"""
Classifies: CHEBI:132155 hydroxynaphthoquinone
"""
"""
Classifies: CHEBI:XXXXX hydroxynaphthoquinone
"""
from rdkit import Chem
from rdkit.Chem import AllChem
from rdkit.Chem import rdMolDescriptors

def is_hydroxynaphthoquinone(smiles: str):
    """
    Determines if a molecule is a hydroxynaphthoquinone based on its SMILES string.
    A hydroxynaphthoquinone is a naphthoquinone with at least one hydroxy group attached.

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

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

    # Define a more general naphthoquinone core pattern
    naphthoquinone_pattern = Chem.MolFromSmarts("c1ccc2C(=O)C=CC(=O)c2c1 |c1:1,2,3,4,5,6,7,8|")
    if not mol.HasSubstructMatch(naphthoquinone_pattern):
        # Try another possible naphthoquinone pattern (1,2-naphthoquinone)
        naphthoquinone_pattern = Chem.MolFromSmarts("c1ccc2C(=O)C(=O)C=Cc2c1 |c1:1,2,3,4,5,6,7,8|")
        if not mol.HasSubstructMatch(naphthoquinone_pattern):
            return False, "No naphthoquinone core found"

    # Define the hydroxy group pattern
    hydroxy_pattern = Chem.MolFromSmarts("[OH]")
    hydroxy_matches = mol.GetSubstructMatches(hydroxy_pattern)
    if len(hydroxy_matches) == 0:
        return False, "No hydroxy group found"

    # Check if at least one hydroxy group is directly attached to the naphthoquinone core
    naphthoquinone_atoms = mol.GetSubstructMatch(naphthoquinone_pattern)
    for match in hydroxy_matches:
        hydroxy_atom = match[0]
        for neighbor in mol.GetAtomWithIdx(hydroxy_atom).GetNeighbors():
            if neighbor.GetIdx() in naphthoquinone_atoms:
                return True, "Contains a naphthoquinone core with at least one hydroxy group attached"

    return False, "Hydroxy group not directly attached to the naphthoquinone core"


__metadata__ = {   'chemical_class': {   'id': 'CHEBI:XXXXX',
                          'name': 'hydroxynaphthoquinone',
                          'definition': 'Any naphthoquinone in which the naphthoquinone moiety is substituted by at least one hydroxy group.',
                          'parents': ['CHEBI:XXXXX', 'CHEBI:XXXXX']},
    'config': {   'llm_model_name': 'lbl/claude-sonnet',
                  'f1_threshold': 0.8,
                  'max_attempts': 5,
                  'max_positive_instances': None,
                  'max_positive_to_test': None,
                  'max_negative_to_test': None,
                  'max_positive_in_prompt': 50,
                  'max_negative_in_prompt': 20,
                  'max_instances_in_prompt': 100,
                  'test_proportion': 0.1},
    'message': None,
    'attempt': 0,
    'success': True,
    'best': True,
    'error': '',
    'stdout': None,
    'num_true_positives': 150,
    'num_false_positives': 4,
    'num_true_negatives': 182407,
    'num_false_negatives': 23,
    'num_negatives': None,
    'precision': 0.974025974025974,
    'recall': 0.8670520231213873,
    'f1': 0.9174311926605504,
    'accuracy': 0.9998521228585199}


__metadata__ = {   'chemical_class': {   'id': 'CHEBI:132155',
                          'name': 'hydroxynaphthoquinone',
                          'definition': 'Any naphthoquinone in which the '
