"""
Classifies: CHEBI:2468 secondary alpha-hydroxy ketone
"""
from rdkit import Chem

def is_secondary_alpha_hydroxy_ketone(smiles: str):
    """
    Determines if a molecule is a secondary alpha-hydroxy ketone based on its SMILES string.
    A secondary alpha-hydroxy ketone typically features a ketone group linked to a secondary alcohol.

    Args:
        smiles (str): SMILES string of the molecule

    Returns:
        bool: True if molecule is a secondary alpha-hydroxy ketone, False otherwise
        str: Reason for classification
    """
    
    # Parse SMILES
    mol = Chem.MolFromSmiles(smiles)
    if mol is None:
        return False, "Invalid SMILES string"

    # Expanded SMARTS pattern for secondary alpha-hydroxy ketone
    # This pattern attempts to capture more configurations
    alpha_hydroxy_ketone_pattern = Chem.MolFromSmarts("[#6][CX3](=O)[CX4][OX2H]")

    # Check for the secondary alpha-hydroxy ketone pattern
    if mol.HasSubstructMatch(alpha_hydroxy_ketone_pattern):
        return True, "Contains secondary alpha-hydroxy ketone structure"
    
    return False, "Does not contain secondary alpha-hydroxy ketone structure"


__metadata__ = {   'chemical_class': {   'id': 'CHEBI:2468',
                          'name': 'secondary alpha-hydroxy ketone',
                          'definition': 'An alpha-hydroxy ketone in which the '
                                        'carbonyl group and the hydroxy group '
                                        'are linked by a carbon bearing one '
                                        'hydrogen and one organyl group. '
                                        'Secondary alpha-hydroxy ketones are '
                                        'also known as acyloins, and are '
                                        'formally derived from reductive '
                                        'coupling of two carboxylic acid '
                                        'groups.',
                          'parents': ['CHEBI:139588', 'CHEBI:35681'],
                          'xrefs': ['Wikipedia:Acyloin'],
                          'all_positive_examples': []},
    'config': None,
    'message': '\n'
               'Attempt failed: F1 score of 0.7105263157894736 is too low.\n'
               'Outcomes:\n'
               '------\n'
               '\n'
               'True positives: SMILES: '
               'C[C@@H]1CC(=O)[C@@H](O)C(O1)OP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C[C@@H]1O)n1cc(C)c(=O)[nH]c1=O '
               'NAME: dTDP-3-dehydro-4,6-dideoxy-D-glucose REASON: CORRECT '
               'Contains secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)C(O)C[C@]34C)[C@@H]1CC[C@@H]2O '
               'NAME: 2-hydroxytestosterone REASON: CORRECT Contains secondary '
               'alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               '[H][C@@]12O[C@]3([H])C=C(C)C(=O)[C@@H](O)[C@]3(CO)[C@@](C)(C[C@H]1O)[C@]21CO1 '
               'NAME: deoxynivalenol REASON: CORRECT Contains secondary '
               'alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'C[C@@H]1CC(=O)[C@@H](O)[C@H](O1)OP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C[C@@H]1O)n1cc(C)c(=O)[nH]c1=O '
               'NAME: dTDP-3-dehydro-4,6-dideoxy-alpha-D-glucose REASON: '
               'CORRECT Contains secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               '[H][C@]1(Cc2cc3cc(O)cc(O)c3c(O)c2C(=O)[C@H]1O)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O '
               'NAME: olivin REASON: CORRECT Contains secondary alpha-hydroxy '
               'ketone structure\n'
               ' * SMILES: C12=C(N[C@@](C(C(C)O)=O)(CN1)[H])C(NC(=N2)N)=O '
               'NAME: (6R)-6-lactoyl-5,6,7,8-tetrahydropterin REASON: CORRECT '
               'Contains secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               '[H][C@@]1(CC[C@@]2(O)C3=CC(=O)[C@]4([H])C[C@@H](O)C(=O)C[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)[C@H](O)CCC(C)(C)O '
               'NAME: 2-dehydroecdysone REASON: CORRECT Contains secondary '
               'alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'O[C@@H]1[C@H](OC2=C(C=CC(O)=C2)C1=O)C1=CC=C(O)C(O)=C1 NAME: '
