C2)CCN(CCOCCO)CC1
inchi:    InChI=1S/C18H27NO4/c1-2-23-17(21)18(16-6-4-3-5-7-16)8-10-19(11-9-18)12-14-22-15-13-20/h3-7,20H,2,8-15H2,1H3
inchiKey:    KJTKYGFGPQSRRA-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#8]-[#6]-[#6]-[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#8]-[#6]-[#6]-[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

fentanylcarbamate: O=C(N(C1=CC=CC=C1)C2CCN(CCC3=CC=CC=C3)CC2)OCC

smiles_non_kekule:    CCOC(=O)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    CCOC(=O)N(C1=CC=CC=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C22H28N2O2/c1-2-26-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h3-12,21H,2,13-18H2,1H3
inchiKey:    BPXVEPWHWMDYCP-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#8]-[#6]-[#6]
smarts_isomeric:    [#8]=[#6](-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#8]-[#6]-[#6]

4-fluoroisobutyrylfentanyl: CC(C)C(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=C(C=C3)F

smiles_non_kekule:    CC(C)C(=O)N(c1ccc(F)cc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    CC(C)C(=O)N(C1=CC=C(F)C=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C23H29FN2O/c1-18(2)23(27)26(21-10-8-20(24)9-11-21)22-13-16-25(17-14-22)15-12-19-6-4-3-5-7-19/h3-11,18,22H,12-17H2,1-2H3
inchiKey:    OZDOSQNUJIXEOR-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#9]
smarts_isomeric:    [#6]-[#6](-[#6])-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#9]

2′-fluoroortho-fluorofentanyl: O=C(CC)N(C1CCN(CCC2=CC=CC=C2F)CC1)C3=C(F)C=CC=C3

smiles_non_kekule:    CCC(=O)N(c1ccccc1F)C1CCN(CCc2ccccc2F)CC1
smiles_kekule:    CCC(=O)N(C1=C(F)C=CC=C1)C1CCN(CCC2=CC=CC=C2F)CC1
inchi:    InChI=1S/C22H26F2N2O/c1-2-22(27)26(21-10-6-5-9-20(21)24)18-12-15-25(16-13-18)14-11-17-7-3-4-8-19(17)23/h3-10,18H,2,11-16H2,1H3
inchiKey:    AUXYZYMWQUXVDV-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6]-[#6])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2-[#9])-[#6]-[#6]-1)-[#6]1:[#6](-[#9]):[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#8]=[#6](-[#6]-[#6])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2-[#9])-[#6]-[#6]-1)-[#6]1:[#6](-[#9]):[#6]:[#6]:[#6]:[#6]:1

furanylfentanyl: C1CN(CCC1N(C2=CC=CC=C2)C(=O)C3=CC=CO3)CCC4=CC=CC=C4

smiles_non_kekule:    O=C(c1ccco1)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    O=C(C1=CC=CO1)N(C1=CC=CC=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C24H26N2O2/c27-24(23-12-7-19-28-23)26(21-10-5-2-6-11-21)22-14-17-25(18-15-22)16-13-20-8-3-1-4-9-20/h1-12,19,22H,13-18H2
inchiKey:    FZJVHWISUGFFQV-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#7](-[#6]-[#6]-[#6]-1-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#8]:1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1-[#6]-[#7](-[#6]-[#6]-[#6]-1-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#8]:1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

furethidine: CCOC(=O)C1(CCN(CC1)CCOCC2CCCO2)C3=CC=CC=C3

smiles_non_kekule:    CCOC(=O)C1(c2ccccc2)CCN(CCOCC2CCCO2)CC1
smiles_kekule:    CCOC(=O)C1(C2=CC=CC=C2)CCN(CCOCC2CCCO2)CC1
inchi:    InChI=1S/C21H31NO4/c1-2-25-20(23)21(18-7-4-3-5-8-18)10-12-22(13-11-21)14-16-24-17-19-9-6-15-26-19/h3-5,7-8,19H,2,6,9-17H2,1H3
inchiKey:    NNCOZXNZFLUYGG-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#8]-[#6]-[#6]1-[#6]-[#6]-[#6]-[#8]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#8]-[#6]-[#6]1-[#6]-[#6]-[#6]-[#8]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

hydroxypethidine: CCOC(=O)C1(CCN(CC1)C)C2=CC(=CC=C2)O

smiles_non_kekule:    CCOC(=O)C1(c2cccc(O)c2)CCN(C)CC1
smiles_kekule:    CCOC(=O)C1(C2=CC(O)=CC=C2)CCN(C)CC1
inchi:    InChI=1S/C15H21NO3/c1-3-19-14(18)15(7-9-16(2)10-8-15)12-5-4-6-13(17)11-12/h4-6,11,17H,3,7-10H2,1-2H3
inchiKey:    WTJBNMUWRKPFRS-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6])-[#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1)-[#8]
smarts_isomeric:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6])-[#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1)-[#8]

isobutyrylfentanyl: CC(C)C(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3

smiles_non_kekule:    CC(C)C(=O)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    CC(C)C(=O)N(C1=CC=CC=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C23H30N2O/c1-19(2)23(26)25(21-11-7-4-8-12-21)22-14-17-24(18-15-22)16-13-20-9-5-3-6-10-20/h3-12,19,22H,13-18H2,1-2H3
inchiKey:    WRPFPNIHTOSMKU-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6](-[#6])-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

isotonitazene: CCN(CC)CCN1C(CC2=CC=C(OC(C)C)C=C2)=NC3=CC([N+]([O-])=O)=CC=C31

smiles_non_kekule:    CCN(CC)CCn1c(Cc2ccc(OC(C)C)cc2)nc2cc([N+](=O)[O-])ccc21
smiles_kekule:    CCN(CC)CCN1C(CC2=CC=C(OC(C)C)C=C2)=NC2=CC([N+](=O)[O-])=CC=C21
inchi:    InChI=1S/C23H30N4O3/c1-5-25(6-2)13-14-26-22-12-9-19(27(28)29)16-21(22)24-23(26)15-18-7-10-20(11-8-18)30-17(3)4/h7-12,16-17H,5-6,13-15H2,1-4H3
inchiKey:    OIOQREYBGDAYGT-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7](-[#6]-[#6])-[#6]-[#6]-[#7]1:[#6](-[#6]-[#6]2:[#6]:[#6]:[#6](-[#8]-[#6](-[#6])-[#6]):[#6]:[#6]:2):[#7]:[#6]2:[#6]:[#6](-[#7+](-[#8-])=[#8]):[#6]:[#6]:[#6]:1:2
smarts_isomeric:    [#6]-[#6]-[#7](-[#6]-[#6])-[#6]-[#6]-[#7]1:[#6](-[#6]-[#6]2:[#6]:[#6]:[#6](-[#8]-[#6](-[#6])-[#6]):[#6]:[#6]:2):[#7]:[#6]2:[#6]:[#6](-[#7+](-[#8-])=[#8]):[#6]:[#6]:[#6]:1:2

ketobemidone: CCC(=O)C1(CCN(CC1)C)C2=CC(=CC=C2)O

smiles_non_kekule:    CCC(=O)C1(c2cccc(O)c2)CCN(C)CC1
smiles_kekule:    CCC(=O)C1(C2=CC(O)=CC=C2)CCN(C)CC1
inchi:    InChI=1S/C15H21NO2/c1-3-14(18)15(7-9-16(2)10-8-15)12-5-4-6-13(17)11-12/h4-6,11,17H,3,7-10H2,1-2H3
inchiKey:    ALFGKMXHOUSVAD-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6])-[#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1)-[#8]
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6])-[#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1)-[#8]

levomoramide: C[C@@H](CN1CCOCC1)C(c1ccccc1)(c1ccccc1)C(=O)N1CCCC1

smiles_non_kekule:    C[C@@H](CN1CCOCC1)C(C(=O)N1CCCC1)(c1ccccc1)c1ccccc1
smiles_kekule:    C[C@@H](CN1CCOCC1)C(C(=O)N1CCCC1)(C1=CC=CC=C1)C1=CC=CC=C1
inchi:    InChI=1S/C25H32N2O2/c1-21(20-26-16-18-29-19-17-26)25(22-10-4-2-5-11-22,23-12-6-3-7-13-23)24(28)27-14-8-9-15-27/h2-7,10-13,21H,8-9,14-20H2,1H3/t21-/m0/s1
inchiKey:    INUNXTSAACVKJS-NRFANRHFSA-N
smarts:    [#6]-[#6H](-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1)-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](=[#8])-[#7]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6@@H](-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1)-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](=[#8])-[#7]1-[#6]-[#6]-[#6]-[#6]-1

levophenacylmorphan: C1CCC23CCN(C(C2C1)CC4=C3C=C(C=C4)O)CC(=O)C5=CC=CC=C5

smiles_non_kekule:    O=C(CN1CCC23CCCCC2C1Cc1ccc(O)cc13)c1ccccc1
smiles_kekule:    O=C(CN1CCC23CCCCC2C1CC1=C3C=C(O)C=C1)C1=CC=CC=C1
inchi:    InChI=1S/C24H27NO2/c26-19-10-9-18-14-22-20-8-4-5-11-24(20,21(18)15-19)12-13-25(22)16-23(27)17-6-2-1-3-7-17/h1-3,6-7,9-10,15,20,22,26H,4-5,8,11-14,16H2
inchiKey:    RCYBMSQOSGJZLO-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#6]23-[#6]-[#6]-[#7](-[#6](-[#6]-2-[#6]-1)-[#6]-[#6]1:[#6]-3:[#6]:[#6](:[#6]:[#6]:1)-[#8])-[#6]-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#6]23-[#6]-[#6]-[#7](-[#6](-[#6]-2-[#6]-1)-[#6]-[#6]1:[#6]-3:[#6]:[#6](:[#6]:[#6]:1)-[#8])-[#6]-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

methoxyacetylfentanyl: c3ccccc3N(C(=O)COC)C1CCN(CC1)CCc2ccccc2

smiles_non_kekule:    COCC(=O)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    COCC(=O)N(C1=CC=CC=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C22H28N2O2/c1-26-18-22(25)24(20-10-6-3-7-11-20)21-13-16-23(17-14-21)15-12-19-8-4-2-5-9-19/h2-11,21H,12-18H2,1H3
inchiKey:    SADNVKRDSWWFTK-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#7](-[#6](=[#8])-[#6]-[#8]-[#6])-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#7](-[#6](=[#8])-[#6]-[#8]-[#6])-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

4′-methylacetylfentanyl: CC(N(C1CCN(CCC2=CC=C(C)C=C2)CC1)C3=CC=CC=C3)=O

smiles_non_kekule:    CC(=O)N(c1ccccc1)C1CCN(CCc2ccc(C)cc2)CC1
smiles_kekule:    CC(=O)N(C1=CC=CC=C1)C1CCN(CCC2=CC=C(C)C=C2)CC1
inchi:    InChI=1S/C22H28N2O/c1-18-8-10-20(11-9-18)12-15-23-16-13-22(14-17-23)24(19(2)25)21-6-4-3-5-7-21/h3-11,22H,12-17H2,1-2H3
inchiKey:    BBMRIHXVAUNKEV-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)=[#8]
smarts_isomeric:    [#6]-[#6](-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)=[#8]

3-methylfentanyl: CCC(=O)N(C1CCN(CC1C)CCC2=CC=CC=C2)C3=CC=CC=C3

smiles_non_kekule:    CCC(=O)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1C
smiles_kekule:    CCC(=O)N(C1=CC=CC=C1)C1CCN(CCC2=CC=CC=C2)CC1C
inchi:    InChI=1S/C23H30N2O/c1-3-23(26)25(21-12-8-5-9-13-21)22-15-17-24(18-19(22)2)16-14-20-10-6-4-7-11-20/h4-13,19,22H,3,14-18H2,1-2H3
inchiKey:    MLQRZXNZHAOCHQ-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1-[#6])-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1-[#6])-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

3-methylthiofentanyl: CCC(=O)N(C1CCN(CC1C)CCC2=CC=CS2)C3=CC=CC=C3

smiles_non_kekule:    CCC(=O)N(c1ccccc1)C1CCN(CCc2cccs2)CC1C
smiles_kekule:    CCC(=O)N(C1=CC=CC=C1)C1CCN(CCC2=CC=CS2)CC1C
inchi:    InChI=1S/C21H28N2OS/c1-3-21(24)23(18-8-5-4-6-9-18)20-12-14-22(16-17(20)2)13-11-19-10-7-15-25-19/h4-10,15,17,20H,3,11-14,16H2,1-2H3
inchiKey:    SRARDYUHGVMEQI-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1-[#6])-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1-[#6])-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

morpheridine: CCOC(=O)C1(CCN(CC1)CCN2CCOCC2)C3=CC=CC=C3

smiles_non_kekule:    CCOC(=O)C1(c2ccccc2)CCN(CCN2CCOCC2)CC1
smiles_kekule:    CCOC(=O)C1(C2=CC=CC=C2)CCN(CCN2CCOCC2)CC1
inchi:    InChI=1S/C20H30N2O3/c1-2-25-19(23)20(18-6-4-3-5-7-18)8-10-21(11-9-20)12-13-22-14-16-24-17-15-22/h3-7H,2,8-17H2,1H3
inchiKey:    JDEDMCKQPKGSAX-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

mppp: O=C(CC3=CC=CC=C3)N(C(C2=CC=CC=C2)CN1CCCC1)C

smiles_non_kekule:    CN(C(=O)Cc1ccccc1)C(CN1CCCC1)c1ccccc1
smiles_kekule:    CN(C(=O)CC1=CC=CC=C1)C(CN1CCCC1)C1=CC=CC=C1
inchi:    InChI=1S/C21H26N2O/c1-22(21(24)16-18-10-4-2-5-11-18)20(17-23-14-8-9-15-23)19-12-6-3-7-13-19/h2-7,10-13,20H,8-9,14-17H2,1H3
inchiKey:    OVZWUDZIAAHNFG-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7](-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-1)-[#6]
smarts_isomeric:    [#8]=[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7](-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-1)-[#6]

mt-45: c3ccccc3CC(c2ccccc2)N(CC1)CCN1C4CCCCC4

smiles_non_kekule:    c1ccc(CC(c2ccccc2)N2CCN(C3CCCCC3)CC2)cc1
smiles_kekule:    C1=CC=C(CC(C2=CC=CC=C2)N2CCN(C3CCCCC3)CC2)C=C1
inchi:    InChI=1S/C24H32N2/c1-4-10-21(11-5-1)20-24(22-12-6-2-7-13-22)26-18-16-25(17-19-26)23-14-8-3-9-15-23/h1-2,4-7,10-13,23-24H,3,8-9,14-20H2
inchiKey:    IGBRRSIHEGCUEN-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

noracymethadol: CCC(C(CC(C)NC)(C1=CC=CC=C1)C2=CC=CC=C2)OC(=O)C

smiles_non_kekule:    CCC(OC(C)=O)C(CC(C)NC)(c1ccccc1)c1ccccc1
smiles_kekule:    CCC(OC(C)=O)C(CC(C)NC)(C1=CC=CC=C1)C1=CC=CC=C1
inchi:    InChI=1S/C22H29NO2/c1-5-21(25-18(3)24)22(16-17(2)23-4,19-12-8-6-9-13-19)20-14-10-7-11-15-20/h6-15,17,21,23H,5,16H2,1-4H3
inchiKey:    VWCUGCYZZGRKEE-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](-[#6](-[#6]-[#6](-[#6])-[#7]-[#6])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8]-[#6](=[#8])-[#6]
smarts_isomeric:    [#6]-[#6]-[#6](-[#6](-[#6]-[#6](-[#6])-[#7]-[#6])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8]-[#6](=[#8])-[#6]

norlevorphanol: C1CCC23CCNC(C2C1)CC4=C3C=C(C=C4)O

smiles_non_kekule:    Oc1ccc2c(c1)C13CCCCC1C(C2)NCC3
smiles_kekule:    OC1=CC2=C(C=C1)CC1NCCC23CCCCC13
inchi:    InChI=1S/C16H21NO/c18-12-5-4-11-9-15-13-3-1-2-6-16(13,7-8-17-15)14(11)10-12/h4-5,10,13,15,17-18H,1-3,6-9H2
inchiKey:    IYNWSQDZXMGGGI-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#6]23-[#6]-[#6]-[#7]-[#6](-[#6]-2-[#6]-1)-[#6]-[#6]1:[#6]-3:[#6]:[#6](:[#6]:[#6]:1)-[#8]
smarts_isomeric:    [#6]1-[#6]-[#6]-[#6]23-[#6]-[#6]-[#7]-[#6](-[#6]-2-[#6]-1)-[#6]-[#6]1:[#6]-3:[#6]:[#6](:[#6]:[#6]:1)-[#8]

normethadone: CCC(=O)C(CCN(C)C)(C1=CC=CC=C1)C2=CC=CC=C2

smiles_non_kekule:    CCC(=O)C(CCN(C)C)(c1ccccc1)c1ccccc1
smiles_kekule:    CCC(=O)C(CCN(C)C)(C1=CC=CC=C1)C1=CC=CC=C1
inchi:    InChI=1S/C20H25NO/c1-4-19(22)20(15-16-21(2)3,17-11-7-5-8-12-17)18-13-9-6-10-14-18/h5-14H,4,15-16H2,1-3H3
inchiKey:    WCJFBSYALHQBSK-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#6](-[#6]-[#6]-[#7](-[#6])-[#6])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#6](-[#6]-[#6]-[#7](-[#6])-[#6])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

norpipanone: CCC(=O)C(CCN1CCCCC1)(C2=CC=CC=C2)C3=CC=CC=C3

smiles_non_kekule:    CCC(=O)C(CCN1CCCCC1)(c1ccccc1)c1ccccc1
smiles_kekule:    CCC(=O)C(CCN1CCCCC1)(C1=CC=CC=C1)C1=CC=CC=C1
inchi:    InChI=1S/C23H29NO/c1-2-22(25)23(20-12-6-3-7-13-20,21-14-8-4-9-15-21)16-19-24-17-10-5-11-18-24/h3-4,6-9,12-15H,2,5,10-11,16-19H2,1H3
inchiKey:    WCDSHELZWCOTMI-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#6](-[#6]-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#6](-[#6]-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

ocfentanil: COCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3F

smiles_non_kekule:    COCC(=O)N(c1ccccc1F)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    COCC(=O)N(C1=CC=CC=C1F)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C22H27FN2O2/c1-27-17-22(26)25(21-10-6-5-9-20(21)23)19-12-15-24(16-13-19)14-11-18-7-3-2-4-8-18/h2-10,19H,11-17H2,1H3
inchiKey:    NYISTOZKVCMVEL-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9]
smarts_isomeric:    [#6]-[#8]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9]

ortho-fluoroacrylfentanyl: O=C(N(C1=CC=CC=C1F)C2CCN(CCC3=CC=CC=C3)CC2)C=C

smiles_non_kekule:    C=CC(=O)N(c1ccccc1F)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    C=CC(=O)N(C1=CC=CC=C1F)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C22H25FN2O/c1-2-22(26)25(21-11-7-6-10-20(21)23)19-13-16-24(17-14-19)15-12-18-8-4-3-5-9-18/h2-11,19H,1,12-17H2
inchiKey:    ROBNYLIAYXEIFM-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9])-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]=[#6]
smarts_isomeric:    [#8]=[#6](-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9])-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]=[#6]

ortho-fluorobutyrylfentanyl: CCCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=C(C=C3)F

smiles_non_kekule:    CCCC(=O)N(c1ccc(F)cc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    CCCC(=O)N(C1=CC=C(F)C=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C23H29FN2O/c1-2-6-23(27)26(21-11-9-20(24)10-12-21)22-14-17-25(18-15-22)16-13-19-7-4-3-5-8-19/h3-5,7-12,22H,2,6,13-18H2,1H3
inchiKey:    QZFMCYUBPSLOBP-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#9]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#9]

ortho-fluorofentanyl: CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3F

smiles_non_kekule:    CCC(=O)N(c1ccccc1F)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    CCC(=O)N(C1=CC=CC=C1F)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C22H27FN2O/c1-2-22(26)25(21-11-7-6-10-20(21)23)19-13-16-24(17-14-19)15-12-18-8-4-3-5-9-18/h3-11,19H,2,12-17H2,1H3
inchiKey:    BKUWDIVZCJNXRA-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9]
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9]

ortho-fluoroisobutyrylfentanyl: CC(C)C(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C3=C(F)C=CC=C3

smiles_non_kekule:    CC(C)C(=O)N(c1ccccc1F)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    CC(C)C(=O)N(C1=C(F)C=CC=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C23H29FN2O/c1-18(2)23(27)26(22-11-7-6-10-21(22)24)20-13-16-25(17-14-20)15-12-19-8-4-3-5-9-19/h3-11,18,20H,12-17H2,1-2H3
inchiKey:    NEWBKHYGTFTPMC-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6](-[#9]):[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6](-[#6])-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6](-[#9]):[#6]:[#6]:[#6]:[#6]:1

ortho-methylacetylfentanyl: CC(N(C1CCN(CCC2=CC=CC=C2)CC1)C3=C(C)C=CC=C3)=O

smiles_non_kekule:    CC(=O)N(c1ccccc1C)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    CC(=O)N(C1=C(C)C=CC=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C22H28N2O/c1-18-8-6-7-11-22(18)24(19(2)25)21-13-16-23(17-14-21)15-12-20-9-4-3-5-10-20/h3-11,21H,12-17H2,1-2H3
inchiKey:    GRDWUDZBHWHLSH-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6](-[#6]):[#6]:[#6]:[#6]:[#6]:1)=[#8]
smarts_isomeric:    [#6]-[#6](-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6](-[#6]):[#6]:[#6]:[#6]:[#6]:1)=[#8]

ortho-methylmethoxyacetylfentanyl: O=C(COC)N(C1CCN(CCC2=CC=CC=C2)CC1)C3=C(C)C=CC=C3

smiles_non_kekule:    COCC(=O)N(c1ccccc1C)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    COCC(=O)N(C1=C(C)C=CC=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C23H30N2O2/c1-19-8-6-7-11-22(19)25(23(26)18-27-2)21-13-16-24(17-14-21)15-12-20-9-4-3-5-10-20/h3-11,21H,12-18H2,1-2H3
inchiKey:    JJNJJOPCUJRZRG-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6]-[#8]-[#6])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6](-[#6]):[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#8]=[#6](-[#6]-[#8]-[#6])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6](-[#6]):[#6]:[#6]:[#6]:[#6]:1

para-chloroisobutyrylfentanyl: O=C(C(C)C)N(C1CCN(CCC2=CC=CC=C2)CC1)C3=CC=C(Cl)C=C3

smiles_non_kekule:    CC(C)C(=O)N(c1ccc(Cl)cc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    CC(C)C(=O)N(C1=CC=C(Cl)C=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C23H29ClN2O/c1-18(2)23(27)26(21-10-8-20(24)9-11-21)22-13-16-25(17-14-22)15-12-19-6-4-3-5-7-19/h3-11,18,22H,12-17H2,1-2H3
inchiKey:    YWHLYGSHOQKCJG-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6](-[#6])-[#6])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1
smarts_isomeric:    [#8]=[#6](-[#6](-[#6])-[#6])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6](-[#17]):[#6]:[#6]:1

para-fluorobutyrylfentanyl: C1C(CCN(C1)CCc1ccccc1)N(c1ccc(cc1)F)C(=O)CCC

smiles_non_kekule:    CCCC(=O)N(c1ccc(F)cc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    CCCC(=O)N(C1=CC=C(F)C=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C23H29FN2O/c1-2-6-23(27)26(21-11-9-20(24)10-12-21)22-14-17-25(18-15-22)16-13-19-7-4-3-5-8-19/h3-5,7-12,22H,2,6,13-18H2,1H3
inchiKey:    QZFMCYUBPSLOBP-UHFFFAOYSA-N
smarts:    [#6]1-[#6](-[#6]-[#6]-[#7](-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7](-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#9])-[#6](=[#8])-[#6]-[#6]-[#6]
smarts_isomeric:    [#6]1-[#6](-[#6]-[#6]-[#7](-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7](-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#9])-[#6](=[#8])-[#6]-[#6]-[#6]

para-fluorofentanyl: CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=C(C=C3)F

smiles_non_kekule:    CCC(=O)N(c1ccc(F)cc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    CCC(=O)N(C1=CC=C(F)C=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C22H27FN2O/c1-2-22(26)25(20-10-8-19(23)9-11-20)21-13-16-24(17-14-21)15-12-18-6-4-3-5-7-18/h3-11,21H,2,12-17H2,1H3
inchiKey:    KXUBAVLIJFTASZ-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#9]
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#9]

para-fluorofuranylfentanyl: O=C(C1=CC=CO1)N(C2CCN(CCC3=CC=CC=C3)CC2)C4=CC=C(F)C=C4

smiles_non_kekule:    O=C(c1ccco1)N(c1ccc(F)cc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    O=C(C1=CC=CO1)N(C1=CC=C(F)C=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C24H25FN2O2/c25-20-8-10-21(11-9-20)27(24(28)23-7-4-18-29-23)22-13-16-26(17-14-22)15-12-19-5-2-1-3-6-19/h1-11,18,22H,12-17H2
inchiKey:    MGEQOAJOFFXWTR-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6]1:[#6]:[#6]:[#6]:[#8]:1)-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6](-[#9]):[#6]:[#6]:1
smarts_isomeric:    [#8]=[#6](-[#6]1:[#6]:[#6]:[#6]:[#8]:1)-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6](-[#9]):[#6]:[#6]:1

para-methoxybutyrylfentanyl: O=C(CCC)N(C1CCN(CCC2=CC=CC=C2)CC1)C3=CC=C(OC)C=C3

smiles_non_kekule:    CCCC(=O)N(c1ccc(OC)cc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    CCCC(=O)N(C1=CC=C(OC)C=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C24H32N2O2/c1-3-7-24(27)26(21-10-12-23(28-2)13-11-21)22-15-18-25(19-16-22)17-14-20-8-5-4-6-9-20/h4-6,8-13,22H,3,7,14-19H2,1-2H3
inchiKey:    FNVSEQCPMXWQKG-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6]-[#6]-[#6])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#8]=[#6](-[#6]-[#6]-[#6])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6]:[#6]:1

para-methylfentanyl: O=C(CC)N(C1CCN(CCC2=CC=CC=C2)CC1)C3=CC=C(C)C=C3

smiles_non_kekule:    CCC(=O)N(c1ccc(C)cc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    CCC(=O)N(C1=CC=C(C)C=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C23H30N2O/c1-3-23(26)25(21-11-9-19(2)10-12-21)22-14-17-24(18-15-22)16-13-20-7-5-4-6-8-20/h4-12,22H,3,13-18H2,1-2H3
inchiKey:    XHWYYMNEJCMADF-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6]-[#6])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#8]=[#6](-[#6]-[#6])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:1

pepap: O=C(C)OC1(CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3

smiles_non_kekule:    CC(=O)OC1(c2ccccc2)CCN(CCc2ccccc2)CC1
smiles_kekule:    CC(=O)OC1(C2=CC=CC=C2)CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C21H25NO2/c1-18(23)24-21(20-10-6-3-7-11-20)13-16-22(17-14-21)15-12-19-8-4-2-5-9-19/h2-11H,12-17H2,1H3
inchiKey:    BVURVTVDNWSNFN-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6])-[#8]-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#8]=[#6](-[#6])-[#8]-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

phenadoxone: CCC(=O)C(CC(C)N1CCOCC1)(C2=CC=CC=C2)C3=CC=CC=C3

smiles_non_kekule:    CCC(=O)C(CC(C)N1CCOCC1)(c1ccccc1)c1ccccc1
smiles_kekule:    CCC(=O)C(CC(C)N1CCOCC1)(C1=CC=CC=C1)C1=CC=CC=C1
inchi:    InChI=1S/C23H29NO2/c1-3-22(25)23(20-10-6-4-7-11-20,21-12-8-5-9-13-21)18-19(2)24-14-16-26-17-15-24/h4-13,19H,3,14-18H2,1-2H3
inchiKey:    LOXCOAXRHYDLOW-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#6](-[#6]-[#6](-[#6])-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#6](-[#6]-[#6](-[#6])-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

phenampromide: CCC(=O)N(C1=CC=CC=C1)C(C)CN2CCCCC2

smiles_non_kekule:    CCC(=O)N(c1ccccc1)C(C)CN1CCCCC1
smiles_kekule:    CCC(=O)N(C1=CC=CC=C1)C(C)CN1CCCCC1
inchi:    InChI=1S/C17H26N2O/c1-3-17(20)19(16-10-6-4-7-11-16)15(2)14-18-12-8-5-9-13-18/h4,6-7,10-11,15H,3,5,8-9,12-14H2,1-2H3
inchiKey:    DHTRHEVNFFZCNU-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](-[#6])-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](-[#6])-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

phenomorphan: C1CCC23CCN(C(C2C1)CC4=C3C=C(C=C4)O)CCC5=CC=CC=C5

smiles_non_kekule:    Oc1ccc2c(c1)C13CCCCC1C(C2)N(CCc1ccccc1)CC3
smiles_kekule:    OC1=CC2=C(C=C1)CC1C3CCCCC23CCN1CCC1=CC=CC=C1
inchi:    InChI=1S/C24H29NO/c26-20-10-9-19-16-23-21-8-4-5-12-24(21,22(19)17-20)13-15-25(23)14-11-18-6-2-1-3-7-18/h1-3,6-7,9-10,17,21,23,26H,4-5,8,11-16H2
inchiKey:    CFBQYWXPZVQQTN-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#6]23-[#6]-[#6]-[#7](-[#6](-[#6]-2-[#6]-1)-[#6]-[#6]1:[#6]-3:[#6]:[#6](:[#6]:[#6]:1)-[#8])-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#6]23-[#6]-[#6]-[#7](-[#6](-[#6]-2-[#6]-1)-[#6]-[#6]1:[#6]-3:[#6]:[#6](:[#6]:[#6]:1)-[#8])-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

phenoperidine: CCOC(=O)C1(CCN(CC1)CCC(C2=CC=CC=C2)O)C3=CC=CC=C3

smiles_non_kekule:    CCOC(=O)C1(c2ccccc2)CCN(CCC(O)c2ccccc2)CC1
smiles_kekule:    CCOC(=O)C1(C2=CC=CC=C2)CCN(CCC(O)C2=CC=CC=C2)CC1
inchi:    InChI=1S/C23H29NO3/c1-2-27-22(26)23(20-11-7-4-8-12-20)14-17-24(18-15-23)16-13-21(25)19-9-5-3-6-10-19/h3-12,21,25H,2,13-18H2,1H3
inchiKey:    IPOPQVVNCFQFRK-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

phenylfentanyl: O=C(C1=CC=CC=C1)N(C2CCN(CCC3=CC=CC=C3)CC2)C4=CC=CC=C4

smiles_non_kekule:    O=C(c1ccccc1)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    O=C(C1=CC=CC=C1)N(C1=CC=CC=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C26H28N2O/c29-26(23-12-6-2-7-13-23)28(24-14-8-3-9-15-24)25-17-20-27(21-18-25)19-16-22-10-4-1-5-11-22/h1-15,25H,16-21H2
inchiKey:    BJPDWVPQDSVQKD-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#8]=[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

piritramide: C1CCN(CC1)C2(CCN(CC2)CCC(C#N)(C3=CC=CC=C3)C4=CC=CC=C4)C(=O)N

smiles_non_kekule:    N#CC(CCN1CCC(C(N)=O)(N2CCCCC2)CC1)(c1ccccc1)c1ccccc1
smiles_kekule:    N#CC(CCN1CCC(C(N)=O)(N2CCCCC2)CC1)(C1=CC=CC=C1)C1=CC=CC=C1
inchi:    InChI=1S/C27H34N4O/c28-22-26(23-10-4-1-5-11-23,24-12-6-2-7-13-24)14-19-30-20-15-27(16-21-30,25(29)32)31-17-8-3-9-18-31/h1-2,4-7,10-13H,3,8-9,14-21H2,(H2,29,32)
inchiKey:    IHEHEFLXQFOQJO-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6](-[#6]#[#7])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](=[#8])-[#7]
smarts_isomeric:    [#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6](-[#6]#[#7])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](=[#8])-[#7]

proheptazine: CCC(=O)OC1(CCCN(CC1C)C)C2=CC=CC=C2

smiles_non_kekule:    CCC(=O)OC1(c2ccccc2)CCCN(C)CC1C
smiles_kekule:    CCC(=O)OC1(C2=CC=CC=C2)CCCN(C)CC1C
inchi:    InChI=1S/C17H25NO2/c1-4-16(19)20-17(15-9-6-5-7-10-15)11-8-12-18(3)13-14(17)2/h5-7,9-10,14H,4,8,11-13H2,1-3H3
inchiKey:    ZXWAUWBYASJEOE-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#8]-[#6]1(-[#6]-[#6]-[#6]-[#7](-[#6]-[#6]-1-[#6])-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#8]-[#6]1(-[#6]-[#6]-[#6]-[#7](-[#6]-[#6]-1-[#6])-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

properidine: CC(C)OC(=O)C1(CCN(CC1)C)C2=CC=CC=C2

smiles_non_kekule:    CC(C)OC(=O)C1(c2ccccc2)CCN(C)CC1
smiles_kekule:    CC(C)OC(=O)C1(C2=CC=CC=C2)CCN(C)CC1
inchi:    InChI=1S/C16H23NO2/c1-13(2)19-15(18)16(9-11-17(3)12-10-16)14-7-5-4-6-8-14/h4-8,13H,9-12H2,1-3H3
inchiKey:    XJKQCILVUHXVIQ-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6](-[#6])-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

propiram: CCC(=O)N(C1=CC=CC=N1)C(C)CN2CCCCC2

smiles_non_kekule:    CCC(=O)N(c1ccccn1)C(C)CN1CCCCC1
smiles_kekule:    CCC(=O)N(C1=CC=CC=N1)C(C)CN1CCCCC1
inchi:    InChI=1S/C16H25N3O/c1-3-16(20)19(15-9-5-6-10-17-15)14(2)13-18-11-7-4-8-12-18/h5-6,9-10,14H,3-4,7-8,11-13H2,1-2H3
inchiKey:    ZBAFFZBKCMWUHM-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#7]:1)-[#6](-[#6])-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#7]:1)-[#6](-[#6])-[#6]-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

racemoramide: CC(CN1CCOCC1)C(C2=CC=CC=C2)(C3=CC=CC=C3)C(=O)N4CCCC4

tetrahydrofuranylfentanyl: C1CC(OC1)C(=O)N(C2CCN(CC2)CCC3=CC=CC=C3)C4=CC=CC=C4

smiles_non_kekule:    O=C(C1CCCO1)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    O=C(C1CCCO1)N(C1=CC=CC=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C24H30N2O2/c27-24(23-12-7-19-28-23)26(21-10-5-2-6-11-21)22-14-17-25(18-15-22)16-13-20-8-3-1-4-9-20/h1-6,8-11,22-23H,7,12-19H2
inchiKey:    OHJNHKUFSKAANI-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6](-[#8]-[#6]-1)-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1-[#6]-[#6](-[#8]-[#6]-1)-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

thiofentanyl: CCC(=O)N(C1CCN(CC1)CCC2=CC=CS2)C3=CC=CC=C3

smiles_non_kekule:    CCC(=O)N(c1ccccc1)C1CCN(CCc2cccs2)CC1
smiles_kekule:    CCC(=O)N(C1=CC=CC=C1)C1CCN(CCC2=CC=CS2)CC1
inchi:    InChI=1S/C20H26N2OS/c1-2-20(23)22(17-7-4-3-5-8-17)18-10-13-21(14-11-18)15-12-19-9-6-16-24-19/h3-9,16,18H,2,10-15H2,1H3
inchiKey:    YMRFZDHYDKZXPA-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

thiofuranylfentanyl: O=C(N(C1CCN(CCC2=CC=CC=C2)CC1)C3=CC=CC=C3)C4=CC=CS4

smiles_non_kekule:    O=C(c1cccs1)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    O=C(C1=CC=CS1)N(C1=CC=CC=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C24H26N2OS/c27-24(23-12-7-19-28-23)26(21-10-5-2-6-11-21)22-14-17-25(18-15-22)16-13-20-8-3-1-4-9-20/h1-12,19,22H,13-18H2
inchiKey:    CCHPKGYUIHSQIE-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#16]:1
smarts_isomeric:    [#8]=[#6](-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#16]:1

tilidine: CCOC(=O)C1(CCC=CC1N(C)C)C2=CC=CC=C2

smiles_non_kekule:    CCOC(=O)C1(c2ccccc2)CCC=CC1N(C)C
smiles_kekule:    CCOC(=O)C1(C2=CC=CC=C2)CCC=CC1N(C)C
inchi:    InChI=1S/C17H23NO2/c1-4-20-16(19)17(14-10-6-5-7-11-14)13-9-8-12-15(17)18(2)3/h5-8,10-12,15H,4,9,13H2,1-3H3
inchiKey:    WDEFBBTXULIOBB-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#6]=[#6]-[#6]-1-[#7](-[#6])-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#6]=[#6]-[#6]-1-[#7](-[#6])-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

trimeperidine: CCC(=O)OC1(CC(N(CC1C)C)C)C2=CC=CC=C2

smiles_non_kekule:    CCC(=O)OC1(c2ccccc2)CC(C)N(C)CC1C
smiles_kekule:    CCC(=O)OC1(C2=CC=CC=C2)CC(C)N(C)CC1C
inchi:    InChI=1S/C17H25NO2/c1-5-16(19)20-17(15-9-7-6-8-10-15)11-14(3)18(4)12-13(17)2/h6-10,13-14H,5,11-12H2,1-4H3
inchiKey:    UVITTYOJFDLOGI-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#8]-[#6]1(-[#6]-[#6](-[#7](-[#6]-[#6]-1-[#6])-[#6])-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#8]-[#6]1(-[#6]-[#6](-[#7](-[#6]-[#6]-1-[#6])-[#6])-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

pinky: CN(C)C1CCCCC1N(C)C(=O)C2=CC(=C(C=C2)Cl)Cl

smiles_non_kekule:    CN(C)C1CCCCC1N(C)C(=O)c1ccc(Cl)c(Cl)c1
smiles_kekule:    CN(C)C1CCCCC1N(C)C(=O)C1=CC(Cl)=C(Cl)C=C1
inchi:    InChI=1S/C16H22Cl2N2O/c1-19(2)14-6-4-5-7-15(14)20(3)16(21)11-8-9-12(17)13(18)10-11/h8-10,14-15H,4-7H2,1-3H3
inchiKey:    JGPNMZWFVRQNGU-UHFFFAOYSA-N
smarts:    [#6]-[#7](-[#6])-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1-[#7](-[#6])-[#6](=[#8])-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1)-[#17])-[#17]
smarts_isomeric:    [#6]-[#7](-[#6])-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1-[#7](-[#6])-[#6](=[#8])-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1)-[#17])-[#17]

valerylfentanyl: CCCCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3

smiles_non_kekule:    CCCCC(=O)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    CCCCC(=O)N(C1=CC=CC=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C24H32N2O/c1-2-3-14-24(27)26(22-12-8-5-9-13-22)23-16-19-25(20-17-23)18-15-21-10-6-4-7-11-21/h4-13,23H,2-3,14-20H2,1H3
inchiKey:    VCCPXHWAJYWQMR-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

acetorphine: CCCC(C)(C1CC23C=CC1(C4C25CCN(C3CC6=C5C(=C(C=C6)OC(=O)C)O4)C)OC)O

smiles_non_kekule:    CCCC(C)(O)C1CC23C=CC1(OC)C1Oc4c(OC(C)=O)ccc5c4C12CCN(C)C3C5
smiles_kekule:    CCCC(C)(O)C1CC23C=CC1(OC)C1OC4=C5C(=CC=C4OC(C)=O)CC2N(C)CCC513
inchi:    InChI=1S/C27H35NO5/c1-6-9-24(3,30)19-15-25-10-11-27(19,31-5)23-26(25)12-13-28(4)20(25)14-17-7-8-18(32-16(2)29)22(33-23)21(17)26/h7-8,10-11,19-20,23,30H,6,9,12-15H2,1-5H3
inchiKey:    LFYBMMHFJIAKFE-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6](-[#6])(-[#6]1-[#6]-[#6]23-[#6]=[#6]-[#6]-1(-[#6]1-[#6]-24-[#6]-[#6]-[#7](-[#6]-3-[#6]-[#6]2:[#6]-4:[#6](:[#6](:[#6]:[#6]:2)-[#8]-[#6](=[#8])-[#6])-[#8]-1)-[#6])-[#8]-[#6])-[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6](-[#6])(-[#6]1-[#6]-[#6]23-[#6]=[#6]-[#6]-1(-[#6]1-[#6]-24-[#6]-[#6]-[#7](-[#6]-3-[#6]-[#6]2:[#6]-4:[#6](:[#6](:[#6]:[#6]:2)-[#8]-[#6](=[#8])-[#6])-[#8]-1)-[#6])-[#8]-[#6])-[#8]

acetyldihydrocodeine: CC(=O)OC1CCC2C3CC4=C5C2(C1OC5=C(C=C4)OC)CCN3C

smiles_non_kekule:    COc1ccc2c3c1OC1C(OC(C)=O)CCC4C(C2)N(C)CCC341
smiles_kekule:    COC1=C2OC3C(OC(C)=O)CCC4C5CC(=C2C43CCN5C)C=C1
inchi:    InChI=1S/C20H25NO4/c1-11(22)24-16-7-5-13-14-10-12-4-6-15(23-3)18-17(12)20(13,19(16)25-18)8-9-21(14)2/h4,6,13-14,16,19H,5,7-10H2,1-3H3
inchiKey:    LGGDXXJAGWBUSL-UHFFFAOYSA-N
smarts:    [#6]-[#6](=[#8])-[#8]-[#6]1-[#6]-[#6]-[#6]2-[#6]3-[#6]-[#6]4:[#6]5-[#6]-2(-[#6]-1-[#8]-[#6]:5:[#6](:[#6]:[#6]:4)-[#8]-[#6])-[#6]-[#6]-[#7]-3-[#6]
smarts_isomeric:    [#6]-[#6](=[#8])-[#8]-[#6]1-[#6]-[#6]-[#6]2-[#6]3-[#6]-[#6]4:[#6]5-[#6]-2(-[#6]-1-[#8]-[#6]:5:[#6](:[#6]:[#6]:4)-[#8]-[#6])-[#6]-[#6]-[#7]-3-[#6]