                                        'naphthaoquinone moiety is substituted '
                                        'by at least one hydroxy group.',
                          'parents': ['CHEBI:132130', 'CHEBI:25481'],
                          'xrefs': ['Wikipedia:Hydroxynaphthoquinone'],
                          'all_positive_examples': []},
    'config': None,
    'message': '\n'
               'Attempt failed: F1 score of 0.34567901234567905 is too low.\n'
               'Outcomes:\n'
               '------\n'
               '\n'
               'True positives: SMILES: Oc1cc(O)c2C(=O)C=C(O)C(=O)c2c1 NAME: '
               'flaviolin REASON: CORRECT Contains a naphthoquinone core with '
               'at least one hydroxy group attached\n'
               ' * SMILES: CC1=C(O)C(=O)c2c(O)c(O)c(C)c(O)c2C1=O NAME: '
               'aureoquinone REASON: CORRECT Contains a naphthoquinone core '
               'with at least one hydroxy group attached\n'
               ' * SMILES: Oc1cccc2C(=O)C(=CC(=O)c12)c1ccc(O)c2c(O)cccc12 '
               'NAME: Hypoxylone REASON: CORRECT Contains a naphthoquinone '
               'core with at least one hydroxy group attached\n'
               ' * SMILES: '
               'OC1=C([C@H]2CC[C@@H](CC2)c2ccc(Cl)cc2)C(=O)c2ccccc2C1=O NAME: '
               'atovaquone REASON: CORRECT Contains a naphthoquinone core with '
               'at least one hydroxy group attached\n'
               ' * SMILES: CC(C)=CC[C@H](O)C1=CC(=O)c2c(O)ccc(O)c2C1=O NAME: '
               'Alkannin REASON: CORRECT Contains a naphthoquinone core with '
               'at least one hydroxy group attached\n'
               ' * SMILES: '
               'CC(C)(COC(=O)c1ccc2OCOc2c1)CC1=C(O)C(=O)c2ccccc2C1=O NAME: '
               'rhinacanthin D REASON: CORRECT Contains a naphthoquinone core '
               'with at least one hydroxy group attached\n'
               ' * SMILES: CC(C)=CC[C@@H](O)C1=CC(=O)c2c(O)ccc(O)c2C1=O NAME: '
               'Shikonin REASON: CORRECT Contains a naphthoquinone core with '
               'at least one hydroxy group attached\n'
               ' * SMILES: '
               'COC1=CC(=O)c2c(O)c(OC)c3C[C@](C)(O)[C@H](C(C)=O)c4c(OC)c(O)c5C(=O)C=C(OC)C(=O)c5c4-c3c2C1=O '
               'NAME: hypocrellin D REASON: CORRECT Contains a naphthoquinone '
               'core with at least one hydroxy group attached\n'
               ' * SMILES: Oc1cccc2C(=O)C=CC(=O)c12 NAME: juglone REASON: '
               'CORRECT Contains a naphthoquinone core with at least one '
               'hydroxy group attached\n'
               ' * SMILES: OCCC1=C(O)C(=O)c2ccccc2C1=O NAME: '
               '2-hydroxy-3-(2-hydroxyethyl)naphthalene-1,4-dione REASON: '
               'CORRECT Contains a naphthoquinone core with at least one '
               'hydroxy group attached\n'
               ' * SMILES: Oc1ccc(O)c2C(=O)C=CC(=O)c12 NAME: naphthazarin '
               'REASON: CORRECT Contains a naphthoquinone core with at least '
               'one hydroxy group attached\n'
               ' * SMILES: COC1=C(C)C(=O)c2c(O)cc(OC\\C=C(/C)CCC=C(C)C)cc2C1=O '
               'NAME: 7-O-geranyl-2-O,3-dimethylflaviolin REASON: CORRECT '
