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