benzylmorphine: CN1CCC23C4C1CC5=C2C(=C(C=C5)OCC6=CC=CC=C6)OC3C(C=C4)O

smiles_non_kekule:    CN1CCC23c4c5ccc(OCc6ccccc6)c4OC2C(O)C=CC3C1C5
smiles_kekule:    CN1CCC23C4=C5C=CC(OCC6=CC=CC=C6)=C4OC2C(O)C=CC3C1C5
inchi:    InChI=1S/C24H25NO3/c1-25-12-11-24-17-8-9-19(26)23(24)28-22-20(27-14-15-5-3-2-4-6-15)10-7-16(21(22)24)13-18(17)25/h2-10,17-19,23,26H,11-14H2,1H3
inchiKey:    RDJGWRFTDZZXSM-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8]
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8]

codeinemethylbromide: C[N+]1(CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)O)C.[Br-]

smiles_non_kekule:    COc1ccc2c3c1OC1C(O)C=CC4C(C2)[N+](C)(C)CCC341.[Br-]
smiles_kekule:    COC1=C2OC3C(O)C=CC4C5CC(=C2C43CC[N+]5(C)C)C=C1.[Br-]
inchi:    InChI=1S/C19H24NO3.BrH/c1-20(2)9-8-19-12-5-6-14(21)18(19)23-17-15(22-3)7-4-11(16(17)19)10-13(12)20;/h4-7,12-14,18,21H,8-10H2,1-3H3;1H/q+1;/p-1
inchiKey:    KIKLDWULAZATJG-UHFFFAOYSA-M
smarts:    [#6]-[#7+]1(-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8])-[#6].[#35-]
smarts_isomeric:    [#6]-[#7+]1(-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8])-[#6].[#35-]

codeine-n-oxide: C[N+]1(CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)O)[O-]

smiles_non_kekule:    COc1ccc2c3c1OC1C(O)C=CC4C(C2)[N+](C)([O-])CCC341
smiles_kekule:    COC1=C2OC3C(O)C=CC4C5CC(=C2C43CC[N+]5(C)[O-])C=C1
inchi:    InChI=1S/C18H21NO4/c1-19(21)8-7-18-11-4-5-13(20)17(18)23-16-14(22-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3
inchiKey:    BDLSDHWCOJPHIE-UHFFFAOYSA-N
smarts:    [#6]-[#7+]1(-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8])-[#8-]
smarts_isomeric:    [#6]-[#7+]1(-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8])-[#8-]

cyprenorphine: CC(C)(C1CC23C=CC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)O

smiles_non_kekule:    COC12C=CC3(CC1C(C)(C)O)C1Cc4ccc(O)c5c4C3(CCN1CC1CC1)C2O5
smiles_kekule:    COC12C=CC3(CC1C(C)(C)O)C1CC4=CC=C(O)C5=C4C3(CCN1CC1CC1)C2O5
inchi:    InChI=1S/C26H33NO4/c1-23(2,29)18-13-24-8-9-26(18,30-3)22-25(24)10-11-27(14-15-4-5-15)19(24)12-16-6-7-17(28)21(31-22)20(16)25/h6-9,15,18-19,22,28-29H,4-5,10-14H2,1-3H3
inchiKey:    VSKIOMHXEUHYSI-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])(-[#6]1-[#6]-[#6]23-[#6]=[#6]-[#6]-1(-[#6]1-[#6]-24-[#6]-[#6]-[#7](-[#6]-3-[#6]-[#6]2:[#6]-4:[#6](:[#6](:[#6]:[#6]:2)-[#8])-[#8]-1)-[#6]-[#6]1-[#6]-[#6]-1)-[#8]-[#6])-[#8]
smarts_isomeric:    [#6]-[#6](-[#6])(-[#6]1-[#6]-[#6]23-[#6]=[#6]-[#6]-1(-[#6]1-[#6]-24-[#6]-[#6]-[#7](-[#6]-3-[#6]-[#6]2:[#6]-4:[#6](:[#6](:[#6]:[#6]:2)-[#8])-[#8]-1)-[#6]-[#6]1-[#6]-[#6]-1)-[#8]-[#6])-[#8]

desomorphine: CN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3CCC4

smiles_non_kekule:    CN1CCC23c4c5ccc(O)c4OC2CCCC3C1C5
smiles_kekule:    CN1CCC23C4=C5C=CC(O)=C4OC2CCCC3C1C5
inchi:    InChI=1S/C17H21NO2/c1-18-8-7-17-11-3-2-4-14(17)20-16-13(19)6-5-10(15(16)17)9-12(11)18/h5-6,11-12,14,19H,2-4,7-9H2,1H3
inchiKey:    LNNWVNGFPYWNQE-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8])-[#8]-[#6]-3-[#6]-[#6]-[#6]-4
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8])-[#8]-[#6]-3-[#6]-[#6]-[#6]-4

dihydromorphine: CN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(CC4)O

smiles_non_kekule:    CN1CCC23c4c5ccc(O)c4OC2C(O)CCC3C1C5
smiles_kekule:    CN1CCC23C4=C5C=CC(O)=C4OC2C(O)CCC3C1C5
inchi:    InChI=1S/C17H21NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2,4,10-11,13,16,19-20H,3,5-8H2,1H3
inchiKey:    IJVCSMSMFSCRME-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8])-[#8]-[#6]-3-[#6](-[#6]-[#6]-4)-[#8]
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8])-[#8]-[#6]-3-[#6](-[#6]-[#6]-4)-[#8]

drotebanol: CN1CCC23CC(CCC2(C1CC4=C3C(=C(C=C4)OC)OC)O)O

smiles_non_kekule:    COc1ccc2c(c1OC)C13CCN(C)C(C2)C1(O)CCC(O)C3
smiles_kekule:    COC1=C(OC)C2=C(C=C1)CC1N(C)CCC23CC(O)CCC13O
inchi:    InChI=1S/C19H27NO4/c1-20-9-8-18-11-13(21)6-7-19(18,22)15(20)10-12-4-5-14(23-2)17(24-3)16(12)18/h4-5,13,15,21-22H,6-11H2,1-3H3
inchiKey:    LCAHPIFLPICNRW-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]-[#6](-[#6]-[#6]-[#6]-2(-[#6]-1-[#6]-[#6]1:[#6]-3:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#8]-[#6])-[#8])-[#8]
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]-[#6](-[#6]-[#6]-[#6]-2(-[#6]-1-[#6]-[#6]1:[#6]-3:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#8]-[#6])-[#8])-[#8]

etorphine: CCCC(C)(C1CC23C=CC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)C)OC)O

smiles_non_kekule:    CCCC(C)(O)C1CC23C=CC1(OC)C1Oc4c(O)ccc5c4C12CCN(C)C3C5
smiles_kekule:    CCCC(C)(O)C1CC23C=CC1(OC)C1OC4=C5C(=CC=C4O)CC2N(C)CCC513
inchi:    InChI=1S/C25H33NO4/c1-5-8-22(2,28)17-14-23-9-10-25(17,29-4)21-24(23)11-12-26(3)18(23)13-15-6-7-16(27)20(30-21)19(15)24/h6-7,9-10,17-18,21,27-28H,5,8,11-14H2,1-4H3
inchiKey:    CAHCBJPUTCKATP-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6](-[#6])(-[#6]1-[#6]-[#6]23-[#6]=[#6]-[#6]-1(-[#6]1-[#6]-24-[#6]-[#6]-[#7](-[#6]-3-[#6]-[#6]2:[#6]-4:[#6](:[#6](:[#6]:[#6]:2)-[#8])-[#8]-1)-[#6])-[#8]-[#6])-[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6](-[#6])(-[#6]1-[#6]-[#6]23-[#6]=[#6]-[#6]-1(-[#6]1-[#6]-24-[#6]-[#6]-[#7](-[#6]-3-[#6]-[#6]2:[#6]-4:[#6](:[#6](:[#6]:[#6]:2)-[#8])-[#8]-1)-[#6])-[#8]-[#6])-[#8]

heroin: CC(=O)OC1C=CC2C3CC4=C5C2(C1OC5=C(C=C4)OC(=O)C)CCN3C

smiles_non_kekule:    CC(=O)Oc1ccc2c3c1OC1C(OC(C)=O)C=CC4C(C2)N(C)CCC341
smiles_kekule:    CC(=O)OC1=C2OC3C(OC(C)=O)C=CC4C5CC(=C2C43CCN5C)C=C1
inchi:    InChI=1S/C21H23NO5/c1-11(23)25-16-6-4-13-10-15-14-5-7-17(26-12(2)24)20-21(14,8-9-22(15)3)18(13)19(16)27-20/h4-7,14-15,17,20H,8-10H2,1-3H3
inchiKey:    GVGLGOZIDCSQPN-UHFFFAOYSA-N
smarts:    [#6]-[#6](=[#8])-[#8]-[#6]1-[#6]=[#6]-[#6]2-[#6]3-[#6]-[#6]4:[#6]5-[#6]-2(-[#6]-1-[#8]-[#6]:5:[#6](:[#6]:[#6]:4)-[#8]-[#6](=[#8])-[#6])-[#6]-[#6]-[#7]-3-[#6]
smarts_isomeric:    [#6]-[#6](=[#8])-[#8]-[#6]1-[#6]=[#6]-[#6]2-[#6]3-[#6]-[#6]4:[#6]5-[#6]-2(-[#6]-1-[#8]-[#6]:5:[#6](:[#6]:[#6]:4)-[#8]-[#6](=[#8])-[#6])-[#6]-[#6]-[#7]-3-[#6]

hydromorphinol: CN1CCC23C4C(CCC2(C1CC5=C3C(=C(C=C5)O)O4)O)O

smiles_non_kekule:    CN1CCC23c4c5ccc(O)c4OC2C(O)CCC3(O)C1C5
smiles_kekule:    CN1CCC23C4=C5C=CC(O)=C4OC2C(O)CCC3(O)C1C5
inchi:    InChI=1S/C17H21NO4/c1-18-7-6-16-13-9-2-3-10(19)14(13)22-15(16)11(20)4-5-17(16,21)12(18)8-9/h2-3,11-12,15,19-21H,4-8H2,1H3
inchiKey:    AABLHGPVOULICI-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6](-[#6]-[#6]-[#6]-2(-[#6]-1-[#6]-[#6]1:[#6]-3:[#6](:[#6](:[#6]:[#6]:1)-[#8])-[#8]-4)-[#8])-[#8]
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6](-[#6]-[#6]-[#6]-2(-[#6]-1-[#6]-[#6]1:[#6]-3:[#6](:[#6](:[#6]:[#6]:1)-[#8])-[#8]-4)-[#8])-[#8]

methyldesorphine: CC1=CCC2C3CC4=C5C2(C1OC5=C(C=C4)O)CCN3C

smiles_non_kekule:    CC1=CCC2C3Cc4ccc(O)c5c4C2(CCN3C)C1O5
smiles_kekule:    CC1=CCC2C3CC4=C5C(=C(O)C=C4)OC1C52CCN3C
inchi:    InChI=1S/C18H21NO2/c1-10-3-5-12-13-9-11-4-6-14(20)16-15(11)18(12,17(10)21-16)7-8-19(13)2/h3-4,6,12-13,17,20H,5,7-9H2,1-2H3
inchiKey:    CUFWYVOFDYVCPM-UHFFFAOYSA-N
smarts:    [#6]-[#6]1=[#6]-[#6]-[#6]2-[#6]3-[#6]-[#6]4:[#6]5-[#6]-2(-[#6]-1-[#8]-[#6]:5:[#6](:[#6]:[#6]:4)-[#8])-[#6]-[#6]-[#7]-3-[#6]
smarts_isomeric:    [#6]-[#6]1=[#6]-[#6]-[#6]2-[#6]3-[#6]-[#6]4:[#6]5-[#6]-2(-[#6]-1-[#8]-[#6]:5:[#6](:[#6]:[#6]:4)-[#8])-[#6]-[#6]-[#7]-3-[#6]

methyldihydromorphine: CC1(CCC2C3CC4=C5C2(C1OC5=C(C=C4)O)CCN3C)O

smiles_non_kekule:    CN1CCC23c4c5ccc(O)c4OC2C(C)(O)CCC3C1C5
smiles_kekule:    CN1CCC23C4=C5C=CC(O)=C4OC2C(C)(O)CCC3C1C5
inchi:    InChI=1S/C18H23NO3/c1-17(21)6-5-11-12-9-10-3-4-13(20)15-14(10)18(11,16(17)22-15)7-8-19(12)2/h3-4,11-12,16,20-21H,5-9H2,1-2H3
inchiKey:    NBKVWIJQJMEQLE-UHFFFAOYSA-N
smarts:    [#6]-[#6]1(-[#6]-[#6]-[#6]2-[#6]3-[#6]-[#6]4:[#6]5-[#6]-2(-[#6]-1-[#8]-[#6]:5:[#6](:[#6]:[#6]:4)-[#8])-[#6]-[#6]-[#7]-3-[#6])-[#8]
smarts_isomeric:    [#6]-[#6]1(-[#6]-[#6]-[#6]2-[#6]3-[#6]-[#6]4:[#6]5-[#6]-2(-[#6]-1-[#8]-[#6]:5:[#6](:[#6]:[#6]:4)-[#8])-[#6]-[#6]-[#7]-3-[#6])-[#8]

morphinemethylbromide: C[N+]1(CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(C=C4)O)C.[Br-]

smiles_non_kekule:    C[N+]1(C)CCC23c4c5ccc(O)c4OC2C(O)C=CC3C1C5.[Br-]
smiles_kekule:    C[N+]1(C)CCC23C4=C5C=CC(O)=C4OC2C(O)C=CC3C1C5.[Br-]
inchi:    InChI=1S/C18H21NO3.BrH/c1-19(2)8-7-18-11-4-6-14(21)17(18)22-16-13(20)5-3-10(15(16)18)9-12(11)19;/h3-6,11-12,14,17,21H,7-9H2,1-2H3;1H
inchiKey:    KQUQZJSQMSHWHP-UHFFFAOYSA-N
smarts:    [#6]-[#7+]1(-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8])-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8])-[#6].[#35-]
smarts_isomeric:    [#6]-[#7+]1(-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8])-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8])-[#6].[#35-]

morphinemethylsulfonate: CN1CCC23C4C1CC5=C2C(=C(C=C5)OS(=O)(=O)C)OC3C(C=C4)O

smiles_non_kekule:    CN1CCC23c4c5ccc(OS(C)(=O)=O)c4OC2C(O)C=CC3C1C5
smiles_kekule:    CN1CCC23C4=C5C=CC(OS(C)(=O)=O)=C4OC2C(O)C=CC3C1C5
inchi:    InChI=1S/C18H21NO5S/c1-19-8-7-18-11-4-5-13(20)17(18)23-16-14(24-25(2,21)22)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3
inchiKey:    ILBGUXQOPBTXLD-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#16](=[#8])(=[#8])-[#6])-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8]
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#16](=[#8])(=[#8])-[#6])-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8]

morphine-n-oxide: C[N+]1(CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(C=C4)O)[O-]

smiles_non_kekule:    C[N+]1([O-])CCC23c4c5ccc(O)c4OC2C(O)C=CC3C1C5
smiles_kekule:    C[N+]1([O-])CCC23C4=C5C=CC(O)=C4OC2C(O)C=CC3C1C5
inchi:    InChI=1S/C17H19NO4/c1-18(21)7-6-17-10-3-5-13(20)16(17)22-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,13,16,19-20H,6-8H2,1H3
inchiKey:    AMAPEXTUMXQULJ-UHFFFAOYSA-N
smarts:    [#6]-[#7+]1(-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8])-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8])-[#8-]
smarts_isomeric:    [#6]-[#7+]1(-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8])-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8])-[#8-]

myrophine: CCCCCCCCCCCCCC(=O)OC1C=CC2C3CC4=C5C2(C1OC5=C(C=C4)OCC6=CC=CC=C6)CCN3C

smiles_non_kekule:    CCCCCCCCCCCCCC(=O)OC1C=CC2C3Cc4ccc(OCc5ccccc5)c5c4C2(CCN3C)C1O5
smiles_kekule:    CCCCCCCCCCCCCC(=O)OC1C=CC2C3CC4=C5C(=C(OCC6=CC=CC=C6)C=C4)OC1C52CCN3C
inchi:    InChI=1S/C38H51NO4/c1-3-4-5-6-7-8-9-10-11-12-16-19-34(40)42-33-23-21-30-31-26-29-20-22-32(41-27-28-17-14-13-15-18-28)36-35(29)38(30,37(33)43-36)24-25-39(31)2/h13-15,17-18,20-23,30-31,33,37H,3-12,16,19,24-27H2,1-2H3
inchiKey:    GODGZZGKTZQSAL-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6](=[#8])-[#8]-[#6]1-[#6]=[#6]-[#6]2-[#6]3-[#6]-[#6]4:[#6]5-[#6]-2(-[#6]-1-[#8]-[#6]:5:[#6](:[#6]:[#6]:4)-[#8]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]-[#6]-[#7]-3-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6](=[#8])-[#8]-[#6]1-[#6]=[#6]-[#6]2-[#6]3-[#6]-[#6]4:[#6]5-[#6]-2(-[#6]-1-[#8]-[#6]:5:[#6](:[#6]:[#6]:4)-[#8]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]-[#6]-[#7]-3-[#6]

nicocodeine: CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)OC(=O)C6=CN=CC=C6

smiles_non_kekule:    COc1ccc2c3c1OC1C(OC(=O)c4cccnc4)C=CC4C(C2)N(C)CCC341
smiles_kekule:    COC1=C2OC3C(OC(=O)C4=CN=CC=C4)C=CC4C5CC(=C2C43CCN5C)C=C1
inchi:    InChI=1S/C24H24N2O4/c1-26-11-9-24-16-6-8-19(29-23(27)15-4-3-10-25-13-15)22(24)30-21-18(28-2)7-5-14(20(21)24)12-17(16)26/h3-8,10,13,16-17,19,22H,9,11-12H2,1-2H3
inchiKey:    RYBGRHAWFUVMST-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8]-[#6](=[#8])-[#6]1:[#6]:[#7]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8]-[#6](=[#8])-[#6]1:[#6]:[#7]:[#6]:[#6]:[#6]:1

nicomorphine: CN1CCC23C4C1CC5=C2C(=C(C=C5)OC(=O)C6=CN=CC=C6)OC3C(C=C4)OC(=O)C7=CN=CC=C7

smiles_non_kekule:    CN1CCC23c4c5ccc(OC(=O)c6cccnc6)c4OC2C(OC(=O)c2cccnc2)C=CC3C1C5
smiles_kekule:    CN1CCC23C4=C5C=CC(OC(=O)C6=CN=CC=C6)=C4OC2C(OC(=O)C2=CN=CC=C2)C=CC3C1C5
inchi:    InChI=1S/C29H25N3O5/c1-32-13-10-29-20-7-9-23(36-28(34)19-5-3-12-31-16-19)26(29)37-25-22(8-6-17(24(25)29)14-21(20)32)35-27(33)18-4-2-11-30-15-18/h2-9,11-12,15-16,20-21,23,26H,10,13-14H2,1H3
inchiKey:    HNDXBGYRMHRUFN-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6](=[#8])-[#6]1:[#6]:[#7]:[#6]:[#6]:[#6]:1)-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8]-[#6](=[#8])-[#6]1:[#6]:[#7]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6](=[#8])-[#6]1:[#6]:[#7]:[#6]:[#6]:[#6]:1)-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8]-[#6](=[#8])-[#6]1:[#6]:[#7]:[#6]:[#6]:[#6]:1

normorphine: C1CNC2CC3=C4C15C2C=CC(C5OC4=C(C=C3)O)O

smiles_non_kekule:    Oc1ccc2c3c1OC1C(O)C=CC4C(C2)NCCC341
smiles_kekule:    OC1=C2OC3C(O)C=CC4C5CC(=C2C43CCN5)C=C1
inchi:    InChI=1S/C16H17NO3/c18-11-3-1-8-7-10-9-2-4-12(19)15-16(9,5-6-17-10)13(8)14(11)20-15/h1-4,9-10,12,15,17-19H,5-7H2
inchiKey:    ONBWJWYUHXVEJS-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#7]-[#6]2-[#6]-[#6]3:[#6]4-[#6]-15-[#6]-2-[#6]=[#6]-[#6](-[#6]-5-[#8]-[#6]:4:[#6](:[#6]:[#6]:3)-[#8])-[#8]
smarts_isomeric:    [#6]1-[#6]-[#7]-[#6]2-[#6]-[#6]3:[#6]4-[#6]-15-[#6]-2-[#6]=[#6]-[#6](-[#6]-5-[#8]-[#6]:4:[#6](:[#6]:[#6]:3)-[#8])-[#8]

pholcodine: CN1CCC23C4C1CC5=C2C(=C(C=C5)OCCN6CCOCC6)OC3C(C=C4)O

smiles_non_kekule:    CN1CCC23c4c5ccc(OCCN6CCOCC6)c4OC2C(O)C=CC3C1C5
smiles_kekule:    CN1CCC23C4=C5C=CC(OCCN6CCOCC6)=C4OC2C(O)C=CC3C1C5
inchi:    InChI=1S/C23H30N2O4/c1-24-7-6-23-16-3-4-18(26)22(23)29-21-19(5-2-15(20(21)23)14-17(16)24)28-13-10-25-8-11-27-12-9-25/h2-5,16-18,22,26H,6-14H2,1H3
inchiKey:    GPFAJKDEDBRFOS-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1)-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8]
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1)-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8]

thebacon: CC(=O)OC1=CCC2C3CC4=C5C2(C1OC5=C(C=C4)OC)CCN3C

smiles_non_kekule:    COc1ccc2c3c1OC1C(OC(C)=O)=CCC4C(C2)N(C)CCC314
smiles_kekule:    COC1=C2OC3C(OC(C)=O)=CCC4C5CC(=C2C34CCN5C)C=C1
inchi:    InChI=1S/C20H23NO4/c1-11(22)24-16-7-5-13-14-10-12-4-6-15(23-3)18-17(12)20(13,19(16)25-18)8-9-21(14)2/h4,6-7,13-14,19H,5,8-10H2,1-3H3
inchiKey:    RRJQTGHQFYTZOW-UHFFFAOYSA-N
smarts:    [#6]-[#6](=[#8])-[#8]-[#6]1=[#6]-[#6]-[#6]2-[#6]3-[#6]-[#6]4:[#6]5-[#6]-2(-[#6]-1-[#8]-[#6]:5:[#6](:[#6]:[#6]:4)-[#8]-[#6])-[#6]-[#6]-[#7]-3-[#6]
smarts_isomeric:    [#6]-[#6](=[#8])-[#8]-[#6]1=[#6]-[#6]-[#6]2-[#6]3-[#6]-[#6]4:[#6]5-[#6]-2(-[#6]-1-[#8]-[#6]:5:[#6](:[#6]:[#6]:4)-[#8]-[#6])-[#6]-[#6]-[#7]-3-[#6]

alpha-ethyltryptamine: CCC(CC1=CNC2=CC=CC=C21)N

smiles_non_kekule:    CCC(N)Cc1c[nH]c2ccccc12
smiles_kekule:    CCC(N)CC1=CNC2=CC=CC=C12
inchi:    InChI=1S/C12H16N2/c1-2-10(13)7-9-8-14-12-6-4-3-5-11(9)12/h3-6,8,10,14H,2,7,13H2,1H3
inchiKey:    ZXUMUPVQYAFTLF-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](-[#6]-[#6]1:[#6]:[#7H]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#7]
smarts_isomeric:    [#6]-[#6]-[#6](-[#6]-[#6]1:[#6]:[#7H]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#7]

4-bromo-2,5-dimethoxy-amphetamine: CC(CC1=CC(=C(C=C1OC)Br)OC)N

smiles_non_kekule:    COc1cc(CC(C)N)c(OC)cc1Br
smiles_kekule:    COC1=C(Br)C=C(OC)C(CC(C)N)=C1
inchi:    InChI=1S/C11H16BrNO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3
inchiKey:    FXMWUTGUCAKGQL-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#8]-[#6])-[#35])-[#8]-[#6])-[#7]
smarts_isomeric:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#8]-[#6])-[#35])-[#8]-[#6])-[#7]

4-bromo-2,5-dimethoxyphenethylamine: COC1=CC(=C(C=C1CCN)OC)Br

smiles_non_kekule:    COc1cc(CCN)c(OC)cc1Br
smiles_kekule:    COC1=C(Br)C=C(OC)C(CCN)=C1
inchi:    InChI=1S/C10H14BrNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3
inchiKey:    YMHOBZXQZVXHBM-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#6]-[#6]-[#7])-[#8]-[#6])-[#35]
smarts_isomeric:    [#6]-[#8]-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#6]-[#6]-[#7])-[#8]-[#6])-[#35]

2,5-dimethoxyamphetamine: CC(CC1=C(C=CC(=C1)OC)OC)N

smiles_non_kekule:    COc1ccc(OC)c(CC(C)N)c1
smiles_kekule:    COC1=CC(CC(C)N)=C(OC)C=C1
inchi:    InChI=1S/C11H17NO2/c1-8(12)6-9-7-10(13-2)4-5-11(9)14-3/h4-5,7-8H,6,12H2,1-3H3
inchiKey:    LATVFYDIBMDBSY-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6]1:[#6](:[#6]:[#6]:[#6](:[#6]:1)-[#8]-[#6])-[#8]-[#6])-[#7]
smarts_isomeric:    [#6]-[#6](-[#6]-[#6]1:[#6](:[#6]:[#6]:[#6](:[#6]:1)-[#8]-[#6])-[#8]-[#6])-[#7]

2,5-dimethoxy-4-ethylamphet-amine: CCC1=CC(=C(C=C1OC)CC(C)N)OC

smiles_non_kekule:    CCc1cc(OC)c(CC(C)N)cc1OC
smiles_kekule:    CCC1=CC(OC)=C(CC(C)N)C=C1OC
inchi:    InChI=1S/C13H21NO2/c1-5-10-7-13(16-4)11(6-9(2)14)8-12(10)15-3/h7-9H,5-6,14H2,1-4H3
inchiKey:    HXJKWPGVENNMCC-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#8]-[#6])-[#6]-[#6](-[#6])-[#7])-[#8]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#8]-[#6])-[#6]-[#6](-[#6])-[#7])-[#8]-[#6]

2,5-dimethoxy-4-(n)-propylthiophenethylamine: CCCSC1=C(C=C(C(=C1)OC)CCN)OC

smiles_non_kekule:    CCCSc1cc(OC)c(CCN)cc1OC
smiles_kekule:    CCCSC1=C(OC)C=C(CCN)C(OC)=C1
inchi:    InChI=1S/C13H21NO2S/c1-4-7-17-13-9-11(15-2)10(5-6-14)8-12(13)16-3/h8-9H,4-7,14H2,1-3H3
inchiKey:    OLEVEPDJOFPJTF-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#16]-[#6]1:[#6](:[#6]:[#6](:[#6](:[#6]:1)-[#8]-[#6])-[#6]-[#6]-[#7])-[#8]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]-[#16]-[#6]1:[#6](:[#6]:[#6](:[#6](:[#6]:1)-[#8]-[#6])-[#6]-[#6]-[#7])-[#8]-[#6]

4-methoxyamphetamine: CC(CC1=CC=C(C=C1)OC)N

smiles_non_kekule:    COc1ccc(CC(C)N)cc1
smiles_kekule:    COC1=CC=C(CC(C)N)C=C1
inchi:    InChI=1S/C10H15NO/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6,8H,7,11H2,1-2H3
inchiKey:    NEGYEDYHPHMHGK-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#7]
smarts_isomeric:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#7]

5-methoxy-3,4-methylenedioxy-amphetamine: CC(CC1=CC2=C(C(=C1)OC)OCO2)N

smiles_non_kekule:    COc1cc(CC(C)N)cc2c1OCO2
smiles_kekule:    COC1=CC(CC(C)N)=CC2=C1OCO2
inchi:    InChI=1S/C11H15NO3/c1-7(12)3-8-4-9(13-2)11-10(5-8)14-6-15-11/h4-5,7H,3,6,12H2,1-2H3
inchiKey:    YQYUWUKDEVZFDB-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]2:[#6](:[#6](:[#6]:1)-[#8]-[#6])-[#8]-[#6]-[#8]-2)-[#7]
smarts_isomeric:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]2:[#6](:[#6](:[#6]:1)-[#8]-[#6])-[#8]-[#6]-[#8]-2)-[#7]

4-methyl-2,5-dimethoxy-amphetamine: CC(CC1=CC(=C(C=C1OC)SC)OC)N

smiles_non_kekule:    COc1cc(SC)c(OC)cc1CC(C)N
smiles_kekule:    COC1=CC(SC)=C(OC)C=C1CC(C)N
inchi:    InChI=1S/C12H19NO2S/c1-8(13)5-9-6-11(15-3)12(16-4)7-10(9)14-2/h6-8H,5,13H2,1-4H3
inchiKey:    COBYBOVXXDQRAU-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#8]-[#6])-[#16]-[#6])-[#8]-[#6])-[#7]
smarts_isomeric:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#8]-[#6])-[#16]-[#6])-[#8]-[#6])-[#7]

3,4-methylenedioxyamphetamine: CC(CC1=CC2=C(C=C1)OCO2)N

smiles_non_kekule:    CC(N)Cc1ccc2c(c1)OCO2
smiles_kekule:    CC(N)CC1=CC2=C(C=C1)OCO2
inchi:    InChI=1S/C10H13NO2/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6,11H2,1H3
inchiKey:    NGBBVGZWCFBOGO-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#8]-2)-[#7]
smarts_isomeric:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#8]-2)-[#7]

3,4-methylenedioxymethamphetamine: CC(CC1=CC2=C(C=C1)OCO2)NC

smiles_non_kekule:    CNC(C)Cc1ccc2c(c1)OCO2
smiles_kekule:    CNC(C)CC1=CC2=C(C=C1)OCO2
inchi:    InChI=1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3
inchiKey:    SHXWCVYOXRDMCX-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#8]-2)-[#7]-[#6]
smarts_isomeric:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#8]-2)-[#7]-[#6]

3,4-methylenedioxy-n-ethylamphetamine: CCNC(C)CC1=CC2=C(C=C1)OCO2

smiles_non_kekule:    CCNC(C)Cc1ccc2c(c1)OCO2
smiles_kekule:    CCNC(C)CC1=CC2=C(C=C1)OCO2
inchi:    InChI=1S/C12H17NO2/c1-3-13-9(2)6-10-4-5-11-12(7-10)15-8-14-11/h4-5,7,9,13H,3,6,8H2,1-2H3
inchiKey:    PVXVWWANJIWJOO-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7]-[#6](-[#6])-[#6]-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#8]-2
smarts_isomeric:    [#6]-[#6]-[#7]-[#6](-[#6])-[#6]-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#8]-2

n-hydroxy-3,4-methylenedioxyamphetamine: CC(CC1=CC2=C(C=C1)OCO2)NO

smiles_non_kekule:    CC(Cc1ccc2c(c1)OCO2)NO
smiles_kekule:    CC(CC1=CC2=C(C=C1)OCO2)NO
inchi:    InChI=1S/C10H13NO3/c1-7(11-12)4-8-2-3-9-10(5-8)14-6-13-9/h2-3,5,7,11-12H,4,6H2,1H3
inchiKey:    FNDCTJYFKOQGTL-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#8]-2)-[#7]-[#8]
smarts_isomeric:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#8]-2)-[#7]-[#8]

3,4,5-trimethoxyamphetamine: CC(CC1=CC(=C(C(=C1)OC)OC)OC)N

smiles_non_kekule:    COc1cc(CC(C)N)cc(OC)c1OC
smiles_kekule:    COC1=CC(CC(C)N)=CC(OC)=C1OC
inchi:    InChI=1S/C12H19NO3/c1-8(13)5-9-6-10(14-2)12(16-4)11(7-9)15-3/h6-8H,5,13H2,1-4H3
inchiKey:    WGTASENVNYJZBK-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6](:[#6](:[#6](:[#6]:1)-[#8]-[#6])-[#8]-[#6])-[#8]-[#6])-[#7]
smarts_isomeric:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6](:[#6](:[#6](:[#6]:1)-[#8]-[#6])-[#8]-[#6])-[#8]-[#6])-[#7]

5-methoxy-n,n-dimethyltryptamine: CN(C)CCC1=CNC2=C1C=C(C=C2)OC

smiles_non_kekule:    COc1ccc2[nH]cc(CCN(C)C)c2c1
smiles_kekule:    COC1=CC2=C(C=C1)NC=C2CCN(C)C
inchi:    InChI=1S/C13H18N2O/c1-15(2)7-6-10-9-14-13-5-4-11(16-3)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3
inchiKey:    ZSTKHSQDNIGFLM-UHFFFAOYSA-N
smarts:    [#6]-[#7](-[#6])-[#6]-[#6]-[#6]1:[#6]:[#7H]:[#6]2:[#6]:1:[#6]:[#6](:[#6]:[#6]:2)-[#8]-[#6]
smarts_isomeric:    [#6]-[#7](-[#6])-[#6]-[#6]-[#6]1:[#6]:[#7H]:[#6]2:[#6]:1:[#6]:[#6](:[#6]:[#6]:2)-[#8]-[#6]

alpha-methyltryptamine: CC(CC1=CNC2=CC=CC=C21)N

smiles_non_kekule:    CC(N)Cc1c[nH]c2ccccc12
smiles_kekule:    CC(N)CC1=CNC2=CC=CC=C12
inchi:    InChI=1S/C11H14N2/c1-8(12)6-9-7-13-11-5-3-2-4-10(9)11/h2-5,7-8,13H,6,12H2,1H3
inchiKey:    QSQQQURBVYWZKJ-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#7H]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#7]
smarts_isomeric:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#7H]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#7]

bufotenine: CN(C)CCC1=CNC2=C1C=C(C=C2)O

smiles_non_kekule:    CN(C)CCc1c[nH]c2ccc(O)cc12
smiles_kekule:    CN(C)CCC1=CNC2=C1C=C(O)C=C2
inchi:    InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3
inchiKey:    VTTONGPRPXSUTJ-UHFFFAOYSA-N
smarts:    [#6]-[#7](-[#6])-[#6]-[#6]-[#6]1:[#6]:[#7H]:[#6]2:[#6]:1:[#6]:[#6](:[#6]:[#6]:2)-[#8]
smarts_isomeric:    [#6]-[#7](-[#6])-[#6]-[#6]-[#6]1:[#6]:[#7H]:[#6]2:[#6]:1:[#6]:[#6](:[#6]:[#6]:2)-[#8]

diethyltryptamine: CCN(CC)CCC1=CNC2=CC=CC=C21

smiles_non_kekule:    CCN(CC)CCc1c[nH]c2ccccc12
smiles_kekule:    CCN(CC)CCC1=CNC2=CC=CC=C12
inchi:    InChI=1S/C14H20N2/c1-3-16(4-2)10-9-12-11-15-14-8-6-5-7-13(12)14/h5-8,11,15H,3-4,9-10H2,1-2H3
inchiKey:    LSSUMOWDTKZHHT-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7](-[#6]-[#6])-[#6]-[#6]-[#6]1:[#6]:[#7H]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2
smarts_isomeric:    [#6]-[#6]-[#7](-[#6]-[#6])-[#6]-[#6]-[#6]1:[#6]:[#7H]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2

dimethyltryptamine: CN(C)CCC1=CNC2=CC=CC=C21

smiles_non_kekule:    CN(C)CCc1c[nH]c2ccccc12
smiles_kekule:    CN(C)CCC1=CNC2=CC=CC=C12
inchi:    InChI=1S/C12H16N2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H3
inchiKey:    DMULVCHRPCFFGV-UHFFFAOYSA-N
smarts:    [#6]-[#7](-[#6])-[#6]-[#6]-[#6]1:[#6]:[#7H]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2
smarts_isomeric:    [#6]-[#7](-[#6])-[#6]-[#6]-[#6]1:[#6]:[#7H]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2

5-methoxy-n,n-diisopropyltryptamine: CC(C)N(CCC1=CNC2=C1C=C(C=C2)OC)C(C)C

smiles_non_kekule:    COc1ccc2[nH]cc(CCN(C(C)C)C(C)C)c2c1
smiles_kekule:    COC1=CC2=C(C=C1)NC=C2CCN(C(C)C)C(C)C
inchi:    InChI=1S/C17H26N2O/c1-12(2)19(13(3)4)9-8-14-11-18-17-7-6-15(20-5)10-16(14)17/h6-7,10-13,18H,8-9H2,1-5H3
inchiKey:    DNBPMBJFRRVTSJ-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])-[#7](-[#6]-[#6]-[#6]1:[#6]:[#7H]:[#6]2:[#6]:1:[#6]:[#6](:[#6]:[#6]:2)-[#8]-[#6])-[#6](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6](-[#6])-[#7](-[#6]-[#6]-[#6]1:[#6]:[#7H]:[#6]2:[#6]:1:[#6]:[#6](:[#6]:[#6]:2)-[#8]-[#6])-[#6](-[#6])-[#6]

ibogaine: CCC1CC2CC3C1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC

smiles_non_kekule:    CCC1CC2CC3c4[nH]c5ccc(OC)cc5c4CCN(C2)C13
smiles_kekule:    CCC1CC2CC3C4=C(CCN(C2)C13)C1=C(C=CC(OC)=C1)N4
inchi:    InChI=1S/C20H26N2O/c1-3-13-8-12-9-17-19-15(6-7-22(11-12)20(13)17)16-10-14(23-2)4-5-18(16)21-19/h4-5,10,12-13,17,20-21H,3,6-9,11H2,1-2H3
inchiKey:    HSIBGVUMFOSJPD-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]1-[#6]-[#6]2-[#6]-[#6]3-[#6]-1-[#7](-[#6]-2)-[#6]-[#6]-[#6]1:[#6]-3:[#7H]:[#6]2:[#6]:1:[#6]:[#6](:[#6]:[#6]:2)-[#8]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]1-[#6]-[#6]2-[#6]-[#6]3-[#6]-1-[#7](-[#6]-2)-[#6]-[#6]-[#6]1:[#6]-3:[#7H]:[#6]2:[#6]:1:[#6]:[#6](:[#6]:[#6]:2)-[#8]-[#6]

lysergicaciddiethylamide: CCN(CC)C(=O)C1CN(C2CC3=CNC4=CC=CC(=C34)C2=C1)C

smiles_non_kekule:    CCN(CC)C(=O)C1C=C2c3cccc4[nH]cc(c34)CC2N(C)C1
smiles_kekule:    CCN(CC)C(=O)C1C=C2C3=C4C(=CNC4=CC=C3)CC2N(C)C1
inchi:    InChI=1S/C20H25N3O/c1-4-23(5-2)20(24)14-9-16-15-7-6-8-17-19(15)13(11-21-17)10-18(16)22(3)12-14/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3
inchiKey:    VAYOSLLFUXYJDT-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7](-[#6]-[#6])-[#6](=[#8])-[#6]1-[#6]-[#7](-[#6]2-[#6]-[#6]3:[#6]:[#7H]:[#6]4:[#6]:[#6]:[#6]:[#6](:[#6]:3:4)-[#6]-2=[#6]-1)-[#6]
smarts_isomeric:    [#6]-[#6]-[#7](-[#6]-[#6])-[#6](=[#8])-[#6]1-[#6]-[#7](-[#6]2-[#6]-[#6]3:[#6]:[#7H]:[#6]4:[#6]:[#6]:[#6]:[#6](:[#6]:3:4)-[#6]-2=[#6]-1)-[#6]

marihuana: CCCCCC1=CC(=C2C3C=C(CCC3C(OC2=C1)(C)C)C)O

smiles_non_kekule:    CCCCCc1cc(O)c2c(c1)OC(C)(C)C1CCC(C)=CC21
smiles_kekule:    CCCCCC1=CC(O)=C2C(=C1)OC(C)(C)C1CCC(C)=CC21
inchi:    InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3
inchiKey:    CYQFCXCEBYINGO-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]1:[#6]:[#6](:[#6]2-[#6]3-[#6]=[#6](-[#6]-[#6]-[#6]-3-[#6](-[#8]-[#6]:2:[#6]:1)(-[#6])-[#6])-[#6])-[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]1:[#6]:[#6](:[#6]2-[#6]3-[#6]=[#6](-[#6]-[#6]-[#6]-3-[#6](-[#8]-[#6]:2:[#6]:1)(-[#6])-[#6])-[#6])-[#8]

mescaline: COC1=CC(=CC(=C1OC)OC)CCN

smiles_non_kekule:    COc1cc(CCN)cc(OC)c1OC
smiles_kekule:    COC1=CC(CCN)=CC(OC)=C1OC
inchi:    InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3
inchiKey:    RHCSKNNOAZULRK-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]1:[#6]:[#6](:[#6]:[#6](:[#6]:1-[#8]-[#6])-[#8]-[#6])-[#6]-[#6]-[#7]
smarts_isomeric:    [#6]-[#8]-[#6]1:[#6]:[#6](:[#6]:[#6](:[#6]:1-[#8]-[#6])-[#8]-[#6])-[#6]-[#6]-[#7]

parahexyl: CCCCCCC1=CC(=C2C3=C(CCC(C3)C)C(OC2=C1)(C)C)O

smiles_non_kekule:    CCCCCCc1cc(O)c2c(c1)OC(C)(C)C1=C2CC(C)CC1
smiles_kekule:    CCCCCCC1=CC(O)=C2C3=C(CCC(C)C3)C(C)(C)OC2=C1
inchi:    InChI=1S/C22H32O2/c1-5-6-7-8-9-16-13-19(23)21-17-12-15(2)10-11-18(17)22(3,4)24-20(21)14-16/h13-15,23H,5-12H2,1-4H3
inchiKey:    OORFXDSWECAQLI-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]1:[#6]:[#6](:[#6]2-[#6]3=[#6](-[#6]-[#6]-[#6](-[#6]-3)-[#6])-[#6](-[#8]-[#6]:2:[#6]:1)(-[#6])-[#6])-[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]1:[#6]:[#6](:[#6]2-[#6]3=[#6](-[#6]-[#6]-[#6](-[#6]-3)-[#6])-[#6](-[#8]-[#6]:2:[#6]:1)(-[#6])-[#6])-[#8]

peyote: COC1=CC(=CC(=C1OC)OC)CCN

n-ethyl-3-piperidylbenzilate: O=C(OC1CCCN(CC)C1)C(O)(c2ccccc2)c3ccccc3

smiles_non_kekule:    CCN1CCCC(OC(=O)C(O)(c2ccccc2)c2ccccc2)C1
smiles_kekule:    CCN1CCCC(OC(=O)C(O)(C2=CC=CC=C2)C2=CC=CC=C2)C1
inchi:    InChI=1S/C21H25NO3/c1-2-22-15-9-14-19(16-22)25-20(23)21(24,17-10-5-3-6-11-17)18-12-7-4-8-13-18/h3-8,10-13,19,24H,2,9,14-16H2,1H3
inchiKey:    OJYOTLHNSMYONM-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#8]-[#6]1-[#6]-[#6]-[#6]-[#7](-[#6]-[#6])-[#6]-1)-[#6](-[#8])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#8]=[#6](-[#8]-[#6]1-[#6]-[#6]-[#6]-[#7](-[#6]-[#6])-[#6]-1)-[#6](-[#8])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

n-methyl-3-piperidylbenzilate: CN1CCCC(C1)OC(=O)C(C2=CC=CC=C2)(C3=CC=CC=C3)O

smiles_non_kekule:    CN1CCCC(OC(=O)C(O)(c2ccccc2)c2ccccc2)C1
smiles_kekule:    CN1CCCC(OC(=O)C(O)(C2=CC=CC=C2)C2=CC=CC=C2)C1
inchi:    InChI=1S/C20H23NO3/c1-21-14-8-13-18(15-21)24-19(22)20(23,16-9-4-2-5-10-16)17-11-6-3-7-12-17/h2-7,9-12,18,23H,8,13-15H2,1H3
inchiKey:    ZBEILXWHVSVDBN-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]-[#6](-[#6]-1)-[#8]-[#6](=[#8])-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8]
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]-[#6](-[#6]-1)-[#8]-[#6](=[#8])-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8]

psilocybin: CN(C)CCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O

smiles_non_kekule:    CN(C)CCc1c[nH]c2cccc(OP(=O)(O)O)c12
smiles_kekule:    CN(C)CCC1=CNC2=C1C(OP(=O)(O)O)=CC=C2
inchi:    InChI=1S/C12H17N2O4P/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)18-19(15,16)17/h3-5,8,13H,6-7H2,1-2H3,(H2,15,16,17)
inchiKey:    QVDSEJDULKLHCG-UHFFFAOYSA-N
smarts:    [#6]-[#7](-[#6])-[#6]-[#6]-[#6]1:[#6]:[#7H]:[#6]2:[#6]:1:[#6](:[#6]:[#6]:[#6]:2)-[#8]-[#15](=[#8])(-[#8])-[#8]
smarts_isomeric:    [#6]-[#7](-[#6])-[#6]-[#6]-[#6]1:[#6]:[#7H]:[#6]2:[#6]:1:[#6](:[#6]:[#6]:[#6]:2)-[#8]-[#15](=[#8])(-[#8])-[#8]

psilocyn: CN(C)CCC1=CNC2=C1C(=CC=C2)O

smiles_non_kekule:    CN(C)CCc1c[nH]c2cccc(O)c12
smiles_kekule:    CN(C)CCC1=CNC2=C1C(O)=CC=C2
inchi:    InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3
inchiKey:    SPCIYGNTAMCTRO-UHFFFAOYSA-N
smarts:    [#6]-[#7](-[#6])-[#6]-[#6]-[#6]1:[#6]:[#7H]:[#6]2:[#6]:1:[#6](:[#6]:[#6]:[#6]:2)-[#8]
smarts_isomeric:    [#6]-[#7](-[#6])-[#6]-[#6]-[#6]1:[#6]:[#7H]:[#6]2:[#6]:1:[#6](:[#6]:[#6]:[#6]:2)-[#8]

tetrahydrocannabinols: CCCCCC1=CC(=C2C3C=C(CCC3C(OC2=C1)(C)C)C)O

n-ethyl-1-phenylcyclohexylamine: ClC(Cl)=C(Cl)Cl

smiles_non_kekule:    ClC(Cl)=C(Cl)Cl
smiles_kekule:    ClC(Cl)=C(Cl)Cl
inchi:    InChI=1S/C2Cl4/c3-1(4)2(5)6
inchiKey:    CYTYCFOTNPOANT-UHFFFAOYSA-N
smarts:    [#17]-[#6](-[#17])=[#6](-[#17])-[#17]
smarts_isomeric:    [#17]-[#6](-[#17])=[#6](-[#17])-[#17]

pyrrolidine-phencyclidine: c1ccccc1C3(N2CCCC2)CCCCC3

smiles_non_kekule:    c1ccc(C2(N3CCCC3)CCCCC2)cc1
smiles_kekule:    C1=CC=C(C2(N3CCCC3)CCCCC2)C=C1
inchi:    InChI=1S/C16H23N/c1-3-9-15(10-4-1)16(11-5-2-6-12-16)17-13-7-8-14-17/h1,3-4,9-10H,2,5-8,11-14H2
inchiKey:    FYOWWXMGDATDQY-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]1(-[#7]2-[#6]-[#6]-[#6]-[#6]-2)-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]1(-[#7]2-[#6]-[#6]-[#6]-[#6]-2)-[#6]-[#6]-[#6]-[#6]-[#6]-1

thiophene-phencyclidine: C1CCC(CC1)(C2=CC=CS2)N3CCCCC3

smiles_non_kekule:    c1csc(C2(N3CCCCC3)CCCCC2)c1
smiles_kekule:    C1=CSC(C2(N3CCCCC3)CCCCC2)=C1
inchi:    InChI=1S/C15H23NS/c1-3-9-15(10-4-1,14-8-7-13-17-14)16-11-5-2-6-12-16/h7-8,13H,1-6,9-12H2
inchiKey:    JUZZEWSCNBCFRL-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)(-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)(-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