               '(+)-trans-fustin REASON: CORRECT Contains secondary '
               'alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'C[C@@H]1C[C@@H](OC(C)=O)[C@H](O)[C@H](O[C@H]2CC[C@]3(C=O)[C@H]4[C@H](O)C(=O)[C@]5(C)[C@H](CC[C@]5(O)[C@@H]4CC[C@]3(O)C2)c2ccc(=O)oc2)O1 '
               'NAME: bryotoxin A REASON: CORRECT Contains secondary '
               'alpha-hydroxy ketone structure\n'
               ' * SMILES: OC(C(O)=O)C(=O)C(O)=O NAME: 2-hydroxy-3-oxosuccinic '
               'acid REASON: CORRECT Contains secondary alpha-hydroxy ketone '
               'structure\n'
               ' * SMILES: '
               'C=1(C=CC(OC1)=O)[C@@H]2[C@]3(C([C@H]([C@@]4([C@]5(C[C@@H]([C@@H](C[C@]5(CC[C@]4([C@]3(CC2)O)[H])O)OC(=O)C)OC(=O)C)C)[H])O)=O)C '
               'NAME: lucibufagin C REASON: CORRECT Contains secondary '
               'alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'C1[C@@]2([C@@]([C@@]3(C(C[C@@H](OS(O)(=O)=O)CC3)=C1)C)(CC[C@]4([C@]2(C[C@H](C4=O)O)[H])C)[H])[H] '
               'NAME: 16alpha-hydroxydehydroepiandrosterone 3-sulfate REASON: '
               'CORRECT Contains secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: N[C@@H]1CC(=CC(=O)[C@H]1O)C(O)=O NAME: '
               '5-amino-5-deoxy-3-dehydroshikimic acid REASON: CORRECT '
               'Contains secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: O[C@H]1[C@@H](Oc2cc(O)cc(O)c2C1=O)c1cc(O)c(O)c(O)c1 '
               'NAME: (-)-dihydromyricetin REASON: CORRECT Contains secondary '
               'alpha-hydroxy ketone structure\n'
               ' * SMILES: O=C(C(O)[C@H]1[C@H](C=C[C@@H]([C@H]1O)O)/C=C/C)C '
               'NAME: Arthropsatriol B REASON: CORRECT Contains secondary '
               'alpha-hydroxy ketone structure\n'
               ' * SMILES: COc1ccc(CC(O)C(=O)c2ccc(OC)cc2OC)cc1 NAME: '
               "2'-O-methylodoratol REASON: CORRECT Contains secondary "
               'alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'C[C@H]1OC(OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)n2ccc(N)nc2=O)[C@H](O)[C@@H](O)C1=O '
               'NAME: CDP-4-dehydro-6-deoxy-D-glucose REASON: CORRECT Contains '
               'secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: O[C@H](C(O)=O)C(=O)C(O)=O NAME: '
               '(2S)-2-hydroxy-3-oxosuccinic acid REASON: CORRECT Contains '
               'secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: COc1cc(O)c(CC=C(C)C)cc1C(=O)[C@@H](O)Cc1ccc(O)cc1 '
               'NAME: lespeflorin C3 REASON: CORRECT Contains secondary '
               'alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'CC1=CC(=O)[C@@H](O)[C@@]2(C)[C@H]1C[C@H]1OC(=O)[C@H](O)[C@H]3[C@@H](CO)[C@@H](O)[C@H](O)[C@H]2[C@@]13C '
               'NAME: yadanziolide T REASON: CORRECT Contains secondary '
               'alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'C[C@H]1C\\C=C\\[C@H]2[C@H](O)C(C)=C(C)[C@H]3[C@H](Cc4c[nH]c5ccccc45)NC(=O)[C@@]23C(=O)\\C=C\\C(=O)[C@H](O)\\C(C)=C\\1 '
               'NAME: chaetoglobosin B REASON: CORRECT Contains secondary '
               'alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'C1[C@]2([C@]3([C@@](C4=C(CC3)C=C(C=C4)O[C@@H]5O[C@@H]([C@H]([C@@H]([C@H]5O)O)O)C(O)=O)(CC[C@@]2(C(=O)[C@@H]1O)C)[H])[H])[H] '
               'NAME: 16alpha-hydroxyestrone 3-O-(beta-D-glucuronide) REASON: '
               'CORRECT Contains secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: COc1ccc(CC(O)C(=O)c2ccc(OC)cc2O)cc1 NAME: odoratol '
               'REASON: CORRECT Contains secondary alpha-hydroxy ketone '
               'structure\n'
               ' * SMILES: O[C@H]1CC[C@@H](CC1=O)C(O)=O NAME: '
               '(1S,4S)-4-hydroxy-3-oxocyclohexane-1-carboxylic acid REASON: '
               'CORRECT Contains secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: CC(O)C(=O)C1=Nc2c(NC1)nc(N)[nH]c2=O NAME: '
               'sepiapterin REASON: CORRECT Contains secondary alpha-hydroxy '
               'ketone structure\n'
               'False positives: SMILES: '
               'C1([C@@H]([C@H]1C=C(C)C)C(=O)SCCNC(CCNC(=O)[C@@H](C(COP(OP(OC[C@H]2O[C@@H](N3C4=C(C(=NC=N4)N)N=C3)[C@@H]([C@@H]2OP([O-])([O-])=O)O)(=O)[O-])(=O)[O-])(C)C)O)=O)(C)C '