               'Contains a naphthoquinone core with at least one hydroxy group '
               'attached\n'
               ' * SMILES: '
               'CC(C)=CC[C@@H](OC(=O)C=C(C)C)C1=CC(=O)c2c(O)ccc(O)c2C1=O NAME: '
               'beta,beta-Dimethylacrylshikonin REASON: CORRECT Contains a '
               'naphthoquinone core with at least one hydroxy group attached\n'
               ' * SMILES: CC(=O)OC(CC=C(C)C)C1=CC(=O)c2c(O)ccc(O)c2C1=O NAME: '
               'Acetylshikonin REASON: CORRECT Contains a naphthoquinone core '
               'with at least one hydroxy group attached\n'
               ' * SMILES: '
               'C\\C=C(/C)CC\\C=C(/C)C(=O)OCC(C)(C)CC1=C(O)C(=O)c2ccccc2C1=O '
               'NAME: rhinacanthin C REASON: CORRECT Contains a naphthoquinone '
               'core with at least one hydroxy group attached\n'
               ' * SMILES: Cc1ccc(O)c2C(=O)C(C)=C(O)C(=O)c12 NAME: '
               'Aristolindiquinone REASON: CORRECT Contains a naphthoquinone '
               'core with at least one hydroxy group attached\n'
               ' * SMILES: '
               'C[C@@H](\\C=C\\C=C(/C)C(O)=O)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](O)[C@H](C)[C@@H](O)C(C)\\C=C(/C)C(=O)c1c(O)c(C)cc2C(=O)C(N)=CC(=O)c12 '
               'NAME: rifamycin-undecaketide carboxylic acid REASON: CORRECT '
               'Contains a naphthoquinone core with at least one hydroxy group '
               'attached\n'
               ' * SMILES: COC1=C(C)C(=O)c2c(O)cc(O)cc2C1=O NAME: '
               '2-O,3-dimethylflaviolin REASON: CORRECT Contains a '
               'naphthoquinone core with at least one hydroxy group attached\n'
               ' * SMILES: COC1=C(OC)C(=O)c2c(O)c3OCOc3c(O)c2C1=O NAME: '
               'Tricrozarin A REASON: CORRECT Contains a naphthoquinone core '
               'with at least one hydroxy group attached\n'
               ' * SMILES: '
               'CC(C)=CC[C@H](OC(=O)C=C(C)C)C1=CC(=O)c2c(O)ccc(O)c2C1=O NAME: '
               'Alkannin beta,beta-dimethylacrylate REASON: CORRECT Contains a '
               'naphthoquinone core with at least one hydroxy group attached\n'
               ' * SMILES: C1=CC=C(C2=C1C(C=C(C2=O)O)=O)O NAME: '
               '2,8-dihydroxy-1,4-naphthoquinone REASON: CORRECT Contains a '
               'naphthoquinone core with at least one hydroxy group attached\n'
               ' * SMILES: Cc1cc(O)c2C(=O)C=CC(=O)c2c1 NAME: Ramentaceone '
               'REASON: CORRECT Contains a naphthoquinone core with at least '
               'one hydroxy group attached\n'
               ' * SMILES: '
               'Cc1cc(O)c2C(=O)C=C(C(=O)c2c1)c1c(C)cc2C(=O)C=CC(=O)c2c1O NAME: '
               'Diospyrin REASON: CORRECT Contains a naphthoquinone core with '
               'at least one hydroxy group attached\n'
               ' * SMILES: C12=C(C(C(C)=C(C1=O)O)=O)C=CC=C2O NAME: Droserone '
               'REASON: CORRECT Contains a naphthoquinone core with at least '
               'one hydroxy group attached\n'
               ' * SMILES: '
               'CC(C)C(=O)O[C@H](CC=C(C)C)C1=CC(=O)c2c(O)ccc(O)c2C1=O NAME: '
               'Isobutylshikonin REASON: CORRECT Contains a naphthoquinone '
               'core with at least one hydroxy group attached\n'