1-[1-(2-thienyl)cyclohexyl]pyrrolidine: C1CCC(CC1)(C2=CC=CS2)N3CCCC3

smiles_non_kekule:    c1csc(C2(N3CCCC3)CCCCC2)c1
smiles_kekule:    C1=CSC(C2(N3CCCC3)CCCCC2)=C1
inchi:    InChI=1S/C14H21NS/c1-2-8-14(9-3-1,13-7-6-12-16-13)15-10-4-5-11-15/h6-7,12H,1-5,8-11H2
inchiKey:    XLQOCWQLDNWQDM-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)(-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#7]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)(-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#7]1-[#6]-[#6]-[#6]-[#6]-1

mephedrone: CC1=CC=C(C=C1)C(=O)C(C)NC

smiles_non_kekule:    CNC(C)C(=O)c1ccc(C)cc1
smiles_kekule:    CNC(C)C(=O)C1=CC=C(C)C=C1
inchi:    InChI=1S/C11H15NO/c1-8-4-6-10(7-5-8)11(13)9(2)12-3/h4-7,9,12H,1-3H3
inchiKey:    YELGFTGWJGBAQU-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6](=[#8])-[#6](-[#6])-[#7]-[#6]
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6](=[#8])-[#6](-[#6])-[#7]-[#6]

mdpv: CCCC(C(=O)C1=CC2=C(C=C1)OCO2)N3CCCC3

smiles_non_kekule:    CCCC(C(=O)c1ccc2c(c1)OCO2)N1CCCC1
smiles_kekule:    CCCC(C(=O)C1=CC2=C(C=C1)OCO2)N1CCCC1
inchi:    InChI=1S/C16H21NO3/c1-2-5-13(17-8-3-4-9-17)16(18)12-6-7-14-15(10-12)20-11-19-14/h6-7,10,13H,2-5,8-9,11H2,1H3
inchiKey:    SYHGEUNFJIGTRX-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#8]-2)-[#7]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6]-[#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#8]-2)-[#7]1-[#6]-[#6]-[#6]-[#6]-1

2c-e: COc1cc(CC)c(cc1CCN)OC

smiles_non_kekule:    CCc1cc(OC)c(CCN)cc1OC
smiles_kekule:    CCC1=C(OC)C=C(CCN)C(OC)=C1
inchi:    InChI=1S/C12H19NO2/c1-4-9-7-12(15-3)10(5-6-13)8-11(9)14-2/h7-8H,4-6,13H2,1-3H3
inchiKey:    VDRGNAMREYBIHA-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]1:[#6]:[#6](-[#6]-[#6]):[#6](:[#6]:[#6]:1-[#6]-[#6]-[#7])-[#8]-[#6]
smarts_isomeric:    [#6]-[#8]-[#6]1:[#6]:[#6](-[#6]-[#6]):[#6](:[#6]:[#6]:1-[#6]-[#6]-[#7])-[#8]-[#6]

2c-d: O(c1cc(c(OC)cc1CCN)C)C

smiles_non_kekule:    COc1cc(CCN)c(OC)cc1C
smiles_kekule:    COC1=C(C)C=C(OC)C(CCN)=C1
inchi:    InChI=1S/C11H17NO2/c1-8-6-11(14-3)9(4-5-12)7-10(8)13-2/h6-7H,4-5,12H2,1-3H3
inchiKey:    UNQQFDCVEMVQHM-UHFFFAOYSA-N
smarts:    [#8](-[#6]1:[#6]:[#6](:[#6](-[#8]-[#6]):[#6]:[#6]:1-[#6]-[#6]-[#7])-[#6])-[#6]
smarts_isomeric:    [#8](-[#6]1:[#6]:[#6](:[#6](-[#8]-[#6]):[#6]:[#6]:1-[#6]-[#6]-[#7])-[#6])-[#6]

2c-c: COc1cc(CCN)c(cc1Cl)OC

smiles_non_kekule:    COc1cc(CCN)c(OC)cc1Cl
smiles_kekule:    COC1=CC(CCN)=C(OC)C=C1Cl
inchi:    InChI=1S/C10H14ClNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3
inchiKey:    CGKQFIWIPSIVAS-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]1:[#6]:[#6](-[#6]-[#6]-[#7]):[#6](:[#6]:[#6]:1-[#17])-[#8]-[#6]
smarts_isomeric:    [#6]-[#8]-[#6]1:[#6]:[#6](-[#6]-[#6]-[#7]):[#6](:[#6]:[#6]:1-[#17])-[#8]-[#6]

2c-i: Ic1cc(OC)c(cc1OC)CCN

smiles_non_kekule:    COc1cc(CCN)c(OC)cc1I
smiles_kekule:    COC1=CC(CCN)=C(OC)C=C1I
inchi:    InChI=1S/C10H14INO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3
inchiKey:    PQHQBRJAAZQXHL-UHFFFAOYSA-N
smarts:    [#53]-[#6]1:[#6]:[#6](-[#8]-[#6]):[#6](:[#6]:[#6]:1-[#8]-[#6])-[#6]-[#6]-[#7]
smarts_isomeric:    [#53]-[#6]1:[#6]:[#6](-[#8]-[#6]):[#6](:[#6]:[#6]:1-[#8]-[#6])-[#6]-[#6]-[#7]

2c-t-2: CCSc1cc(OC)c(cc1OC)CCN

smiles_non_kekule:    CCSc1cc(OC)c(CCN)cc1OC
smiles_kekule:    CCSC1=CC(OC)=C(CCN)C=C1OC
inchi:    InChI=1S/C12H19NO2S/c1-4-16-12-8-10(14-2)9(5-6-13)7-11(12)15-3/h7-8H,4-6,13H2,1-3H3
inchiKey:    HCWQGDLBIKOJPM-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#16]-[#6]1:[#6]:[#6](-[#8]-[#6]):[#6](:[#6]:[#6]:1-[#8]-[#6])-[#6]-[#6]-[#7]
smarts_isomeric:    [#6]-[#6]-[#16]-[#6]1:[#6]:[#6](-[#8]-[#6]):[#6](:[#6]:[#6]:1-[#8]-[#6])-[#6]-[#6]-[#7]

2c-t-4: CC(C)Sc1cc(OC)c(cc1OC)CCN

smiles_non_kekule:    COc1cc(SC(C)C)c(OC)cc1CCN
smiles_kekule:    COC1=C(CCN)C=C(OC)C(SC(C)C)=C1
inchi:    InChI=1S/C13H21NO2S/c1-9(2)17-13-8-11(15-3)10(5-6-14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3
inchiKey:    HDYZSVKZKDPLDT-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])-[#16]-[#6]1:[#6]:[#6](-[#8]-[#6]):[#6](:[#6]:[#6]:1-[#8]-[#6])-[#6]-[#6]-[#7]
smarts_isomeric:    [#6]-[#6](-[#6])-[#16]-[#6]1:[#6]:[#6](-[#8]-[#6]):[#6](:[#6]:[#6]:1-[#8]-[#6])-[#6]-[#6]-[#7]

2c-h: O(c1ccc(OC)cc1CCN)C

smiles_non_kekule:    COc1ccc(OC)c(CCN)c1
smiles_kekule:    COC1=CC=C(OC)C(CCN)=C1
inchi:    InChI=1S/C10H15NO2/c1-12-9-3-4-10(13-2)8(7-9)5-6-11/h3-4,7H,5-6,11H2,1-2H3
inchiKey:    WNCUVUUEJZEATP-UHFFFAOYSA-N
smarts:    [#8](-[#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6]:[#6]:1-[#6]-[#6]-[#7])-[#6]
smarts_isomeric:    [#8](-[#6]1:[#6]:[#6]:[#6](-[#8]-[#6]):[#6]:[#6]:1-[#6]-[#6]-[#7])-[#6]

2c-n: [O-][N+](=O)c1cc(OC)c(cc1OC)CCN

smiles_non_kekule:    COc1cc([N+](=O)[O-])c(OC)cc1CCN
smiles_kekule:    COC1=C(CCN)C=C(OC)C([N+](=O)[O-])=C1
inchi:    InChI=1S/C10H14N2O4/c1-15-9-6-8(12(13)14)10(16-2)5-7(9)3-4-11/h5-6H,3-4,11H2,1-2H3
inchiKey:    ZMUSDZGRRJGRAO-UHFFFAOYSA-N
smarts:    [#8-]-[#7+](=[#8])-[#6]1:[#6]:[#6](-[#8]-[#6]):[#6](:[#6]:[#6]:1-[#8]-[#6])-[#6]-[#6]-[#7]
smarts_isomeric:    [#8-]-[#7+](=[#8])-[#6]1:[#6]:[#6](-[#8]-[#6]):[#6](:[#6]:[#6]:1-[#8]-[#6])-[#6]-[#6]-[#7]

2c-p: COC1=C(CCN)C=C(OC)C(CCC)=C1

smiles_non_kekule:    CCCc1cc(OC)c(CCN)cc1OC
smiles_kekule:    CCCC1=CC(OC)=C(CCN)C=C1OC
inchi:    InChI=1S/C13H21NO2/c1-4-5-10-8-13(16-3)11(6-7-14)9-12(10)15-2/h8-9H,4-7,14H2,1-3H3
inchiKey:    PZJOKFZGPTVNBF-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]1:[#6](-[#6]-[#6]-[#7]):[#6]:[#6](-[#8]-[#6]):[#6](-[#6]-[#6]-[#6]):[#6]:1
smarts_isomeric:    [#6]-[#8]-[#6]1:[#6](-[#6]-[#6]-[#7]):[#6]:[#6](-[#8]-[#6]):[#6](-[#6]-[#6]-[#6]):[#6]:1

methylone: CC(C(=O)C1=CC2=C(C=C1)OCO2)NC

smiles_non_kekule:    CNC(C)C(=O)c1ccc2c(c1)OCO2
smiles_kekule:    CNC(C)C(=O)C1=CC2=C(C=C1)OCO2
inchi:    InChI=1S/C11H13NO3/c1-7(12-2)11(13)8-3-4-9-10(5-8)15-6-14-9/h3-5,7,12H,6H2,1-2H3
inchiKey:    VKEQBMCRQDSRET-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#8]-2)-[#7]-[#6]
smarts_isomeric:    [#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#8]-2)-[#7]-[#6]

ur-144: CCCCCN1C=C(C2=CC=CC=C21)C(=O)C3C(C3(C)C)(C)C

smiles_non_kekule:    CCCCCn1cc(C(=O)C2C(C)(C)C2(C)C)c2ccccc21
smiles_kekule:    CCCCCN1C=C(C(=O)C2C(C)(C)C2(C)C)C2=CC=CC=C21
inchi:    InChI=1S/C21H29NO/c1-6-7-10-13-22-14-16(15-11-8-9-12-17(15)22)18(23)19-20(2,3)21(19,4)5/h8-9,11-12,14,19H,6-7,10,13H2,1-5H3
inchiKey:    NBMMIBNZVQFQEO-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#7]1:[#6]:[#6](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6](=[#8])-[#6]1-[#6](-[#6]-1(-[#6])-[#6])(-[#6])-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#7]1:[#6]:[#6](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6](=[#8])-[#6]1-[#6](-[#6]-1(-[#6])-[#6])(-[#6])-[#6]

5-fluoro-ur-144: FCCCCCN1C=C(C(C2C(C)(C)C2(C)C)=O)C3=C1C=CC=C3

smiles_non_kekule:    CC1(C)C(C(=O)c2cn(CCCCCF)c3ccccc23)C1(C)C
smiles_kekule:    CC1(C)C(C(=O)C2=CN(CCCCCF)C3=C2C=CC=C3)C1(C)C
inchi:    InChI=1S/C21H28FNO/c1-20(2)19(21(20,3)4)18(24)16-14-23(13-9-5-8-12-22)17-11-7-6-10-15(16)17/h6-7,10-11,14,19H,5,8-9,12-13H2,1-4H3
inchiKey:    PXLDPUUMIHVLEC-UHFFFAOYSA-N
smarts:    [#9]-[#6]-[#6]-[#6]-[#6]-[#6]-[#7]1:[#6]:[#6](-[#6](-[#6]2-[#6](-[#6])(-[#6])-[#6]-2(-[#6])-[#6])=[#8]):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#9]-[#6]-[#6]-[#6]-[#6]-[#6]-[#7]1:[#6]:[#6](-[#6](-[#6]2-[#6](-[#6])(-[#6])-[#6]-2(-[#6])-[#6])=[#8]):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2

apinaca: C3C4CC2CC3CC(C4)(C2)NC(=O)c(nn1CCCCC)c5c1cccc5

smiles_non_kekule:    CCCCCn1nc(C(=O)NC23CC4CC(CC(C4)C2)C3)c2ccccc21
smiles_kekule:    CCCCCN1N=C(C(=O)NC23CC4CC(CC(C4)C2)C3)C2=C1C=CC=C2
inchi:    InChI=1S/C23H31N3O/c1-2-3-6-9-26-20-8-5-4-7-19(20)21(25-26)22(27)24-23-13-16-10-17(14-23)12-18(11-16)15-23/h4-5,7-8,16-18H,2-3,6,9-15H2,1H3,(H,24,27)
inchiKey:    UCTCCIPCJZKWEZ-UHFFFAOYSA-N
smarts:    [#6]1-[#6]2-[#6]-[#6]3-[#6]-[#6]-1-[#6]-[#6](-[#6]-2)(-[#6]-3)-[#7]-[#6](=[#8])-[#6]1:[#7]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#6]1-[#6]2-[#6]-[#6]3-[#6]-[#6]-1-[#6]-[#6](-[#6]-2)(-[#6]-3)-[#7]-[#6](=[#8])-[#6]1:[#7]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2

quinolin-8-yl 5-fluoro-1-pentylindole-3-carboxylate: CCCCCN1C=C(C2=C1C=CC(=C2)F)C(=O)OC3=CC=CC4=C3N=CC=C4

smiles_non_kekule:    CCCCCn1cc(C(=O)Oc2cccc3cccnc23)c2cc(F)ccc21
smiles_kekule:    CCCCCN1C=C(C(=O)OC2=CC=CC3=C2N=CC=C3)C2=C1C=CC(F)=C2
inchi:    InChI=1S/C23H21FN2O2/c1-2-3-4-13-26-15-19(18-14-17(24)10-11-20(18)26)23(27)28-21-9-5-7-16-8-6-12-25-22(16)21/h5-12,14-15H,2-4,13H2,1H3
inchiKey:    MOYVWIALGMWFFL-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#7]1:[#6]:[#6](:[#6]2:[#6]:1:[#6]:[#6]:[#6](:[#6]:2)-[#9])-[#6](=[#8])-[#8]-[#6]1:[#6]:[#6]:[#6]:[#6]2:[#6]:1:[#7]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#7]1:[#6]:[#6](:[#6]2:[#6]:1:[#6]:[#6]:[#6](:[#6]:2)-[#9])-[#6](=[#8])-[#8]-[#6]1:[#6]:[#6]:[#6]:[#6]2:[#6]:1:[#7]:[#6]:[#6]:[#6]:2

quinolin-8-yl1-(5-fluoropentyl)-1h-indole-3-carboxylate: C1=CC=C2C(=C1)C(=CN2CCCCCF)C(=O)OC3=CC=CC4=C3N=CC=C4

smiles_non_kekule:    O=C(Oc1cccc2cccnc12)c1cn(CCCCCF)c2ccccc12
smiles_kekule:    O=C(OC1=CC=CC2=C1N=CC=C2)C1=CN(CCCCCF)C2=CC=CC=C12
inchi:    InChI=1S/C23H21FN2O2/c24-13-4-1-5-15-26-16-19(18-10-2-3-11-20(18)26)23(27)28-21-12-6-8-17-9-7-14-25-22(17)21/h2-3,6-12,14,16H,1,4-5,13,15H2
inchiKey:    MBOCMBFDYVSGLJ-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]2:[#6](:[#6]:1):[#6](:[#6]:[#7]:2-[#6]-[#6]-[#6]-[#6]-[#6]-[#9])-[#6](=[#8])-[#8]-[#6]1:[#6]:[#6]:[#6]:[#6]2:[#6]:1:[#7]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]2:[#6](:[#6]:1):[#6](:[#6]:[#7]:2-[#6]-[#6]-[#6]-[#6]-[#6]-[#9])-[#6](=[#8])-[#8]-[#6]1:[#6]:[#6]:[#6]:[#6]2:[#6]:1:[#7]:[#6]:[#6]:[#6]:2

n-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1h-indazole-3-carboxamide: CC(C)C(C(=O)N)NC(=O)C1=NN(C2=CC=CC=C21)CC3=CC=C(C=C3)F

smiles_non_kekule:    CC(C)C(NC(=O)c1nn(Cc2ccc(F)cc2)c2ccccc12)C(N)=O
smiles_kekule:    CC(C)C(NC(=O)C1=NN(CC2=CC=C(F)C=C2)C2=CC=CC=C12)C(N)=O
inchi:    InChI=1S/C20H21FN4O2/c1-12(2)17(19(22)26)23-20(27)18-15-5-3-4-6-16(15)25(24-18)11-13-7-9-14(21)10-8-13/h3-10,12,17H,11H2,1-2H3,(H2,22,26)(H,23,27)
inchiKey:    AKOOIMKXADOPDA-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])-[#6](-[#6](=[#8])-[#7])-[#7]-[#6](=[#8])-[#6]1:[#7]:[#7](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#9]
smarts_isomeric:    [#6]-[#6](-[#6])-[#6](-[#6](=[#8])-[#7])-[#7]-[#6](=[#8])-[#6]1:[#7]:[#7](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#9]

n-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-pentyl-1h-indazole-3-carboxamide: O=C(C1=NN(CCCCC)C2=C1C=CC=C2)NC(C(C)(C)C)C(N)=O

smiles_non_kekule:    CCCCCn1nc(C(=O)NC(C(N)=O)C(C)(C)C)c2ccccc21
smiles_kekule:    CCCCCN1N=C(C(=O)NC(C(N)=O)C(C)(C)C)C2=C1C=CC=C2
inchi:    InChI=1S/C19H28N4O2/c1-5-6-9-12-23-14-11-8-7-10-13(14)15(22-23)18(25)21-16(17(20)24)19(2,3)4/h7-8,10-11,16H,5-6,9,12H2,1-4H3,(H2,20,24)(H,21,25)
inchiKey:    FWTARAXQGJRQKN-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6]1:[#7]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#7]-[#6](-[#6](-[#6])(-[#6])-[#6])-[#6](-[#7])=[#8]
smarts_isomeric:    [#8]=[#6](-[#6]1:[#7]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#7]-[#6](-[#6](-[#6])(-[#6])-[#6])-[#6](-[#7])=[#8]

2c-i-nbome: COC1=CC=CC=C1CNCCC2=CC(=C(C=C2OC)I)OC

smiles_non_kekule:    COc1cc(CCNCc2ccccc2OC)c(OC)cc1I
smiles_kekule:    COC1=C(I)C=C(OC)C(CCNCC2=CC=CC=C2OC)=C1
inchi:    InChI=1S/C18H22INO3/c1-21-16-7-5-4-6-14(16)12-20-9-8-13-10-18(23-3)15(19)11-17(13)22-2/h4-7,10-11,20H,8-9,12H2,1-3H3
inchiKey:    ZFUOLNAKPBFDIJ-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#7]-[#6]-[#6]-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#8]-[#6])-[#53])-[#8]-[#6]
smarts_isomeric:    [#6]-[#8]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#7]-[#6]-[#6]-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#8]-[#6])-[#53])-[#8]-[#6]

2c-c-nbome: COc2ccccc2CNCCc(cc1OC)c(OC)cc1Cl

smiles_non_kekule:    COc1cc(CCNCc2ccccc2OC)c(OC)cc1Cl
smiles_kekule:    COC1=C(Cl)C=C(OC)C(CCNCC2=CC=CC=C2OC)=C1
inchi:    InChI=1S/C18H22ClNO3/c1-21-16-7-5-4-6-14(16)12-20-9-8-13-10-18(23-3)15(19)11-17(13)22-2/h4-7,10-11,20H,8-9,12H2,1-3H3
inchiKey:    FJFPOGCVVLUYAQ-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#7]-[#6]-[#6]-[#6]1:[#6]:[#6](-[#8]-[#6]):[#6](:[#6]:[#6]:1-[#8]-[#6])-[#17]
smarts_isomeric:    [#6]-[#8]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#7]-[#6]-[#6]-[#6]1:[#6]:[#6](-[#8]-[#6]):[#6](:[#6]:[#6]:1-[#8]-[#6])-[#17]

2c-b-nbome: COC1=CC=CC=C1CNCCC2=CC(=C(C=C2OC)Br)OC

smiles_non_kekule:    COc1cc(CCNCc2ccccc2OC)c(OC)cc1Br
smiles_kekule:    COC1=C(Br)C=C(OC)C(CCNCC2=CC=CC=C2OC)=C1
inchi:    InChI=1S/C18H22BrNO3/c1-21-16-7-5-4-6-14(16)12-20-9-8-13-10-18(23-3)15(19)11-17(13)22-2/h4-7,10-11,20H,8-9,12H2,1-3H3
inchiKey:    SUXGNJVVBGJEFB-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#7]-[#6]-[#6]-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#8]-[#6])-[#35])-[#8]-[#6]
smarts_isomeric:    [#6]-[#8]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#7]-[#6]-[#6]-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1-[#8]-[#6])-[#35])-[#8]-[#6]

4-mec: CCNC(C)C(=O)C1=CC=C(C=C1)C

smiles_non_kekule:    CCNC(C)C(=O)c1ccc(C)cc1
smiles_kekule:    CCNC(C)C(=O)C1=CC=C(C)C=C1
inchi:    InChI=1S/C12H17NO/c1-4-13-10(3)12(14)11-7-5-9(2)6-8-11/h5-8,10,13H,4H2,1-3H3
inchiKey:    ZOXZWYWOECCBSH-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7]-[#6](-[#6])-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]
smarts_isomeric:    [#6]-[#6]-[#7]-[#6](-[#6])-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]

4-meppp: CC1=CC=C(C=C1)C(=O)C(C)N2CCCC2

smiles_non_kekule:    Cc1ccc(C(=O)C(C)N2CCCC2)cc1
smiles_kekule:    CC1=CC=C(C(=O)C(C)N2CCCC2)C=C1
inchi:    InChI=1S/C14H19NO/c1-11-5-7-13(8-6-11)14(16)12(2)15-9-3-4-10-15/h5-8,12H,3-4,9-10H2,1-2H3
inchiKey:    APSJUNFBAXIXLK-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6](=[#8])-[#6](-[#6])-[#7]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6](=[#8])-[#6](-[#6])-[#7]1-[#6]-[#6]-[#6]-[#6]-1

alpha-pvp: CCCC(C(C1=CC=CC=C1)=O)N2CCCC2

smiles_non_kekule:    CCCC(C(=O)c1ccccc1)N1CCCC1
smiles_kekule:    CCCC(C(=O)C1=CC=CC=C1)N1CCCC1
inchi:    InChI=1S/C15H21NO/c1-2-8-14(16-11-6-7-12-16)15(17)13-9-4-3-5-10-13/h3-5,9-10,14H,2,6-8,11-12H2,1H3
inchiKey:    YDIIDRWHPFMLGR-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6](-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)=[#8])-[#7]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6]-[#6]-[#6](-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)=[#8])-[#7]1-[#6]-[#6]-[#6]-[#6]-1

butylone: CCC(C(=O)C1=CC2=C(C=C1)OCO2)NC

smiles_non_kekule:    CCC(NC)C(=O)c1ccc2c(c1)OCO2
smiles_kekule:    CCC(NC)C(=O)C1=CC2=C(C=C1)OCO2
inchi:    InChI=1S/C12H15NO3/c1-3-9(13-2)12(14)8-4-5-10-11(6-8)16-7-15-10/h4-6,9,13H,3,7H2,1-2H3
inchiKey:    CGKQZIULZRXRRJ-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#8]-2)-[#7]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#8]-2)-[#7]-[#6]

pentedrone: CCCC(C(=O)C1=CC=CC=C1)NC

smiles_non_kekule:    CCCC(NC)C(=O)c1ccccc1
smiles_kekule:    CCCC(NC)C(=O)C1=CC=CC=C1
inchi:    InChI=1S/C12H17NO/c1-3-7-11(13-2)12(14)10-8-5-4-6-9-10/h4-6,8-9,11,13H,3,7H2,1-2H3
inchiKey:    WLIWIUNEJRETFX-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]-[#6]

pentylone: CCCC(C(=O)C1=CC2=C(C=C1)OCO2)NC

smiles_non_kekule:    CCCC(NC)C(=O)c1ccc2c(c1)OCO2
smiles_kekule:    CCCC(NC)C(=O)C1=CC2=C(C=C1)OCO2
inchi:    InChI=1S/C13H17NO3/c1-3-4-10(14-2)13(15)9-5-6-11-12(7-9)17-8-16-11/h5-7,10,14H,3-4,8H2,1-2H3
inchiKey:    DFMLULIEUUXXSA-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#8]-2)-[#7]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#8]-2)-[#7]-[#6]

flephedrone: CC(C(=O)C1=CC=C(C=C1)F)NC

smiles_non_kekule:    CNC(C)C(=O)c1ccc(F)cc1
smiles_kekule:    CNC(C)C(=O)C1=CC=C(F)C=C1
inchi:    InChI=1S/C10H12FNO/c1-7(12-2)10(13)8-3-5-9(11)6-4-8/h3-7,12H,1-2H3
inchiKey:    MWKQPIROPJSFRI-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#9])-[#7]-[#6]
smarts_isomeric:    [#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#9])-[#7]-[#6]

3-fmc: FC1=CC=CC(=C1)C(C(C)NC)=O

smiles_non_kekule:    CNC(C)C(=O)c1cccc(F)c1
smiles_kekule:    CNC(C)C(=O)C1=CC(F)=CC=C1
inchi:    InChI=1S/C10H12FNO/c1-7(12-2)10(13)8-4-3-5-9(11)6-8/h3-7,12H,1-2H3
inchiKey:    PQIBROLLUQSNQI-UHFFFAOYSA-N
smarts:    [#9]-[#6]1:[#6]:[#6]:[#6]:[#6](:[#6]:1)-[#6](-[#6](-[#6])-[#7]-[#6])=[#8]
smarts_isomeric:    [#9]-[#6]1:[#6]:[#6]:[#6]:[#6](:[#6]:1)-[#6](-[#6](-[#6])-[#7]-[#6])=[#8]

naphyrone: CCCC(C(C1=CC2=C(C=C1)C=CC=C2)=O)N3CCCC3

smiles_non_kekule:    CCCC(C(=O)c1ccc2ccccc2c1)N1CCCC1
smiles_kekule:    CCCC(C(=O)C1=CC2=C(C=CC=C2)C=C1)N1CCCC1
inchi:    InChI=1S/C19H23NO/c1-2-7-18(20-12-5-6-13-20)19(21)17-11-10-15-8-3-4-9-16(15)14-17/h3-4,8-11,14,18H,2,5-7,12-13H2,1H3
inchiKey:    DTNUPBSOODGRKW-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6](-[#6](-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1):[#6]:[#6]:[#6]:[#6]:2)=[#8])-[#7]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6]-[#6]-[#6](-[#6](-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1):[#6]:[#6]:[#6]:[#6]:2)=[#8])-[#7]1-[#6]-[#6]-[#6]-[#6]-1

alpha-pbp: C2CCCN2C(CC)C(=O)c1ccccc1

smiles_non_kekule:    CCC(C(=O)c1ccccc1)N1CCCC1
smiles_kekule:    CCC(C(=O)C1=CC=CC=C1)N1CCCC1
inchi:    InChI=1S/C14H19NO/c1-2-13(15-10-6-7-11-15)14(16)12-8-4-3-5-9-12/h3-5,8-9,13H,2,6-7,10-11H2,1H3
inchiKey:    GSESDIFGJCCBHN-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#6]-[#7]-1-[#6](-[#6]-[#6])-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#6]-[#7]-1-[#6](-[#6]-[#6])-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

ab-chminaca: CC(C)C(C(=O)N)NC(=O)C1=NN(C2=CC=CC=C21)CC3CCCCC3

smiles_non_kekule:    CC(C)C(NC(=O)c1nn(CC2CCCCC2)c2ccccc12)C(N)=O
smiles_kekule:    CC(C)C(NC(=O)C1=NN(CC2CCCCC2)C2=CC=CC=C12)C(N)=O
inchi:    InChI=1S/C20H28N4O2/c1-13(2)17(19(21)25)22-20(26)18-15-10-6-7-11-16(15)24(23-18)12-14-8-4-3-5-9-14/h6-7,10-11,13-14,17H,3-5,8-9,12H2,1-2H3,(H2,21,25)(H,22,26)
inchiKey:    KJNZIEGLNLCWTQ-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])-[#6](-[#6](=[#8])-[#7])-[#7]-[#6](=[#8])-[#6]1:[#7]:[#7](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6](-[#6])-[#6](-[#6](=[#8])-[#7])-[#7]-[#6](=[#8])-[#6]1:[#7]:[#7](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

ab-pinaca: CCCCCN1C2=CC=CC=C2C(=N1)C(=O)NC(C(C)C)C(=O)N

smiles_non_kekule:    CCCCCn1nc(C(=O)NC(C(N)=O)C(C)C)c2ccccc21
smiles_kekule:    CCCCCN1N=C(C(=O)NC(C(N)=O)C(C)C)C2=CC=CC=C21
inchi:    InChI=1S/C18H26N4O2/c1-4-5-8-11-22-14-10-7-6-9-13(14)16(21-22)18(24)20-15(12(2)3)17(19)23/h6-7,9-10,12,15H,4-5,8,11H2,1-3H3,(H2,19,23)(H,20,24)
inchiKey:    GIMHPAQOAAZSHS-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#7]1:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#6](:[#7]:1)-[#6](=[#8])-[#7]-[#6](-[#6](-[#6])-[#6])-[#6](=[#8])-[#7]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#7]1:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#6](:[#7]:1)-[#6](=[#8])-[#7]-[#6](-[#6](-[#6])-[#6])-[#6](=[#8])-[#7]

thj-2201: O=C(C1=CC=CC2=C1C=CC=C2)C3=NN(CCCCCF)C4=C3C=CC=C4

smiles_non_kekule:    O=C(c1cccc2ccccc12)c1nn(CCCCCF)c2ccccc12
smiles_kekule:    O=C(C1=CC=CC2=C1C=CC=C2)C1=NN(CCCCCF)C2=C1C=CC=C2
inchi:    InChI=1S/C23H21FN2O/c24-15-6-1-7-16-26-21-14-5-4-12-20(21)22(25-26)23(27)19-13-8-10-17-9-2-3-11-18(17)19/h2-5,8-14H,1,6-7,15-16H2
inchiKey:    DULWRYKFTVFPTL-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#6]1:[#7]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]-[#9]):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#8]=[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#6]1:[#7]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]-[#9]):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2

mab-chminaca: O=C(NC(C(N)=O)C(C)(C)C)C1=NN(CC2CCCCC2)C3=C1C=CC=C3

smiles_non_kekule:    CC(C)(C)C(NC(=O)c1nn(CC2CCCCC2)c2ccccc12)C(N)=O
smiles_kekule:    CC(C)(C)C(NC(=O)C1=NN(CC2CCCCC2)C2=C1C=CC=C2)C(N)=O
inchi:    InChI=1S/C21H30N4O2/c1-21(2,3)18(19(22)26)23-20(27)17-15-11-7-8-12-16(15)25(24-17)13-14-9-5-4-6-10-14/h7-8,11-12,14,18H,4-6,9-10,13H2,1-3H3,(H2,22,26)(H,23,27)
inchiKey:    ZWCCSIUBHCZKOY-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#7]-[#6](-[#6](-[#7])=[#8])-[#6](-[#6])(-[#6])-[#6])-[#6]1:[#7]:[#7](-[#6]-[#6]2-[#6]-[#6]-[#6]-[#6]-[#6]-2):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#8]=[#6](-[#7]-[#6](-[#6](-[#7])=[#8])-[#6](-[#6])(-[#6])-[#6])-[#6]1:[#7]:[#7](-[#6]-[#6]2-[#6]-[#6]-[#6]-[#6]-[#6]-2):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2

5f-mdmb-pinaca: COC(=O)C(NC(=O)c1nn(CCCCCF)c2ccccc12)C(C)(C)C

smiles_non_kekule:    COC(=O)C(NC(=O)c1nn(CCCCCF)c2ccccc12)C(C)(C)C
smiles_kekule:    COC(=O)C(NC(=O)C1=NN(CCCCCF)C2=CC=CC=C12)C(C)(C)C
inchi:    InChI=1S/C20H28FN3O3/c1-20(2,3)17(19(26)27-4)22-18(25)16-14-10-6-7-11-15(14)24(23-16)13-9-5-8-12-21/h6-7,10-11,17H,5,8-9,12-13H2,1-4H3,(H,22,25)
inchiKey:    PWEKNGSNNAKWBL-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6](=[#8])-[#6](-[#7]-[#6](=[#8])-[#6]1:[#7]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]-[#9]):[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6](-[#6])(-[#6])-[#6]
smarts_isomeric:    [#6]-[#8]-[#6](=[#8])-[#6](-[#7]-[#6](=[#8])-[#6]1:[#7]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]-[#9]):[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6](-[#6])(-[#6])-[#6]

5f-amb: CC(C)C(C(=O)OC)NC(=O)C1=NN(C2=CC=CC=C21)CCCCCF

smiles_non_kekule:    COC(=O)C(NC(=O)c1nn(CCCCCF)c2ccccc12)C(C)C
smiles_kekule:    COC(=O)C(NC(=O)C1=NN(CCCCCF)C2=CC=CC=C12)C(C)C
inchi:    InChI=1S/C19H26FN3O3/c1-13(2)16(19(25)26-3)21-18(24)17-14-9-5-6-10-15(14)23(22-17)12-8-4-7-11-20/h5-6,9-10,13,16H,4,7-8,11-12H2,1-3H3,(H,21,24)
inchiKey:    SAFXSUZMRLTBMM-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])-[#6](-[#6](=[#8])-[#8]-[#6])-[#7]-[#6](=[#8])-[#6]1:[#7]:[#7](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6]-[#6]-[#6]-[#6]-[#6]-[#9]
smarts_isomeric:    [#6]-[#6](-[#6])-[#6](-[#6](=[#8])-[#8]-[#6])-[#7]-[#6](=[#8])-[#6]1:[#7]:[#7](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6]-[#6]-[#6]-[#6]-[#6]-[#9]