               'NAME: (R,R)-chrysanthemoyl-CoA(4-) REASON: WRONGLY CLASSIFIED '
               'Contains secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'O=C(N[C@H]([C@H](O)/C=C/CC/C=C(/CCCCCC)\\C)CO[C@@H]1O[C@@H]([C@@H](O)[C@@H]([C@H]1O)O)CO)[C@H](O)CCCCCCCCCCCCCCCC '
               'NAME: Cerebroside E REASON: WRONGLY CLASSIFIED Contains '
               'secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: C1([C@@H]([C@H]([C@@H](C([C@@H]1O)=O)O)O)O)=O NAME: '
               '3-dehydro-scyllo-inosose REASON: WRONGLY CLASSIFIED Contains '
               'secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               '[C@@H]1(N2C3=C(C(=NC=N3)N)N=C2)O[C@H](COP(OP(OCC(C)([C@H](C(NCCC(NCCSC(=O)C(CC(=O)[O-])C=4C=CC=CC4)=O)=O)O)C)(=O)[O-])(=O)[O-])[C@H]([C@H]1O)OP([O-])([O-])=O '
               'NAME: 2-phenylsuccinyl-CoA(5-) REASON: WRONGLY CLASSIFIED '
               'Contains secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: O(C(C[N+](C)(C)C)CC([O-])=O)C(=O)C(O)CCCCCCCCCCCC '
               'NAME: 2-Hydroxymyristoylcarnitine REASON: WRONGLY CLASSIFIED '
               'Contains secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'CCCCCCCCCCCCCCCCCCCCCCCCCCC(O)C(=O)N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCC(C)C '
               'NAME: '
               'N-(2-hydroxyoctacosanoyl)-4-hydroxy-15-methylhexadecasphinganine '
               'REASON: WRONGLY CLASSIFIED Contains secondary alpha-hydroxy '
               'ketone structure\n'
               ' * SMILES: '
               'O=C(NCCCC(NC(=O)/C=C\\CCCCCCC)C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(CO)CC(=O)N)C(O)C(=O)N)CCNC(=O)C(N)C(O)C)C(O)C)N '
               'NAME: Rotihibin C REASON: WRONGLY CLASSIFIED Contains '
               'secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)C(C3=CC=CC=C3)O NAME: '
               '2-hydroxy-2-phenylacetic acid '
               '[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] ester REASON: '
               'WRONGLY CLASSIFIED Contains secondary alpha-hydroxy ketone '
               'structure\n'
               ' * SMILES: '
               'O[C@H]([C@@H](O)C(O)=O)C(O)=O.C1C2CNCC1c1cc3nccnc3cc21 NAME: '
               'varenicline tartrate REASON: WRONGLY CLASSIFIED Contains '
               'secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'CC(C)(COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCO '
               'NAME: 4-hydroxybutyryl-CoA(4-) REASON: WRONGLY CLASSIFIED '
               'Contains secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'C[C@H](CCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O '
               'NAME: ascr#10-CoA REASON: WRONGLY CLASSIFIED Contains '
               'secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: OC(CCCC([O-])=O)C([O-])=O NAME: '
               '2-hydroxyadipate(2-) REASON: WRONGLY CLASSIFIED Contains '
               'secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'O=C(N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](CC(=O)N[C@H](C(=O)N[C@@H](C(=O)O)[C@@H](O)C(C)C)C(C)C)CCCCCCC)[C@H](O)C)CC(C)C)[C@H]1N(C(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](N(C(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](N)C)[C@@H](O)C(C)C)CCC(=O)N)C)[C@H](CC)C)[C@@H](O)C(=O)N)[C@H](O)C)CCC1 '
               'NAME: Acyclolaxaphycin B REASON: WRONGLY CLASSIFIED Contains '
               'secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'OC(CCCCCCCCCCC(C)C)CC(=O)NC(CCCCN)C(OCCOC(=O)C(O)CCCCCCCCCCC(C)C)=O '
               'NAME: Lysine-containing siolipin REASON: WRONGLY CLASSIFIED '
               'Contains secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'CC(C)(COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C1=CC(O)CC=C1 '
               'NAME: 3-hydroxycyclohexa-1,5-diene-1-carbonyl-CoA(4-) REASON: '
               'WRONGLY CLASSIFIED Contains secondary alpha-hydroxy ketone '
               'structure\n'
               ' * SMILES: '
               'O=C([C@@]1([C@@H]2[C@@H](C=C[C@@H]1C)C[C@H](C)CC2)C)C(O)CO '
               'NAME: Phomodiol REASON: WRONGLY CLASSIFIED Contains secondary '
               'alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               '[C@@H]1(N2C3=C(C(=NC=N3)N)N=C2)O[C@H](COP(OP(OCC([C@H](C(NCCC(NCCSC(=O)C[C@@H](O)CCCCCCCCCCCCCCCCCCCCC)=O)=O)O)(C)C)(=O)O)(=O)O)[C@H]([C@H]1O)OP(O)(O)=O '
               'NAME: (3S)-3-hydroxytetracosanoyl-CoA REASON: WRONGLY '
               'CLASSIFIED Contains secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               '[C@@H]1(N2C=3C(=C(N=CN3)N)N=C2)O[C@H](COP(OP(OCC([C@H](C(NCCC(NCCSC(=O)CCC4=CC(=CC=C4)O)=O)=O)O)(C)C)(=O)[O-])(=O)[O-])[C@H]([C@H]1O)OP([O-])([O-])=O '
               'NAME: 3-(m-hydroxyphenyl)propanoyl-CoA(4-) REASON: WRONGLY '
               'CLASSIFIED Contains secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'CC(C)CCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12 '
               'NAME: isomyristoyl-CoA(4-) REASON: WRONGLY CLASSIFIED Contains '
               'secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'O=C(N[C@@H](C1=CC=CC=C1)CC(=O)O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N)C(C)C)C(C)C)CC(C)C)CO '
               'NAME: Pyloricidin A REASON: WRONGLY CLASSIFIED Contains '
               'secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'CC\\C=C/C\\C=C/C\\C=C/C\\C=C/C\\C=C/CCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12 '
               'NAME: (9Z,12Z,15Z,18Z,21Z)-tetracosapentaenoyl-CoA(4-) REASON: '
               'WRONGLY CLASSIFIED Contains secondary alpha-hydroxy ketone '
               'structure\n'
               ' * SMILES: CC(C)(COP([O-])([O-])=O)[C@@H](O)C(=O)NCCC([O-])=O '
               "NAME: (R)-4'-phosphonatopantothenate(3-) REASON: WRONGLY "
               'CLASSIFIED Contains secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'CC(C)(COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCCCCCCCCCO '
               'NAME: 15-hydroxypentadecanoyl-CoA(4-) REASON: WRONGLY '
               'CLASSIFIED Contains secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'OC[C@@H](O)[C@@H](OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@H](O)C=O '
               'NAME: D-glucopyranosyl-(1->4)-aldehydo-D-mannose REASON: '
               'WRONGLY CLASSIFIED Contains secondary alpha-hydroxy ketone '
               'structure\n'
               ' * SMILES: '
               'P(OCCNC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO)(O)(O)=O NAME: '
               'N-Gluconyl ethanolamine phosphate REASON: WRONGLY CLASSIFIED '
               'Contains secondary alpha-hydroxy ketone structure\n'
               'False negatives: SMILES: '
               'OC1(C(O)=C(C(O)=C(C1=O)C(=O)CC(C)C)CC=C(C)C)CC=C(C)C NAME: '
               '(R)-Humulone REASON: MISSED Does not contain secondary '
               'alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'O=C1/C(/C(=O)[C@]2([C@H]3C(=C(O)C(=C([C@]3(O[C@]2([C@]1(O)C)O)C)O)C)C(=O)CC/C=C/C)C)=C(/O)\\C=C\\C=C\\C '
               'NAME: 10,11-dihydrobisvertinolone REASON: MISSED Does not '
               'contain secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'O=C1C(=CC([C@@]1(O)C[C@H]2C(=C)CC[C@@H]3[C@@]2(CCCC3(C)C)C)=O)C '
               'NAME: Penicilliumin B REASON: MISSED Does not contain '
               'secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'O=C1/C(=C(\\O)/C=C/C=C/C)/[C@H]2[C@@](O)(C)C([C@@]1([C@H]3C[C@@](O)(CO)O[C@@H]23)C)=O '
               'NAME: Sorbicillfuran A REASON: MISSED Does not contain '
               'secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: O=C1C=C[C@H]([C@]1(O)C(=O)CCCCCCCCCCCC)O NAME: '
               'Hygrophorone C12 REASON: MISSED Does not contain secondary '
               'alpha-hydroxy ketone structure\n'
               ' * SMILES: O=C1NC(=C(C)C)C([C@]1(O)C/C=C/CC(O)C)=O NAME: '
               'Cladosporiumin D REASON: MISSED Does not contain secondary '
               'alpha-hydroxy ketone structure\n'
               ' * SMILES: '
               'O=C1/C(=C(/O)\\C=C\\C=C\\C)/[C@H]2[C@@](O)(C)C([C@@]1(C(OCCCC)C2)C)=O '
               'NAME: Rezishanone B REASON: MISSED Does not contain secondary '
               'alpha-hydroxy ketone structure\n'