               'False positives: SMILES: O=C1C(O)=C(O)C(=O)C=2C1=C(O)C=C(OC)C2 '
               'NAME: 7-O-methylspinochrome B (2, 3,5trihydroxy-7-methoxy-l , '
               '4-naphthoquinone) REASON: WRONGLY CLASSIFIED Contains a '
               'naphthoquinone core with at least one hydroxy group attached\n'
               ' * SMILES: O=C1C2=C(C(=O)C=C1C)C=C(O)C(=C2)C NAME: '
               '6-hydroxy-2,7-dimethyl-1,4-naphthoquinone REASON: WRONGLY '
               'CLASSIFIED Contains a naphthoquinone core with at least one '
               'hydroxy group attached\n'
               ' * SMILES: '
               'O=C1C2=C(C(=O)C3=C1[C@H]4[C@](O)(C[C@H](C)C[C@H]4O)[C@H](C3)O)C(O)=CC=C2 '
               'NAME: Saccharosporone B REASON: WRONGLY CLASSIFIED Contains a '
               'naphthoquinone core with at least one hydroxy group attached\n'
               ' * SMILES: '
               'O=C1NC=2C(=O)C3=C(O)C(=C(O)C(=C3C(C2)=O)C(=O)C(=CC4OC4[C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]([C@H](C=CC=C1C)C)O)C)O)C)O)C)C)C '
               'NAME: 27,28-epoxy-28-desmethylrifamycin W REASON: WRONGLY '
               'CLASSIFIED Contains a naphthoquinone core with at least one '
               'hydroxy group attached\n'
               ' * SMILES: '
               'O=C1O[C@H](CC=C[C@@H](CCC(C=2C=3C(C=4[C@]1(C=CC(=O)NC4C(=O)C3C=C(C)C2O)C)=O)=O)CC)CC(C)C '
               'NAME: Olimycin A REASON: WRONGLY CLASSIFIED Contains a '
               'naphthoquinone core with at least one hydroxy group attached\n'
               ' * SMILES: '
               'O=C1C(=CC([C@H](O)[C@H]([C@@H](O)[C@@H]([C@H](O)[C@@H]([C@@H](O)[C@@H](C)C=CC=CC(NC=2C(C3=C(C1=C(O)C(=C3O)C)C(=O)C2)=O)=O)C)C)C)C)C '
               'NAME: 16-demethyl-34a-dehydroxy rifamycin W REASON: WRONGLY '
               'CLASSIFIED Contains a naphthoquinone core with at least one '
               'hydroxy group attached\n'
               ' * SMILES: '
               'O=C1C2=C(O)C3=C(OC)C(=CC=C3C=C2C(=O)C4=C1CC[C@@](C4)(O)C)C '
               'NAME: M-4 REASON: WRONGLY CLASSIFIED Contains a naphthoquinone '
               'core with at least one hydroxy group attached\n'
               ' * SMILES: '
               'O=C1C2=C(O)C(=CC=C2C(=O)C3=C1C=C[C@]4([C@@]3(O)C(=O)C[C@@](OC5OC(C(OC6OC(C(=O)C=C6)C)CC5)C)(C)C4)O)C7O[C@@H]([C@H]8OC9O[C@@H](C)[C@@H](C[C@@H]9O[C@@H]8C7)O)C '
               'NAME: PI-083 REASON: WRONGLY CLASSIFIED Contains a '
               'naphthoquinone core with at least one hydroxy group attached\n'
               ' * SMILES: '
               'S(C1=C2NC(=O)C=CC=CC=C[C@H]([C@@H](O)CC(=O)C(C)=CC[C@H](C=C[C@@H]([C@@H]([C@H](C=C(C(C=3C(C1=O)=C(C2=O)C=C(C)C3O)=O)C)C)O)C)O)C)C '
               'NAME: Naphthoquinomycin B REASON: WRONGLY CLASSIFIED Contains '
               'a naphthoquinone core with at least one hydroxy group '
               'attached\n'
               ' * SMILES: '
               'C[C@@H]1O[C@H](CC[C@@H]1O)O[C@]12C(=O)C[C@](C)(O)C[C@@]1(O)C=CC1=C2C(=O)c2ccc([C@H]3C[C@@H](O[C@H]4CC[C@H](O[C@H]5C[C@@H](O)[C@H](O)[C@@H](C)O5)[C@H](C)O4)[C@H](O)[C@@H](C)O3)c(O)c2C1=O '
               'NAME: urdamycin A REASON: WRONGLY CLASSIFIED Contains a '