5f-apinaca: O=C(C1=NN(C2=C1C=CC=C2)CCCCCF)NC34CC5CC(C4)CC(C5)C3

smiles_non_kekule:    O=C(NC12CC3CC(CC(C3)C1)C2)c1nn(CCCCCF)c2ccccc12
smiles_kekule:    O=C(NC12CC3CC(CC(C3)C1)C2)C1=NN(CCCCCF)C2=C1C=CC=C2
inchi:    InChI=1S/C23H30FN3O/c24-8-4-1-5-9-27-20-7-3-2-6-19(20)21(26-27)22(28)25-23-13-16-10-17(14-23)12-18(11-16)15-23/h2-3,6-7,16-18H,1,4-5,8-15H2,(H,25,28)
inchiKey:    UCMFSGVIEPXYIV-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6]1:[#7]:[#7](:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-[#6]-[#6]-[#6]-[#9])-[#7]-[#6]12-[#6]-[#6]3-[#6]-[#6](-[#6]-1)-[#6]-[#6](-[#6]-3)-[#6]-2
smarts_isomeric:    [#8]=[#6](-[#6]1:[#7]:[#7](:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-[#6]-[#6]-[#6]-[#9])-[#7]-[#6]12-[#6]-[#6]3-[#6]-[#6](-[#6]-1)-[#6]-[#6](-[#6]-3)-[#6]-2

adb-fubinaca: CC(C)(C)C(C(=O)N)NC(=O)C1=NN(C2=CC=CC=C21)CC3=CC=C(C=C3)F

smiles_non_kekule:    CC(C)(C)C(NC(=O)c1nn(Cc2ccc(F)cc2)c2ccccc12)C(N)=O
smiles_kekule:    CC(C)(C)C(NC(=O)C1=NN(CC2=CC=C(F)C=C2)C2=CC=CC=C12)C(N)=O
inchi:    InChI=1S/C21H23FN4O2/c1-21(2,3)18(19(23)27)24-20(28)17-15-6-4-5-7-16(15)26(25-17)12-13-8-10-14(22)11-9-13/h4-11,18H,12H2,1-3H3,(H2,23,27)(H,24,28)
inchiKey:    ZSSGCSINPVBLQD-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])(-[#6])-[#6](-[#6](=[#8])-[#7])-[#7]-[#6](=[#8])-[#6]1:[#7]:[#7](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#9]
smarts_isomeric:    [#6]-[#6](-[#6])(-[#6])-[#6](-[#6](=[#8])-[#7])-[#7]-[#6](=[#8])-[#6]1:[#7]:[#7](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#9]

mdmb-chmica: COC(=O)[C@@H](NC(=O)c1cn(CC2CCCCC2)c3ccccc13)C(C)(C)C

smiles_non_kekule:    COC(=O)[C@@H](NC(=O)c1cn(CC2CCCCC2)c2ccccc12)C(C)(C)C
smiles_kekule:    COC(=O)[C@@H](NC(=O)C1=CN(CC2CCCCC2)C2=CC=CC=C12)C(C)(C)C
inchi:    InChI=1S/C23H32N2O3/c1-23(2,3)20(22(27)28-4)24-21(26)18-15-25(14-16-10-6-5-7-11-16)19-13-9-8-12-17(18)19/h8-9,12-13,15-16,20H,5-7,10-11,14H2,1-4H3,(H,24,26)/t20-/m1/s1
inchiKey:    SRJKCVHWIDFUBO-HXUWFJFHSA-N
smarts:    [#6]-[#8]-[#6](=[#8])-[#6H](-[#7]-[#6](=[#8])-[#6]1:[#6]:[#7](-[#6]-[#6]2-[#6]-[#6]-[#6]-[#6]-[#6]-2):[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6](-[#6])(-[#6])-[#6]
smarts_isomeric:    [#6]-[#8]-[#6](=[#8])-[#6@@H](-[#7]-[#6](=[#8])-[#6]1:[#6]:[#7](-[#6]-[#6]2-[#6]-[#6]-[#6]-[#6]-[#6]-2):[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6](-[#6])(-[#6])-[#6]

mdmb-fubinaca: CC(C)(C)C(C(=O)OC)NC(=O)C1=NN(C2=CC=CC=C21)CC3=CC=C(C=C3)F

smiles_non_kekule:    COC(=O)C(NC(=O)c1nn(Cc2ccc(F)cc2)c2ccccc12)C(C)(C)C
smiles_kekule:    COC(=O)C(NC(=O)C1=NN(CC2=CC=C(F)C=C2)C2=CC=CC=C12)C(C)(C)C
inchi:    InChI=1S/C22H24FN3O3/c1-22(2,3)19(21(28)29-4)24-20(27)18-16-7-5-6-8-17(16)26(25-18)13-14-9-11-15(23)12-10-14/h5-12,19H,13H2,1-4H3,(H,24,27)
inchiKey:    RFCDVEHNYDVCMU-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])(-[#6])-[#6](-[#6](=[#8])-[#8]-[#6])-[#7]-[#6](=[#8])-[#6]1:[#7]:[#7](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#9]
smarts_isomeric:    [#6]-[#6](-[#6])(-[#6])-[#6](-[#6](=[#8])-[#8]-[#6])-[#7]-[#6](=[#8])-[#6]1:[#7]:[#7](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#9]

mmb-fubinaca: FC(C=C1)=CC=C1CN2N=C(C(N[C@H](C(OC)=O)C(C)C)=O)C3=CC=CC=C32

smiles_non_kekule:    COC(=O)[C@@H](NC(=O)c1nn(Cc2ccc(F)cc2)c2ccccc12)C(C)C
smiles_kekule:    COC(=O)[C@@H](NC(=O)C1=NN(CC2=CC=C(F)C=C2)C2=CC=CC=C12)C(C)C
inchi:    InChI=1S/C21H22FN3O3/c1-13(2)18(21(27)28-3)23-20(26)19-16-6-4-5-7-17(16)25(24-19)12-14-8-10-15(22)11-9-14/h4-11,13,18H,12H2,1-3H3,(H,23,26)/t18-/m0/s1
inchiKey:    FRFFLYJQPCIIQB-SFHVURJKSA-N
smarts:    [#9]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]-[#7]1:[#7]:[#6](-[#6](-[#7]-[#6H](-[#6](-[#8]-[#6])=[#8])-[#6](-[#6])-[#6])=[#8]):[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2
smarts_isomeric:    [#9]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]-[#7]1:[#7]:[#6](-[#6](-[#7]-[#6@H](-[#6](-[#8]-[#6])=[#8])-[#6](-[#6])-[#6])=[#8]):[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2

ethylone: CCNC(C)C(=O)C1=CC2=C(C=C1)OCO2

smiles_non_kekule:    CCNC(C)C(=O)c1ccc2c(c1)OCO2
smiles_kekule:    CCNC(C)C(=O)C1=CC2=C(C=C1)OCO2
inchi:    InChI=1S/C12H15NO3/c1-3-13-8(2)12(14)9-4-5-10-11(6-9)16-7-15-10/h4-6,8,13H,3,7H2,1-2H3
inchiKey:    MJEMIOXXNCZZFK-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7]-[#6](-[#6])-[#6](=[#8])-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#8]-2
smarts_isomeric:    [#6]-[#6]-[#7]-[#6](-[#6])-[#6](=[#8])-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#8]-2

nm2201: FCCCCCN1C=C(C(OC2=C(C=CC=C3)C3=CC=C2)=O)C4=CC=CC=C41

smiles_non_kekule:    O=C(Oc1cccc2ccccc12)c1cn(CCCCCF)c2ccccc12
smiles_kekule:    O=C(OC1=CC=CC2=CC=CC=C12)C1=CN(CCCCCF)C2=CC=CC=C12
inchi:    InChI=1S/C24H22FNO2/c25-15-6-1-7-16-26-17-21(20-12-4-5-13-22(20)26)24(27)28-23-14-8-10-18-9-2-3-11-19(18)23/h2-5,8-14,17H,1,6-7,15-16H2
inchiKey:    PRGFSQYZCKCBQO-UHFFFAOYSA-N
smarts:    [#9]-[#6]-[#6]-[#6]-[#6]-[#6]-[#7]1:[#6]:[#6](-[#6](-[#8]-[#6]2:[#6]3:[#6]:[#6]:[#6]:[#6]:[#6]:3:[#6]:[#6]:[#6]:2)=[#8]):[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2
smarts_isomeric:    [#9]-[#6]-[#6]-[#6]-[#6]-[#6]-[#7]1:[#6]:[#6](-[#6](-[#8]-[#6]2:[#6]3:[#6]:[#6]:[#6]:[#6]:[#6]:3:[#6]:[#6]:[#6]:2)=[#8]):[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2

5f-ab-pinaca: CC(C)C(C(=O)N)NC(=O)C1=NN(C2=CC=CC=C21)CCCCCF

smiles_non_kekule:    CC(C)C(NC(=O)c1nn(CCCCCF)c2ccccc12)C(N)=O
smiles_kekule:    CC(C)C(NC(=O)C1=NN(CCCCCF)C2=CC=CC=C12)C(N)=O
inchi:    InChI=1S/C18H25FN4O2/c1-12(2)15(17(20)24)21-18(25)16-13-8-4-5-9-14(13)23(22-16)11-7-3-6-10-19/h4-5,8-9,12,15H,3,6-7,10-11H2,1-2H3,(H2,20,24)(H,21,25)
inchiKey:    WCBYXIBEPFZUBG-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])-[#6](-[#6](=[#8])-[#7])-[#7]-[#6](=[#8])-[#6]1:[#7]:[#7](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6]-[#6]-[#6]-[#6]-[#6]-[#9]
smarts_isomeric:    [#6]-[#6](-[#6])-[#6](-[#6](=[#8])-[#7])-[#7]-[#6](=[#8])-[#6]1:[#7]:[#7](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6]-[#6]-[#6]-[#6]-[#6]-[#9]

4-cn-cumyl-butinaca: O=C(NC(C)(C)C1=CC=CC=C1)C2=NN(CCCCC#N)C3=C2C=CC=C3

smiles_non_kekule:    CC(C)(NC(=O)c1nn(CCCCC#N)c2ccccc12)c1ccccc1
smiles_kekule:    CC(C)(NC(=O)C1=NN(CCCCC#N)C2=C1C=CC=C2)C1=CC=CC=C1
inchi:    InChI=1S/C22H24N4O/c1-22(2,17-11-5-3-6-12-17)24-21(27)20-18-13-7-8-14-19(18)26(25-20)16-10-4-9-15-23/h3,5-8,11-14H,4,9-10,16H2,1-2H3,(H,24,27)
inchiKey:    JGTSOWOPISVAHG-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#7]-[#6](-[#6])(-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#7]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]#[#7]):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#8]=[#6](-[#7]-[#6](-[#6])(-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#7]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]#[#7]):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2

mmb-chmica: CC(C)C(C(=O)OC)NC(=O)C1=CN(C2=CC=CC=C21)CC3CCCCC3

smiles_non_kekule:    COC(=O)C(NC(=O)c1cn(CC2CCCCC2)c2ccccc12)C(C)C
smiles_kekule:    COC(=O)C(NC(=O)C1=CN(CC2CCCCC2)C2=CC=CC=C12)C(C)C
inchi:    InChI=1S/C22H30N2O3/c1-15(2)20(22(26)27-3)23-21(25)18-14-24(13-16-9-5-4-6-10-16)19-12-8-7-11-17(18)19/h7-8,11-12,14-16,20H,4-6,9-10,13H2,1-3H3,(H,23,25)
inchiKey:    ROWZIXRLVUOMCJ-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])-[#6](-[#6](=[#8])-[#8]-[#6])-[#7]-[#6](=[#8])-[#6]1:[#6]:[#7](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6](-[#6])-[#6](-[#6](=[#8])-[#8]-[#6])-[#7]-[#6](=[#8])-[#6]1:[#6]:[#7](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

5f-cumyl-p7aica: CC(C)(C1=CC=CC=C1)NC(=O)C2=CN(C3=C2C=CC=N3)CCCCCF

smiles_non_kekule:    CC(C)(NC(=O)c1cn(CCCCCF)c2ncccc12)c1ccccc1
smiles_kekule:    CC(C)(NC(=O)C1=CN(CCCCCF)C2=C1C=CC=N2)C1=CC=CC=C1
inchi:    InChI=1S/C22H26FN3O/c1-22(2,17-10-5-3-6-11-17)25-21(27)19-16-26(15-8-4-7-13-23)20-18(19)12-9-14-24-20/h3,5-6,9-12,14,16H,4,7-8,13,15H2,1-2H3,(H,25,27)
inchiKey:    MXJYOUMYJGNQEY-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]-[#6](=[#8])-[#6]1:[#6]:[#7](:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#7]:2)-[#6]-[#6]-[#6]-[#6]-[#6]-[#9]
smarts_isomeric:    [#6]-[#6](-[#6])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]-[#6](=[#8])-[#6]1:[#6]:[#7](:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#7]:2)-[#6]-[#6]-[#6]-[#6]-[#6]-[#9]

n-ethylpentylone: CCCC(C(=O)C1=CC2=C(C=C1)OCO2)NCC

smiles_non_kekule:    CCCC(NCC)C(=O)c1ccc2c(c1)OCO2
smiles_kekule:    CCCC(NCC)C(=O)C1=CC2=C(C=C1)OCO2
inchi:    InChI=1S/C14H19NO3/c1-3-5-11(15-4-2)14(16)10-6-7-12-13(8-10)18-9-17-12/h6-8,11,15H,3-5,9H2,1-2H3
inchiKey:    VERDHJIMZYXGIW-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#8]-2)-[#7]-[#6]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]2:[#6](:[#6]:[#6]:1)-[#8]-[#6]-[#8]-2)-[#7]-[#6]-[#6]

4f-mdmb-binaca: O=C(N[C@H](C(OC)=O)C(C)(C)C)C1=NN(CCCCF)C2=C1C=CC=C2

smiles_non_kekule:    COC(=O)[C@@H](NC(=O)c1nn(CCCCF)c2ccccc12)C(C)(C)C
smiles_kekule:    COC(=O)[C@@H](NC(=O)C1=NN(CCCCF)C2=C1C=CC=C2)C(C)(C)C
inchi:    InChI=1S/C19H26FN3O3/c1-19(2,3)16(18(25)26-4)21-17(24)15-13-9-5-6-10-14(13)23(22-15)12-8-7-11-20/h5-6,9-10,16H,7-8,11-12H2,1-4H3,(H,21,24)/t16-/m1/s1
inchiKey:    GZGKSDAMWRWYOZ-MRXNPFEDSA-N
smarts:    [#8]=[#6](-[#7]-[#6H](-[#6](-[#8]-[#6])=[#8])-[#6](-[#6])(-[#6])-[#6])-[#6]1:[#7]:[#7](-[#6]-[#6]-[#6]-[#6]-[#9]):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#8]=[#6](-[#7]-[#6@H](-[#6](-[#8]-[#6])=[#8])-[#6](-[#6])(-[#6])-[#6])-[#6]1:[#7]:[#7](-[#6]-[#6]-[#6]-[#6]-[#9]):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2

para-methoxymethamphetamine: CC(CC1=CC=C(C=C1)OC)NC

smiles_non_kekule:    CNC(C)Cc1ccc(OC)cc1
smiles_kekule:    CNC(C)CC1=CC=C(OC)C=C1
inchi:    InChI=1S/C11H17NO/c1-9(12-2)8-10-4-6-11(13-3)7-5-10/h4-7,9,12H,8H2,1-3H3
inchiKey:    UGFMBZYKVQSQFX-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#7]-[#6]
smarts_isomeric:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#7]-[#6]

gamma-hydroxybutyricacid: C(CC(=O)O)CO

smiles_non_kekule:    O=C(O)CCCO
smiles_kekule:    O=C(O)CCCO
inchi:    InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7)
inchiKey:    SJZRECIVHVDYJC-UHFFFAOYSA-N
smarts:    [#6](-[#6]-[#6](=[#8])-[#8])-[#6]-[#8]
smarts_isomeric:    [#6](-[#6]-[#6](=[#8])-[#8])-[#6]-[#8]

mecloqualone: CC1=NC2=CC=CC=C2C(=O)N1C3=CC=CC=C3Cl

smiles_non_kekule:    Cc1nc2ccccc2c(=O)n1-c1ccccc1Cl
smiles_kekule:    CC1=NC2=CC=CC=C2C(=O)N1C1=CC=CC=C1Cl
inchi:    InChI=1S/C15H11ClN2O/c1-10-17-13-8-4-2-6-11(13)15(19)18(10)14-9-5-3-7-12(14)16/h2-9H,1H3
inchiKey:    SFITWQDBYUMAPS-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#7]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#6](=[#8]):[#7]:1-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17]
smarts_isomeric:    [#6]-[#6]1:[#7]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#6](=[#8]):[#7]:1-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17]

methaqualone: CC1=CC=CC=C1N2C(=NC3=CC=CC=C3C2=O)C

smiles_non_kekule:    Cc1ccccc1-n1c(C)nc2ccccc2c1=O
smiles_kekule:    CC1=CC=CC=C1N1C(C)=NC2=CC=CC=C2C1=O
inchi:    InChI=1S/C16H14N2O/c1-11-7-3-6-10-15(11)18-12(2)17-14-9-5-4-8-13(14)16(18)19/h3-10H,1-2H3
inchiKey:    JEYCTXHKTXCGPB-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#7]1:[#6](:[#7]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#6]:1=[#8])-[#6]
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#7]1:[#6](:[#7]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#6]:1=[#8])-[#6]

aminorex: C1C(OC(=N1)N)C2=CC=CC=C2

smiles_non_kekule:    NC1=NCC(c2ccccc2)O1
smiles_kekule:    NC1=NCC(C2=CC=CC=C2)O1
inchi:    InChI=1S/C9H10N2O/c10-9-11-6-8(12-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H2,10,11)
inchiKey:    SYAKTDIEAPMBAL-UHFFFAOYSA-N
smarts:    [#6]1-[#6](-[#8]-[#6](=[#7]-1)-[#7])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1-[#6](-[#8]-[#6](=[#7]-1)-[#7])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

n-benzylpiperazine: C1CN(CCN1)CC2=CC=CC=C2

smiles_non_kekule:    c1ccc(CN2CCNCC2)cc1
smiles_kekule:    C1=CC=C(CN2CCNCC2)C=C1
inchi:    InChI=1S/C11H16N2/c1-2-4-11(5-3-1)10-13-8-6-12-7-9-13/h1-5,12H,6-10H2
inchiKey:    IQXXEPZFOOTTBA-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#7](-[#6]-[#6]-[#7]-1)-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1-[#6]-[#7](-[#6]-[#6]-[#7]-1)-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

cathinone: CC(C(=O)C1=CC=CC=C1)N

smiles_non_kekule:    CC(N)C(=O)c1ccccc1
smiles_kekule:    CC(N)C(=O)C1=CC=CC=C1
inchi:    InChI=1S/C9H11NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7H,10H2,1H3
inchiKey:    PUAQLLVFLMYYJJ-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]
smarts_isomeric:    [#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]

4,4′-dimethylaminorex: CC(N=C(N)O1)C1C2=CC=C(C)C=C2

smiles_non_kekule:    Cc1ccc(C2OC(N)=NC2C)cc1
smiles_kekule:    CC1=CC=C(C2OC(N)=NC2C)C=C1
inchi:    InChI=1S/C11H14N2O/c1-7-3-5-9(6-4-7)10-8(2)13-11(12)14-10/h3-6,8,10H,1-2H3,(H2,12,13)
inchiKey:    NPILLHMQNMXXTL-UHFFFAOYSA-N
smarts:    [#6]-[#6]1-[#7]=[#6](-[#7])-[#8]-[#6]-1-[#6]1:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]1-[#7]=[#6](-[#7])-[#8]-[#6]-1-[#6]1:[#6]:[#6]:[#6](-[#6]):[#6]:[#6]:1

fenethylline: CC(CC1=CC=CC=C1)NCCN2C=NC3=C2C(=O)N(C(=O)N3C)C

smiles_non_kekule:    CC(Cc1ccccc1)NCCn1cnc2c1c(=O)n(C)c(=O)n2C
smiles_kekule:    CC(CC1=CC=CC=C1)NCCN1C=NC2=C1C(=O)N(C)C(=O)N2C
inchi:    InChI=1S/C18H23N5O2/c1-13(11-14-7-5-4-6-8-14)19-9-10-23-12-20-16-15(23)17(24)22(3)18(25)21(16)2/h4-8,12-13,19H,9-11H2,1-3H3
inchiKey:    NMCHYWGKBADVMK-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]-[#6]-[#6]-[#7]1:[#6]:[#7]:[#6]2:[#6]:1:[#6](=[#8]):[#7](:[#6](=[#8]):[#7]:2-[#6])-[#6]
smarts_isomeric:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]-[#6]-[#6]-[#7]1:[#6]:[#7]:[#6]2:[#6]:1:[#6](=[#8]):[#7](:[#6](=[#8]):[#7]:2-[#6])-[#6]

methcathinone: CC(C(=O)C1=CC=CC=C1)NC

smiles_non_kekule:    CNC(C)C(=O)c1ccccc1
smiles_kekule:    CNC(C)C(=O)C1=CC=CC=C1
inchi:    InChI=1S/C10H13NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,11H,1-2H3
inchiKey:    LPLLVINFLBSFRP-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]-[#6]
smarts_isomeric:    [#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]-[#6]

(±)cis-4-methylaminorex: CC1C(OC(=N1)N)C2=CC=CC=C2

smiles_non_kekule:    CC1N=C(N)OC1c1ccccc1
smiles_kekule:    CC1N=C(N)OC1C1=CC=CC=C1
inchi:    InChI=1S/C10H12N2O/c1-7-9(13-10(11)12-7)8-5-3-2-4-6-8/h2-7,9H,1H3,(H2,11,12)
inchiKey:    LJQBMYDFWFGESC-UHFFFAOYSA-N
smarts:    [#6]-[#6]1-[#6](-[#8]-[#6](=[#7]-1)-[#7])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]1-[#6](-[#8]-[#6](=[#7]-1)-[#7])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

n-ethylamphetamine: CC(NCC)CC1=CC=CC=C1

smiles_non_kekule:    CCNC(C)Cc1ccccc1
smiles_kekule:    CCNC(C)CC1=CC=CC=C1
inchi:    InChI=1S/C11H17N/c1-3-12-10(2)9-11-7-5-4-6-8-11/h4-8,10,12H,3,9H2,1-2H3
inchiKey:    YAGBSNMZQKEFCO-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#7]-[#6]-[#6])-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6](-[#7]-[#6]-[#6])-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

n,n-dimethylamphetamine: CC(CC1=CC=CC=C1)N(C)C

smiles_non_kekule:    CC(Cc1ccccc1)N(C)C
smiles_kekule:    CC(CC1=CC=CC=C1)N(C)C
inchi:    InChI=1S/C11H17N/c1-10(12(2)3)9-11-7-5-4-6-8-11/h4-8,10H,9H2,1-3H3
inchiKey:    OBDSVYOSYSKVMX-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7](-[#6])-[#6]

cp-47,479: CCCCCCC(C)(C)c1ccc(c(c1)O)[C@H]2CCC[C@H](C2)O

smiles_non_kekule:    CCCCCCC(C)(C)c1ccc([C@H]2CCC[C@@H](O)C2)c(O)c1
smiles_kekule:    CCCCCCC(C)(C)C1=CC=C([C@H]2CCC[C@@H](O)C2)C(O)=C1
inchi:    InChI=1S/C21H34O2/c1-4-5-6-7-13-21(2,3)17-11-12-19(20(23)15-17)16-9-8-10-18(22)14-16/h11-12,15-16,18,22-23H,4-10,13-14H2,1-3H3/t16-,18+/m0/s1
inchiKey:    ZWWRREXSUJTKNN-FUHWJXTLSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6](-[#6])(-[#6])-[#6]1:[#6]:[#6]:[#6](:[#6](:[#6]:1)-[#8])-[#6H]1-[#6]-[#6]-[#6]-[#6H](-[#6]-1)-[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6](-[#6])(-[#6])-[#6]1:[#6]:[#6]:[#6](:[#6](:[#6]:1)-[#8])-[#6@H]1-[#6]-[#6]-[#6]-[#6@H](-[#6]-1)-[#8]

cannabicyclohexanol: CCCCCCCC(C)(C)C1=CC(=C(C=C1)C2CCCC(C2)O)O

smiles_non_kekule:    CCCCCCCC(C)(C)c1ccc(C2CCCC(O)C2)c(O)c1
smiles_kekule:    CCCCCCCC(C)(C)C1=CC(O)=C(C2CCCC(O)C2)C=C1
inchi:    InChI=1S/C22H36O2/c1-4-5-6-7-8-14-22(2,3)18-12-13-20(21(24)16-18)17-10-9-11-19(23)15-17/h12-13,16-17,19,23-24H,4-11,14-15H2,1-3H3
inchiKey:    HNMJDLVMIUDJNH-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6](-[#6])(-[#6])-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1)-[#6]1-[#6]-[#6]-[#6]-[#6](-[#6]-1)-[#8])-[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6](-[#6])(-[#6])-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1)-[#6]1-[#6]-[#6]-[#6]-[#6](-[#6]-1)-[#8])-[#8]

jwh-018: CCCCCN1C=C(C(C2=CC=CC3=CC=CC=C32)=O)C4=CC=CC=C41

smiles_non_kekule:    CCCCCn1cc(C(=O)c2cccc3ccccc23)c2ccccc21
smiles_kekule:    CCCCCN1C=C(C(=O)C2=CC=CC3=CC=CC=C23)C2=CC=CC=C21
inchi:    InChI=1S/C24H23NO/c1-2-3-8-16-25-17-22(20-13-6-7-15-23(20)25)24(26)21-14-9-11-18-10-4-5-12-19(18)21/h4-7,9-15,17H,2-3,8,16H2,1H3
inchiKey:    JDNLPKCAXICMBW-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#7]1:[#6]:[#6](-[#6](-[#6]2:[#6]:[#6]:[#6]:[#6]3:[#6]:[#6]:[#6]:[#6]:[#6]:2:3)=[#8]):[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#7]1:[#6]:[#6](-[#6](-[#6]2:[#6]:[#6]:[#6]:[#6]3:[#6]:[#6]:[#6]:[#6]:[#6]:2:3)=[#8]):[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2

jwh-073: CCCCN1C=C(C2=CC=CC=C21)C(=O)C3=CC=CC4=CC=CC=C43

smiles_non_kekule:    CCCCn1cc(C(=O)c2cccc3ccccc23)c2ccccc21
smiles_kekule:    CCCCN1C=C(C(=O)C2=CC=CC3=CC=CC=C23)C2=CC=CC=C21
inchi:    InChI=1S/C23H21NO/c1-2-3-15-24-16-21(19-12-6-7-14-22(19)24)23(25)20-13-8-10-17-9-4-5-11-18(17)20/h4-14,16H,2-3,15H2,1H3
inchiKey:    VCHHHSMPMLNVGS-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#7]1:[#6]:[#6](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#7]1:[#6]:[#6](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2

jwh-019: c3cccc2c3cccc2C(=O)c1cn(CCCCCC)c4c1cccc4

smiles_non_kekule:    CCCCCCn1cc(C(=O)c2cccc3ccccc23)c2ccccc21
smiles_kekule:    CCCCCCN1C=C(C(=O)C2=CC=CC3=C2C=CC=C3)C2=C1C=CC=C2
inchi:    InChI=1S/C25H25NO/c1-2-3-4-9-17-26-18-23(21-14-7-8-16-24(21)26)25(27)22-15-10-12-19-11-5-6-13-20(19)22/h5-8,10-16,18H,2-4,9,17H2,1H3
inchiKey:    PALJPGHWDUHUPO-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6]:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2-[#6](=[#8])-[#6]1:[#6]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6]:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2-[#6](=[#8])-[#6]1:[#6]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]-[#6]):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2

jwh-200: O=C(C1=CC=CC2=C1C=CC=C2)C3=CN(C4=C3C=CC=C4)CCN5CCOCC5

smiles_non_kekule:    O=C(c1cccc2ccccc12)c1cn(CCN2CCOCC2)c2ccccc12
smiles_kekule:    O=C(C1=CC=CC2=C1C=CC=C2)C1=CN(CCN2CCOCC2)C2=C1C=CC=C2
inchi:    InChI=1S/C25H24N2O2/c28-25(22-10-5-7-19-6-1-2-8-20(19)22)23-18-27(24-11-4-3-9-21(23)24)13-12-26-14-16-29-17-15-26/h1-11,18H,12-17H2
inchiKey:    SZWYXJHTNGJPKU-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#6]1:[#6]:[#7](:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1
smarts_isomeric:    [#8]=[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#6]1:[#6]:[#7](:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1

jwh-250: COc2ccccc2CC(=O)c(c3ccccc13)cn1CCCCC

smiles_non_kekule:    CCCCCn1cc(C(=O)Cc2ccccc2OC)c2ccccc21
smiles_kekule:    CCCCCN1C=C(C(=O)CC2=CC=CC=C2OC)C2=CC=CC=C21
inchi:    InChI=1S/C22H25NO2/c1-3-4-9-14-23-16-19(18-11-6-7-12-20(18)23)21(24)15-17-10-5-8-13-22(17)25-2/h5-8,10-13,16H,3-4,9,14-15H2,1-2H3
inchiKey:    FFLSJIQJQKDDCM-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6](=[#8])-[#6]1:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#7](:[#6]:1)-[#6]-[#6]-[#6]-[#6]-[#6]
smarts_isomeric:    [#6]-[#8]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6](=[#8])-[#6]1:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#7](:[#6]:1)-[#6]-[#6]-[#6]-[#6]-[#6]

jwh-081: CCCCCn3c1ccccc1c(c3)C(=O)c4c2ccccc2c(OC)cc4

smiles_non_kekule:    CCCCCn1cc(C(=O)c2ccc(OC)c3ccccc23)c2ccccc21
smiles_kekule:    CCCCCN1C=C(C(=O)C2=CC=C(OC)C3=CC=CC=C23)C2=CC=CC=C21
inchi:    InChI=1S/C25H25NO2/c1-3-4-9-16-26-17-22(19-11-7-8-13-23(19)26)25(27)21-14-15-24(28-2)20-12-6-5-10-18(20)21/h5-8,10-15,17H,3-4,9,16H2,1-2H3
inchiKey:    UBMPKJKGUQDHRM-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#7]1:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#6](:[#6]:1)-[#6](=[#8])-[#6]1:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#6](-[#8]-[#6]):[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#7]1:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#6](:[#6]:1)-[#6](=[#8])-[#6]1:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#6](-[#8]-[#6]):[#6]:[#6]:1

jwh-122: CCCCCn1cc(c2c1cccc2)C(=O)c3ccc(c4c3cccc4)C

smiles_non_kekule:    CCCCCn1cc(C(=O)c2ccc(C)c3ccccc23)c2ccccc21
smiles_kekule:    CCCCCN1C=C(C(=O)C2=CC=C(C)C3=C2C=CC=C3)C2=C1C=CC=C2
inchi:    InChI=1S/C25H25NO/c1-3-4-9-16-26-17-23(21-12-7-8-13-24(21)26)25(27)22-15-14-18(2)19-10-5-6-11-20(19)22/h5-8,10-15,17H,3-4,9,16H2,1-2H3
inchiKey:    HUKJQMKQFWYIHS-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#7]1:[#6]:[#6](:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6](:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#7]1:[#6]:[#6](:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6](:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#6]

jwh-398: c14ccccc1n(CCCCC)cc4C(=O)c(cc3)c2ccccc2c3Cl

smiles_non_kekule:    CCCCCn1cc(C(=O)c2ccc(Cl)c3ccccc23)c2ccccc21
smiles_kekule:    CCCCCN1C=C(C(=O)C2=CC=C(Cl)C3=CC=CC=C23)C2=CC=CC=C21
inchi:    InChI=1S/C24H22ClNO/c1-2-3-8-15-26-16-21(19-11-6-7-12-23(19)26)24(27)20-13-14-22(25)18-10-5-4-9-17(18)20/h4-7,9-14,16H,2-3,8,15H2,1H3
inchiKey:    IUWBHGFOHXVVKV-UHFFFAOYSA-N
smarts:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]):[#6]:[#6]:2-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6](:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#17]
smarts_isomeric:    [#6]12:[#6]:[#6]:[#6]:[#6]:[#6]:1:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]):[#6]:[#6]:2-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6](:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#17]

am-2201: O=C(C1=CN(CCCCCF)C2=C1C=CC=C2)C3=CC=CC4=C3C=CC=C4

smiles_non_kekule:    O=C(c1cccc2ccccc12)c1cn(CCCCCF)c2ccccc12
smiles_kekule:    O=C(C1=CC=CC2=C1C=CC=C2)C1=CN(CCCCCF)C2=C1C=CC=C2
inchi:    InChI=1S/C24H22FNO/c25-15-6-1-7-16-26-17-22(20-12-4-5-14-23(20)26)24(27)21-13-8-10-18-9-2-3-11-19(18)21/h2-5,8-14,17H,1,6-7,15-16H2
inchiKey:    ALQFAGFPQCBPED-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6]1:[#6]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]-[#9]):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#6]1:[#6]:[#6]:[#6]:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#8]=[#6](-[#6]1:[#6]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]-[#9]):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#6]1:[#6]:[#6]:[#6]:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2

am-694: Ic2ccccc2C(=O)c1cn(CCCCCF)c3ccccc13

smiles_non_kekule:    O=C(c1ccccc1I)c1cn(CCCCCF)c2ccccc12
smiles_kekule:    O=C(C1=CC=CC=C1I)C1=CN(CCCCCF)C2=CC=CC=C12
inchi:    InChI=1S/C20H19FINO/c21-12-6-1-7-13-23-14-17(15-8-3-5-11-19(15)23)20(24)16-9-2-4-10-18(16)22/h2-5,8-11,14H,1,6-7,12-13H2
inchiKey:    LFFIIZFINPPEMC-UHFFFAOYSA-N
smarts:    [#53]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6](=[#8])-[#6]1:[#6]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]-[#9]):[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2
smarts_isomeric:    [#53]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6](=[#8])-[#6]1:[#6]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]-[#9]):[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2

rcs-4: CCCCCn1cc(c2c1cccc2)C(=O)c3ccc(cc3)OC

smiles_non_kekule:    CCCCCn1cc(C(=O)c2ccc(OC)cc2)c2ccccc21
smiles_kekule:    CCCCCN1C=C(C(=O)C2=CC=C(OC)C=C2)C2=C1C=CC=C2
inchi:    InChI=1S/C21H23NO2/c1-3-4-7-14-22-15-19(18-8-5-6-9-20(18)22)21(23)16-10-12-17(24-2)13-11-16/h5-6,8-13,15H,3-4,7,14H2,1-2H3
inchiKey:    OZCYJKDWRUIFFE-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#7]1:[#6]:[#6](:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#8]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#7]1:[#6]:[#6](:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#8]-[#6]

rcs-8: COc1ccccc1CC(=O)c2cn(c3c2cccc3)CCC4CCCCC4

smiles_non_kekule:    COc1ccccc1CC(=O)c1cn(CCC2CCCCC2)c2ccccc12
smiles_kekule:    COC1=CC=CC=C1CC(=O)C1=CN(CCC2CCCCC2)C2=C1C=CC=C2
inchi:    InChI=1S/C25H29NO2/c1-28-25-14-8-5-11-20(25)17-24(27)22-18-26(23-13-7-6-12-21(22)23)16-15-19-9-3-2-4-10-19/h5-8,11-14,18-19H,2-4,9-10,15-17H2,1H3
inchiKey:    BSQFBMXCQIKYNI-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6](=[#8])-[#6]1:[#6]:[#7](:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#8]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6](=[#8])-[#6]1:[#6]:[#7](:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

jwh-203: Clc2ccccc2CC(=O)c1cn(CCCCC)c3ccccc13

smiles_non_kekule:    CCCCCn1cc(C(=O)Cc2ccccc2Cl)c2ccccc21
smiles_kekule:    CCCCCN1C=C(C(=O)CC2=CC=CC=C2Cl)C2=CC=CC=C21
inchi:    InChI=1S/C21H22ClNO/c1-2-3-8-13-23-15-18(17-10-5-7-12-20(17)23)21(24)14-16-9-4-6-11-19(16)22/h4-7,9-12,15H,2-3,8,13-14H2,1H3
inchiKey:    YDINKDBAZJOSLV-UHFFFAOYSA-N
smarts:    [#17]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6](=[#8])-[#6]1:[#6]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]):[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2
smarts_isomeric:    [#17]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-[#6](=[#8])-[#6]1:[#6]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]):[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2

5f-edmb-pinaca: CC(C)(C)C(NC(C1=NN(CCCCCF)C2=C1C=CC=C2)=O)C(OCC)=O

smiles_non_kekule:    CCOC(=O)C(NC(=O)c1nn(CCCCCF)c2ccccc12)C(C)(C)C
smiles_kekule:    CCOC(=O)C(NC(=O)C1=NN(CCCCCF)C2=C1C=CC=C2)C(C)(C)C
inchi:    InChI=1S/C21H30FN3O3/c1-5-28-20(27)18(21(2,3)4)23-19(26)17-15-11-7-8-12-16(15)25(24-17)14-10-6-9-13-22/h7-8,11-12,18H,5-6,9-10,13-14H2,1-4H3,(H,23,26)
inchiKey:    VDEACSPMBSUVRD-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])(-[#6])-[#6](-[#7]-[#6](-[#6]1:[#7]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]-[#9]):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)=[#8])-[#6](-[#8]-[#6]-[#6])=[#8]
smarts_isomeric:    [#6]-[#6](-[#6])(-[#6])-[#6](-[#7]-[#6](-[#6]1:[#7]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]-[#9]):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)=[#8])-[#6](-[#8]-[#6]-[#6])=[#8]

5f-mdmb-pica: O=C(N[C@H](C(OC)=O)C(C)(C)C)C1=CN(CCCCCF)C2=C1C=CC=C2

smiles_non_kekule:    COC(=O)[C@@H](NC(=O)c1cn(CCCCCF)c2ccccc12)C(C)(C)C
smiles_kekule:    COC(=O)[C@@H](NC(=O)C1=CN(CCCCCF)C2=C1C=CC=C2)C(C)(C)C
inchi:    InChI=1S/C21H29FN2O3/c1-21(2,3)18(20(26)27-4)23-19(25)16-14-24(13-9-5-8-12-22)17-11-7-6-10-15(16)17/h6-7,10-11,14,18H,5,8-9,12-13H2,1-4H3,(H,23,25)/t18-/m1/s1
inchiKey:    CHSUEEBESACQDV-GOSISDBHSA-N
smarts:    [#8]=[#6](-[#7]-[#6H](-[#6](-[#8]-[#6])=[#8])-[#6](-[#6])(-[#6])-[#6])-[#6]1:[#6]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]-[#9]):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2
smarts_isomeric:    [#8]=[#6](-[#7]-[#6@H](-[#6](-[#8]-[#6])=[#8])-[#6](-[#6])(-[#6])-[#6])-[#6]1:[#6]:[#7](-[#6]-[#6]-[#6]-[#6]-[#6]-[#9]):[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2

fub-apinaca: C1C2CC3CC1CC(C2)(C3)NC(=O)C4=NN(C5=CC=CC=C54)CC6=CC=C(C=C6)F

smiles_non_kekule:    O=C(NC12CC3CC(CC(C3)C1)C2)c1nn(Cc2ccc(F)cc2)c2ccccc12
smiles_kekule:    O=C(NC12CC3CC(CC(C3)C1)C2)C1=NN(CC2=CC=C(F)C=C2)C2=CC=CC=C12
inchi:    InChI=1S/C25H26FN3O/c26-20-7-5-16(6-8-20)15-29-22-4-2-1-3-21(22)23(28-29)24(30)27-25-12-17-9-18(13-25)11-19(10-17)14-25/h1-8,17-19H,9-15H2,(H,27,30)
inchiKey:    MWBHSNBPUSKVDD-UHFFFAOYSA-N
smarts:    [#6]1-[#6]2-[#6]-[#6]3-[#6]-[#6]-1-[#6]-[#6](-[#6]-2)(-[#6]-3)-[#7]-[#6](=[#8])-[#6]1:[#7]:[#7](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#9]
smarts_isomeric:    [#6]1-[#6]2-[#6]-[#6]3-[#6]-[#6]-1-[#6]-[#6](-[#6]-2)(-[#6]-3)-[#7]-[#6](=[#8])-[#6]1:[#7]:[#7](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#9]

5f-cumyl-pinaca: CC(C)(C1=CC=CC=C1)NC(=O)C2=NN(C3=CC=CC=C32)CCCCCF

smiles_non_kekule:    CC(C)(NC(=O)c1nn(CCCCCF)c2ccccc12)c1ccccc1
smiles_kekule:    CC(C)(NC(=O)C1=NN(CCCCCF)C2=CC=CC=C12)C1=CC=CC=C1
inchi:    InChI=1S/C22H26FN3O/c1-22(2,17-11-5-3-6-12-17)24-21(27)20-18-13-7-8-14-19(18)26(25-20)16-10-4-9-15-23/h3,5-8,11-14H,4,9-10,15-16H2,1-2H3,(H,24,27)
inchiKey:    XSHGVIPHMOTDCS-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]-[#6](=[#8])-[#6]1:[#7]:[#7](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6]-[#6]-[#6]-[#6]-[#6]-[#9]
smarts_isomeric:    [#6]-[#6](-[#6])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]-[#6](=[#8])-[#6]1:[#7]:[#7](:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:1:2)-[#6]-[#6]-[#6]-[#6]-[#6]-[#9]

fub-144: Fc1ccc(cc1)Cn1cc(c2c1cccc2)C(=O)C1C(C1(C)C)(C)C

smiles_non_kekule:    CC1(C)C(C(=O)c2cn(Cc3ccc(F)cc3)c3ccccc23)C1(C)C
smiles_kekule:    CC1(C)C(C(=O)C2=CN(CC3=CC=C(F)C=C3)C3=C2C=CC=C3)C1(C)C
inchi:    InChI=1S/C23H24FNO/c1-22(2)21(23(22,3)4)20(26)18-14-25(19-8-6-5-7-17(18)19)13-15-9-11-16(24)12-10-15/h5-12,14,21H,13H2,1-4H3
inchiKey:    UXOFEILQVZFLRH-UHFFFAOYSA-N
smarts:    [#9]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]-[#7]1:[#6]:[#6](:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#6](=[#8])-[#6]1-[#6](-[#6]-1(-[#6])-[#6])(-[#6])-[#6]
smarts_isomeric:    [#9]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]-[#7]1:[#6]:[#6](:[#6]2:[#6]:1:[#6]:[#6]:[#6]:[#6]:2)-[#6](=[#8])-[#6]1-[#6](-[#6]-1(-[#6])-[#6])(-[#6])-[#6]

2-(ethylamino)-1-phenylhexan-1-one: CCCCC(C(=O)C1=CC=CC=C1)NCC

smiles_non_kekule:    CCCCC(NCC)C(=O)c1ccccc1
smiles_kekule:    CCCCC(NCC)C(=O)C1=CC=CC=C1
inchi:    InChI=1S/C14H21NO/c1-3-5-11-13(15-4-2)14(16)12-9-7-6-8-10-12/h6-10,13,15H,3-5,11H2,1-2H3
inchiKey:    CWNKMHIETKEBCA-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]-[#6]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]-[#6]-[#6]

alpha-pyrrolidinohexiophenone: C1(=CC=CC=C1)C(C(CCCC)N2CCCC2)=O

smiles_non_kekule:    CCCCC(C(=O)c1ccccc1)N1CCCC1
smiles_kekule:    CCCCC(C(=O)C1=CC=CC=C1)N1CCCC1
inchi:    InChI=1S/C16H23NO/c1-2-3-11-15(17-12-7-8-13-17)16(18)14-9-5-4-6-10-14/h4-6,9-10,15H,2-3,7-8,11-13H2,1H3
inchiKey:    KYIJLDDXQWBNGX-UHFFFAOYSA-N
smarts:    [#6]1(:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](-[#6](-[#6]-[#6]-[#6]-[#6])-[#7]1-[#6]-[#6]-[#6]-[#6]-1)=[#8]
smarts_isomeric:    [#6]1(:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](-[#6](-[#6]-[#6]-[#6]-[#6])-[#7]1-[#6]-[#6]-[#6]-[#6]-1)=[#8]

4-meap: CC1=CC=C(C(C(CCC)NCC)=O)C=C1

smiles_non_kekule:    CCCC(NCC)C(=O)c1ccc(C)cc1
smiles_kekule:    CCCC(NCC)C(=O)C1=CC=C(C)C=C1
inchi:    InChI=1S/C14H21NO/c1-4-6-13(15-5-2)14(16)12-9-7-11(3)8-10-12/h7-10,13,15H,4-6H2,1-3H3
inchiKey:    IKIANZXWCBSIGA-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6](-[#6](-[#6](-[#6]-[#6]-[#6])-[#7]-[#6]-[#6])=[#8]):[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6](-[#6](-[#6](-[#6]-[#6]-[#6])-[#7]-[#6]-[#6])=[#8]):[#6]:[#6]:1

4′-methyl-alpha-pyrrolidinohexanophenone: CC1=CC=C(C(C(CCCC)N2CCCC2)=O)C=C1

smiles_non_kekule:    CCCCC(C(=O)c1ccc(C)cc1)N1CCCC1
smiles_kekule:    CCCCC(C(=O)C1=CC=C(C)C=C1)N1CCCC1
inchi:    InChI=1S/C17H25NO/c1-3-4-7-16(18-12-5-6-13-18)17(19)15-10-8-14(2)9-11-15/h8-11,16H,3-7,12-13H2,1-2H3
inchiKey:    YOSQVMGMENUCDX-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6](-[#6](-[#6](-[#6]-[#6]-[#6]-[#6])-[#7]2-[#6]-[#6]-[#6]-[#6]-2)=[#8]):[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6](-[#6](-[#6](-[#6]-[#6]-[#6]-[#6])-[#7]2-[#6]-[#6]-[#6]-[#6]-2)=[#8]):[#6]:[#6]:1

1-phenyl-2-(pyrrolidin-1-yl)heptan-1-one: CCCCCC(C(=O)C1=CC=CC=C1)N2CCCC2

smiles_non_kekule:    CCCCCC(C(=O)c1ccccc1)N1CCCC1
smiles_kekule:    CCCCCC(C(=O)C1=CC=CC=C1)N1CCCC1
inchi:    InChI=1S/C17H25NO/c1-2-3-5-12-16(18-13-8-9-14-18)17(19)15-10-6-4-7-11-15/h4,6-7,10-11,16H,2-3,5,8-9,12-14H2,1H3
inchiKey:    DLRWKNLMJAIFQB-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]1-[#6]-[#6]-[#6]-[#6]-1

4′-chloro-alpha-pvp: CCCC(C(=O)C1=CC=C(C=C1)Cl)N2CCCC2

smiles_non_kekule:    CCCC(C(=O)c1ccc(Cl)cc1)N1CCCC1
smiles_kekule:    CCCC(C(=O)C1=CC=C(Cl)C=C1)N1CCCC1
inchi:    InChI=1S/C15H20ClNO/c1-2-5-14(17-10-3-4-11-17)15(18)12-6-8-13(16)9-7-12/h6-9,14H,2-5,10-11H2,1H3
inchiKey:    NIGBFBTVONRYQN-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#17])-[#7]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6]-[#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#17])-[#7]1-[#6]-[#6]-[#6]-[#6]-1

brorphine: CC(C1=CC=C(Br)C=C1)N2CCC(N3C(NC4=C3C=CC=C4)=O)CC2

smiles_non_kekule:    CC(c1ccc(Br)cc1)N1CCC(n2c(=O)[nH]c3ccccc32)CC1
smiles_kekule:    CC(C1=CC=C(Br)C=C1)N1CCC(N2C(=O)NC3=C2C=CC=C3)CC1
inchi:    InChI=1S/C20H22BrN3O/c1-14(15-6-8-16(21)9-7-15)23-12-10-17(11-13-23)24-19-5-3-2-4-18(19)22-20(24)25/h2-9,14,17H,10-13H2,1H3,(H,22,25)
inchiKey:    CNOFBGYRMCBVLO-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]1:[#6]:[#6]:[#6](-[#35]):[#6]:[#6]:1)-[#7]1-[#6]-[#6]-[#6](-[#7]2:[#6](:[#7H]:[#6]3:[#6]:2:[#6]:[#6]:[#6]:[#6]:3)=[#8])-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6](-[#6]1:[#6]:[#6]:[#6](-[#35]):[#6]:[#6]:1)-[#7]1-[#6]-[#6]-[#6](-[#7]2:[#6](:[#7H]:[#6]3:[#6]:2:[#6]:[#6]:[#6]:[#6]:3)=[#8])-[#6]-[#6]-1

problem_type: 22/25 (loop 0/0)

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

Problem Template: _problem_schedule_two

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

[15:23:45] WARNING: Omitted undefined stereo

Write structure of schedule two molecules.