               ' * SMILES: OC(C)(C)C(=O)C NAME: 3-Hydroxy-3-methylbutan-2-one '
               'REASON: MISSED Does not contain secondary alpha-hydroxy ketone '
               'structure\n'
               ' * SMILES: OC1(CCCC(C1=O)(C)C)C NAME: '
               '2-Hydroxy-2,6,6-trimethylcyclohexanone REASON: MISSED Does not '
               'contain secondary alpha-hydroxy ketone structure\n'
               ' * SMILES: O=C1C=CC(C1(O)CO)=O NAME: G2201-C REASON: MISSED '
               'Does not contain secondary alpha-hydroxy ketone structure\n'
               '------\n'
               '\n'
               'In your reasoning step, analyze the previous program and the '
               'above outcomes, hypothesizing about what went wrong, and how '
               'to improve.\n',
    'sample_true_negatives': [   {   'smiles': 'P(OCC(OC(=O)CC/C=C\\C/C=C\\C/C=C\\C/C=C\\C/C=C\\C/C=C\\CC)COC(=O)CCC/C=C\\C/C=C\\C/C=C\\CCCCCCCC)(OCCN(C)C)(O)=O',
                                     'name': 'Pe-nme2(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))',
                                     'reason': 'Does not contain secondary '
                                               'alpha-hydroxy ketone '
                                               'structure'},
                                 {   'smiles': 'O1[C@]2([C@@H](O)[C@H](O)[C@@H](O)[C@@]1(OCC[C@H](CCC=C(C(OC[C@]3(O)[C@@H](O)[C@@](OC3)(OC2)[H])=O)C)C)[H])[H]',
                                     'name': 'Urceolide',
                                     'reason': 'Does not contain secondary '
                                               'alpha-hydroxy ketone '
                                               'structure'},
                                 {   'smiles': 'CC1=CC(=C(C=C1)C)C(=O)CSC2=NN=C(S2)C',
                                     'name': '1-(2,5-dimethylphenyl)-2-[(5-methyl-1,3,4-thiadiazol-2-yl)thio]ethanone',
                                     'reason': 'Does not contain secondary '
                                               'alpha-hydroxy ketone '
                                               'structure'},
                                 {   'smiles': 'CCCC[C@](Cn1cncn1)(C#N)c1ccc(Cl)cc1',
                                     'name': '(S)-myclobutanil',
                                     'reason': 'Does not contain secondary '
                                               'alpha-hydroxy ketone '
                                               'structure'},
                                 {   'smiles': 'O=C1O[C@@H]([C@H](NC(=O)[C@@H](NC(=O)CCCCC)CC(=O)O)C(=O)N[C@H](C(=O)N[C@H]2CC[C@H](N([C@H](C(N([C@H](C(N[C@H]1C(C)C)=O)CC3=CC=CC=C3)C)=O)CC(C)C)C2=O)O)CCCCN(C)C)C',
                                     'name': 'Cyanopeptolin D',
                                     'reason': 'Does not contain secondary '
                                               'alpha-hydroxy ketone '
                                               'structure'},
                                 {   'smiles': 'O1[C@]2(O)N([C@H](C(=O)N3[C@]2(CCC3)[H])C(C)C)C(=O)[C@@]1(NC(=O)[C@H]4CN([C@]5(C(=C4)C6=C7C(C5)=CNC7=CC=C6)[H])C)C',
                                     'name': 'Ergovaline',
                                     'reason': 'Does not contain secondary '
                                               'alpha-hydroxy ketone '
                                               'structure'},
                                 {   'smiles': 'OC(=O)CCCCCCC#CCCCC',
                                     'name': '8-tridecynoic acid',
                                     'reason': 'Does not contain secondary '
                                               'alpha-hydroxy ketone '
                                               'structure'},
                                 {   'smiles': 'CC(=O)N([O-])CCC[C@H](N)C(=O)N[C@@H](CCCN([O-])C(C)=O)C(=O)N[C@@H](CCCN([O-])C(C)=O)C(=O)N[C@@H](CO)C(=O)N[C@H]([C@H](O)[C@H]1S[C@H]([C@H](O)[C@H]1O)n1ccc(=N)n(C)c1=O)C(O)=O',
                                     'name': 'desferrialbomycin epsilon(3-)',
                                     'reason': 'Does not contain secondary '
                                               'alpha-hydroxy ketone '