               'naphthoquinone core with at least one hydroxy group attached\n'
               ' * SMILES: '
               'O=C1C=2OC([C@H]3C[C@H](O)C(=C[C@H]3C2C(=O)C=4C1=C(O)C(=C(O)C4)C)C)(C)C '
               'NAME: Unnamed naphterpin 1 REASON: WRONGLY CLASSIFIED Contains '
               'a naphthoquinone core with at least one hydroxy group '
               'attached\n'
               ' * SMILES: '
               'O=C1C2=C(C(=O)C=C1C)C(=C(O)C=C2)[C@]3(O)NC(=O)C4=C3C=CC=C4OC '
               'NAME: '
               '6-hydroxy-5-(1-hydroxy-4-methoxy-3-oxo-2H-isoindol-1-yl)-2-methylnaphthalene-1,4-dione '
               'REASON: WRONGLY CLASSIFIED Contains a naphthoquinone core with '
               'at least one hydroxy group attached\n'
               ' * SMILES: '
               'O=C1C2=C(C(O)=C(C)C=C2C(=O)C=3C1=C(O)C=C(OC)C3)C4=C(O)C=5C(=O)C6=C(C(O)C(O)(C)C(C6O)O)C(C5C=C4OC)=O '
               'NAME: Alterporriol C REASON: WRONGLY CLASSIFIED Contains a '
               'naphthoquinone core with at least one hydroxy group attached\n'
               ' * SMILES: '
               'C[C@@H]1C[C@@H](OC(C)=O)[C@H](O)[C@]2(O1)O[C@H](CC(O)=O)CC1=C2C(=O)c2c(O)cccc2C1=O '
               'NAME: griseusin B REASON: WRONGLY CLASSIFIED Contains a '
               'naphthoquinone core with at least one hydroxy group attached\n'
               ' * SMILES: '
               'O=C1NC=2C(=O)C3=C(O)C(=C4O[C@@](C(C4=C3C(C2)=O)=O)(OC=C[C@H](OC)[C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]([C@H](C=CC=C1)C)O)C)O)C)OC(=O)C)C)C)C '
               'NAME: 16-demethylrifamycin S REASON: WRONGLY CLASSIFIED '
               'Contains a naphthoquinone core with at least one hydroxy group '
               'attached\n'
               ' * SMILES: '
               'O=C1C2=C(C(=O)C3=C1C=C(OC)C=C3O)[C@@H](OC(=C2)C)OC[C@@H]4C(=O)CC[C@@H]4C '
               'NAME: 1R, 4′S, 5′R -ulosporin G REASON: WRONGLY CLASSIFIED '
               'Contains a naphthoquinone core with at least one hydroxy group '
               'attached\n'
               ' * SMILES: '
               'O=C1C2=C(O)C(=CC=C2C(=O)C3=C1C=C[C@]4([C@]3(O)C(=O)C[C@@](OC5OC(C(=O)C=C5)C)(C)C4)O)[C@H]6O[C@H]([C@H](OC7OC(C(=O)C=C7)C)[C@H](C6)O)C '
               'NAME: Saprolmycin A REASON: WRONGLY CLASSIFIED Contains a '
               'naphthoquinone core with at least one hydroxy group attached\n'
               ' * SMILES: '
               'O=C1OC(C(=O)O)=CC=2C1=C(O)C=3O[C@]4(OC=5C(O)=C6C(=O)C(OC)=CC(C6=C(C5C4)O)=O)CCC3C2 '
               'NAME: Rubromycin CA1 REASON: WRONGLY CLASSIFIED Contains a '
               'naphthoquinone core with at least one hydroxy group attached\n'
               ' * SMILES: '
               'O=C1O[C@@H](C=C[C@@H](CCC(C=2C=3C(C=4[C@@]1(C=CC(=O)NC4C(=O)C3C=C(C)C2O)C)=O)=O)CC)[C@@H](O)C=C(C)C '
               'NAME: Divergolide I REASON: WRONGLY CLASSIFIED Contains a '
               'naphthoquinone core with at least one hydroxy group attached\n'
               ' * SMILES: '
               'O=C1NC=2C(=O)C3=C(C(C(=O)C(=C[C@@H]([C@H](O)[C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]([C@H](C=CC=C1C)C)O)C)O)C)O)C)C)C)=C(O)C(=C3)C)C(C2)=O '
               'NAME: Proansamycin B REASON: WRONGLY CLASSIFIED Contains a '