Answer:

structure of schedule two molecules:

codeine: CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)O

dihydroetorphine: CCCC(C)(C1CC23CCC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)C)OC)O

ethylmorphine: CCOC1=C2C3=C(CC4C5C3(CCN4C)C(O2)C(C=C5)O)C=C1

etorphinehydrochloride: CCCC(C)(C1CC23C=CC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)C)OC)O.Cl

granulated-opium: CN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(C=C4)O

hydrocodone: CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(=O)CC4

hydromorphone: CN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(=O)CC4

metopon: CC12C(=O)CCC3C14CCN(C3CC5=C4C(=C(C=C5)O)O2)C

morphine: CN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(C=C4)O

noroxymorphone: C1CC2(C3CC4=C5C2(CCN3)C(C1=O)OC5=C(C=C4)O)O

oripavine: CN1CCC23C4C(=CC=C2C1CC5=C3C(=C(C=C5)O)O4)OC

oxycodone: CN1CCC23C4C(=O)CCC2(C1CC5=C3C(=C(C=C5)OC)O4)O

oxymorphone: CN1CC[C@]23[C@H]4OC5=C(O)C=CC(C[C@@H]1[C@]2(O)CCC4=O)=C35

thebaine: CN1CCC23C4C(=CC=C2C1CC5=C3C(=C(C=C5)OC)O4)OC

alfentanil: CCC(=O)N(C1=CC=CC=C1)C2(CCN(CC2)CCN3C(=O)N(N=N3)CC)COC

alphaprodine: CCC(=O)OC1(CCN(CC1C)C)C2=CC=CC=C2

anileridine: CCOC(=O)C1(CCN(CC1)CCC2=CC=C(C=C2)N)C3=CC=CC=C3

bezitramide: CCC(=O)N1C2=CC=CC=C2N(C1=O)C3CCN(CC3)CCC(C#N)(C4=CC=CC=C4)C5=CC=CC=C5

dextropropoxyphene: CCC(=O)OC(CC1=CC=CC=C1)(C2=CC=CC=C2)C(C)CN(C)C

carfentanil: CCC(=O)N(C1=CC=CC=C1)C2(CCN(CC2)CCC3=CC=CC=C3)C(=O)OC

dihydrocodeine: CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(CC4)O

diphenoxylate: CCOC(=O)C1(CCN(CC1)CCC(C#N)(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4

fentanyl: CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3

isomethadone: CCC(=O)C(C1=CC=CC=C1)(C2=CC=CC=C2)C(C)CN(C)C

levo-alphacetylmethadol: CC[C@]([H])(C(C[C@@]([H])(C)N(C)C)(c1ccccc1)c2ccccc2)OC(=O)C

levomethorphan: CN1CCC23CCCCC2C1CC4=C3C=C(C=C4)OC

levorphanol: CN1CCC23CCCCC2C1CC4=C3C=C(C=C4)O

metazocine: CC1C2CC3=C(C1(CCN2C)C)C=C(C=C3)O

methadone: CCC(=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2

methadone-intermediate: CC(CC(C#N)(C1=CC=CC=C1)C2=CC=CC=C2)N(C)C

moramide-intermediate: O=C(O)C(c1ccccc1)(c2ccccc2)C(C)CN3CCOCC3

oliceridine: COC1=C(SC=C1)CNCCC2(CCOC3(C2)CCCC3)C4=CC=CC=N4

pethidine: O=C(C1(CCN(CC1)C)C2=CC=CC=C2)OCC

pethidine-intermediate-a: CN1CCC(CC1)(C#N)c2ccccc2

pethidine-intermediate-b: O=C(OCC)C2(c1ccccc1)CCNCC2

pethidine-intermediate-c: CN1CCC(CC1)(C2=CC=CC=C2)C(=O)O

phenazocine: CC1C2CC3=C(C1(CCN2CCC4=CC=CC=C4)C)C=C(C=C3)O

piminodine: CCOC(=O)C1(CCN(CC1)CCCNC2=CC=CC=C2)C3=CC=CC=C3

racemethorphan: CN1CCC23CCCCC2C1CC4=C3C=C(C=C4)OC

racemorphan: CN1CCC23CCCCC2C1CC4=C3C=C(C=C4)O

remifentanil: CCC(=O)N(C1=CC=CC=C1)C2(CCN(CC2)CCC(=O)OC)C(=O)OC

sufentanil: CCC(=O)N(C1=CC=CC=C1)C2(CCN(CC2)CCC3=CC=CS3)COC

tapentadol: CCC(C1=CC(=CC=C1)O)C(C)CN(C)C

thiafentanil: COCC(=O)N(C1=CC=CC=C1)C2(CCN(CC2)CCC3=CC=CS3)C(=O)OC

amphetamine: CC(CC1=CC=CC=C1)N

methamphetamine: CC(CC1=CC=CC=C1)NC

phenmetrazine: CC1C(OCCN1)C2=CC=CC=C2

methylphenidate: COC(=O)C(C1CCCCN1)C2=CC=CC=C2

lisdexamfetamine: CC(CC1=CC=CC=C1)NC(=O)C(CCCCN)N

amobarbital: CCC1(C(=O)NC(=O)NC1=O)CCC(C)C

glutethimide: CCC1(CCC(=O)NC1=O)C2=CC=CC=C2

pentobarbital: CCCC(C)C1(C(=O)NC(=O)NC1=O)CC

phencyclidine: C1CCC(CC1)(C2=CC=CC=C2)N3CCCCC3

secobarbital: CCCC(C)C1(C(=O)NC(=O)NC1=O)CC=C

nabilone: CCCCCCC(C)(C)C1=CC(=C2C3CC(=O)CCC3C(OC2=C1)(C)C)O

dronabinol: CCCCCC1=CC(=C2C3C=C(CCC3C(OC2=C1)(C)C)C)O

phenylacetone: CC(=O)CC1=CC=CC=C1

1-phenylcyclohexylamine: C1CCC(CC1)(C2=CC=CC=C2)N

1-piperidinocyclohexanecarbonitrile: C1CCC(CC1)(C#N)N2CCCCC2

4-anilino-n-phenethylpiperidine: C1CN(CCC1NC2=CC=CC=C2)CCC3=CC=CC=C3

Solution:

structure of schedule two molecules:

codeine: CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)O

smiles_non_kekule:    COc1ccc2c3c1OC1C(O)C=CC4C(C2)N(C)CCC341
smiles_kekule:    COC1=C2OC3C(O)C=CC4C5CC(=C2C43CCN5C)C=C1
inchi:    InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3
inchiKey:    OROGSEYTTFOCAN-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8]
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8]

dihydroetorphine: CCCC(C)(C1CC23CCC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)C)OC)O

smiles_non_kekule:    CCCC(C)(O)C1CC23CCC1(OC)C1Oc4c(O)ccc5c4C12CCN(C)C3C5
smiles_kekule:    CCCC(C)(O)C1CC23CCC1(OC)C1OC4=C5C(=CC=C4O)CC2N(C)CCC513
inchi:    InChI=1S/C25H35NO4/c1-5-8-22(2,28)17-14-23-9-10-25(17,29-4)21-24(23)11-12-26(3)18(23)13-15-6-7-16(27)20(30-21)19(15)24/h6-7,17-18,21,27-28H,5,8-14H2,1-4H3
inchiKey:    BRTSNYPDACNMIP-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6](-[#6])(-[#6]1-[#6]-[#6]23-[#6]-[#6]-[#6]-1(-[#6]1-[#6]-24-[#6]-[#6]-[#7](-[#6]-3-[#6]-[#6]2:[#6]-4:[#6](:[#6](:[#6]:[#6]:2)-[#8])-[#8]-1)-[#6])-[#8]-[#6])-[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6](-[#6])(-[#6]1-[#6]-[#6]23-[#6]-[#6]-[#6]-1(-[#6]1-[#6]-24-[#6]-[#6]-[#7](-[#6]-3-[#6]-[#6]2:[#6]-4:[#6](:[#6](:[#6]:[#6]:2)-[#8])-[#8]-1)-[#6])-[#8]-[#6])-[#8]

ethylmorphine: CCOC1=C2C3=C(CC4C5C3(CCN4C)C(O2)C(C=C5)O)C=C1

smiles_non_kekule:    CCOc1ccc2c3c1OC1C(O)C=CC4C(C2)N(C)CCC341
smiles_kekule:    CCOC1=C2OC3C(O)C=CC4C5CC(=C2C43CCN5C)C=C1
inchi:    InChI=1S/C19H23NO3/c1-3-22-15-7-4-11-10-13-12-5-6-14(21)18-19(12,8-9-20(13)2)16(11)17(15)23-18/h4-7,12-14,18,21H,3,8-10H2,1-2H3
inchiKey:    OGDVEMNWJVYAJL-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]-[#6]1:[#6]2:[#6]3:[#6](-[#6]-[#6]4-[#6]5-[#6]-3(-[#6]-[#6]-[#7]-4-[#6])-[#6](-[#8]-2)-[#6](-[#6]=[#6]-5)-[#8]):[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#8]-[#6]1:[#6]2:[#6]3:[#6](-[#6]-[#6]4-[#6]5-[#6]-3(-[#6]-[#6]-[#7]-4-[#6])-[#6](-[#8]-2)-[#6](-[#6]=[#6]-5)-[#8]):[#6]:[#6]:1

etorphinehydrochloride: CCCC(C)(C1CC23C=CC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)C)OC)O.Cl

smiles_non_kekule:    CCCC(C)(O)C1CC23C=CC1(OC)C1Oc4c(O)ccc5c4C12CCN(C)C3C5.Cl
smiles_kekule:    CCCC(C)(O)C1CC23C=CC1(OC)C1OC4=C5C(=CC=C4O)CC2N(C)CCC513.Cl
inchi:    InChI=1S/C25H33NO4.ClH/c1-5-8-22(2,28)17-14-23-9-10-25(17,29-4)21-24(23)11-12-26(3)18(23)13-15-6-7-16(27)20(30-21)19(15)24;/h6-7,9-10,17-18,21,27-28H,5,8,11-14H2,1-4H3;1H
inchiKey:    JNHPUZURWFYYHW-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6](-[#6])(-[#6]1-[#6]-[#6]23-[#6]=[#6]-[#6]-1(-[#6]1-[#6]-24-[#6]-[#6]-[#7](-[#6]-3-[#6]-[#6]2:[#6]-4:[#6](:[#6](:[#6]:[#6]:2)-[#8])-[#8]-1)-[#6])-[#8]-[#6])-[#8].[#17]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6](-[#6])(-[#6]1-[#6]-[#6]23-[#6]=[#6]-[#6]-1(-[#6]1-[#6]-24-[#6]-[#6]-[#7](-[#6]-3-[#6]-[#6]2:[#6]-4:[#6](:[#6](:[#6]:[#6]:2)-[#8])-[#8]-1)-[#6])-[#8]-[#6])-[#8].[#17]

granulated-opium: CN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(C=C4)O

smiles_non_kekule:    CN1CCC23c4c5ccc(O)c4OC2C(O)C=CC3C1C5
smiles_kekule:    CN1CCC23C4=C5C=CC(O)=C4OC2C(O)C=CC3C1C5
inchi:    InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,13,16,19-20H,6-8H2,1H3
inchiKey:    BQJCRHHNABKAKU-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8])-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8]
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8])-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8]

hydrocodone: CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(=O)CC4

smiles_non_kekule:    COc1ccc2c3c1OC1C(=O)CCC4C(C2)N(C)CCC314
smiles_kekule:    COC1=C2OC3C(=O)CCC4C5CC(=C2C34CCN5C)C=C1
inchi:    InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-12,17H,4-5,7-9H2,1-2H3
inchiKey:    LLPOLZWFYMWNKH-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#8]-[#6]-3-[#6](=[#8])-[#6]-[#6]-4
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#8]-[#6]-3-[#6](=[#8])-[#6]-[#6]-4

hydromorphone: CN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(=O)CC4

smiles_non_kekule:    CN1CCC23c4c5ccc(O)c4OC2C(=O)CCC3C1C5
smiles_kekule:    CN1CCC23C4=C5C=CC(O)=C4OC2C(=O)CCC3C1C5
inchi:    InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2,4,10-11,16,19H,3,5-8H2,1H3
inchiKey:    WVLOADHCBXTIJK-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8])-[#8]-[#6]-3-[#6](=[#8])-[#6]-[#6]-4
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8])-[#8]-[#6]-3-[#6](=[#8])-[#6]-[#6]-4

metopon: CC12C(=O)CCC3C14CCN(C3CC5=C4C(=C(C=C5)O)O2)C

smiles_non_kekule:    CN1CCC23c4c5ccc(O)c4OC2(C)C(=O)CCC3C1C5
smiles_kekule:    CN1CCC23C4=C5C=CC(O)=C4OC2(C)C(=O)CCC3C1C5
inchi:    InChI=1S/C18H21NO3/c1-17-14(21)6-4-11-12-9-10-3-5-13(20)16(22-17)15(10)18(11,17)7-8-19(12)2/h3,5,11-12,20H,4,6-9H2,1-2H3
inchiKey:    NPZXCTIHHUUEEJ-UHFFFAOYSA-N
smarts:    [#6]-[#6]12-[#6](=[#8])-[#6]-[#6]-[#6]3-[#6]-14-[#6]-[#6]-[#7](-[#6]-3-[#6]-[#6]1:[#6]-4:[#6](:[#6](:[#6]:[#6]:1)-[#8])-[#8]-2)-[#6]
smarts_isomeric:    [#6]-[#6]12-[#6](=[#8])-[#6]-[#6]-[#6]3-[#6]-14-[#6]-[#6]-[#7](-[#6]-3-[#6]-[#6]1:[#6]-4:[#6](:[#6](:[#6]:[#6]:1)-[#8])-[#8]-2)-[#6]

morphine: CN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(C=C4)O

noroxymorphone: C1CC2(C3CC4=C5C2(CCN3)C(C1=O)OC5=C(C=C4)O)O

smiles_non_kekule:    O=C1CCC2(O)C3Cc4ccc(O)c5c4C2(CCN3)C1O5
smiles_kekule:    O=C1CCC2(O)C3CC4=C5C(=C(O)C=C4)OC1C52CCN3
inchi:    InChI=1S/C16H17NO4/c18-9-2-1-8-7-11-16(20)4-3-10(19)14-15(16,5-6-17-11)12(8)13(9)21-14/h1-2,11,14,17-18,20H,3-7H2
inchiKey:    HLMSIZPQBSYUNL-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]2(-[#6]3-[#6]-[#6]4:[#6]5-[#6]-2(-[#6]-[#6]-[#7]-3)-[#6](-[#6]-1=[#8])-[#8]-[#6]:5:[#6](:[#6]:[#6]:4)-[#8])-[#8]
smarts_isomeric:    [#6]1-[#6]-[#6]2(-[#6]3-[#6]-[#6]4:[#6]5-[#6]-2(-[#6]-[#6]-[#7]-3)-[#6](-[#6]-1=[#8])-[#8]-[#6]:5:[#6](:[#6]:[#6]:4)-[#8])-[#8]

oripavine: CN1CCC23C4C(=CC=C2C1CC5=C3C(=C(C=C5)O)O4)OC

smiles_non_kekule:    COC1=CC=C2C3Cc4ccc(O)c5c4C2(CCN3C)C1O5
smiles_kekule:    COC1=CC=C2C3CC4=C5C(=C(O)C=C4)OC1C25CCN3C
inchi:    InChI=1S/C18H19NO3/c1-19-8-7-18-11-4-6-14(21-2)17(18)22-16-13(20)5-3-10(15(16)18)9-12(11)19/h3-6,12,17,20H,7-9H2,1-2H3
inchiKey:    ZKLXUUYLEHCAMF-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6](=[#6]-[#6]=[#6]-2-[#6]-1-[#6]-[#6]1:[#6]-3:[#6](:[#6](:[#6]:[#6]:1)-[#8])-[#8]-4)-[#8]-[#6]
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6](=[#6]-[#6]=[#6]-2-[#6]-1-[#6]-[#6]1:[#6]-3:[#6](:[#6](:[#6]:[#6]:1)-[#8])-[#8]-4)-[#8]-[#6]

oxycodone: CN1CCC23C4C(=O)CCC2(C1CC5=C3C(=C(C=C5)OC)O4)O

smiles_non_kekule:    COc1ccc2c3c1OC1C(=O)CCC4(O)C(C2)N(C)CCC314
smiles_kekule:    COC1=C2OC3C(=O)CCC4(O)C5CC(=C2C34CCN5C)C=C1
inchi:    InChI=1S/C18H21NO4/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10/h3-4,13,16,21H,5-9H2,1-2H3
inchiKey:    BRUQQQPBMZOVGD-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6](=[#8])-[#6]-[#6]-[#6]-2(-[#6]-1-[#6]-[#6]1:[#6]-3:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#8]-4)-[#8]
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6](=[#8])-[#6]-[#6]-[#6]-2(-[#6]-1-[#6]-[#6]1:[#6]-3:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#8]-4)-[#8]

oxymorphone: CN1CC[C@]23[C@H]4OC5=C(O)C=CC(C[C@@H]1[C@]2(O)CCC4=O)=C35

smiles_non_kekule:    CN1CC[C@]23c4c5ccc(O)c4O[C@H]2C(=O)CC[C@@]3(O)[C@H]1C5
smiles_kekule:    CN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2C(=O)CC[C@@]3(O)[C@H]1C5
inchi:    InChI=1S/C17H19NO4/c1-18-7-6-16-13-9-2-3-10(19)14(13)22-15(16)11(20)4-5-17(16,21)12(18)8-9/h2-3,12,15,19,21H,4-8H2,1H3/t12-,15+,16+,17-/m1/s1
inchiKey:    UQCNKQCJZOAFTQ-ISWURRPUSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6H]4-[#8]-[#6]5:[#6](-[#8]):[#6]:[#6]:[#6](-[#6]-[#6H]-1-[#6]-2(-[#8])-[#6]-[#6]-[#6]-4=[#8]):[#6]:5-3
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6@]23-[#6@H]4-[#8]-[#6]5:[#6](-[#8]):[#6]:[#6]:[#6](-[#6]-[#6@@H]-1-[#6@]-2(-[#8])-[#6]-[#6]-[#6]-4=[#8]):[#6]:5-3

thebaine: CN1CCC23C4C(=CC=C2C1CC5=C3C(=C(C=C5)OC)O4)OC

smiles_non_kekule:    COC1=CC=C2C3Cc4ccc(OC)c5c4C2(CCN3C)C1O5
smiles_kekule:    COC1=CC=C2C3CC4=C5C(=C(OC)C=C4)OC1C25CCN3C
inchi:    InChI=1S/C19H21NO3/c1-20-9-8-19-12-5-7-15(22-3)18(19)23-17-14(21-2)6-4-11(16(17)19)10-13(12)20/h4-7,13,18H,8-10H2,1-3H3
inchiKey:    FQXXSQDCDRQNQE-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6](=[#6]-[#6]=[#6]-2-[#6]-1-[#6]-[#6]1:[#6]-3:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#8]-4)-[#8]-[#6]
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6](=[#6]-[#6]=[#6]-2-[#6]-1-[#6]-[#6]1:[#6]-3:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#8]-4)-[#8]-[#6]

alfentanil: CCC(=O)N(C1=CC=CC=C1)C2(CCN(CC2)CCN3C(=O)N(N=N3)CC)COC

smiles_non_kekule:    CCC(=O)N(c1ccccc1)C1(COC)CCN(CCn2nnn(CC)c2=O)CC1
smiles_kekule:    CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN(CCN2N=NN(CC)C2=O)CC1
inchi:    InChI=1S/C21H32N6O3/c1-4-19(28)27(18-9-7-6-8-10-18)21(17-30-3)11-13-24(14-12-21)15-16-26-20(29)25(5-2)22-23-26/h6-10H,4-5,11-17H2,1-3H3
inchiKey:    IDBPHNDTYPBSNI-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#7]1:[#6](=[#8]):[#7](:[#7]:[#7]:1)-[#6]-[#6])-[#6]-[#8]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#7]1:[#6](=[#8]):[#7](:[#7]:[#7]:1)-[#6]-[#6])-[#6]-[#8]-[#6]

alphaprodine: CCC(=O)OC1(CCN(CC1C)C)C2=CC=CC=C2

anileridine: CCOC(=O)C1(CCN(CC1)CCC2=CC=C(C=C2)N)C3=CC=CC=C3

smiles_non_kekule:    CCOC(=O)C1(c2ccccc2)CCN(CCc2ccc(N)cc2)CC1
smiles_kekule:    CCOC(=O)C1(C2=CC=CC=C2)CCN(CCC2=CC=C(N)C=C2)CC1
inchi:    InChI=1S/C22H28N2O2/c1-2-26-21(25)22(19-6-4-3-5-7-19)13-16-24(17-14-22)15-12-18-8-10-20(23)11-9-18/h3-11H,2,12-17,23H2,1H3
inchiKey:    LKYQLAWMNBFNJT-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#7])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#7])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

bezitramide: CCC(=O)N1C2=CC=CC=C2N(C1=O)C3CCN(CC3)CCC(C#N)(C4=CC=CC=C4)C5=CC=CC=C5

smiles_non_kekule:    CCC(=O)n1c(=O)n(C2CCN(CCC(C#N)(c3ccccc3)c3ccccc3)CC2)c2ccccc21
smiles_kekule:    CCC(=O)N1C(=O)N(C2CCN(CCC(C#N)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)C2=CC=CC=C21
inchi:    InChI=1S/C31H32N4O2/c1-2-29(36)35-28-16-10-9-15-27(28)34(30(35)37)26-17-20-33(21-18-26)22-19-31(23-32,24-11-5-3-6-12-24)25-13-7-4-8-14-25/h3-16,26H,2,17-22H2,1H3
inchiKey:    FLKWNFFCSSJANB-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#7]1:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#7](:[#6]:1=[#8])-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6](-[#6]#[#7])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#7]1:[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2:[#7](:[#6]:1=[#8])-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6](-[#6]#[#7])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

dextropropoxyphene: CCC(=O)OC(CC1=CC=CC=C1)(C2=CC=CC=C2)C(C)CN(C)C

smiles_non_kekule:    CCC(=O)OC(Cc1ccccc1)(c1ccccc1)C(C)CN(C)C
smiles_kekule:    CCC(=O)OC(CC1=CC=CC=C1)(C1=CC=CC=C1)C(C)CN(C)C
inchi:    InChI=1S/C22H29NO2/c1-5-21(24)25-22(18(2)17-23(3)4,20-14-10-7-11-15-20)16-19-12-8-6-9-13-19/h6-15,18H,5,16-17H2,1-4H3
inchiKey:    XLMALTXPSGQGBX-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#8]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](-[#6])-[#6]-[#7](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#8]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](-[#6])-[#6]-[#7](-[#6])-[#6]

carfentanil: CCC(=O)N(C1=CC=CC=C1)C2(CCN(CC2)CCC3=CC=CC=C3)C(=O)OC

smiles_non_kekule:    CCC(=O)N(c1ccccc1)C1(C(=O)OC)CCN(CCc2ccccc2)CC1
smiles_kekule:    CCC(=O)N(C1=CC=CC=C1)C1(C(=O)OC)CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C24H30N2O3/c1-3-22(27)26(21-12-8-5-9-13-21)24(23(28)29-2)15-18-25(19-16-24)17-14-20-10-6-4-7-11-20/h4-13H,3,14-19H2,1-2H3
inchiKey:    YDSDEBIZUNNPOB-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](=[#8])-[#8]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](=[#8])-[#8]-[#6]

dihydrocodeine: CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(CC4)O

smiles_non_kekule:    COc1ccc2c3c1OC1C(O)CCC4C(C2)N(C)CCC341
smiles_kekule:    COC1=C2OC3C(O)CCC4C5CC(=C2C43CCN5C)C=C1
inchi:    InChI=1S/C18H23NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3
inchiKey:    RBOXVHNMENFORY-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#8]-[#6]-3-[#6](-[#6]-[#6]-4)-[#8]
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#8]-[#6]-3-[#6](-[#6]-[#6]-4)-[#8]

diphenoxylate: CCOC(=O)C1(CCN(CC1)CCC(C#N)(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4

smiles_non_kekule:    CCOC(=O)C1(c2ccccc2)CCN(CCC(C#N)(c2ccccc2)c2ccccc2)CC1
smiles_kekule:    CCOC(=O)C1(C2=CC=CC=C2)CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC1
inchi:    InChI=1S/C30H32N2O2/c1-2-34-28(33)29(25-12-6-3-7-13-25)18-21-32(22-19-29)23-20-30(24-31,26-14-8-4-9-15-26)27-16-10-5-11-17-27/h3-17H,2,18-23H2,1H3
inchiKey:    HYPPXZBJBPSRLK-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6](-[#6]#[#7])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6](-[#6]#[#7])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

fentanyl: CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3

smiles_non_kekule:    CCC(=O)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1
smiles_kekule:    CCC(=O)N(C1=CC=CC=C1)C1CCN(CCC2=CC=CC=C2)CC1
inchi:    InChI=1S/C22H28N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h3-12,21H,2,13-18H2,1H3
inchiKey:    PJMPHNIQZUBGLI-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

isomethadone: CCC(=O)C(C1=CC=CC=C1)(C2=CC=CC=C2)C(C)CN(C)C

smiles_non_kekule:    CCC(=O)C(c1ccccc1)(c1ccccc1)C(C)CN(C)C
smiles_kekule:    CCC(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)C(C)CN(C)C
inchi:    InChI=1S/C21H27NO/c1-5-20(23)21(17(2)16-22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17H,5,16H2,1-4H3
inchiKey:    IFKPLJWIEQBPGG-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](-[#6])-[#6]-[#7](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](-[#6])-[#6]-[#7](-[#6])-[#6]

levo-alphacetylmethadol: CC[C@]([H])(C(C[C@@]([H])(C)N(C)C)(c1ccccc1)c2ccccc2)OC(=O)C

smiles_non_kekule:    CC[C@@H](OC(C)=O)C(C[C@@H](C)N(C)C)(c1ccccc1)c1ccccc1
smiles_kekule:    CC[C@@H](OC(C)=O)C(C[C@@H](C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1
inchi:    InChI=1S/C23H31NO2/c1-6-22(26-19(3)25)23(17-18(2)24(4)5,20-13-9-7-10-14-20)21-15-11-8-12-16-21/h7-16,18,22H,6,17H2,1-5H3/t18-,22-/m1/s1
inchiKey:    XBMIVRRWGCYBTQ-XMSQKQJNSA-N
smarts:    [#6]-[#6]-[#6H](-[#6](-[#6]-[#6H](-[#6])-[#7](-[#6])-[#6])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8]-[#6](=[#8])-[#6]
smarts_isomeric:    [#6]-[#6]-[#6@H](-[#6](-[#6]-[#6@@H](-[#6])-[#7](-[#6])-[#6])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8]-[#6](=[#8])-[#6]

levomethorphan: CN1CCC23CCCCC2C1CC4=C3C=C(C=C4)OC

smiles_non_kekule:    COc1ccc2c(c1)C13CCCCC1C(C2)N(C)CC3
smiles_kekule:    COC1=CC2=C(C=C1)CC1C3CCCCC23CCN1C
inchi:    InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3
inchiKey:    MKXZASYAUGDDCJ-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]-[#6]-[#6]-[#6]-[#6]-2-[#6]-1-[#6]-[#6]1:[#6]-3:[#6]:[#6](:[#6]:[#6]:1)-[#8]-[#6]
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]-[#6]-[#6]-[#6]-[#6]-2-[#6]-1-[#6]-[#6]1:[#6]-3:[#6]:[#6](:[#6]:[#6]:1)-[#8]-[#6]

levorphanol: CN1CCC23CCCCC2C1CC4=C3C=C(C=C4)O

smiles_non_kekule:    CN1CCC23CCCCC2C1Cc1ccc(O)cc13
smiles_kekule:    CN1CCC23CCCCC2C1CC1=C3C=C(O)C=C1
inchi:    InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3
inchiKey:    JAQUASYNZVUNQP-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]-[#6]-[#6]-[#6]-[#6]-2-[#6]-1-[#6]-[#6]1:[#6]-3:[#6]:[#6](:[#6]:[#6]:1)-[#8]
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]-[#6]-[#6]-[#6]-[#6]-2-[#6]-1-[#6]-[#6]1:[#6]-3:[#6]:[#6](:[#6]:[#6]:1)-[#8]

metazocine: CC1C2CC3=C(C1(CCN2C)C)C=C(C=C3)O

smiles_non_kekule:    CC1C2Cc3ccc(O)cc3C1(C)CCN2C
smiles_kekule:    CC1C2CC3=C(C=C(O)C=C3)C1(C)CCN2C
inchi:    InChI=1S/C15H21NO/c1-10-14-8-11-4-5-12(17)9-13(11)15(10,2)6-7-16(14)3/h4-5,9-10,14,17H,6-8H2,1-3H3
inchiKey:    YGSVZRIZCHZUHB-UHFFFAOYSA-N
smarts:    [#6]-[#6]1-[#6]2-[#6]-[#6]3:[#6](-[#6]-1(-[#6]-[#6]-[#7]-2-[#6])-[#6]):[#6]:[#6](:[#6]:[#6]:3)-[#8]
smarts_isomeric:    [#6]-[#6]1-[#6]2-[#6]-[#6]3:[#6](-[#6]-1(-[#6]-[#6]-[#7]-2-[#6])-[#6]):[#6]:[#6](:[#6]:[#6]:3)-[#8]

methadone: CCC(=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2

smiles_non_kekule:    CCC(=O)C(CC(C)N(C)C)(c1ccccc1)c1ccccc1
smiles_kekule:    CCC(=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1
inchi:    InChI=1S/C21H27NO/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17H,5,16H2,1-4H3
inchiKey:    USSIQXCVUWKGNF-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#6](-[#6]-[#6](-[#6])-[#7](-[#6])-[#6])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#6](-[#6]-[#6](-[#6])-[#7](-[#6])-[#6])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

methadone-intermediate: CC(CC(C#N)(C1=CC=CC=C1)C2=CC=CC=C2)N(C)C

smiles_non_kekule:    CC(CC(C#N)(c1ccccc1)c1ccccc1)N(C)C
smiles_kekule:    CC(CC(C#N)(C1=CC=CC=C1)C1=CC=CC=C1)N(C)C
inchi:    InChI=1S/C19H22N2/c1-16(21(2)3)14-19(15-20,17-10-6-4-7-11-17)18-12-8-5-9-13-18/h4-13,16H,14H2,1-3H3
inchiKey:    GJJQIGFCGLPOQK-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6](-[#6]#[#7])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6](-[#6]-[#6](-[#6]#[#7])(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7](-[#6])-[#6]

moramide-intermediate: O=C(O)C(c1ccccc1)(c2ccccc2)C(C)CN3CCOCC3

smiles_non_kekule:    CC(CN1CCOCC1)C(C(=O)O)(c1ccccc1)c1ccccc1
smiles_kekule:    CC(CN1CCOCC1)C(C(=O)O)(C1=CC=CC=C1)C1=CC=CC=C1
inchi:    InChI=1S/C21H25NO3/c1-17(16-22-12-14-25-15-13-22)21(20(23)24,18-8-4-2-5-9-18)19-10-6-3-7-11-19/h2-11,17H,12-16H2,1H3,(H,23,24)
inchiKey:    AWLNVHVUYACOMZ-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#8])-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](-[#6])-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1
smarts_isomeric:    [#8]=[#6](-[#8])-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](-[#6])-[#6]-[#7]1-[#6]-[#6]-[#8]-[#6]-[#6]-1

oliceridine: COC1=C(SC=C1)CNCCC2(CCOC3(C2)CCCC3)C4=CC=CC=N4

smiles_non_kekule:    COc1ccsc1CNCCC1(c2ccccn2)CCOC2(CCCC2)C1
smiles_kekule:    COC1=C(CNCCC2(C3=CC=CC=N3)CCOC3(CCCC3)C2)SC=C1
inchi:    InChI=1S/C22H30N2O2S/c1-25-18-7-15-27-19(18)16-23-13-10-21(20-6-2-5-12-24-20)11-14-26-22(17-21)8-3-4-9-22/h2,5-7,12,15,23H,3-4,8-11,13-14,16-17H2,1H3
inchiKey:    DMNOVGJWPASQDL-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]1:[#6](:[#16]:[#6]:[#6]:1)-[#6]-[#7]-[#6]-[#6]-[#6]1(-[#6]-[#6]-[#8]-[#6]2(-[#6]-1)-[#6]-[#6]-[#6]-[#6]-2)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#7]:1
smarts_isomeric:    [#6]-[#8]-[#6]1:[#6](:[#16]:[#6]:[#6]:1)-[#6]-[#7]-[#6]-[#6]-[#6]1(-[#6]-[#6]-[#8]-[#6]2(-[#6]-1)-[#6]-[#6]-[#6]-[#6]-2)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#7]:1

pethidine: O=C(C1(CCN(CC1)C)C2=CC=CC=C2)OCC

smiles_non_kekule:    CCOC(=O)C1(c2ccccc2)CCN(C)CC1
smiles_kekule:    CCOC(=O)C1(C2=CC=CC=C2)CCN(C)CC1
inchi:    InChI=1S/C15H21NO2/c1-3-18-14(17)15(9-11-16(2)12-10-15)13-7-5-4-6-8-13/h4-8H,3,9-12H2,1-2H3
inchiKey:    XADCESSVHJOZHK-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8]-[#6]-[#6]
smarts_isomeric:    [#8]=[#6](-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8]-[#6]-[#6]

pethidine-intermediate-a: CN1CCC(CC1)(C#N)c2ccccc2

smiles_non_kekule:    CN1CCC(C#N)(c2ccccc2)CC1
smiles_kekule:    CN1CCC(C#N)(C2=CC=CC=C2)CC1
inchi:    InChI=1S/C13H16N2/c1-15-9-7-13(11-14,8-10-15)12-5-3-2-4-6-12/h2-6H,7-10H2,1H3
inchiKey:    ZLFQTZYFXYOGLS-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)(-[#6]#[#7])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)(-[#6]#[#7])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

pethidine-intermediate-b: O=C(OCC)C2(c1ccccc1)CCNCC2

smiles_non_kekule:    CCOC(=O)C1(c2ccccc2)CCNCC1
smiles_kekule:    CCOC(=O)C1(C2=CC=CC=C2)CCNCC1
inchi:    InChI=1S/C14H19NO2/c1-2-17-13(16)14(8-10-15-11-9-14)12-6-4-3-5-7-12/h3-7,15H,2,8-11H2,1H3
inchiKey:    QKHMFBKXTNQCTM-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#8]-[#6]-[#6])-[#6]1(-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-[#7]-[#6]-[#6]-1
smarts_isomeric:    [#8]=[#6](-[#8]-[#6]-[#6])-[#6]1(-[#6]2:[#6]:[#6]:[#6]:[#6]:[#6]:2)-[#6]-[#6]-[#7]-[#6]-[#6]-1

pethidine-intermediate-c: CN1CCC(CC1)(C2=CC=CC=C2)C(=O)O

smiles_non_kekule:    CN1CCC(C(=O)O)(c2ccccc2)CC1
smiles_kekule:    CN1CCC(C(=O)O)(C2=CC=CC=C2)CC1
inchi:    InChI=1S/C13H17NO2/c1-14-9-7-13(8-10-14,12(15)16)11-5-3-2-4-6-11/h2-6H,7-10H2,1H3,(H,15,16)
inchiKey:    KHUPPYUUMRDAAX-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](=[#8])-[#8]
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6](=[#8])-[#8]

phenazocine: CC1C2CC3=C(C1(CCN2CCC4=CC=CC=C4)C)C=C(C=C3)O

smiles_non_kekule:    CC1C2Cc3ccc(O)cc3C1(C)CCN2CCc1ccccc1
smiles_kekule:    CC1C2CC3=C(C=C(O)C=C3)C1(C)CCN2CCC1=CC=CC=C1
inchi:    InChI=1S/C22H27NO/c1-16-21-14-18-8-9-19(24)15-20(18)22(16,2)11-13-23(21)12-10-17-6-4-3-5-7-17/h3-9,15-16,21,24H,10-14H2,1-2H3
inchiKey:    ZQHYKVKNPWDQSL-UHFFFAOYSA-N
smarts:    [#6]-[#6]1-[#6]2-[#6]-[#6]3:[#6](-[#6]-1(-[#6]-[#6]-[#7]-2-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]):[#6]:[#6](:[#6]:[#6]:3)-[#8]
smarts_isomeric:    [#6]-[#6]1-[#6]2-[#6]-[#6]3:[#6](-[#6]-1(-[#6]-[#6]-[#7]-2-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]):[#6]:[#6](:[#6]:[#6]:3)-[#8]

piminodine: CCOC(=O)C1(CCN(CC1)CCCNC2=CC=CC=C2)C3=CC=CC=C3

smiles_non_kekule:    CCOC(=O)C1(c2ccccc2)CCN(CCCNc2ccccc2)CC1
smiles_kekule:    CCOC(=O)C1(C2=CC=CC=C2)CCN(CCCNC2=CC=CC=C2)CC1
inchi:    InChI=1S/C23H30N2O2/c1-2-27-22(26)23(20-10-5-3-6-11-20)14-18-25(19-15-23)17-9-16-24-21-12-7-4-8-13-21/h3-8,10-13,24H,2,9,14-19H2,1H3
inchiKey:    PXXKIYPSXYFATG-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]-[#7]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]-[#7]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

racemethorphan: CN1CCC23CCCCC2C1CC4=C3C=C(C=C4)OC

racemorphan: CN1CCC23CCCCC2C1CC4=C3C=C(C=C4)O

remifentanil: CCC(=O)N(C1=CC=CC=C1)C2(CCN(CC2)CCC(=O)OC)C(=O)OC

smiles_non_kekule:    CCC(=O)N(c1ccccc1)C1(C(=O)OC)CCN(CCC(=O)OC)CC1
smiles_kekule:    CCC(=O)N(C1=CC=CC=C1)C1(C(=O)OC)CCN(CCC(=O)OC)CC1
inchi:    InChI=1S/C20H28N2O5/c1-4-17(23)22(16-8-6-5-7-9-16)20(19(25)27-3)11-14-21(15-12-20)13-10-18(24)26-2/h5-9H,4,10-15H2,1-3H3
inchiKey:    ZTVQQQVZCWLTDF-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6](=[#8])-[#8]-[#6])-[#6](=[#8])-[#8]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6](=[#8])-[#8]-[#6])-[#6](=[#8])-[#8]-[#6]