                                               'structure'},
                                 {   'smiles': 'OC[C@H]1O[C@H](O[C@@H]2[C@@H](CO)O[C@H](O[C@@H]3[C@@H](CO)O[C@H](O[C@@H]4[C@@H](CO)O[C@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O',
                                     'name': 'alpha-maltotetraose',
                                     'reason': 'Does not contain secondary '
                                               'alpha-hydroxy ketone '
                                               'structure'},
                                 {   'smiles': 'SC[C@H](N)C(=O)N[C@H](C(=O)N[C@@H](CCC(=O)N)C(O)=O)CO',
                                     'name': 'Cys-Ser-Gln',
                                     'reason': 'Does not contain secondary '
                                               'alpha-hydroxy ketone '
                                               'structure'}],
    'sample_false_negatives': [],
    'attempt': 3,
    'reasoning': '### Reasoning\n'
                 '\n'
                 'The previous code attempts to identify whether a given '
                 'molecule contains a secondary alpha-hydroxy ketone structure '
                 'by using a SMARTS pattern. However, the low F1 score '
                 'suggests that the pattern may not be accurately capturing '
                 'the chemical substructure in question, leading to both false '
                 'positives and false negatives.\n'
                 '\n'
                 "Let's break down the previous approach and possible reasons "
                 'for its failure:\n'
                 '\n'
                 '1. **SMARTS Pattern:** The pattern used was '
                 '`[CX3](=O)[CX4;H1]([OX2H])[#6]`. This pattern is meant to '
                 'identify a ketone `C(=O)` adjacent to a secondary carbon '
                 '(`[CX4;H1]` indicates a carbon with one hydrogen) bonded to '
                 'a hydroxyl group (`[OX2H]`). However, this pattern may not '
                 'correctly identify all stereo and positional variations of '
                 'secondary alpha-hydroxy ketones.\n'
                 '\n'
                 '2. **Substructure Matching:** The substructure pattern might '
                 'be too restrictive or misaligned with the diversity seen in '
                 'this class of compounds. For instance, certain '
                 'stereochemical configurations or ring structures might not '
                 'match the pattern even though they fit the class '
                 'description.\n'
                 '\n'
                 '3. **False Positives/Negatives:** The pattern might be '
                 'either too broad, capturing structures not belonging to the '
                 'class (false positives), or too narrow, missing legitimate '
                 'secondary alpha-hydroxy ketones (false negatives).\n'
                 '\n'
                 '### Improvement Steps\n'
                 '\n'
                 '1. **Expand the SMARTS Pattern:** Consider more flexibility '
                 'in both stereochemistry and connectivity of atoms. '
                 'Investigate if the missed cases have common substructures '
                 'that can be explicitly included.\n'
                 '\n'
                 '2. **Debug and Iteratively Test:** Use a variety of known '
                 'positives and negatives to iteratively refine the SMARTS '
                 'pattern, ensuring it captures the right structures.\n'
                 '\n'
                 '3. **Analyze Failure Cases:** Identify patterns in the false '
                 'positives and negatives to guide the adjustment of the '
                 'SMARTS string.\n'
                 '\n'
                 '### Revised Code',
    'success': True,
    'best': True,
    'error': '',
    'stdout': None,
    'num_true_positives': 194,
    'num_false_positives': 100,
    'num_true_negatives': 4677,
    'num_false_negatives': 0,
    'num_negatives': None,
    'precision': 0.6598639455782312,
    'recall': 1.0,
    'f1': 0.7950819672131146,
    'accuracy': 0.9798833232749949,
    'negative_predictive_value': 1.0}