               'naphthoquinone core with at least one hydroxy group attached\n'
               ' * SMILES: '
               'O=C1C2=C(C3=C4C(=O)C5=C(C[C@@H](O)[C@]([C@@H]5O)(O)C)C(C4=C(O)C=C3OC)=O)C(OC)=CC(=C2C(=O)C6=C1[C@@H](O)[C@@](O)(C)[C@@H](C6)O)O '
               'NAME: Alterporriol N REASON: WRONGLY CLASSIFIED Contains a '
               'naphthoquinone core with at least one hydroxy group attached\n'
               ' * SMILES: O=C1C2=C(C(=O)C=C1C(O)C(O)CC(=O)OC)C(O)=CC=C2 NAME: '
               'Khatmiamycin REASON: WRONGLY CLASSIFIED Contains a '
               'naphthoquinone core with at least one hydroxy group attached\n'
               ' * SMILES: '
               'O=C1C=2OC([C@H]3CC[C@@](C=C3C2C(=O)C=4C1=C(O)C(=C(O)C4)C)(O)C)(C)C '
               'NAME: Naphterpin A REASON: WRONGLY CLASSIFIED Contains a '
               'naphthoquinone core with at least one hydroxy group attached\n'
               ' * SMILES: '
               'CC(C)C1=C(O)C(=O)c2c(C)c3c(OC(O)[C@]3(C)CC=C)c(O)c2C1=O NAME: '
               'Coleone A REASON: WRONGLY CLASSIFIED Contains a naphthoquinone '
               'core with at least one hydroxy group attached\n'
               ' * SMILES: '
               'O=C1C(OC)=CC(=O)C2=C1C=C3C[C@@H]4[C@@H](O[C@@H]5O[C@@H]([C@@H](O[C@@H]6O[C@H]([C@@H](O[C@@H]7O[C@H]([C@@H](O[C@@H]8O[C@H]([C@@H](OC(=O)C(C(=O)O)(C)C)CC8)C)CC7)C)CC6)C)CC5)C)C(=O)C(=C([C@@]4(C(C3=C2O)=O)O[C@@H]9O[C@@H]([C@@H](O[C@@H]%10O[C@@H]([C@@H](O)CC%10)C)CC9)C)O)C(=O)N '
               'NAME: Cervimycin C REASON: WRONGLY CLASSIFIED Contains a '
               'naphthoquinone core with at least one hydroxy group attached\n'
               'False negatives: SMILES: '
               '[C@H](C)([C@@H]([C@@H]([C@H](\\C=C\\O[C@]1(OC=2C(C1=O)=C3C(C(C(C(=C3[O-])/C=N/N4CCN(CC4)C)=O)=O)=C(C2C)[O-])C)OC)C)OC(=O)C)[C@H](O)[C@@H]([C@@H](O)[C@@H](C)/C=C/C=C(/C)\\C(N)=O)C '
               'NAME: rifampicin ortho-naphthoquinone carboxamide(2-) REASON: '
               'MISSED No naphthoquinone core found\n'
               ' * SMILES: '
               '[C@H](C)([C@@H]([C@@H]([C@H](\\C=C\\O[C@]1(OC=2C(C1=O)=C3C(C(C(C=C3[O-])=O)=O)=C(C2C)[O-])C)OC)C)OC(=O)C)[C@H](O)[C@@H]([C@@H](O)[C@@H](C)/C=C/C=C(/C)\\C(N)=O)C '
               'NAME: rifamycin SV ortho-naphthoquinone carboxamide(2-) '
               'REASON: MISSED No naphthoquinone core found\n'
               ' * SMILES: '
               '[C@H](C)([C@@H]([C@@H]([C@H](\\C=C\\O[C@]1(OC=2C(C1=O)=C3C(C(C(=CC3=O)[O-])=O)=C(C2C)[O-])C)OC)C)OC(=O)C)[C@H](O)[C@@H]([C@@H](O)[C@@H](C)/C=C/C=C(/C)\\C(N)=O)C '
               'NAME: rifamycin SV para-naphthoquinone carboxamide(2-) REASON: '
               'MISSED Hydroxy group not attached to the naphthoquinone core\n'
               ' * SMILES: '
               '[C@H](C)([C@@H]([C@@H]([C@H](\\C=C\\O[C@]1(OC=2C(C1=O)=C3C(C(C(=C(C3=O)/C=N/N4CCN(CC4)C)[O-])=O)=C(C2C)[O-])C)OC)C)OC(=O)C)[C@H](O)[C@@H]([C@@H](O)[C@@H](C)/C=C/C=C(/C)\\C(N)=O)C '
               'NAME: rifampicin para-naphthoquinone carboxamide(2-) REASON: '
               'MISSED Hydroxy group not attached to the naphthoquinone core\n'
               ' * SMILES: CC(C)c1cc(O)c(C=O)c2C(=O)C(=O)C(C)=Cc12 NAME: '
               'Hibiscoquinone A REASON: MISSED No naphthoquinone core found\n'