sufentanil: CCC(=O)N(C1=CC=CC=C1)C2(CCN(CC2)CCC3=CC=CS3)COC

smiles_non_kekule:    CCC(=O)N(c1ccccc1)C1(COC)CCN(CCc2cccs2)CC1
smiles_kekule:    CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN(CCC2=CC=CS2)CC1
inchi:    InChI=1S/C22H30N2O2S/c1-3-21(25)24(19-8-5-4-6-9-19)22(18-26-2)12-15-23(16-13-22)14-11-20-10-7-17-27-20/h4-10,17H,3,11-16,18H2,1-2H3
inchiKey:    GGCSSNBKKAUURC-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#6]-[#8]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#6]-[#8]-[#6]

tapentadol: CCC(C1=CC(=CC=C1)O)C(C)CN(C)C

smiles_non_kekule:    CCC(c1cccc(O)c1)C(C)CN(C)C
smiles_kekule:    CCC(C1=CC(O)=CC=C1)C(C)CN(C)C
inchi:    InChI=1S/C14H23NO/c1-5-14(11(2)10-15(3)4)12-7-6-8-13(16)9-12/h6-9,11,14,16H,5,10H2,1-4H3
inchiKey:    KWTWDQCKEHXFFR-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](-[#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1)-[#8])-[#6](-[#6])-[#6]-[#7](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6]-[#6](-[#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1)-[#8])-[#6](-[#6])-[#6]-[#7](-[#6])-[#6]

thiafentanil: COCC(=O)N(C1=CC=CC=C1)C2(CCN(CC2)CCC3=CC=CS3)C(=O)OC

smiles_non_kekule:    COCC(=O)N(c1ccccc1)C1(C(=O)OC)CCN(CCc2cccs2)CC1
smiles_kekule:    COCC(=O)N(C1=CC=CC=C1)C1(C(=O)OC)CCN(CCC2=CC=CS2)CC1
inchi:    InChI=1S/C22H28N2O4S/c1-27-17-20(25)24(18-7-4-3-5-8-18)22(21(26)28-2)11-14-23(15-12-22)13-10-19-9-6-16-29-19/h3-9,16H,10-15,17H2,1-2H3
inchiKey:    HFRKHTCPWUOGHM-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6]-[#6](=[#8])-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#6](=[#8])-[#8]-[#6]
smarts_isomeric:    [#6]-[#8]-[#6]-[#6](=[#8])-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1(-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#16]:1)-[#6](=[#8])-[#8]-[#6]

amphetamine: CC(CC1=CC=CC=C1)N

smiles_non_kekule:    CC(N)Cc1ccccc1
smiles_kekule:    CC(N)CC1=CC=CC=C1
inchi:    InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3
inchiKey:    KWTSXDURSIMDCE-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]
smarts_isomeric:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]

methamphetamine: CC(CC1=CC=CC=C1)NC

smiles_non_kekule:    CNC(C)Cc1ccccc1
smiles_kekule:    CNC(C)CC1=CC=CC=C1
inchi:    InChI=1S/C10H15N/c1-9(11-2)8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3
inchiKey:    MYWUZJCMWCOHBA-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]-[#6]
smarts_isomeric:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]-[#6]

phenmetrazine: CC1C(OCCN1)C2=CC=CC=C2

smiles_non_kekule:    CC1NCCOC1c1ccccc1
smiles_kekule:    CC1NCCOC1C1=CC=CC=C1
inchi:    InChI=1S/C11H15NO/c1-9-11(13-8-7-12-9)10-5-3-2-4-6-10/h2-6,9,11-12H,7-8H2,1H3
inchiKey:    OOBHFESNSZDWIU-UHFFFAOYSA-N
smarts:    [#6]-[#6]1-[#6](-[#8]-[#6]-[#6]-[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]1-[#6](-[#8]-[#6]-[#6]-[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

methylphenidate: COC(=O)C(C1CCCCN1)C2=CC=CC=C2

smiles_non_kekule:    COC(=O)C(c1ccccc1)C1CCCCN1
smiles_kekule:    COC(=O)C(C1=CC=CC=C1)C1CCCCN1
inchi:    InChI=1S/C14H19NO2/c1-17-14(16)13(11-7-3-2-4-8-11)12-9-5-6-10-15-12/h2-4,7-8,12-13,15H,5-6,9-10H2,1H3
inchiKey:    DUGOZIWVEXMGBE-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6](=[#8])-[#6](-[#6]1-[#6]-[#6]-[#6]-[#6]-[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#8]-[#6](=[#8])-[#6](-[#6]1-[#6]-[#6]-[#6]-[#6]-[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

lisdexamfetamine: CC(CC1=CC=CC=C1)NC(=O)C(CCCCN)N

smiles_non_kekule:    CC(Cc1ccccc1)NC(=O)C(N)CCCCN
smiles_kekule:    CC(CC1=CC=CC=C1)NC(=O)C(N)CCCCN
inchi:    InChI=1S/C15H25N3O/c1-12(11-13-7-3-2-4-8-13)18-15(19)14(17)9-5-6-10-16/h2-4,7-8,12,14H,5-6,9-11,16-17H2,1H3,(H,18,19)
inchiKey:    VOBHXZCDAVEXEY-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]-[#6](=[#8])-[#6](-[#6]-[#6]-[#6]-[#6]-[#7])-[#7]
smarts_isomeric:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]-[#6](=[#8])-[#6](-[#6]-[#6]-[#6]-[#6]-[#7])-[#7]

amobarbital: CCC1(C(=O)NC(=O)NC1=O)CCC(C)C

smiles_non_kekule:    CCC1(CCC(C)C)C(=O)NC(=O)NC1=O
smiles_kekule:    CCC1(CCC(C)C)C(=O)NC(=O)NC1=O
inchi:    InChI=1S/C11H18N2O3/c1-4-11(6-5-7(2)3)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16)
inchiKey:    VIROVYVQCGLCII-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]1(-[#6](=[#8])-[#7]-[#6](=[#8])-[#7]-[#6]-1=[#8])-[#6]-[#6]-[#6](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]1(-[#6](=[#8])-[#7]-[#6](=[#8])-[#7]-[#6]-1=[#8])-[#6]-[#6]-[#6](-[#6])-[#6]

glutethimide: CCC1(CCC(=O)NC1=O)C2=CC=CC=C2

smiles_non_kekule:    CCC1(c2ccccc2)CCC(=O)NC1=O
smiles_kekule:    CCC1(C2=CC=CC=C2)CCC(=O)NC1=O
inchi:    InChI=1S/C13H15NO2/c1-2-13(10-6-4-3-5-7-10)9-8-11(15)14-12(13)16/h3-7H,2,8-9H2,1H3,(H,14,15,16)
inchiKey:    JMBQKKAJIKAWKF-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]1(-[#6]-[#6]-[#6](=[#8])-[#7]-[#6]-1=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6]1(-[#6]-[#6]-[#6](=[#8])-[#7]-[#6]-1=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

pentobarbital: CCCC(C)C1(C(=O)NC(=O)NC1=O)CC

smiles_non_kekule:    CCCC(C)C1(CC)C(=O)NC(=O)NC1=O
smiles_kekule:    CCCC(C)C1(CC)C(=O)NC(=O)NC1=O
inchi:    InChI=1S/C11H18N2O3/c1-4-6-7(3)11(5-2)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16)
inchiKey:    WEXRUCMBJFQVBZ-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6](-[#6])-[#6]1(-[#6](=[#8])-[#7]-[#6](=[#8])-[#7]-[#6]-1=[#8])-[#6]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6](-[#6])-[#6]1(-[#6](=[#8])-[#7]-[#6](=[#8])-[#7]-[#6]-1=[#8])-[#6]-[#6]

phencyclidine: C1CCC(CC1)(C2=CC=CC=C2)N3CCCCC3

smiles_non_kekule:    c1ccc(C2(N3CCCCC3)CCCCC2)cc1
smiles_kekule:    C1=CC=C(C2(N3CCCCC3)CCCCC2)C=C1
inchi:    InChI=1S/C17H25N/c1-4-10-16(11-5-1)17(12-6-2-7-13-17)18-14-8-3-9-15-18/h1,4-5,10-11H,2-3,6-9,12-15H2
inchiKey:    JTJMJGYZQZDUJJ-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

secobarbital: CCCC(C)C1(C(=O)NC(=O)NC1=O)CC=C

smiles_non_kekule:    C=CCC1(C(C)CCC)C(=O)NC(=O)NC1=O
smiles_kekule:    C=CCC1(C(C)CCC)C(=O)NC(=O)NC1=O
inchi:    InChI=1S/C12H18N2O3/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17)
inchiKey:    KQPKPCNLIDLUMF-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6](-[#6])-[#6]1(-[#6](=[#8])-[#7]-[#6](=[#8])-[#7]-[#6]-1=[#8])-[#6]-[#6]=[#6]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6](-[#6])-[#6]1(-[#6](=[#8])-[#7]-[#6](=[#8])-[#7]-[#6]-1=[#8])-[#6]-[#6]=[#6]

nabilone: CCCCCCC(C)(C)C1=CC(=C2C3CC(=O)CCC3C(OC2=C1)(C)C)O

smiles_non_kekule:    CCCCCCC(C)(C)c1cc(O)c2c(c1)OC(C)(C)C1CCC(=O)CC21
smiles_kekule:    CCCCCCC(C)(C)C1=CC(O)=C2C(=C1)OC(C)(C)C1CCC(=O)CC21
inchi:    InChI=1S/C24H36O3/c1-6-7-8-9-12-23(2,3)16-13-20(26)22-18-15-17(25)10-11-19(18)24(4,5)27-21(22)14-16/h13-14,18-19,26H,6-12,15H2,1-5H3
inchiKey:    GECBBEABIDMGGL-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6](-[#6])(-[#6])-[#6]1:[#6]:[#6](:[#6]2-[#6]3-[#6]-[#6](=[#8])-[#6]-[#6]-[#6]-3-[#6](-[#8]-[#6]:2:[#6]:1)(-[#6])-[#6])-[#8]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]-[#6]-[#6]-[#6](-[#6])(-[#6])-[#6]1:[#6]:[#6](:[#6]2-[#6]3-[#6]-[#6](=[#8])-[#6]-[#6]-[#6]-3-[#6](-[#8]-[#6]:2:[#6]:1)(-[#6])-[#6])-[#8]

dronabinol: CCCCCC1=CC(=C2C3C=C(CCC3C(OC2=C1)(C)C)C)O

phenylacetone: CC(=O)CC1=CC=CC=C1

smiles_non_kekule:    CC(=O)Cc1ccccc1
smiles_kekule:    CC(=O)CC1=CC=CC=C1
inchi:    InChI=1S/C9H10O/c1-8(10)7-9-5-3-2-4-6-9/h2-6H,7H2,1H3
inchiKey:    QCCDLTOVEPVEJK-UHFFFAOYSA-N
smarts:    [#6]-[#6](=[#8])-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6](=[#8])-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

1-phenylcyclohexylamine: C1CCC(CC1)(C2=CC=CC=C2)N

smiles_non_kekule:    NC1(c2ccccc2)CCCCC1
smiles_kekule:    NC1(C2=CC=CC=C2)CCCCC1
inchi:    InChI=1S/C12H17N/c13-12(9-5-2-6-10-12)11-7-3-1-4-8-11/h1,3-4,7-8H,2,5-6,9-10,13H2
inchiKey:    RGZGRPPQZUQUCR-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]
smarts_isomeric:    [#6]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]

1-piperidinocyclohexanecarbonitrile: C1CCC(CC1)(C#N)N2CCCCC2

smiles_non_kekule:    N#CC1(N2CCCCC2)CCCCC1
smiles_kekule:    N#CC1(N2CCCCC2)CCCCC1
inchi:    InChI=1S/C12H20N2/c13-11-12(7-3-1-4-8-12)14-9-5-2-6-10-14/h1-10H2
inchiKey:    WWSAYKJWUZJLRT-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)(-[#6]#[#7])-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)(-[#6]#[#7])-[#7]1-[#6]-[#6]-[#6]-[#6]-[#6]-1

4-anilino-n-phenethylpiperidine: C1CN(CCC1NC2=CC=CC=C2)CCC3=CC=CC=C3

smiles_non_kekule:    c1ccc(CCN2CCC(Nc3ccccc3)CC2)cc1
smiles_kekule:    C1=CC=C(CCN2CCC(NC3=CC=CC=C3)CC2)C=C1
inchi:    InChI=1S/C19H24N2/c1-3-7-17(8-4-1)11-14-21-15-12-19(13-16-21)20-18-9-5-2-6-10-18/h1-10,19-20H,11-16H2
inchiKey:    ZCMDXDQUYIWEKB-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#7](-[#6]-[#6]-[#6]-1-[#7]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1-[#6]-[#7](-[#6]-[#6]-[#6]-1-[#7]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

problem_type: 23/25 (loop 0/0)

[15:24:00] WARNING: Omitted undefined stereo

[15:24:00] WARNING: Omitted undefined stereo

[15:24:00] WARNING: Omitted undefined stereo

[15:24:00] WARNING: Omitted undefined stereo

[15:24:00] WARNING: Omitted undefined stereo

[15:24:00] WARNING: Omitted undefined stereo

[15:24:00] WARNING: Omitted undefined stereo

[15:24:00] WARNING: Omitted undefined stereo

[15:24:00] WARNING: Omitted undefined stereo

[15:24:00] WARNING: Omitted undefined stereo

[15:24:00] WARNING: Omitted undefined stereo

[15:24:00] WARNING: Omitted undefined stereo

[15:24:00] WARNING: Omitted undefined stereo

Problem Template: _problem_schedule_three

Write structure of schedule three molecules.

Answer:

structure of schedule three molecules:

norfentanyl: CCC(=O)N(C1CCNCC1)C2=CC=CC=C2

benzphetamine: CC(CC1=CC=CC=C1)N(C)CC2=CC=CC=C2

chlorphentermine: CN(C)CCC(C1=CC=C(C=C1)Cl)C2=CC=CC=N2

clortermine: CC(C)(CC1=CC=CC=C1Cl)N

phendimetrazine: CC1C(OCCN1C)C2=CC=CC=C2

amobarbital: CCC1(C(=O)NC(=O)NC1=O)CCC(C)C

secobarbital: CCCC(C)C1(C(=O)NC(=O)NC1=O)CC=C

pentobarbital: CCCC(C)C1(C(=O)NC(=O)NC1=O)CC

chlorhexadol: CC(CC(C)(C)O)OC(C(Cl)(Cl)Cl)O

embutramide: CCC(CC)(CNC(=O)CCCO)C1=CC(=CC=C1)OC

ketamine: CNC1(CCCCC1=O)C2=CC=CC=C2Cl

lysergicacid: CN1CC(C=C2C1CC3=CNC4=CC=CC2=C34)C(=O)O

lysergicacidamide: CN1CC(C=C2C1CC3=CNC4=CC=CC2=C34)C(=O)N

methyprylon: CCC1(C(=O)C(CNC1=O)C)CC

perampanel: C1=CC=C(C=C1)N2C=C(C=C(C2=O)C3=CC=CC=C3C#N)C4=CC=CC=N4

sulfondiethylmethane: CCC(CC)(S(=O)(=O)CC)S(=O)(=O)CC

sulfonethylmethane: CCC(C)(S(=O)(=O)CC)S(=O)(=O)CC

sulfonmethane: O=S(=O)(C(C)(C)S(=O)(=O)CC)CC

tiletamine: CCNC1(CCCCC1=O)C2=CC=CS2

nalorphine_9400: C=CCN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(C=C4)O

flupyrazapon: CC1=NN(C2=C1C(=NCC(=O)N2C)C3=CC=CC=C3F)C

buprenorphine: CC(C)(C)C(C)(C1CC23CCC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)O

Solution:

structure of schedule three molecules:

norfentanyl: CCC(=O)N(C1CCNCC1)C2=CC=CC=C2

smiles_non_kekule:    CCC(=O)N(c1ccccc1)C1CCNCC1
smiles_kekule:    CCC(=O)N(C1=CC=CC=C1)C1CCNCC1
inchi:    InChI=1S/C14H20N2O/c1-2-14(17)16(12-6-4-3-5-7-12)13-8-10-15-11-9-13/h3-7,13,15H,2,8-11H2,1H3
inchiKey:    PMCBDBWCQQBSRJ-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7]-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6](=[#8])-[#7](-[#6]1-[#6]-[#6]-[#7]-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

benzphetamine: CC(CC1=CC=CC=C1)N(C)CC2=CC=CC=C2

smiles_non_kekule:    CC(Cc1ccccc1)N(C)Cc1ccccc1
smiles_kekule:    CC(CC1=CC=CC=C1)N(C)CC1=CC=CC=C1
inchi:    InChI=1S/C17H21N/c1-15(13-16-9-5-3-6-10-16)18(2)14-17-11-7-4-8-12-17/h3-12,15H,13-14H2,1-2H3
inchiKey:    YXKTVDFXDRQTKV-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7](-[#6])-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7](-[#6])-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

chlorphentermine: CN(C)CCC(C1=CC=C(C=C1)Cl)C2=CC=CC=N2

smiles_non_kekule:    CN(C)CCC(c1ccc(Cl)cc1)c1ccccn1
smiles_kekule:    CN(C)CCC(C1=CC=C(Cl)C=C1)C1=CC=CC=N1
inchi:    InChI=1S/C16H19ClN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3
inchiKey:    SOYKEARSMXGVTM-UHFFFAOYSA-N
smarts:    [#6]-[#7](-[#6])-[#6]-[#6]-[#6](-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#17])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#7]:1
smarts_isomeric:    [#6]-[#7](-[#6])-[#6]-[#6]-[#6](-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#17])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#7]:1

clortermine: CC(C)(CC1=CC=CC=C1Cl)N

smiles_non_kekule:    CC(C)(N)Cc1ccccc1Cl
smiles_kekule:    CC(C)(N)CC1=CC=CC=C1Cl
inchi:    InChI=1S/C10H14ClN/c1-10(2,12)7-8-5-3-4-6-9(8)11/h3-6H,7,12H2,1-2H3
inchiKey:    HXCXASJHZQXCKK-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])(-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17])-[#7]
smarts_isomeric:    [#6]-[#6](-[#6])(-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17])-[#7]

phendimetrazine: CC1C(OCCN1C)C2=CC=CC=C2

smiles_non_kekule:    CC1C(c2ccccc2)OCCN1C
smiles_kekule:    CC1C(C2=CC=CC=C2)OCCN1C
inchi:    InChI=1S/C12H17NO/c1-10-12(14-9-8-13(10)2)11-6-4-3-5-7-11/h3-7,10,12H,8-9H2,1-2H3
inchiKey:    MFOCDFTXLCYLKU-UHFFFAOYSA-N
smarts:    [#6]-[#6]1-[#6](-[#8]-[#6]-[#6]-[#7]-1-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]1-[#6](-[#8]-[#6]-[#6]-[#7]-1-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

amobarbital: CCC1(C(=O)NC(=O)NC1=O)CCC(C)C

secobarbital: CCCC(C)C1(C(=O)NC(=O)NC1=O)CC=C

pentobarbital: CCCC(C)C1(C(=O)NC(=O)NC1=O)CC

chlorhexadol: CC(CC(C)(C)O)OC(C(Cl)(Cl)Cl)O

smiles_non_kekule:    CC(CC(C)(C)O)OC(O)C(Cl)(Cl)Cl
smiles_kekule:    CC(CC(C)(C)O)OC(O)C(Cl)(Cl)Cl
inchi:    InChI=1S/C8H15Cl3O3/c1-5(4-7(2,3)13)14-6(12)8(9,10)11/h5-6,12-13H,4H2,1-3H3
inchiKey:    QVFWZNCVPCJQOP-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6](-[#6])(-[#6])-[#8])-[#8]-[#6](-[#6](-[#17])(-[#17])-[#17])-[#8]
smarts_isomeric:    [#6]-[#6](-[#6]-[#6](-[#6])(-[#6])-[#8])-[#8]-[#6](-[#6](-[#17])(-[#17])-[#17])-[#8]

embutramide: CCC(CC)(CNC(=O)CCCO)C1=CC(=CC=C1)OC

smiles_non_kekule:    CCC(CC)(CNC(=O)CCCO)c1cccc(OC)c1
smiles_kekule:    CCC(CC)(CNC(=O)CCCO)C1=CC(OC)=CC=C1
inchi:    InChI=1S/C17H27NO3/c1-4-17(5-2,13-18-16(20)10-7-11-19)14-8-6-9-15(12-14)21-3/h6,8-9,12,19H,4-5,7,10-11,13H2,1-3H3,(H,18,20)
inchiKey:    LMBMDLOSPKIWAP-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](-[#6]-[#6])(-[#6]-[#7]-[#6](=[#8])-[#6]-[#6]-[#6]-[#8])-[#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1)-[#8]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6](-[#6]-[#6])(-[#6]-[#7]-[#6](=[#8])-[#6]-[#6]-[#6]-[#8])-[#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1)-[#8]-[#6]

ketamine: CNC1(CCCCC1=O)C2=CC=CC=C2Cl

smiles_non_kekule:    CNC1(c2ccccc2Cl)CCCCC1=O
smiles_kekule:    CNC1(C2=CC=CC=C2Cl)CCCCC1=O
inchi:    InChI=1S/C13H16ClNO/c1-15-13(9-5-4-8-12(13)16)10-6-2-3-7-11(10)14/h2-3,6-7,15H,4-5,8-9H2,1H3
inchiKey:    YQEZLKZALYSWHR-UHFFFAOYSA-N
smarts:    [#6]-[#7]-[#6]1(-[#6]-[#6]-[#6]-[#6]-[#6]-1=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17]
smarts_isomeric:    [#6]-[#7]-[#6]1(-[#6]-[#6]-[#6]-[#6]-[#6]-1=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17]

lysergicacid: CN1CC(C=C2C1CC3=CNC4=CC=CC2=C34)C(=O)O

smiles_non_kekule:    CN1CC(C(=O)O)C=C2c3cccc4[nH]cc(c34)CC21
smiles_kekule:    CN1CC(C(=O)O)C=C2C3=C4C(=CNC4=CC=C3)CC21
inchi:    InChI=1S/C16H16N2O2/c1-18-8-10(16(19)20)5-12-11-3-2-4-13-15(11)9(7-17-13)6-14(12)18/h2-5,7,10,14,17H,6,8H2,1H3,(H,19,20)
inchiKey:    ZAGRKAFMISFKIO-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6](-[#6]=[#6]2-[#6]-1-[#6]-[#6]1:[#6]:[#7H]:[#6]3:[#6]:[#6]:[#6]:[#6]-2:[#6]:1:3)-[#6](=[#8])-[#8]
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6](-[#6]=[#6]2-[#6]-1-[#6]-[#6]1:[#6]:[#7H]:[#6]3:[#6]:[#6]:[#6]:[#6]-2:[#6]:1:3)-[#6](=[#8])-[#8]

lysergicacidamide: CN1CC(C=C2C1CC3=CNC4=CC=CC2=C34)C(=O)N

smiles_non_kekule:    CN1CC(C(N)=O)C=C2c3cccc4[nH]cc(c34)CC21
smiles_kekule:    CN1CC(C(N)=O)C=C2C3=C4C(=CNC4=CC=C3)CC21
inchi:    InChI=1S/C16H17N3O/c1-19-8-10(16(17)20)5-12-11-3-2-4-13-15(11)9(7-18-13)6-14(12)19/h2-5,7,10,14,18H,6,8H2,1H3,(H2,17,20)
inchiKey:    GENAHGKEFJLNJB-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6](-[#6]=[#6]2-[#6]-1-[#6]-[#6]1:[#6]:[#7H]:[#6]3:[#6]:[#6]:[#6]:[#6]-2:[#6]:1:3)-[#6](=[#8])-[#7]
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6](-[#6]=[#6]2-[#6]-1-[#6]-[#6]1:[#6]:[#7H]:[#6]3:[#6]:[#6]:[#6]:[#6]-2:[#6]:1:3)-[#6](=[#8])-[#7]

methyprylon: CCC1(C(=O)C(CNC1=O)C)CC

smiles_non_kekule:    CCC1(CC)C(=O)NCC(C)C1=O
smiles_kekule:    CCC1(CC)C(=O)NCC(C)C1=O
inchi:    InChI=1S/C10H17NO2/c1-4-10(5-2)8(12)7(3)6-11-9(10)13/h7H,4-6H2,1-3H3,(H,11,13)
inchiKey:    SIDLZWOQUZRBRU-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]1(-[#6](=[#8])-[#6](-[#6]-[#7]-[#6]-1=[#8])-[#6])-[#6]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]1(-[#6](=[#8])-[#6](-[#6]-[#7]-[#6]-1=[#8])-[#6])-[#6]-[#6]

perampanel: C1=CC=C(C=C1)N2C=C(C=C(C2=O)C3=CC=CC=C3C#N)C4=CC=CC=N4

smiles_non_kekule:    N#Cc1ccccc1-c1cc(-c2ccccn2)cn(-c2ccccc2)c1=O
smiles_kekule:    N#CC1=CC=CC=C1C1=CC(C2=CC=CC=N2)=CN(C2=CC=CC=C2)C1=O
inchi:    InChI=1S/C23H15N3O/c24-15-17-8-4-5-11-20(17)21-14-18(22-12-6-7-13-25-22)16-26(23(21)27)19-9-2-1-3-10-19/h1-14,16H
inchiKey:    PRMWGUBFXWROHD-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#7]1:[#6]:[#6](:[#6]:[#6](:[#6]:1=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]#[#7])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#7]:1
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#7]1:[#6]:[#6](:[#6]:[#6](:[#6]:1=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]#[#7])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#7]:1

sulfondiethylmethane: CCC(CC)(S(=O)(=O)CC)S(=O)(=O)CC

smiles_non_kekule:    CCC(CC)(S(=O)(=O)CC)S(=O)(=O)CC
smiles_kekule:    CCC(CC)(S(=O)(=O)CC)S(=O)(=O)CC
inchi:    InChI=1S/C9H20O4S2/c1-5-9(6-2,14(10,11)7-3)15(12,13)8-4/h5-8H2,1-4H3
inchiKey:    VTZYVPLHCQBWSP-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](-[#6]-[#6])(-[#16](=[#8])(=[#8])-[#6]-[#6])-[#16](=[#8])(=[#8])-[#6]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6](-[#6]-[#6])(-[#16](=[#8])(=[#8])-[#6]-[#6])-[#16](=[#8])(=[#8])-[#6]-[#6]

sulfonethylmethane: CCC(C)(S(=O)(=O)CC)S(=O)(=O)CC

smiles_non_kekule:    CCC(C)(S(=O)(=O)CC)S(=O)(=O)CC
smiles_kekule:    CCC(C)(S(=O)(=O)CC)S(=O)(=O)CC
inchi:    InChI=1S/C8H18O4S2/c1-5-8(4,13(9,10)6-2)14(11,12)7-3/h5-7H2,1-4H3
inchiKey:    LKACJLUUJRMGFK-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](-[#6])(-[#16](=[#8])(=[#8])-[#6]-[#6])-[#16](=[#8])(=[#8])-[#6]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6](-[#6])(-[#16](=[#8])(=[#8])-[#6]-[#6])-[#16](=[#8])(=[#8])-[#6]-[#6]

sulfonmethane: O=S(=O)(C(C)(C)S(=O)(=O)CC)CC

smiles_non_kekule:    CCS(=O)(=O)C(C)(C)S(=O)(=O)CC
smiles_kekule:    CCS(=O)(=O)C(C)(C)S(=O)(=O)CC
inchi:    InChI=1S/C7H16O4S2/c1-5-12(8,9)7(3,4)13(10,11)6-2/h5-6H2,1-4H3
inchiKey:    CESKLHVYGRFMFP-UHFFFAOYSA-N
smarts:    [#8]=[#16](=[#8])(-[#6](-[#6])(-[#6])-[#16](=[#8])(=[#8])-[#6]-[#6])-[#6]-[#6]
smarts_isomeric:    [#8]=[#16](=[#8])(-[#6](-[#6])(-[#6])-[#16](=[#8])(=[#8])-[#6]-[#6])-[#6]-[#6]

tiletamine: CCNC1(CCCCC1=O)C2=CC=CS2

smiles_non_kekule:    CCNC1(c2cccs2)CCCCC1=O
smiles_kekule:    CCNC1(C2=CC=CS2)CCCCC1=O
inchi:    InChI=1S/C12H17NOS/c1-2-13-12(11-7-5-9-15-11)8-4-3-6-10(12)14/h5,7,9,13H,2-4,6,8H2,1H3
inchiKey:    QAXBVGVYDCAVLV-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7]-[#6]1(-[#6]-[#6]-[#6]-[#6]-[#6]-1=[#8])-[#6]1:[#6]:[#6]:[#6]:[#16]:1
smarts_isomeric:    [#6]-[#6]-[#7]-[#6]1(-[#6]-[#6]-[#6]-[#6]-[#6]-1=[#8])-[#6]1:[#6]:[#6]:[#6]:[#16]:1

nalorphine_9400: C=CCN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(C=C4)O

smiles_non_kekule:    C=CCN1CCC23c4c5ccc(O)c4OC2C(O)C=CC3C1C5
smiles_kekule:    C=CCN1CCC23C4=C5C=CC(O)=C4OC2C(O)C=CC3C1C5
inchi:    InChI=1S/C19H21NO3/c1-2-8-20-9-7-19-12-4-6-15(22)18(19)23-17-14(21)5-3-11(16(17)19)10-13(12)20/h2-6,12-13,15,18,21-22H,1,7-10H2
inchiKey:    UIQMVEYFGZJHCZ-UHFFFAOYSA-N
smarts:    [#6]=[#6]-[#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8])-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8]
smarts_isomeric:    [#6]=[#6]-[#6]-[#7]1-[#6]-[#6]-[#6]23-[#6]4-[#6]-1-[#6]-[#6]1:[#6]-2:[#6](:[#6](:[#6]:[#6]:1)-[#8])-[#8]-[#6]-3-[#6](-[#6]=[#6]-4)-[#8]

flupyrazapon: CC1=NN(C2=C1C(=NCC(=O)N2C)C3=CC=CC=C3F)C

smiles_non_kekule:    Cc1nn(C)c2c1C(c1ccccc1F)=NCC(=O)N2C
smiles_kekule:    CC1=NN(C)C2=C1C(C1=CC=CC=C1F)=NCC(=O)N2C
inchi:    InChI=1S/C15H15FN4O/c1-9-13-14(10-6-4-5-7-11(10)16)17-8-12(21)19(2)15(13)20(3)18-9/h4-7H,8H2,1-3H3
inchiKey:    GDSCFOSHSOWNDL-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#7]:[#7](:[#6]2:[#6]:1-[#6](=[#7]-[#6]-[#6](=[#8])-[#7]-2-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9])-[#6]
smarts_isomeric:    [#6]-[#6]1:[#7]:[#7](:[#6]2:[#6]:1-[#6](=[#7]-[#6]-[#6](=[#8])-[#7]-2-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9])-[#6]

buprenorphine: CC(C)(C)C(C)(C1CC23CCC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)O

smiles_non_kekule:    COC12CCC3(CC1C(C)(O)C(C)(C)C)C1Cc4ccc(O)c5c4C3(CCN1CC1CC1)C2O5
smiles_kekule:    COC12CCC3(CC1C(C)(O)C(C)(C)C)C1CC4=CC=C(O)C5=C4C3(CCN1CC1CC1)C2O5
inchi:    InChI=1S/C29H41NO4/c1-25(2,3)26(4,32)20-15-27-10-11-29(20,33-5)24-28(27)12-13-30(16-17-6-7-17)21(27)14-18-8-9-19(31)23(34-24)22(18)28/h8-9,17,20-21,24,31-32H,6-7,10-16H2,1-5H3
inchiKey:    RMRJXGBAOAMLHD-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])(-[#6])-[#6](-[#6])(-[#6]1-[#6]-[#6]23-[#6]-[#6]-[#6]-1(-[#6]1-[#6]-24-[#6]-[#6]-[#7](-[#6]-3-[#6]-[#6]2:[#6]-4:[#6](:[#6](:[#6]:[#6]:2)-[#8])-[#8]-1)-[#6]-[#6]1-[#6]-[#6]-1)-[#8]-[#6])-[#8]
smarts_isomeric:    [#6]-[#6](-[#6])(-[#6])-[#6](-[#6])(-[#6]1-[#6]-[#6]23-[#6]-[#6]-[#6]-1(-[#6]1-[#6]-24-[#6]-[#6]-[#7](-[#6]-3-[#6]-[#6]2:[#6]-4:[#6](:[#6](:[#6]:[#6]:2)-[#8])-[#8]-1)-[#6]-[#6]1-[#6]-[#6]-1)-[#8]-[#6])-[#8]

problem_type: 24/25 (loop 0/0)

Problem Template: _problem_schedule_five

[15:24:04] WARNING: Omitted undefined stereo

[15:24:04] WARNING: Omitted undefined stereo

[15:24:04] WARNING: Omitted undefined stereo

[15:24:04] WARNING: Omitted undefined stereo

[15:24:04] WARNING: Omitted undefined stereo

[15:24:04] WARNING: Omitted undefined stereo

Write structure of schedule five molecules.

Answer:

structure of schedule five molecules:

eluxadoline: CC1=CC(=CC(=C1CC(C(=O)N(CC2=CC(=C(C=C2)OC)C(=O)O)C(C)C3=NC=C(N3)C4=CC=CC=C4)N)C)C(=O)N

pyrovalerone: CCCC(C(=O)C1=CC=C(C=C1)C)N2CCCC2

brivaracetam: CCCC1CC(=O)N(C1)C(CC)C(=O)N

cenobamate: C1=CC=C(C(=C1)C(CN2N=CN=N2)OC(=O)N)Cl

ezogabine: CCOC(=O)NC1=C(C=C(C=C1)NCC2=CC=C(C=C2)F)N

lacosamide: CC(=O)NC(COC)C(=O)NCC1=CC=CC=C1

lasmiditan: CN1CCC(CC1)C(=O)C2=NC(=CC=C2)NC(=O)C3=C(C=C(C=C3F)F)F

pregabalin: CC(C)CC(CC(=O)O)CN

Solution:

structure of schedule five molecules:

eluxadoline: CC1=CC(=CC(=C1CC(C(=O)N(CC2=CC(=C(C=C2)OC)C(=O)O)C(C)C3=NC=C(N3)C4=CC=CC=C4)N)C)C(=O)N

smiles_non_kekule:    COc1ccc(CN(C(=O)C(N)Cc2c(C)cc(C(N)=O)cc2C)C(C)c2ncc(-c3ccccc3)[nH]2)cc1C(=O)O
smiles_kekule:    COC1=C(C(=O)O)C=C(CN(C(=O)C(N)CC2=C(C)C=C(C(N)=O)C=C2C)C(C)C2=NC=C(C3=CC=CC=C3)N2)C=C1
inchi:    InChI=1S/C32H35N5O5/c1-18-12-23(29(34)38)13-19(2)24(18)15-26(33)31(39)37(17-21-10-11-28(42-4)25(14-21)32(40)41)20(3)30-35-16-27(36-30)22-8-6-5-7-9-22/h5-14,16,20,26H,15,17,33H2,1-4H3,(H2,34,38)(H,35,36)(H,40,41)
inchiKey:    QFNHIDANIVGXPE-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6](:[#6]:[#6](:[#6]:1-[#6]-[#6](-[#6](=[#8])-[#7](-[#6]-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#6](=[#8])-[#8])-[#6](-[#6])-[#6]1:[#7]:[#6]:[#6](:[#7H]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7])-[#6])-[#6](=[#8])-[#7]
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6](:[#6]:[#6](:[#6]:1-[#6]-[#6](-[#6](=[#8])-[#7](-[#6]-[#6]1:[#6]:[#6](:[#6](:[#6]:[#6]:1)-[#8]-[#6])-[#6](=[#8])-[#8])-[#6](-[#6])-[#6]1:[#7]:[#6]:[#6](:[#7H]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7])-[#6])-[#6](=[#8])-[#7]

pyrovalerone: CCCC(C(=O)C1=CC=C(C=C1)C)N2CCCC2

smiles_non_kekule:    CCCC(C(=O)c1ccc(C)cc1)N1CCCC1
smiles_kekule:    CCCC(C(=O)C1=CC=C(C)C=C1)N1CCCC1
inchi:    InChI=1S/C16H23NO/c1-3-6-15(17-11-4-5-12-17)16(18)14-9-7-13(2)8-10-14/h7-10,15H,3-6,11-12H2,1-2H3
inchiKey:    SWUVZKWCOBGPTH-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6])-[#7]1-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#6]-[#6]-[#6](-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6])-[#7]1-[#6]-[#6]-[#6]-[#6]-1

brivaracetam: CCCC1CC(=O)N(C1)C(CC)C(=O)N

smiles_non_kekule:    CCCC1CC(=O)N(C(CC)C(N)=O)C1
smiles_kekule:    CCCC1CC(=O)N(C(CC)C(N)=O)C1
inchi:    InChI=1S/C11H20N2O2/c1-3-5-8-6-10(14)13(7-8)9(4-2)11(12)15/h8-9H,3-7H2,1-2H3,(H2,12,15)
inchiKey:    MSYKRHVOOPPJKU-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6]1-[#6]-[#6](=[#8])-[#7](-[#6]-1)-[#6](-[#6]-[#6])-[#6](=[#8])-[#7]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6]1-[#6]-[#6](=[#8])-[#7](-[#6]-1)-[#6](-[#6]-[#6])-[#6](=[#8])-[#7]

cenobamate: C1=CC=C(C(=C1)C(CN2N=CN=N2)OC(=O)N)Cl

smiles_non_kekule:    NC(=O)OC(Cn1ncnn1)c1ccccc1Cl
smiles_kekule:    NC(=O)OC(CN1N=CN=N1)C1=CC=CC=C1Cl
inchi:    InChI=1S/C10H10ClN5O2/c11-8-4-2-1-3-7(8)9(18-10(12)17)5-16-14-6-13-15-16/h1-4,6,9H,5H2,(H2,12,17)
inchiKey:    GFHAXPJGXSQLPT-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](:[#6](:[#6]:1)-[#6](-[#6]-[#7]1:[#7]:[#6]:[#7]:[#7]:1)-[#8]-[#6](=[#8])-[#7])-[#17]
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](:[#6](:[#6]:1)-[#6](-[#6]-[#7]1:[#7]:[#6]:[#7]:[#7]:1)-[#8]-[#6](=[#8])-[#7])-[#17]

ezogabine: CCOC(=O)NC1=C(C=C(C=C1)NCC2=CC=C(C=C2)F)N

smiles_non_kekule:    CCOC(=O)Nc1ccc(NCc2ccc(F)cc2)cc1N
smiles_kekule:    CCOC(=O)NC1=C(N)C=C(NCC2=CC=C(F)C=C2)C=C1
inchi:    InChI=1S/C16H18FN3O2/c1-2-22-16(21)20-15-8-7-13(9-14(15)18)19-10-11-3-5-12(17)6-4-11/h3-9,19H,2,10,18H2,1H3,(H,20,21)
inchiKey:    PCOBBVZJEWWZFR-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]-[#6](=[#8])-[#7]-[#6]1:[#6](:[#6]:[#6](:[#6]:[#6]:1)-[#7]-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#9])-[#7]
smarts_isomeric:    [#6]-[#6]-[#8]-[#6](=[#8])-[#7]-[#6]1:[#6](:[#6]:[#6](:[#6]:[#6]:1)-[#7]-[#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#9])-[#7]

lacosamide: CC(=O)NC(COC)C(=O)NCC1=CC=CC=C1

smiles_non_kekule:    COCC(NC(C)=O)C(=O)NCc1ccccc1
smiles_kekule:    COCC(NC(C)=O)C(=O)NCC1=CC=CC=C1
inchi:    InChI=1S/C13H18N2O3/c1-10(16)15-12(9-18-2)13(17)14-8-11-6-4-3-5-7-11/h3-7,12H,8-9H2,1-2H3,(H,14,17)(H,15,16)
inchiKey:    VPPJLAIAVCUEMN-UHFFFAOYSA-N
smarts:    [#6]-[#6](=[#8])-[#7]-[#6](-[#6]-[#8]-[#6])-[#6](=[#8])-[#7]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6](=[#8])-[#7]-[#6](-[#6]-[#8]-[#6])-[#6](=[#8])-[#7]-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

lasmiditan: CN1CCC(CC1)C(=O)C2=NC(=CC=C2)NC(=O)C3=C(C=C(C=C3F)F)F

smiles_non_kekule:    CN1CCC(C(=O)c2cccc(NC(=O)c3c(F)cc(F)cc3F)n2)CC1
smiles_kekule:    CN1CCC(C(=O)C2=NC(NC(=O)C3=C(F)C=C(F)C=C3F)=CC=C2)CC1
inchi:    InChI=1S/C19H18F3N3O2/c1-25-7-5-11(6-8-25)18(26)15-3-2-4-16(23-15)24-19(27)17-13(21)9-12(20)10-14(17)22/h2-4,9-11H,5-8H2,1H3,(H,23,24,27)
inchiKey:    XEDHVZKDSYZQBF-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)-[#6](=[#8])-[#6]1:[#7]:[#6](:[#6]:[#6]:[#6]:1)-[#7]-[#6](=[#8])-[#6]1:[#6](:[#6]:[#6](:[#6]:[#6]:1-[#9])-[#9])-[#9]
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#6](-[#6]-[#6]-1)-[#6](=[#8])-[#6]1:[#7]:[#6](:[#6]:[#6]:[#6]:1)-[#7]-[#6](=[#8])-[#6]1:[#6](:[#6]:[#6](:[#6]:[#6]:1-[#9])-[#9])-[#9]

pregabalin: CC(C)CC(CC(=O)O)CN

smiles_non_kekule:    CC(C)CC(CN)CC(=O)O
smiles_kekule:    CC(C)CC(CN)CC(=O)O
inchi:    InChI=1S/C8H17NO2/c1-6(2)3-7(5-9)4-8(10)11/h6-7H,3-5,9H2,1-2H3,(H,10,11)
inchiKey:    AYXYPKUFHZROOJ-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])-[#6]-[#6](-[#6]-[#6](=[#8])-[#8])-[#6]-[#7]
smarts_isomeric:    [#6]-[#6](-[#6])-[#6]-[#6](-[#6]-[#6](=[#8])-[#8])-[#6]-[#7]

problem_type: 25/25 (loop 0/0)

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Charges were rearranged

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Charges were rearranged

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Charges were rearranged; Omitted undefined stereo

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Charges were rearranged

[15:24:06] WARNING: Charges were rearranged

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Omitted undefined stereo

[15:24:06] WARNING: Omitted undefined stereo

[15:24:07] WARNING: Omitted undefined stereo

[15:24:07] WARNING: Omitted undefined stereo

[15:24:07] WARNING: Omitted undefined stereo

[15:24:07] WARNING: Omitted undefined stereo

[15:24:07] WARNING: Omitted undefined stereo

[15:24:07] WARNING: Omitted undefined stereo

[15:24:07] WARNING: Omitted undefined stereo

[15:24:07] WARNING: Omitted undefined stereo

[15:24:07] WARNING: Omitted undefined stereo

[15:24:07] WARNING: Omitted undefined stereo

[15:24:07] WARNING: Omitted undefined stereo

[15:24:07] WARNING: Omitted undefined stereo

[15:24:07] WARNING: Omitted undefined stereo

[15:24:07] WARNING: Omitted undefined stereo

[15:24:07] WARNING: Omitted undefined stereo

[15:24:07] WARNING: Omitted undefined stereo

[15:24:07] WARNING: Omitted undefined stereo

[15:24:07] WARNING: Omitted undefined stereo

[15:24:07] WARNING: Omitted undefined stereo

Problem Template: _problem_schedule_four

Write structure of schedule four molecules.

Answer:

structure of schedule four molecules:

dextropropoxyphene: CCC(=O)OC(CC1=CC=CC=C1)(C2=CC=CC=C2)C(C)CN(C)C

2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol: CN(C)CC1CCCCC1(C2=CC(=CC=C2)OC)O

alfaxalone: CC(=O)C1CCC2C1(CC(=O)C3C2CCC4C3(CCC(C4)O)C)C

alprazolam: CC1=NN=C2N1C3=C(C=C(C=C3)Cl)C(=NC2)C4=CC=CC=C4

barbital: CCC1(C(=O)NC(=O)NC1=O)CC

brexanolone: CC(=O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C

bromazepam: C1C(=O)NC2=C(C=C(C=C2)Br)C(=N1)C3=CC=CC=N3

camazepam: CN1C2=C(C=C(C=C2)Cl)C(=NC(C1=O)OC(=O)N(C)C)C3=CC=CC=C3

carisoprodol: CCCC(C)(COC(=O)N)COC(=O)NC(C)C

chloralbetaine: C[N+](C)(C)CC(=O)[O-].C(C(Cl)(Cl)Cl)(O)O

chloralhydrate: C(C(Cl)(Cl)Cl)(O)O

chlordiazepoxide: CN=C1CN(C(=C2C=C(C=CC2=N1)Cl)C3=CC=CC=C3)O

clobazam: CN1C(=O)CC(=O)N(C2=C1C=CC(=C2)Cl)C3=CC=CC=C3

clonazepam: C1C(=O)NC2=C(C=C(C=C2)[N+](=O)[O-])C(=N1)C3=CC=CC=C3Cl

clorazepate: C1=CC=C(C=C1)C2=NC(C(=O)NC3=C2C=C(C=C3)Cl)C(=O)O

clotiazepam: CCC1=CC2=C(S1)N(C(=O)CN=C2C3=CC=CC=C3Cl)C

cloxazolam: C1COC2(N1CC(=O)NC3=C2C=C(C=C3)Cl)C4=CC=CC=C4Cl

delorazepam: C1C(=O)NC2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CC=C3Cl

diazepam: CN1C(=O)CN=C(C2=C1C=CC(=C2)Cl)C3=CC=CC=C3

dichloralphenazone: CC1=CC(=O)N(N1C)C2=CC=CC=C2.C(C(Cl)(Cl)Cl)(O)O.C(C(Cl)(Cl)Cl)(O)O

estazolam: C1C2=NN=CN2C3=C(C=C(C=C3)Cl)C(=N1)C4=CC=CC=C4

ethchlorvynol: CCC(C=CCl)(C#C)O

ethinamate: O=C(OC1(C#C)CCCCC1)N

ethyl loflazepate: CCOC(=O)C1C(=O)NC2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CC=C3F

fludiazepam: CN1C(=O)CN=C(C2=C1C=CC(=C2)Cl)C3=CC=CC=C3F

flunitrazepam: CN1C(=O)CN=C(C2=C1C=CC(=C2)[N+](=O)[O-])C3=CC=CC=C3F

flurazepam: CCN(CC)CCN1C(=O)CN=C(C2=C1C=CC(=C2)Cl)C3=CC=CC=C3F

fospropofol: CC(C)C1=C(C(=CC=C1)C(C)C)OCOP(=O)(O)O

halazepam: C1C(=O)N(C2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CC=C3)CC(F)(F)F

haloxazolam: C1COC2(N1CC(=O)NC3=C2C=C(C=C3)Br)C4=CC=CC=C4F

ketazolam: CC1=CC(=O)N2CC(=O)N(C3=C(C2(O1)C4=CC=CC=C4)C=C(C=C3)Cl)C

lemborexant: CC1=NC(=NC=C1OCC2(CC2C(=O)NC3=NC=C(C=C3)F)C4=CC(=CC=C4)F)C

loprazolam: CN1CCN(CC1)C=C2C(=O)N3C(=N2)CN=C(C4=C3C=CC(=C4)[N+](=O)[O-])C5=CC=CC=C5Cl

lorazepam: C1=CC=C(C(=C1)C2=NC(C(=O)NC3=C2C=C(C=C3)Cl)O)Cl

lormetazepam: CN1C2=C(C=C(C=C2)Cl)C(=NC(C1=O)O)C3=CC=CC=C3Cl

mebutamate: CCC(C)C(C)(COC(=O)N)COC(=O)N

medazepam: CN1CCN=C(C2=C1C=CC(=C2)Cl)C3=CC=CC=C3

meprobamate: CCCC(C)(COC(=O)N)COC(=O)N

methohexital: CCC#CC(C)C1(C(=O)NC(=O)N(C1=O)C)CC=C

methylphenobarbital: CCC1(C(=O)NC(=O)N(C1=O)C)C2=CC=CC=C2

midazolam: CC1=NC=C2N1C3=C(C=C(C=C3)Cl)C(=NC2)C4=CC=CC=C4F

nimetazepam: CN1C(=O)CN=C(C2=C1C=CC(=C2)[N+](=O)[O-])C3=CC=CC=C3

nitrazepam: C1C(=O)NC2=C(C=C(C=C2)[N+](=O)[O-])C(=N1)C3=CC=CC=C3

nordiazepam: C1C(=O)NC2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CC=C3

oxazepam: C1=CC=C(C=C1)C2=NC(C(=O)NC3=C2C=C(C=C3)Cl)O

oxazolam: CC1CN2CC(=O)NC3=C(C2(O1)C4=CC=CC=C4)C=C(C=C3)Cl

paraldehyde: CC1OC(OC(O1)C)C

petrichloral: C(C(COC(C(Cl)(Cl)Cl)O)(COC(C(Cl)(Cl)Cl)O)COC(C(Cl)(Cl)Cl)O)OC(C(Cl)(Cl)Cl)O

phenobarbital: CCC1(C(=O)NC(=O)NC1=O)C2=CC=CC=C2

pinazepam: C#CCN1C(=O)CN=C(C2=C1C=CC(=C2)Cl)C3=CC=CC=C3

prazepam: C1CC1CN2C(=O)CN=C(C3=C2C=CC(=C3)Cl)C4=CC=CC=C4

quazepam: C1C(=S)N(C2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CC=C3F)CC(F)(F)F

remimazolam: CC1=CN=C2N1C3=C(C=C(C=C3)Br)C(=NC2CCC(=O)OC)C4=CC=CC=N4

suvorexant: CC1CCN(CCN1C(=O)C2=C(C=CC(=C2)C)N3N=CC=N3)C4=NC5=C(O4)C=CC(=C5)Cl

temazepam: CN1C2=C(C=C(C=C2)Cl)C(=NC(C1=O)O)C3=CC=CC=C3

tetrazepam: CN1C(=O)CN=C(C2=C1C=CC(=C2)Cl)C3=CCCCC3

triazolam: CC1=NN=C2N1C3=C(C=C(C=C3)Cl)C(=NC2)C4=CC=CC=C4Cl

zaleplon: CCN(C1=CC=CC(=C1)C2=CC=NC3=C(C=NN23)C#N)C(=O)C

zolpidem: CC1=CC=C(C=C1)C2=C(N3C=C(C=CC3=N2)C)CC(=O)N(C)C

zopiclone: CN1CCN(CC1)C(=O)OC2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl

fenfluramine: CCNC(C)CC1=CC(=CC=C1)C(F)(F)F

lorcaserin: CC1CNCCC2=C1C=C(C=C2)Cl

(+)-norpseudoephedrine: CC(C(C1=CC=CC=C1)O)N

diethylpropion: CCN(CC)C(C)C(=O)C1=CC=CC=C1

fencamfamin: CCNC1C2CCC(C2)C1C3=CC=CC=C3

fenproporex: CC(CC1=CC=CC=C1)NCCC#N

mazindol: C1CN2C(=N1)C3=CC=CC=C3C2(C4=CC=C(C=C4)Cl)O

mefenorex: CC(CC1=CC=CC=C1)NCCCCl

pemoline: C1=CC=C(C=C1)C2C(=O)N=C(O2)N

phentermine: CC(C)(CC1=CC=CC=C1)N

pipradrol: C1CCNC(C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)O

serdexmethylphenidate: COC(=O)C(C1CCCCN1C(=O)OC[N+]2=CC=CC(=C2)C(=O)NC(CO)C(=O)[O-])C3=CC=CC=C3

sibutramine: CC(C)CC(C1(CCC1)C2=CC=C(C=C2)Cl)N(C)C

solriamfetol: C1=CC=C(C=C1)CC(COC(=O)N)N

spa((-)-1-dimethylamino-1,2-diphenylethane): CN(C)C(CC1=CC=CC=C1)C2=CC=CC=C2

pentazocine: CC1C2CC3=C(C1(CCN2CC=C(C)C)C)C=C(C=C3)O

butorphanol: C1CCC2(C3CC4=C(C2(C1)CCN3CC5CCC5)C=C(C=C4)O)O

Solution:

structure of schedule four molecules:

dextropropoxyphene: CCC(=O)OC(CC1=CC=CC=C1)(C2=CC=CC=C2)C(C)CN(C)C

2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol: CN(C)CC1CCCCC1(C2=CC(=CC=C2)OC)O

smiles_non_kekule:    COc1cccc(C2(O)CCCCC2CN(C)C)c1
smiles_kekule:    COC1=CC=CC(C2(O)CCCCC2CN(C)C)=C1
inchi:    InChI=1S/C16H25NO2/c1-17(2)12-14-7-4-5-10-16(14,18)13-8-6-9-15(11-13)19-3/h6,8-9,11,14,18H,4-5,7,10,12H2,1-3H3
inchiKey:    TVYLLZQTGLZFBW-UHFFFAOYSA-N
smarts:    [#6]-[#7](-[#6])-[#6]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1(-[#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1)-[#8]-[#6])-[#8]
smarts_isomeric:    [#6]-[#7](-[#6])-[#6]-[#6]1-[#6]-[#6]-[#6]-[#6]-[#6]-1(-[#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1)-[#8]-[#6])-[#8]

alfaxalone: CC(=O)C1CCC2C1(CC(=O)C3C2CCC4C3(CCC(C4)O)C)C

smiles_non_kekule:    CC(=O)C1CCC2C3CCC4CC(O)CCC4(C)C3C(=O)CC12C
smiles_kekule:    CC(=O)C1CCC2C3CCC4CC(O)CCC4(C)C3C(=O)CC12C
inchi:    InChI=1S/C21H32O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h13-17,19,23H,4-11H2,1-3H3
inchiKey:    DUHUCHOQIDJXAT-UHFFFAOYSA-N
smarts:    [#6]-[#6](=[#8])-[#6]1-[#6]-[#6]-[#6]2-[#6]-1(-[#6]-[#6](=[#8])-[#6]1-[#6]-2-[#6]-[#6]-[#6]2-[#6]-1(-[#6]-[#6]-[#6](-[#6]-2)-[#8])-[#6])-[#6]
smarts_isomeric:    [#6]-[#6](=[#8])-[#6]1-[#6]-[#6]-[#6]2-[#6]-1(-[#6]-[#6](=[#8])-[#6]1-[#6]-2-[#6]-[#6]-[#6]2-[#6]-1(-[#6]-[#6]-[#6](-[#6]-2)-[#8])-[#6])-[#6]

alprazolam: CC1=NN=C2N1C3=C(C=C(C=C3)Cl)C(=NC2)C4=CC=CC=C4

smiles_non_kekule:    Cc1nnc2n1-c1ccc(Cl)cc1C(c1ccccc1)=NC2
smiles_kekule:    CC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12
inchi:    InChI=1S/C17H13ClN4/c1-11-20-21-16-10-19-17(12-5-3-2-4-6-12)14-9-13(18)7-8-15(14)22(11)16/h2-9H,10H2,1H3
inchiKey:    VREFGVBLTWBCJP-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#7]:[#7]:[#6]2:[#7]:1-[#6]1:[#6](:[#6]:[#6](:[#6]:[#6]:1)-[#17])-[#6](=[#7]-[#6]-2)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]1:[#7]:[#7]:[#6]2:[#7]:1-[#6]1:[#6](:[#6]:[#6](:[#6]:[#6]:1)-[#17])-[#6](=[#7]-[#6]-2)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

barbital: CCC1(C(=O)NC(=O)NC1=O)CC

smiles_non_kekule:    CCC1(CC)C(=O)NC(=O)NC1=O
smiles_kekule:    CCC1(CC)C(=O)NC(=O)NC1=O
inchi:    InChI=1S/C8H12N2O3/c1-3-8(4-2)5(11)9-7(13)10-6(8)12/h3-4H2,1-2H3,(H2,9,10,11,12,13)
inchiKey:    FTOAOBMCPZCFFF-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]1(-[#6](=[#8])-[#7]-[#6](=[#8])-[#7]-[#6]-1=[#8])-[#6]-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]1(-[#6](=[#8])-[#7]-[#6](=[#8])-[#7]-[#6]-1=[#8])-[#6]-[#6]

brexanolone: CC(=O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C

smiles_non_kekule:    CC(=O)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C
smiles_kekule:    CC(=O)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C
inchi:    InChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3
inchiKey:    AURFZBICLPNKBZ-UHFFFAOYSA-N
smarts:    [#6]-[#6](=[#8])-[#6]1-[#6]-[#6]-[#6]2-[#6]-1(-[#6]-[#6]-[#6]1-[#6]-2-[#6]-[#6]-[#6]2-[#6]-1(-[#6]-[#6]-[#6](-[#6]-2)-[#8])-[#6])-[#6]
smarts_isomeric:    [#6]-[#6](=[#8])-[#6]1-[#6]-[#6]-[#6]2-[#6]-1(-[#6]-[#6]-[#6]1-[#6]-2-[#6]-[#6]-[#6]2-[#6]-1(-[#6]-[#6]-[#6](-[#6]-2)-[#8])-[#6])-[#6]

bromazepam: C1C(=O)NC2=C(C=C(C=C2)Br)C(=N1)C3=CC=CC=N3

smiles_non_kekule:    O=C1CN=C(c2ccccn2)c2cc(Br)ccc2N1
smiles_kekule:    O=C1CN=C(C2=CC=CC=N2)C2=C(C=CC(Br)=C2)N1
inchi:    InChI=1S/C14H10BrN3O/c15-9-4-5-11-10(7-9)14(17-8-13(19)18-11)12-3-1-2-6-16-12/h1-7H,8H2,(H,18,19)
inchiKey:    VMIYHDSEFNYJSL-UHFFFAOYSA-N
smarts:    [#6]1-[#6](=[#8])-[#7]-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#35])-[#6](=[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#7]:1
smarts_isomeric:    [#6]1-[#6](=[#8])-[#7]-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#35])-[#6](=[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#7]:1

camazepam: CN1C2=C(C=C(C=C2)Cl)C(=NC(C1=O)OC(=O)N(C)C)C3=CC=CC=C3

smiles_non_kekule:    CN(C)C(=O)OC1N=C(c2ccccc2)c2cc(Cl)ccc2N(C)C1=O
smiles_kekule:    CN(C)C(=O)OC1N=C(C2=CC=CC=C2)C2=C(C=CC(Cl)=C2)N(C)C1=O
inchi:    InChI=1S/C19H18ClN3O3/c1-22(2)19(25)26-17-18(24)23(3)15-10-9-13(20)11-14(15)16(21-17)12-7-5-4-6-8-12/h4-11,17H,1-3H3
inchiKey:    PXBVEXGRHZFEOF-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#6](=[#7]-[#6](-[#6]-1=[#8])-[#8]-[#6](=[#8])-[#7](-[#6])-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#7]1-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#6](=[#7]-[#6](-[#6]-1=[#8])-[#8]-[#6](=[#8])-[#7](-[#6])-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

carisoprodol: CCCC(C)(COC(=O)N)COC(=O)NC(C)C

smiles_non_kekule:    CCCC(C)(COC(N)=O)COC(=O)NC(C)C
smiles_kekule:    CCCC(C)(COC(N)=O)COC(=O)NC(C)C
inchi:    InChI=1S/C12H24N2O4/c1-5-6-12(4,7-17-10(13)15)8-18-11(16)14-9(2)3/h9H,5-8H2,1-4H3,(H2,13,15)(H,14,16)
inchiKey:    OFZCIYFFPZCNJE-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6](-[#6])(-[#6]-[#8]-[#6](=[#8])-[#7])-[#6]-[#8]-[#6](=[#8])-[#7]-[#6](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6](-[#6])(-[#6]-[#8]-[#6](=[#8])-[#7])-[#6]-[#8]-[#6](=[#8])-[#7]-[#6](-[#6])-[#6]

chloralbetaine: C[N+](C)(C)CC(=O)[O-].C(C(Cl)(Cl)Cl)(O)O

smiles_non_kekule:    C[N+](C)(C)CC(=O)[O-].OC(O)C(Cl)(Cl)Cl
smiles_kekule:    C[N+](C)(C)CC(=O)[O-].OC(O)C(Cl)(Cl)Cl
inchi:    InChI=1S/C5H11NO2.C2H3Cl3O2/c1-6(2,3)4-5(7)8;3-2(4,5)1(6)7/h4H2,1-3H3;1,6-7H
inchiKey:    ONAOIDNSINNZOA-UHFFFAOYSA-N
smarts:    [#6]-[#7+](-[#6])(-[#6])-[#6]-[#6](=[#8])-[#8-].[#6](-[#6](-[#17])(-[#17])-[#17])(-[#8])-[#8]
smarts_isomeric:    [#6]-[#7+](-[#6])(-[#6])-[#6]-[#6](=[#8])-[#8-].[#6](-[#6](-[#17])(-[#17])-[#17])(-[#8])-[#8]

chloralhydrate: C(C(Cl)(Cl)Cl)(O)O

smiles_non_kekule:    OC(O)C(Cl)(Cl)Cl
smiles_kekule:    OC(O)C(Cl)(Cl)Cl
inchi:    InChI=1S/C2H3Cl3O2/c3-2(4,5)1(6)7/h1,6-7H
inchiKey:    RNFNDJAIBTYOQL-UHFFFAOYSA-N
smarts:    [#6](-[#6](-[#17])(-[#17])-[#17])(-[#8])-[#8]
smarts_isomeric:    [#6](-[#6](-[#17])(-[#17])-[#17])(-[#8])-[#8]

chlordiazepoxide: CN=C1CN(C(=C2C=C(C=CC2=N1)Cl)C3=CC=CC=C3)O

smiles_non_kekule:    CN=C1CN(O)C(c2ccccc2)=c2cc(Cl)ccc2=N1
smiles_kekule:    CN=C1CN(O)C(C2=CC=CC=C2)=C2C=C(Cl)C=CC2=N1
inchi:    InChI=1S/C16H14ClN3O/c1-18-15-10-20(21)16(11-5-3-2-4-6-11)13-9-12(17)7-8-14(13)19-15/h2-9,21H,10H2,1H3
inchiKey:    BUCORZSTKDOEKQ-UHFFFAOYSA-N
smarts:    [#6]-[#7]=[#6]1-[#6]-[#7](-[#6](=[#6]2:[#6]:[#6](:[#6]:[#6]:[#6]:2=[#7]-1)-[#17])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8]
smarts_isomeric:    [#6]-[#7]=[#6]1-[#6]-[#7](-[#6](=[#6]2:[#6]:[#6](:[#6]:[#6]:[#6]:2=[#7]-1)-[#17])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8]

clobazam: CN1C(=O)CC(=O)N(C2=C1C=CC(=C2)Cl)C3=CC=CC=C3

smiles_non_kekule:    CN1C(=O)CC(=O)N(c2ccccc2)c2cc(Cl)ccc21
smiles_kekule:    CN1C(=O)CC(=O)N(C2=CC=CC=C2)C2=C1C=CC(Cl)=C2
inchi:    InChI=1S/C16H13ClN2O2/c1-18-13-8-7-11(17)9-14(13)19(16(21)10-15(18)20)12-5-3-2-4-6-12/h2-9H,10H2,1H3
inchiKey:    CXOXHMZGEKVPMT-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6](=[#8])-[#6]-[#6](=[#8])-[#7](-[#6]2:[#6]-1:[#6]:[#6]:[#6](:[#6]:2)-[#17])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#7]1-[#6](=[#8])-[#6]-[#6](=[#8])-[#7](-[#6]2:[#6]-1:[#6]:[#6]:[#6](:[#6]:2)-[#17])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

clonazepam: C1C(=O)NC2=C(C=C(C=C2)[N+](=O)[O-])C(=N1)C3=CC=CC=C3Cl

smiles_non_kekule:    O=C1CN=C(c2ccccc2Cl)c2cc([N+](=O)[O-])ccc2N1
smiles_kekule:    O=C1CN=C(C2=CC=CC=C2Cl)C2=C(C=CC([N+](=O)[O-])=C2)N1
inchi:    InChI=1S/C15H10ClN3O3/c16-12-4-2-1-3-10(12)15-11-7-9(19(21)22)5-6-13(11)18-14(20)8-17-15/h1-7H,8H2,(H,18,20)
inchiKey:    DGBIGWXXNGSACT-UHFFFAOYSA-N
smarts:    [#6]1-[#6](=[#8])-[#7]-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#7+](=[#8])-[#8-])-[#6](=[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17]
smarts_isomeric:    [#6]1-[#6](=[#8])-[#7]-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#7+](=[#8])-[#8-])-[#6](=[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17]

clorazepate: C1=CC=C(C=C1)C2=NC(C(=O)NC3=C2C=C(C=C3)Cl)C(=O)O

smiles_non_kekule:    O=C(O)C1N=C(c2ccccc2)c2cc(Cl)ccc2NC1=O
smiles_kekule:    O=C(O)C1N=C(C2=CC=CC=C2)C2=C(C=CC(Cl)=C2)NC1=O
inchi:    InChI=1S/C16H11ClN2O3/c17-10-6-7-12-11(8-10)13(9-4-2-1-3-5-9)19-14(16(21)22)15(20)18-12/h1-8,14H,(H,18,20)(H,21,22)
inchiKey:    XDDJGVMJFWAHJX-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]1=[#7]-[#6](-[#6](=[#8])-[#7]-[#6]2:[#6]-1:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#6](=[#8])-[#8]
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]1=[#7]-[#6](-[#6](=[#8])-[#7]-[#6]2:[#6]-1:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#6](=[#8])-[#8]

clotiazepam: CCC1=CC2=C(S1)N(C(=O)CN=C2C3=CC=CC=C3Cl)C

smiles_non_kekule:    CCc1cc2c(s1)N(C)C(=O)CN=C2c1ccccc1Cl
smiles_kekule:    CCC1=CC2=C(S1)N(C)C(=O)CN=C2C1=CC=CC=C1Cl
inchi:    InChI=1S/C16H15ClN2OS/c1-3-10-8-12-15(11-6-4-5-7-13(11)17)18-9-14(20)19(2)16(12)21-10/h4-8H,3,9H2,1-2H3
inchiKey:    CHBRHODLKOZEPZ-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]1:[#6]:[#6]2:[#6](:[#16]:1)-[#7](-[#6](=[#8])-[#6]-[#7]=[#6]-2-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17])-[#6]
smarts_isomeric:    [#6]-[#6]-[#6]1:[#6]:[#6]2:[#6](:[#16]:1)-[#7](-[#6](=[#8])-[#6]-[#7]=[#6]-2-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17])-[#6]

cloxazolam: C1COC2(N1CC(=O)NC3=C2C=C(C=C3)Cl)C4=CC=CC=C4Cl

smiles_non_kekule:    O=C1CN2CCOC2(c2ccccc2Cl)c2cc(Cl)ccc2N1
smiles_kekule:    O=C1CN2CCOC2(C2=CC=CC=C2Cl)C2=C(C=CC(Cl)=C2)N1
inchi:    InChI=1S/C17H14Cl2N2O2/c18-11-5-6-15-13(9-11)17(12-3-1-2-4-14(12)19)21(7-8-23-17)10-16(22)20-15/h1-6,9H,7-8,10H2,(H,20,22)
inchiKey:    ZIXNZOBDFKSQTC-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#8]-[#6]2(-[#7]-1-[#6]-[#6](=[#8])-[#7]-[#6]1:[#6]-2:[#6]:[#6](:[#6]:[#6]:1)-[#17])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17]
smarts_isomeric:    [#6]1-[#6]-[#8]-[#6]2(-[#7]-1-[#6]-[#6](=[#8])-[#7]-[#6]1:[#6]-2:[#6]:[#6](:[#6]:[#6]:1)-[#17])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17]

delorazepam: C1C(=O)NC2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CC=C3Cl

smiles_non_kekule:    O=C1CN=C(c2ccccc2Cl)c2cc(Cl)ccc2N1
smiles_kekule:    O=C1CN=C(C2=CC=CC=C2Cl)C2=C(C=CC(Cl)=C2)N1
inchi:    InChI=1S/C15H10Cl2N2O/c16-9-5-6-13-11(7-9)15(18-8-14(20)19-13)10-3-1-2-4-12(10)17/h1-7H,8H2,(H,19,20)
inchiKey:    CHIFCDOIPRCHCF-UHFFFAOYSA-N
smarts:    [#6]1-[#6](=[#8])-[#7]-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#6](=[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17]
smarts_isomeric:    [#6]1-[#6](=[#8])-[#7]-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#6](=[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17]

diazepam: CN1C(=O)CN=C(C2=C1C=CC(=C2)Cl)C3=CC=CC=C3

smiles_non_kekule:    CN1C(=O)CN=C(c2ccccc2)c2cc(Cl)ccc21
smiles_kekule:    CN1C(=O)CN=C(C2=CC=CC=C2)C2=C1C=CC(Cl)=C2
inchi:    InChI=1S/C16H13ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3
inchiKey:    AAOVKJBEBIDNHE-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6](=[#8])-[#6]-[#7]=[#6](-[#6]2:[#6]-1:[#6]:[#6]:[#6](:[#6]:2)-[#17])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#7]1-[#6](=[#8])-[#6]-[#7]=[#6](-[#6]2:[#6]-1:[#6]:[#6]:[#6](:[#6]:2)-[#17])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

dichloralphenazone: CC1=CC(=O)N(N1C)C2=CC=CC=C2.C(C(Cl)(Cl)Cl)(O)O.C(C(Cl)(Cl)Cl)(O)O

smiles_non_kekule:    Cc1cc(=O)n(-c2ccccc2)n1C.OC(O)C(Cl)(Cl)Cl.OC(O)C(Cl)(Cl)Cl
smiles_kekule:    CC1=CC(=O)N(C2=CC=CC=C2)N1C.OC(O)C(Cl)(Cl)Cl.OC(O)C(Cl)(Cl)Cl
inchi:    InChI=1S/C11H12N2O.2C2H3Cl3O2/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10;2*3-2(4,5)1(6)7/h3-8H,1-2H3;2*1,6-7H
inchiKey:    ATKXDQOHNICLQW-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6](=[#8]):[#7](:[#7]:1-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1.[#6](-[#6](-[#17])(-[#17])-[#17])(-[#8])-[#8].[#6](-[#6](-[#17])(-[#17])-[#17])(-[#8])-[#8]
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6](=[#8]):[#7](:[#7]:1-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1.[#6](-[#6](-[#17])(-[#17])-[#17])(-[#8])-[#8].[#6](-[#6](-[#17])(-[#17])-[#17])(-[#8])-[#8]

estazolam: C1C2=NN=CN2C3=C(C=C(C=C3)Cl)C(=N1)C4=CC=CC=C4

smiles_non_kekule:    Clc1ccc2c(c1)C(c1ccccc1)=NCc1nncn1-2
smiles_kekule:    ClC1=CC2=C(C=C1)N1C=NN=C1CN=C2C1=CC=CC=C1
inchi:    InChI=1S/C16H11ClN4/c17-12-6-7-14-13(8-12)16(11-4-2-1-3-5-11)18-9-15-20-19-10-21(14)15/h1-8,10H,9H2
inchiKey:    CDCHDCWJMGXXRH-UHFFFAOYSA-N
smarts:    [#6]1-[#6]2:[#7]:[#7]:[#6]:[#7]:2-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#6](=[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1-[#6]2:[#7]:[#7]:[#6]:[#7]:2-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#6](=[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

ethchlorvynol: CCC(C=CCl)(C#C)O

smiles_non_kekule:    C#CC(O)(C=CCl)CC
smiles_kekule:    C#CC(O)(C=CCl)CC
inchi:    InChI=1S/C7H9ClO/c1-3-7(9,4-2)5-6-8/h1,5-6,9H,4H2,2H3
inchiKey:    ZEHYJZXQEQOSON-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](-[#6]=[#6]-[#17])(-[#6]#[#6])-[#8]
smarts_isomeric:    [#6]-[#6]-[#6](-[#6]=[#6]-[#17])(-[#6]#[#6])-[#8]

ethinamate: O=C(OC1(C#C)CCCCC1)N

smiles_non_kekule:    C#CC1(OC(N)=O)CCCCC1
smiles_kekule:    C#CC1(OC(N)=O)CCCCC1
inchi:    InChI=1S/C9H13NO2/c1-2-9(12-8(10)11)6-4-3-5-7-9/h1H,3-7H2,(H2,10,11)
inchiKey:    GXRZIMHKGDIBEW-UHFFFAOYSA-N
smarts:    [#8]=[#6](-[#8]-[#6]1(-[#6]#[#6])-[#6]-[#6]-[#6]-[#6]-[#6]-1)-[#7]
smarts_isomeric:    [#8]=[#6](-[#8]-[#6]1(-[#6]#[#6])-[#6]-[#6]-[#6]-[#6]-[#6]-1)-[#7]

ethyl loflazepate: CCOC(=O)C1C(=O)NC2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CC=C3F

smiles_non_kekule:    CCOC(=O)C1N=C(c2ccccc2F)c2cc(Cl)ccc2NC1=O
smiles_kekule:    CCOC(=O)C1N=C(C2=CC=CC=C2F)C2=C(C=CC(Cl)=C2)NC1=O
inchi:    InChI=1S/C18H14ClFN2O3/c1-2-25-18(24)16-17(23)21-14-8-7-10(19)9-12(14)15(22-16)11-5-3-4-6-13(11)20/h3-9,16H,2H2,1H3,(H,21,23)
inchiKey:    CUCHJCMWNFEYOM-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1-[#6](=[#8])-[#7]-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#6](=[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9]
smarts_isomeric:    [#6]-[#6]-[#8]-[#6](=[#8])-[#6]1-[#6](=[#8])-[#7]-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#6](=[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9]

fludiazepam: CN1C(=O)CN=C(C2=C1C=CC(=C2)Cl)C3=CC=CC=C3F

smiles_non_kekule:    CN1C(=O)CN=C(c2ccccc2F)c2cc(Cl)ccc21
smiles_kekule:    CN1C(=O)CN=C(C2=CC=CC=C2F)C2=C1C=CC(Cl)=C2
inchi:    InChI=1S/C16H12ClFN2O/c1-20-14-7-6-10(17)8-12(14)16(19-9-15(20)21)11-4-2-3-5-13(11)18/h2-8H,9H2,1H3
inchiKey:    ROYOYTLGDLIGBX-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6](=[#8])-[#6]-[#7]=[#6](-[#6]2:[#6]-1:[#6]:[#6]:[#6](:[#6]:2)-[#17])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9]
smarts_isomeric:    [#6]-[#7]1-[#6](=[#8])-[#6]-[#7]=[#6](-[#6]2:[#6]-1:[#6]:[#6]:[#6](:[#6]:2)-[#17])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9]

flunitrazepam: CN1C(=O)CN=C(C2=C1C=CC(=C2)[N+](=O)[O-])C3=CC=CC=C3F

smiles_non_kekule:    CN1C(=O)CN=C(c2ccccc2F)c2cc([N+](=O)[O-])ccc21
smiles_kekule:    CN1C(=O)CN=C(C2=CC=CC=C2F)C2=C1C=CC([N+](=O)[O-])=C2
inchi:    InChI=1S/C16H12FN3O3/c1-19-14-7-6-10(20(22)23)8-12(14)16(18-9-15(19)21)11-4-2-3-5-13(11)17/h2-8H,9H2,1H3
inchiKey:    PPTYJKAXVCCBDU-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6](=[#8])-[#6]-[#7]=[#6](-[#6]2:[#6]-1:[#6]:[#6]:[#6](:[#6]:2)-[#7+](=[#8])-[#8-])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9]
smarts_isomeric:    [#6]-[#7]1-[#6](=[#8])-[#6]-[#7]=[#6](-[#6]2:[#6]-1:[#6]:[#6]:[#6](:[#6]:2)-[#7+](=[#8])-[#8-])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9]

flurazepam: CCN(CC)CCN1C(=O)CN=C(C2=C1C=CC(=C2)Cl)C3=CC=CC=C3F

smiles_non_kekule:    CCN(CC)CCN1C(=O)CN=C(c2ccccc2F)c2cc(Cl)ccc21
smiles_kekule:    CCN(CC)CCN1C(=O)CN=C(C2=CC=CC=C2F)C2=C1C=CC(Cl)=C2
inchi:    InChI=1S/C21H23ClFN3O/c1-3-25(4-2)11-12-26-19-10-9-15(22)13-17(19)21(24-14-20(26)27)16-7-5-6-8-18(16)23/h5-10,13H,3-4,11-12,14H2,1-2H3
inchiKey:    SAADBVWGJQAEFS-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7](-[#6]-[#6])-[#6]-[#6]-[#7]1-[#6](=[#8])-[#6]-[#7]=[#6](-[#6]2:[#6]-1:[#6]:[#6]:[#6](:[#6]:2)-[#17])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9]
smarts_isomeric:    [#6]-[#6]-[#7](-[#6]-[#6])-[#6]-[#6]-[#7]1-[#6](=[#8])-[#6]-[#7]=[#6](-[#6]2:[#6]-1:[#6]:[#6]:[#6](:[#6]:2)-[#17])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9]

fospropofol: CC(C)C1=C(C(=CC=C1)C(C)C)OCOP(=O)(O)O

smiles_non_kekule:    CC(C)c1cccc(C(C)C)c1OCOP(=O)(O)O
smiles_kekule:    CC(C)C1=C(OCOP(=O)(O)O)C(C(C)C)=CC=C1
inchi:    InChI=1S/C13H21O5P/c1-9(2)11-6-5-7-12(10(3)4)13(11)17-8-18-19(14,15)16/h5-7,9-10H,8H2,1-4H3,(H2,14,15,16)
inchiKey:    QVNNONOFASOXQV-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])-[#6]1:[#6](:[#6](:[#6]:[#6]:[#6]:1)-[#6](-[#6])-[#6])-[#8]-[#6]-[#8]-[#15](=[#8])(-[#8])-[#8]
smarts_isomeric:    [#6]-[#6](-[#6])-[#6]1:[#6](:[#6](:[#6]:[#6]:[#6]:1)-[#6](-[#6])-[#6])-[#8]-[#6]-[#8]-[#15](=[#8])(-[#8])-[#8]

halazepam: C1C(=O)N(C2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CC=C3)CC(F)(F)F

smiles_non_kekule:    O=C1CN=C(c2ccccc2)c2cc(Cl)ccc2N1CC(F)(F)F
smiles_kekule:    O=C1CN=C(C2=CC=CC=C2)C2=C(C=CC(Cl)=C2)N1CC(F)(F)F
inchi:    InChI=1S/C17H12ClF3N2O/c18-12-6-7-14-13(8-12)16(11-4-2-1-3-5-11)22-9-15(24)23(14)10-17(19,20)21/h1-8H,9-10H2
inchiKey:    WYCLKVQLVUQKNZ-UHFFFAOYSA-N
smarts:    [#6]1-[#6](=[#8])-[#7](-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#6](=[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]-[#6](-[#9])(-[#9])-[#9]
smarts_isomeric:    [#6]1-[#6](=[#8])-[#7](-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#6](=[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]-[#6](-[#9])(-[#9])-[#9]

haloxazolam: C1COC2(N1CC(=O)NC3=C2C=C(C=C3)Br)C4=CC=CC=C4F

smiles_non_kekule:    O=C1CN2CCOC2(c2ccccc2F)c2cc(Br)ccc2N1
smiles_kekule:    O=C1CN2CCOC2(C2=CC=CC=C2F)C2=C(C=CC(Br)=C2)N1
inchi:    InChI=1S/C17H14BrFN2O2/c18-11-5-6-15-13(9-11)17(12-3-1-2-4-14(12)19)21(7-8-23-17)10-16(22)20-15/h1-6,9H,7-8,10H2,(H,20,22)
inchiKey:    XDKCGKQHVBOOHC-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#8]-[#6]2(-[#7]-1-[#6]-[#6](=[#8])-[#7]-[#6]1:[#6]-2:[#6]:[#6](:[#6]:[#6]:1)-[#35])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9]
smarts_isomeric:    [#6]1-[#6]-[#8]-[#6]2(-[#7]-1-[#6]-[#6](=[#8])-[#7]-[#6]1:[#6]-2:[#6]:[#6](:[#6]:[#6]:1)-[#35])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9]

ketazolam: CC1=CC(=O)N2CC(=O)N(C3=C(C2(O1)C4=CC=CC=C4)C=C(C=C3)Cl)C

smiles_non_kekule:    CC1=CC(=O)N2CC(=O)N(C)c3ccc(Cl)cc3C2(c2ccccc2)O1
smiles_kekule:    CC1=CC(=O)N2CC(=O)N(C)C3=C(C=C(Cl)C=C3)C2(C2=CC=CC=C2)O1
inchi:    InChI=1S/C20H17ClN2O3/c1-13-10-18(24)23-12-19(25)22(2)17-9-8-15(21)11-16(17)20(23,26-13)14-6-4-3-5-7-14/h3-11H,12H2,1-2H3
inchiKey:    PWAJCNITSBZRBL-UHFFFAOYSA-N
smarts:    [#6]-[#6]1=[#6]-[#6](=[#8])-[#7]2-[#6]-[#6](=[#8])-[#7](-[#6]3:[#6](-[#6]-2(-[#8]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1):[#6]:[#6](:[#6]:[#6]:3)-[#17])-[#6]
smarts_isomeric:    [#6]-[#6]1=[#6]-[#6](=[#8])-[#7]2-[#6]-[#6](=[#8])-[#7](-[#6]3:[#6](-[#6]-2(-[#8]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1):[#6]:[#6](:[#6]:[#6]:3)-[#17])-[#6]

lemborexant: CC1=NC(=NC=C1OCC2(CC2C(=O)NC3=NC=C(C=C3)F)C4=CC(=CC=C4)F)C

smiles_non_kekule:    Cc1ncc(OCC2(c3cccc(F)c3)CC2C(=O)Nc2ccc(F)cn2)c(C)n1
smiles_kekule:    CC1=NC=C(OCC2(C3=CC(F)=CC=C3)CC2C(=O)NC2=NC=C(F)C=C2)C(C)=N1
inchi:    InChI=1S/C22H20F2N4O2/c1-13-19(11-25-14(2)27-13)30-12-22(15-4-3-5-16(23)8-15)9-18(22)21(29)28-20-7-6-17(24)10-26-20/h3-8,10-11,18H,9,12H2,1-2H3,(H,26,28,29)
inchiKey:    MUGXRYIUWFITCP-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#7]:[#6](:[#7]:[#6]:[#6]:1-[#8]-[#6]-[#6]1(-[#6]-[#6]-1-[#6](=[#8])-[#7]-[#6]1:[#7]:[#6]:[#6](:[#6]:[#6]:1)-[#9])-[#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1)-[#9])-[#6]
smarts_isomeric:    [#6]-[#6]1:[#7]:[#6](:[#7]:[#6]:[#6]:1-[#8]-[#6]-[#6]1(-[#6]-[#6]-1-[#6](=[#8])-[#7]-[#6]1:[#7]:[#6]:[#6](:[#6]:[#6]:1)-[#9])-[#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1)-[#9])-[#6]

loprazolam: CN1CCN(CC1)C=C2C(=O)N3C(=N2)CN=C(C4=C3C=CC(=C4)[N+](=O)[O-])C5=CC=CC=C5Cl

smiles_non_kekule:    CN1CCN(C=C2N=C3CN=C(c4ccccc4Cl)c4cc([N+](=O)[O-])ccc4N3C2=O)CC1
smiles_kekule:    CN1CCN(C=C2N=C3CN=C(C4=CC=CC=C4Cl)C4=C(C=CC([N+](=O)[O-])=C4)N3C2=O)CC1
inchi:    InChI=1S/C23H21ClN6O3/c1-27-8-10-28(11-9-27)14-19-23(31)29-20-7-6-15(30(32)33)12-17(20)22(25-13-21(29)26-19)16-4-2-3-5-18(16)24/h2-7,12,14H,8-11,13H2,1H3
inchiKey:    UTEFBSAVJNEPTR-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]=[#6]1-[#6](=[#8])-[#7]2-[#6](=[#7]-1)-[#6]-[#7]=[#6](-[#6]1:[#6]-2:[#6]:[#6]:[#6](:[#6]:1)-[#7+](=[#8])-[#8-])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17]
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6]=[#6]1-[#6](=[#8])-[#7]2-[#6](=[#7]-1)-[#6]-[#7]=[#6](-[#6]1:[#6]-2:[#6]:[#6]:[#6](:[#6]:1)-[#7+](=[#8])-[#8-])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17]

lorazepam: C1=CC=C(C(=C1)C2=NC(C(=O)NC3=C2C=C(C=C3)Cl)O)Cl

smiles_non_kekule:    O=C1Nc2ccc(Cl)cc2C(c2ccccc2Cl)=NC1O
smiles_kekule:    O=C1NC2=C(C=C(Cl)C=C2)C(C2=CC=CC=C2Cl)=NC1O
inchi:    InChI=1S/C15H10Cl2N2O2/c16-8-5-6-12-10(7-8)13(19-15(21)14(20)18-12)9-3-1-2-4-11(9)17/h1-7,15,21H,(H,18,20)
inchiKey:    DIWRORZWFLOCLC-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](:[#6](:[#6]:1)-[#6]1=[#7]-[#6](-[#6](=[#8])-[#7]-[#6]2:[#6]-1:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#8])-[#17]
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](:[#6](:[#6]:1)-[#6]1=[#7]-[#6](-[#6](=[#8])-[#7]-[#6]2:[#6]-1:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#8])-[#17]

lormetazepam: CN1C2=C(C=C(C=C2)Cl)C(=NC(C1=O)O)C3=CC=CC=C3Cl

smiles_non_kekule:    CN1C(=O)C(O)N=C(c2ccccc2Cl)c2cc(Cl)ccc21
smiles_kekule:    CN1C(=O)C(O)N=C(C2=CC=CC=C2Cl)C2=C1C=CC(Cl)=C2
inchi:    InChI=1S/C16H12Cl2N2O2/c1-20-13-7-6-9(17)8-11(13)14(19-15(21)16(20)22)10-4-2-3-5-12(10)18/h2-8,15,21H,1H3
inchiKey:    FJIKWRGCXUCUIG-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#6](=[#7]-[#6](-[#6]-1=[#8])-[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17]
smarts_isomeric:    [#6]-[#7]1-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#6](=[#7]-[#6](-[#6]-1=[#8])-[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17]

mebutamate: CCC(C)C(C)(COC(=O)N)COC(=O)N

smiles_non_kekule:    CCC(C)C(C)(COC(N)=O)COC(N)=O
smiles_kekule:    CCC(C)C(C)(COC(N)=O)COC(N)=O
inchi:    InChI=1S/C10H20N2O4/c1-4-7(2)10(3,5-15-8(11)13)6-16-9(12)14/h7H,4-6H2,1-3H3,(H2,11,13)(H2,12,14)
inchiKey:    LEROTMJVBFSIMP-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6](-[#6])-[#6](-[#6])(-[#6]-[#8]-[#6](=[#8])-[#7])-[#6]-[#8]-[#6](=[#8])-[#7]
smarts_isomeric:    [#6]-[#6]-[#6](-[#6])-[#6](-[#6])(-[#6]-[#8]-[#6](=[#8])-[#7])-[#6]-[#8]-[#6](=[#8])-[#7]

medazepam: CN1CCN=C(C2=C1C=CC(=C2)Cl)C3=CC=CC=C3

smiles_non_kekule:    CN1CCN=C(c2ccccc2)c2cc(Cl)ccc21
smiles_kekule:    CN1CCN=C(C2=CC=CC=C2)C2=C1C=CC(Cl)=C2
inchi:    InChI=1S/C16H15ClN2/c1-19-10-9-18-16(12-5-3-2-4-6-12)14-11-13(17)7-8-15(14)19/h2-8,11H,9-10H2,1H3
inchiKey:    YLCXGBZIZBEVPZ-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#7]=[#6](-[#6]2:[#6]-1:[#6]:[#6]:[#6](:[#6]:2)-[#17])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#7]=[#6](-[#6]2:[#6]-1:[#6]:[#6]:[#6](:[#6]:2)-[#17])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

meprobamate: CCCC(C)(COC(=O)N)COC(=O)N

smiles_non_kekule:    CCCC(C)(COC(N)=O)COC(N)=O
smiles_kekule:    CCCC(C)(COC(N)=O)COC(N)=O
inchi:    InChI=1S/C9H18N2O4/c1-3-4-9(2,5-14-7(10)12)6-15-8(11)13/h3-6H2,1-2H3,(H2,10,12)(H2,11,13)
inchiKey:    NPPQSCRMBWNHMW-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]-[#6](-[#6])(-[#6]-[#8]-[#6](=[#8])-[#7])-[#6]-[#8]-[#6](=[#8])-[#7]
smarts_isomeric:    [#6]-[#6]-[#6]-[#6](-[#6])(-[#6]-[#8]-[#6](=[#8])-[#7])-[#6]-[#8]-[#6](=[#8])-[#7]

methohexital: CCC#CC(C)C1(C(=O)NC(=O)N(C1=O)C)CC=C

smiles_non_kekule:    C=CCC1(C(C)C#CCC)C(=O)NC(=O)N(C)C1=O
smiles_kekule:    C=CCC1(C(C)C#CCC)C(=O)NC(=O)N(C)C1=O
inchi:    InChI=1S/C14H18N2O3/c1-5-7-8-10(3)14(9-6-2)11(17)15-13(19)16(4)12(14)18/h6,10H,2,5,9H2,1,3-4H3,(H,15,17,19)
inchiKey:    NZXKDOXHBHYTKP-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]#[#6]-[#6](-[#6])-[#6]1(-[#6](=[#8])-[#7]-[#6](=[#8])-[#7](-[#6]-1=[#8])-[#6])-[#6]-[#6]=[#6]
smarts_isomeric:    [#6]-[#6]-[#6]#[#6]-[#6](-[#6])-[#6]1(-[#6](=[#8])-[#7]-[#6](=[#8])-[#7](-[#6]-1=[#8])-[#6])-[#6]-[#6]=[#6]

methylphenobarbital: CCC1(C(=O)NC(=O)N(C1=O)C)C2=CC=CC=C2

smiles_non_kekule:    CCC1(c2ccccc2)C(=O)NC(=O)N(C)C1=O
smiles_kekule:    CCC1(C2=CC=CC=C2)C(=O)NC(=O)N(C)C1=O
inchi:    InChI=1S/C13H14N2O3/c1-3-13(9-7-5-4-6-8-9)10(16)14-12(18)15(2)11(13)17/h4-8H,3H2,1-2H3,(H,14,16,18)
inchiKey:    ALARQZQTBTVLJV-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]1(-[#6](=[#8])-[#7]-[#6](=[#8])-[#7](-[#6]-1=[#8])-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6]1(-[#6](=[#8])-[#7]-[#6](=[#8])-[#7](-[#6]-1=[#8])-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

midazolam: CC1=NC=C2N1C3=C(C=C(C=C3)Cl)C(=NC2)C4=CC=CC=C4F

smiles_non_kekule:    Cc1ncc2n1-c1ccc(Cl)cc1C(c1ccccc1F)=NC2
smiles_kekule:    CC1=NC=C2CN=C(C3=CC=CC=C3F)C3=C(C=CC(Cl)=C3)N21
inchi:    InChI=1S/C18H13ClFN3/c1-11-21-9-13-10-22-18(14-4-2-3-5-16(14)20)15-8-12(19)6-7-17(15)23(11)13/h2-9H,10H2,1H3
inchiKey:    DDLIGBOFAVUZHB-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#7]:[#6]:[#6]2:[#7]:1-[#6]1:[#6](:[#6]:[#6](:[#6]:[#6]:1)-[#17])-[#6](=[#7]-[#6]-2)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9]
smarts_isomeric:    [#6]-[#6]1:[#7]:[#6]:[#6]2:[#7]:1-[#6]1:[#6](:[#6]:[#6](:[#6]:[#6]:1)-[#17])-[#6](=[#7]-[#6]-2)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9]

nimetazepam: CN1C(=O)CN=C(C2=C1C=CC(=C2)[N+](=O)[O-])C3=CC=CC=C3

smiles_non_kekule:    CN1C(=O)CN=C(c2ccccc2)c2cc([N+](=O)[O-])ccc21
smiles_kekule:    CN1C(=O)CN=C(C2=CC=CC=C2)C2=C1C=CC([N+](=O)[O-])=C2
inchi:    InChI=1S/C16H13N3O3/c1-18-14-8-7-12(19(21)22)9-13(14)16(17-10-15(18)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3
inchiKey:    GWUSZQUVEVMBPI-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6](=[#8])-[#6]-[#7]=[#6](-[#6]2:[#6]-1:[#6]:[#6]:[#6](:[#6]:2)-[#7+](=[#8])-[#8-])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#7]1-[#6](=[#8])-[#6]-[#7]=[#6](-[#6]2:[#6]-1:[#6]:[#6]:[#6](:[#6]:2)-[#7+](=[#8])-[#8-])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

nitrazepam: C1C(=O)NC2=C(C=C(C=C2)[N+](=O)[O-])C(=N1)C3=CC=CC=C3

smiles_non_kekule:    O=C1CN=C(c2ccccc2)c2cc([N+](=O)[O-])ccc2N1
smiles_kekule:    O=C1CN=C(C2=CC=CC=C2)C2=C(C=CC([N+](=O)[O-])=C2)N1
inchi:    InChI=1S/C15H11N3O3/c19-14-9-16-15(10-4-2-1-3-5-10)12-8-11(18(20)21)6-7-13(12)17-14/h1-8H,9H2,(H,17,19)
inchiKey:    KJONHKAYOJNZEC-UHFFFAOYSA-N
smarts:    [#6]1-[#6](=[#8])-[#7]-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#7+](=[#8])-[#8-])-[#6](=[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1-[#6](=[#8])-[#7]-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#7+](=[#8])-[#8-])-[#6](=[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

nordiazepam: C1C(=O)NC2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CC=C3

smiles_non_kekule:    O=C1CN=C(c2ccccc2)c2cc(Cl)ccc2N1
smiles_kekule:    O=C1CN=C(C2=CC=CC=C2)C2=C(C=CC(Cl)=C2)N1
inchi:    InChI=1S/C15H11ClN2O/c16-11-6-7-13-12(8-11)15(17-9-14(19)18-13)10-4-2-1-3-5-10/h1-8H,9H2,(H,18,19)
inchiKey:    AKPLHCDWDRPJGD-UHFFFAOYSA-N
smarts:    [#6]1-[#6](=[#8])-[#7]-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#6](=[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1-[#6](=[#8])-[#7]-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#6](=[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

oxazepam: C1=CC=C(C=C1)C2=NC(C(=O)NC3=C2C=C(C=C3)Cl)O

smiles_non_kekule:    O=C1Nc2ccc(Cl)cc2C(c2ccccc2)=NC1O
smiles_kekule:    O=C1NC2=C(C=C(Cl)C=C2)C(C2=CC=CC=C2)=NC1O
inchi:    InChI=1S/C15H11ClN2O2/c16-10-6-7-12-11(8-10)13(9-4-2-1-3-5-9)18-15(20)14(19)17-12/h1-8,15,20H,(H,17,19)
inchiKey:    ADIMAYPTOBDMTL-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]1=[#7]-[#6](-[#6](=[#8])-[#7]-[#6]2:[#6]-1:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#8]
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]1=[#7]-[#6](-[#6](=[#8])-[#7]-[#6]2:[#6]-1:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#8]

oxazolam: CC1CN2CC(=O)NC3=C(C2(O1)C4=CC=CC=C4)C=C(C=C3)Cl

smiles_non_kekule:    CC1CN2CC(=O)Nc3ccc(Cl)cc3C2(c2ccccc2)O1
smiles_kekule:    CC1CN2CC(=O)NC3=C(C=C(Cl)C=C3)C2(C2=CC=CC=C2)O1
inchi:    InChI=1S/C18H17ClN2O2/c1-12-10-21-11-17(22)20-16-8-7-14(19)9-15(16)18(21,23-12)13-5-3-2-4-6-13/h2-9,12H,10-11H2,1H3,(H,20,22)
inchiKey:    VCCZBYPHZRWKFY-UHFFFAOYSA-N
smarts:    [#6]-[#6]1-[#6]-[#7]2-[#6]-[#6](=[#8])-[#7]-[#6]3:[#6](-[#6]-2(-[#8]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1):[#6]:[#6](:[#6]:[#6]:3)-[#17]
smarts_isomeric:    [#6]-[#6]1-[#6]-[#7]2-[#6]-[#6](=[#8])-[#7]-[#6]3:[#6](-[#6]-2(-[#8]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1):[#6]:[#6](:[#6]:[#6]:3)-[#17]

paraldehyde: CC1OC(OC(O1)C)C

smiles_non_kekule:    CC1OC(C)OC(C)O1
smiles_kekule:    CC1OC(C)OC(C)O1
inchi:    InChI=1S/C6H12O3/c1-4-7-5(2)9-6(3)8-4/h4-6H,1-3H3
inchiKey:    SQYNKIJPMDEDEG-UHFFFAOYSA-N
smarts:    [#6]-[#6]1-[#8]-[#6](-[#8]-[#6](-[#8]-1)-[#6])-[#6]
smarts_isomeric:    [#6]-[#6]1-[#8]-[#6](-[#8]-[#6](-[#8]-1)-[#6])-[#6]

petrichloral: C(C(COC(C(Cl)(Cl)Cl)O)(COC(C(Cl)(Cl)Cl)O)COC(C(Cl)(Cl)Cl)O)OC(C(Cl)(Cl)Cl)O

smiles_non_kekule:    OC(OCC(COC(O)C(Cl)(Cl)Cl)(COC(O)C(Cl)(Cl)Cl)COC(O)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl
smiles_kekule:    OC(OCC(COC(O)C(Cl)(Cl)Cl)(COC(O)C(Cl)(Cl)Cl)COC(O)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl
inchi:    InChI=1S/C13H16Cl12O8/c14-10(15,16)5(26)30-1-9(2-31-6(27)11(17,18)19,3-32-7(28)12(20,21)22)4-33-8(29)13(23,24)25/h5-8,26-29H,1-4H2
inchiKey:    OKACKALPXHBEMA-UHFFFAOYSA-N
smarts:    [#6](-[#6](-[#6]-[#8]-[#6](-[#6](-[#17])(-[#17])-[#17])-[#8])(-[#6]-[#8]-[#6](-[#6](-[#17])(-[#17])-[#17])-[#8])-[#6]-[#8]-[#6](-[#6](-[#17])(-[#17])-[#17])-[#8])-[#8]-[#6](-[#6](-[#17])(-[#17])-[#17])-[#8]
smarts_isomeric:    [#6](-[#6](-[#6]-[#8]-[#6](-[#6](-[#17])(-[#17])-[#17])-[#8])(-[#6]-[#8]-[#6](-[#6](-[#17])(-[#17])-[#17])-[#8])-[#6]-[#8]-[#6](-[#6](-[#17])(-[#17])-[#17])-[#8])-[#8]-[#6](-[#6](-[#17])(-[#17])-[#17])-[#8]

phenobarbital: CCC1(C(=O)NC(=O)NC1=O)C2=CC=CC=C2

smiles_non_kekule:    CCC1(c2ccccc2)C(=O)NC(=O)NC1=O
smiles_kekule:    CCC1(C2=CC=CC=C2)C(=O)NC(=O)NC1=O
inchi:    InChI=1S/C12H12N2O3/c1-2-12(8-6-4-3-5-7-8)9(15)13-11(17)14-10(12)16/h3-7H,2H2,1H3,(H2,13,14,15,16,17)
inchiKey:    DDBREPKUVSBGFI-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#6]1(-[#6](=[#8])-[#7]-[#6](=[#8])-[#7]-[#6]-1=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#6]1(-[#6](=[#8])-[#7]-[#6](=[#8])-[#7]-[#6]-1=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

pinazepam: C#CCN1C(=O)CN=C(C2=C1C=CC(=C2)Cl)C3=CC=CC=C3

smiles_non_kekule:    C#CCN1C(=O)CN=C(c2ccccc2)c2cc(Cl)ccc21
smiles_kekule:    C#CCN1C(=O)CN=C(C2=CC=CC=C2)C2=C1C=CC(Cl)=C2
inchi:    InChI=1S/C18H13ClN2O/c1-2-10-21-16-9-8-14(19)11-15(16)18(20-12-17(21)22)13-6-4-3-5-7-13/h1,3-9,11H,10,12H2
inchiKey:    MFZOSKPPVCIFMT-UHFFFAOYSA-N
smarts:    [#6]#[#6]-[#6]-[#7]1-[#6](=[#8])-[#6]-[#7]=[#6](-[#6]2:[#6]-1:[#6]:[#6]:[#6](:[#6]:2)-[#17])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]#[#6]-[#6]-[#7]1-[#6](=[#8])-[#6]-[#7]=[#6](-[#6]2:[#6]-1:[#6]:[#6]:[#6](:[#6]:2)-[#17])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

prazepam: C1CC1CN2C(=O)CN=C(C3=C2C=CC(=C3)Cl)C4=CC=CC=C4

smiles_non_kekule:    O=C1CN=C(c2ccccc2)c2cc(Cl)ccc2N1CC1CC1
smiles_kekule:    O=C1CN=C(C2=CC=CC=C2)C2=C(C=CC(Cl)=C2)N1CC1CC1
inchi:    InChI=1S/C19H17ClN2O/c20-15-8-9-17-16(10-15)19(14-4-2-1-3-5-14)21-11-18(23)22(17)12-13-6-7-13/h1-5,8-10,13H,6-7,11-12H2
inchiKey:    MWQCHHACWWAQLJ-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-1-[#6]-[#7]1-[#6](=[#8])-[#6]-[#7]=[#6](-[#6]2:[#6]-1:[#6]:[#6]:[#6](:[#6]:2)-[#17])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]1-[#6]-[#6]-1-[#6]-[#7]1-[#6](=[#8])-[#6]-[#7]=[#6](-[#6]2:[#6]-1:[#6]:[#6]:[#6](:[#6]:2)-[#17])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

quazepam: C1C(=S)N(C2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CC=C3F)CC(F)(F)F

smiles_non_kekule:    Fc1ccccc1C1=NCC(=S)N(CC(F)(F)F)c2ccc(Cl)cc21
smiles_kekule:    FC1=CC=CC=C1C1=NCC(=S)N(CC(F)(F)F)C2=C1C=C(Cl)C=C2
inchi:    InChI=1S/C17H11ClF4N2S/c18-10-5-6-14-12(7-10)16(11-3-1-2-4-13(11)19)23-8-15(25)24(14)9-17(20,21)22/h1-7H,8-9H2
inchiKey:    IKMPWMZBZSAONZ-UHFFFAOYSA-N
smarts:    [#6]1-[#6](=[#16])-[#7](-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#6](=[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9])-[#6]-[#6](-[#9])(-[#9])-[#9]
smarts_isomeric:    [#6]1-[#6](=[#16])-[#7](-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#6](=[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#9])-[#6]-[#6](-[#9])(-[#9])-[#9]

remimazolam: CC1=CN=C2N1C3=C(C=C(C=C3)Br)C(=NC2CCC(=O)OC)C4=CC=CC=N4

smiles_non_kekule:    COC(=O)CCC1N=C(c2ccccn2)c2cc(Br)ccc2-n2c(C)cnc21
smiles_kekule:    COC(=O)CCC1N=C(C2=CC=CC=N2)C2=C(C=CC(Br)=C2)N2C(C)=CN=C12
inchi:    InChI=1S/C21H19BrN4O2/c1-13-12-24-21-17(7-9-19(27)28-2)25-20(16-5-3-4-10-23-16)15-11-14(22)6-8-18(15)26(13)21/h3-6,8,10-12,17H,7,9H2,1-2H3
inchiKey:    CYHWMBVXXDIZNZ-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#7]:[#6]2:[#7]:1-[#6]1:[#6](:[#6]:[#6](:[#6]:[#6]:1)-[#35])-[#6](=[#7]-[#6]-2-[#6]-[#6]-[#6](=[#8])-[#8]-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#7]:1
smarts_isomeric:    [#6]-[#6]1:[#6]:[#7]:[#6]2:[#7]:1-[#6]1:[#6](:[#6]:[#6](:[#6]:[#6]:1)-[#35])-[#6](=[#7]-[#6]-2-[#6]-[#6]-[#6](=[#8])-[#8]-[#6])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#7]:1

suvorexant: CC1CCN(CCN1C(=O)C2=C(C=CC(=C2)C)N3N=CC=N3)C4=NC5=C(O4)C=CC(=C5)Cl

smiles_non_kekule:    Cc1ccc(-n2nccn2)c(C(=O)N2CCN(c3nc4cc(Cl)ccc4o3)CCC2C)c1
smiles_kekule:    CC1=CC=C(N2N=CC=N2)C(C(=O)N2CCN(C3=NC4=C(C=CC(Cl)=C4)O3)CCC2C)=C1
inchi:    InChI=1S/C23H23ClN6O2/c1-15-3-5-20(30-25-8-9-26-30)18(13-15)22(31)29-12-11-28(10-7-16(29)2)23-27-19-14-17(24)4-6-21(19)32-23/h3-6,8-9,13-14,16H,7,10-12H2,1-2H3
inchiKey:    JYTNQNCOQXFQPK-UHFFFAOYSA-N
smarts:    [#6]-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#7]-1-[#6](=[#8])-[#6]1:[#6](:[#6]:[#6]:[#6](:[#6]:1)-[#6])-[#7]1:[#7]:[#6]:[#6]:[#7]:1)-[#6]1:[#7]:[#6]2:[#6](:[#8]:1):[#6]:[#6]:[#6](:[#6]:2)-[#17]
smarts_isomeric:    [#6]-[#6]1-[#6]-[#6]-[#7](-[#6]-[#6]-[#7]-1-[#6](=[#8])-[#6]1:[#6](:[#6]:[#6]:[#6](:[#6]:1)-[#6])-[#7]1:[#7]:[#6]:[#6]:[#7]:1)-[#6]1:[#7]:[#6]2:[#6](:[#8]:1):[#6]:[#6]:[#6](:[#6]:2)-[#17]

temazepam: CN1C2=C(C=C(C=C2)Cl)C(=NC(C1=O)O)C3=CC=CC=C3

smiles_non_kekule:    CN1C(=O)C(O)N=C(c2ccccc2)c2cc(Cl)ccc21
smiles_kekule:    CN1C(=O)C(O)N=C(C2=CC=CC=C2)C2=C1C=CC(Cl)=C2
inchi:    InChI=1S/C16H13ClN2O2/c1-19-13-8-7-11(17)9-12(13)14(18-15(20)16(19)21)10-5-3-2-4-6-10/h2-9,15,20H,1H3
inchiKey:    SEQDDYPDSLOBDC-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#6](=[#7]-[#6](-[#6]-1=[#8])-[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#7]1-[#6]2:[#6](:[#6]:[#6](:[#6]:[#6]:2)-[#17])-[#6](=[#7]-[#6](-[#6]-1=[#8])-[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

tetrazepam: CN1C(=O)CN=C(C2=C1C=CC(=C2)Cl)C3=CCCCC3

smiles_non_kekule:    CN1C(=O)CN=C(C2=CCCCC2)c2cc(Cl)ccc21
smiles_kekule:    CN1C(=O)CN=C(C2=CCCCC2)C2=C1C=CC(Cl)=C2
inchi:    InChI=1S/C16H17ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h5,7-9H,2-4,6,10H2,1H3
inchiKey:    IQWYAQCHYZHJOS-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6](=[#8])-[#6]-[#7]=[#6](-[#6]2:[#6]-1:[#6]:[#6]:[#6](:[#6]:2)-[#17])-[#6]1=[#6]-[#6]-[#6]-[#6]-[#6]-1
smarts_isomeric:    [#6]-[#7]1-[#6](=[#8])-[#6]-[#7]=[#6](-[#6]2:[#6]-1:[#6]:[#6]:[#6](:[#6]:2)-[#17])-[#6]1=[#6]-[#6]-[#6]-[#6]-[#6]-1

triazolam: CC1=NN=C2N1C3=C(C=C(C=C3)Cl)C(=NC2)C4=CC=CC=C4Cl

smiles_non_kekule:    Cc1nnc2n1-c1ccc(Cl)cc1C(c1ccccc1Cl)=NC2
smiles_kekule:    CC1=NN=C2CN=C(C3=CC=CC=C3Cl)C3=C(C=CC(Cl)=C3)N12
inchi:    InChI=1S/C17H12Cl2N4/c1-10-21-22-16-9-20-17(12-4-2-3-5-14(12)19)13-8-11(18)6-7-15(13)23(10)16/h2-8H,9H2,1H3
inchiKey:    JOFWLTCLBGQGBO-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#7]:[#7]:[#6]2:[#7]:1-[#6]1:[#6](:[#6]:[#6](:[#6]:[#6]:1)-[#17])-[#6](=[#7]-[#6]-2)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17]
smarts_isomeric:    [#6]-[#6]1:[#7]:[#7]:[#6]2:[#7]:1-[#6]1:[#6](:[#6]:[#6](:[#6]:[#6]:1)-[#17])-[#6](=[#7]-[#6]-2)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#17]

zaleplon: CCN(C1=CC=CC(=C1)C2=CC=NC3=C(C=NN23)C#N)C(=O)C

smiles_non_kekule:    CCN(C(C)=O)c1cccc(-c2ccnc3c(C#N)cnn23)c1
smiles_kekule:    CCN(C(C)=O)C1=CC=CC(C2=CC=NC3=C(C#N)C=NN23)=C1
inchi:    InChI=1S/C17H15N5O/c1-3-21(12(2)23)15-6-4-5-13(9-15)16-7-8-19-17-14(10-18)11-20-22(16)17/h4-9,11H,3H2,1-2H3
inchiKey:    HUNXMJYCHXQEGX-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6](:[#6]:1)-[#6]1:[#6]:[#6]:[#7]:[#6]2:[#6](:[#6]:[#7]:[#7]:1:2)-[#6]#[#7])-[#6](=[#8])-[#6]
smarts_isomeric:    [#6]-[#6]-[#7](-[#6]1:[#6]:[#6]:[#6]:[#6](:[#6]:1)-[#6]1:[#6]:[#6]:[#7]:[#6]2:[#6](:[#6]:[#7]:[#7]:1:2)-[#6]#[#7])-[#6](=[#8])-[#6]

zolpidem: CC1=CC=C(C=C1)C2=C(N3C=C(C=CC3=N2)C)CC(=O)N(C)C

smiles_non_kekule:    Cc1ccc(-c2nc3ccc(C)cn3c2CC(=O)N(C)C)cc1
smiles_kekule:    CC1=CC=C(C2=C(CC(=O)N(C)C)N3C=C(C)C=CC3=N2)C=C1
inchi:    InChI=1S/C19H21N3O/c1-13-5-8-15(9-6-13)19-16(11-18(23)21(3)4)22-12-14(2)7-10-17(22)20-19/h5-10,12H,11H2,1-4H3
inchiKey:    ZAFYATHCZYHLPB-UHFFFAOYSA-N
smarts:    [#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]1:[#6](:[#7]2:[#6]:[#6](:[#6]:[#6]:[#6]:2:[#7]:1)-[#6])-[#6]-[#6](=[#8])-[#7](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]1:[#6](:[#7]2:[#6]:[#6](:[#6]:[#6]:[#6]:2:[#7]:1)-[#6])-[#6]-[#6](=[#8])-[#7](-[#6])-[#6]

zopiclone: CN1CCN(CC1)C(=O)OC2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl

smiles_non_kekule:    CN1CCN(C(=O)OC2c3nccnc3C(=O)N2c2ccc(Cl)cn2)CC1
smiles_kekule:    CN1CCN(C(=O)OC2C3=NC=CN=C3C(=O)N2C2=NC=C(Cl)C=C2)CC1
inchi:    InChI=1S/C17H17ClN6O3/c1-22-6-8-23(9-7-22)17(26)27-16-14-13(19-4-5-20-14)15(25)24(16)12-3-2-11(18)10-21-12/h2-5,10,16H,6-9H2,1H3
inchiKey:    GBBSUAFBMRNDJC-UHFFFAOYSA-N
smarts:    [#6]-[#7]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6](=[#8])-[#8]-[#6]1-[#6]2:[#7]:[#6]:[#6]:[#7]:[#6]:2-[#6](=[#8])-[#7]-1-[#6]1:[#7]:[#6]:[#6](:[#6]:[#6]:1)-[#17]
smarts_isomeric:    [#6]-[#7]1-[#6]-[#6]-[#7](-[#6]-[#6]-1)-[#6](=[#8])-[#8]-[#6]1-[#6]2:[#7]:[#6]:[#6]:[#7]:[#6]:2-[#6](=[#8])-[#7]-1-[#6]1:[#7]:[#6]:[#6](:[#6]:[#6]:1)-[#17]

fenfluramine: CCNC(C)CC1=CC(=CC=C1)C(F)(F)F

smiles_non_kekule:    CCNC(C)Cc1cccc(C(F)(F)F)c1
smiles_kekule:    CCNC(C)CC1=CC(C(F)(F)F)=CC=C1
inchi:    InChI=1S/C12H16F3N/c1-3-16-9(2)7-10-5-4-6-11(8-10)12(13,14)15/h4-6,8-9,16H,3,7H2,1-2H3
inchiKey:    DBGIVFWFUFKIQN-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7]-[#6](-[#6])-[#6]-[#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1)-[#6](-[#9])(-[#9])-[#9]
smarts_isomeric:    [#6]-[#6]-[#7]-[#6](-[#6])-[#6]-[#6]1:[#6]:[#6](:[#6]:[#6]:[#6]:1)-[#6](-[#9])(-[#9])-[#9]

lorcaserin: CC1CNCCC2=C1C=C(C=C2)Cl

smiles_non_kekule:    CC1CNCCc2ccc(Cl)cc21
smiles_kekule:    CC1CNCCC2=C1C=C(Cl)C=C2
inchi:    InChI=1S/C11H14ClN/c1-8-7-13-5-4-9-2-3-10(12)6-11(8)9/h2-3,6,8,13H,4-5,7H2,1H3
inchiKey:    XTTZERNUQAFMOF-UHFFFAOYSA-N
smarts:    [#6]-[#6]1-[#6]-[#7]-[#6]-[#6]-[#6]2:[#6]-1:[#6]:[#6](:[#6]:[#6]:2)-[#17]
smarts_isomeric:    [#6]-[#6]1-[#6]-[#7]-[#6]-[#6]-[#6]2:[#6]-1:[#6]:[#6](:[#6]:[#6]:2)-[#17]

(+)-norpseudoephedrine: CC(C(C1=CC=CC=C1)O)N

smiles_non_kekule:    CC(N)C(O)c1ccccc1
smiles_kekule:    CC(N)C(O)C1=CC=CC=C1
inchi:    InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3
inchiKey:    DLNKOYKMWOXYQA-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8])-[#7]
smarts_isomeric:    [#6]-[#6](-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8])-[#7]

diethylpropion: CCN(CC)C(C)C(=O)C1=CC=CC=C1

smiles_non_kekule:    CCN(CC)C(C)C(=O)c1ccccc1
smiles_kekule:    CCN(CC)C(C)C(=O)C1=CC=CC=C1
inchi:    InChI=1S/C13H19NO/c1-4-14(5-2)11(3)13(15)12-9-7-6-8-10-12/h6-11H,4-5H2,1-3H3
inchiKey:    XXEPPPIWZFICOJ-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7](-[#6]-[#6])-[#6](-[#6])-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#7](-[#6]-[#6])-[#6](-[#6])-[#6](=[#8])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

fencamfamin: CCNC1C2CCC(C2)C1C3=CC=CC=C3

smiles_non_kekule:    CCNC1C2CCC(C2)C1c1ccccc1
smiles_kekule:    CCNC1C2CCC(C2)C1C1=CC=CC=C1
inchi:    InChI=1S/C15H21N/c1-2-16-15-13-9-8-12(10-13)14(15)11-6-4-3-5-7-11/h3-7,12-16H,2,8-10H2,1H3
inchiKey:    IKFBPFGUINLYQI-UHFFFAOYSA-N
smarts:    [#6]-[#6]-[#7]-[#6]1-[#6]2-[#6]-[#6]-[#6](-[#6]-2)-[#6]-1-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#6]-[#7]-[#6]1-[#6]2-[#6]-[#6]-[#6](-[#6]-2)-[#6]-1-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

fenproporex: CC(CC1=CC=CC=C1)NCCC#N

smiles_non_kekule:    CC(Cc1ccccc1)NCCC#N
smiles_kekule:    CC(CC1=CC=CC=C1)NCCC#N
inchi:    InChI=1S/C12H16N2/c1-11(14-9-5-8-13)10-12-6-3-2-4-7-12/h2-4,6-7,11,14H,5,9-10H2,1H3
inchiKey:    IQUFSXIQAFPIMR-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]-[#6]-[#6]-[#6]#[#7]
smarts_isomeric:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]-[#6]-[#6]-[#6]#[#7]

mazindol: C1CN2C(=N1)C3=CC=CC=C3C2(C4=CC=C(C=C4)Cl)O

smiles_non_kekule:    OC1(c2ccc(Cl)cc2)c2ccccc2C2=NCCN21
smiles_kekule:    OC1(C2=CC=C(Cl)C=C2)C2=CC=CC=C2C2=NCCN21
inchi:    InChI=1S/C16H13ClN2O/c17-12-7-5-11(6-8-12)16(20)14-4-2-1-3-13(14)15-18-9-10-19(15)16/h1-8,20H,9-10H2
inchiKey:    ZPXSCAKFGYXMGA-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#7]2-[#6](=[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-2(-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#17])-[#8]
smarts_isomeric:    [#6]1-[#6]-[#7]2-[#6](=[#7]-1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1-[#6]-2(-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#17])-[#8]

mefenorex: CC(CC1=CC=CC=C1)NCCCCl

smiles_non_kekule:    CC(Cc1ccccc1)NCCCCl
smiles_kekule:    CC(CC1=CC=CC=C1)NCCCCl
inchi:    InChI=1S/C12H18ClN/c1-11(14-9-5-8-13)10-12-6-3-2-4-7-12/h2-4,6-7,11,14H,5,8-10H2,1H3
inchiKey:    XXVROGAVTTXONC-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]-[#6]-[#6]-[#6]-[#17]
smarts_isomeric:    [#6]-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]-[#6]-[#6]-[#6]-[#17]

pemoline: C1=CC=C(C=C1)C2C(=O)N=C(O2)N

smiles_non_kekule:    NC1=NC(=O)C(c2ccccc2)O1
smiles_kekule:    NC1=NC(=O)C(C2=CC=CC=C2)O1
inchi:    InChI=1S/C9H8N2O2/c10-9-11-8(12)7(13-9)6-4-2-1-3-5-6/h1-5,7H,(H2,10,11,12)
inchiKey:    NRNCYVBFPDDJNE-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]1-[#6](=[#8])-[#7]=[#6](-[#8]-1)-[#7]
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]1-[#6](=[#8])-[#7]=[#6](-[#8]-1)-[#7]

phentermine: CC(C)(CC1=CC=CC=C1)N

smiles_non_kekule:    CC(C)(N)Cc1ccccc1
smiles_kekule:    CC(C)(N)CC1=CC=CC=C1
inchi:    InChI=1S/C10H15N/c1-10(2,11)8-9-6-4-3-5-7-9/h3-7H,8,11H2,1-2H3
inchiKey:    DHHVAGZRUROJKS-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])(-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]
smarts_isomeric:    [#6]-[#6](-[#6])(-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#7]

pipradrol: C1CCNC(C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)O

smiles_non_kekule:    OC(c1ccccc1)(c1ccccc1)C1CCCCN1
smiles_kekule:    OC(C1=CC=CC=C1)(C1=CC=CC=C1)C1CCCCN1
inchi:    InChI=1S/C18H21NO/c20-18(15-9-3-1-4-10-15,16-11-5-2-6-12-16)17-13-7-8-14-19-17/h1-6,9-12,17,19-20H,7-8,13-14H2
inchiKey:    XSWHNYGMWWVAIE-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#7]-[#6](-[#6]-1)-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8]
smarts_isomeric:    [#6]1-[#6]-[#6]-[#7]-[#6](-[#6]-1)-[#6](-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)(-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#8]

serdexmethylphenidate: COC(=O)C(C1CCCCN1C(=O)OC[N+]2=CC=CC(=C2)C(=O)NC(CO)C(=O)[O-])C3=CC=CC=C3

smiles_non_kekule:    COC(=O)C(c1ccccc1)C1CCCCN1C(=O)OC[n+]1cccc(C(=O)NC(CO)C(=O)[O-])c1
smiles_kekule:    COC(=O)C(C1=CC=CC=C1)C1CCCCN1C(=O)OC[N+]1=CC=CC(C(=O)NC(CO)C(=O)[O-])=C1
inchi:    InChI=1S/C25H29N3O8/c1-35-24(33)21(17-8-3-2-4-9-17)20-11-5-6-13-28(20)25(34)36-16-27-12-7-10-18(14-27)22(30)26-19(15-29)23(31)32/h2-4,7-10,12,14,19-21,29H,5-6,11,13,15-16H2,1H3,(H-,26,30,31,32)
inchiKey:    UBZPNQRBUOBBLN-UHFFFAOYSA-N
smarts:    [#6]-[#8]-[#6](=[#8])-[#6](-[#6]1-[#6]-[#6]-[#6]-[#6]-[#7]-1-[#6](=[#8])-[#8]-[#6]-[#7+]1:[#6]:[#6]:[#6]:[#6](:[#6]:1)-[#6](=[#8])-[#7]-[#6](-[#6]-[#8])-[#6](=[#8])-[#8-])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#8]-[#6](=[#8])-[#6](-[#6]1-[#6]-[#6]-[#6]-[#6]-[#7]-1-[#6](=[#8])-[#8]-[#6]-[#7+]1:[#6]:[#6]:[#6]:[#6](:[#6]:1)-[#6](=[#8])-[#7]-[#6](-[#6]-[#8])-[#6](=[#8])-[#8-])-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

sibutramine: CC(C)CC(C1(CCC1)C2=CC=C(C=C2)Cl)N(C)C

smiles_non_kekule:    CC(C)CC(N(C)C)C1(c2ccc(Cl)cc2)CCC1
smiles_kekule:    CC(C)CC(N(C)C)C1(C2=CC=C(Cl)C=C2)CCC1
inchi:    InChI=1S/C17H26ClN/c1-13(2)12-16(19(3)4)17(10-5-11-17)14-6-8-15(18)9-7-14/h6-9,13,16H,5,10-12H2,1-4H3
inchiKey:    UNAANXDKBXWMLN-UHFFFAOYSA-N
smarts:    [#6]-[#6](-[#6])-[#6]-[#6](-[#6]1(-[#6]-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#17])-[#7](-[#6])-[#6]
smarts_isomeric:    [#6]-[#6](-[#6])-[#6]-[#6](-[#6]1(-[#6]-[#6]-[#6]-1)-[#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#17])-[#7](-[#6])-[#6]

solriamfetol: C1=CC=C(C=C1)CC(COC(=O)N)N

smiles_non_kekule:    NC(=O)OCC(N)Cc1ccccc1
smiles_kekule:    NC(=O)OCC(N)CC1=CC=CC=C1
inchi:    InChI=1S/C10H14N2O2/c11-9(7-14-10(12)13)6-8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H2,12,13)
inchiKey:    UCTRAOBQFUDCSR-UHFFFAOYSA-N
smarts:    [#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]-[#6](-[#6]-[#8]-[#6](=[#8])-[#7])-[#7]
smarts_isomeric:    [#6]1:[#6]:[#6]:[#6](:[#6]:[#6]:1)-[#6]-[#6](-[#6]-[#8]-[#6](=[#8])-[#7])-[#7]

spa((-)-1-dimethylamino-1,2-diphenylethane): CN(C)C(CC1=CC=CC=C1)C2=CC=CC=C2

smiles_non_kekule:    CN(C)C(Cc1ccccc1)c1ccccc1
smiles_kekule:    CN(C)C(CC1=CC=CC=C1)C1=CC=CC=C1
inchi:    InChI=1S/C16H19N/c1-17(2)16(15-11-7-4-8-12-15)13-14-9-5-3-6-10-14/h3-12,16H,13H2,1-2H3
inchiKey:    YEJZJVJJPVZXGX-UHFFFAOYSA-N
smarts:    [#6]-[#7](-[#6])-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1
smarts_isomeric:    [#6]-[#7](-[#6])-[#6](-[#6]-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1)-[#6]1:[#6]:[#6]:[#6]:[#6]:[#6]:1

pentazocine: CC1C2CC3=C(C1(CCN2CC=C(C)C)C)C=C(C=C3)O

smiles_non_kekule:    CC(C)=CCN1CCC2(C)c3cc(O)ccc3CC1C2C
smiles_kekule:    CC(C)=CCN1CCC2(C)C3=C(C=CC(O)=C3)CC1C2C
inchi:    InChI=1S/C19H27NO/c1-13(2)7-9-20-10-8-19(4)14(3)18(20)11-15-5-6-16(21)12-17(15)19/h5-7,12,14,18,21H,8-11H2,1-4H3
inchiKey:    VOKSWYLNZZRQPF-UHFFFAOYSA-N
smarts:    [#6]-[#6]1-[#6]2-[#6]-[#6]3:[#6](-[#6]-1(-[#6]-[#6]-[#7]-2-[#6]-[#6]=[#6](-[#6])-[#6])-[#6]):[#6]:[#6](:[#6]:[#6]:3)-[#8]
smarts_isomeric:    [#6]-[#6]1-[#6]2-[#6]-[#6]3:[#6](-[#6]-1(-[#6]-[#6]-[#7]-2-[#6]-[#6]=[#6](-[#6])-[#6])-[#6]):[#6]:[#6](:[#6]:[#6]:3)-[#8]

butorphanol: C1CCC2(C3CC4=C(C2(C1)CCN3CC5CCC5)C=C(C=C4)O)O

smiles_non_kekule:    Oc1ccc2c(c1)C13CCCCC1(O)C(C2)N(CC1CCC1)CC3
smiles_kekule:    OC1=CC2=C(C=C1)CC1N(CC3CCC3)CCC23CCCCC13O
inchi:    InChI=1S/C21H29NO2/c23-17-7-6-16-12-19-21(24)9-2-1-8-20(21,18(16)13-17)10-11-22(19)14-15-4-3-5-15/h6-7,13,15,19,23-24H,1-5,8-12,14H2
inchiKey:    IFKLAQQSCNILHL-UHFFFAOYSA-N
smarts:    [#6]1-[#6]-[#6]-[#6]2(-[#6]3-[#6]-[#6]4:[#6](-[#6]-2(-[#6]-1)-[#6]-[#6]-[#7]-3-[#6]-[#6]1-[#6]-[#6]-[#6]-1):[#6]:[#6](:[#6]:[#6]:4)-[#8])-[#8]
smarts_isomeric:    [#6]1-[#6]-[#6]-[#6]2(-[#6]3-[#6]-[#6]4:[#6](-[#6]-2(-[#6]-1)-[#6]-[#6]-[#7]-3-[#6]-[#6]1-[#6]-[#6]-[#6]-1):[#6]:[#6](:[#6]:[#6]:4)-[#8])-[#8]