               ' * SMILES: '
               'C1CC(CCC1C2=CC=C(C=C2)Cl)C3=C(C4=CC=CC=C4C(=O)C3=O)O NAME: '
               '3-[4-(p-chlorophenyl)cyclohexyl]-4-hydroxy-1,2-naphthoquinone '
               'REASON: MISSED No naphthoquinone core found\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': 'O(C(=O)CCCCCCCCCCC/C=C\\CCCCCCCC)C[C@H](OC(=O)CCCCCCC/C=C\\CCCCCC)COC(=O)CCCC/C=C\\C/C=C\\C/C=C\\C/C=C\\CC',
                                     'name': 'TG(22:1(13Z)/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))',
                                     'reason': 'No naphthoquinone core found'},
                                 {   'smiles': 'O1C2C(C3(C(C4C(C5(C(CC4)CC(OC6OC(C(OC7OC(C(O)C(O)C7O)C)C(O)C6O)COC8OC(C(O)C(O)C8O)CO)CC5)C)CC3)C2)C)C(C19OCC(CC9)C)C',
                                     'name': 'Desglucoparillin',
                                     'reason': 'No naphthoquinone core found'},
                                 {   'smiles': '[C@H]1(O)C(O)O[C@H](C=O)[C@H]([C@@H]1O)O',
                                     'name': '6-dehydro-D-glucose',
                                     'reason': 'No naphthoquinone core found'},
                                 {   'smiles': 'C1=CC(=CC=C1NC2=C(C=NC=C2)S(=O)(=O)N)Cl',
                                     'name': '4-(4-chloroanilino)-3-pyridinesulfonamide',
                                     'reason': 'No naphthoquinone core found'},
                                 {   'smiles': 'C=1([NH+]=C(C=C(N1)NCC=2ON=C(N2)C(N)=O)C(C)C)N',
                                     'name': '2-amino-4-{[(3-carbamoyl-1,2,4-oxadiazol-5-yl)methyl]amino}-6-isopropylpyrimidin-1-ium',
                                     'reason': 'No naphthoquinone core found'},
                                 {   'smiles': 'O([C@@H]1[C@@H](O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O[C@@H]([C@@H]1O)CO)O)[C@H]3O[C@@H]([C@@H](O)[C@H](O)[C@@H]3O)CO',
                                     'name': '(2R,3S,4S,5S,6R)-2-[(2S,3R,4S,5S,6R)-2,5-Dihydroxy-6-(hydroxymethyl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol',
                                     'reason': 'No naphthoquinone core found'},
                                 {   'smiles': 'COC1=CC=C(C=C1)S(=O)(=O)NC2=CC3=C(C=C2)O[C@@H]4[C@H]3C[C@@H](O[C@@H]4CO)CC(=O)O',
                                     'name': '2-[(1R,3R,4aS,9aR)-1-(hydroxymethyl)-6-[(4-methoxyphenyl)sulfonylamino]-3,4,4a,9a-tetrahydro-1H-pyrano[3,4-b]benzofuran-3-yl]acetic '
                                             'acid',
                                     'reason': 'No naphthoquinone core found'},
                                 {   'smiles': 'O=C(C=1NC=CC1)[C@@H]2[C@@H](C=C[C@H]3[C@H]2CCC3)C=CC=C([C@@H]4O[C@@H]([C@H](C(=O)O)C)CC[C@@H]4C)CC',
                                     'name': 'A83094A',
                                     'reason': 'No naphthoquinone core found'},
                                 {   'smiles': 'C[C@H](O)[C@H](O)[C@@H](O)C(=O)COP(O)(O)=O',
                                     'name': 'L-rhamnulose 1-phosphate',
                                     'reason': 'No naphthoquinone core found'},
                                 {   'smiles': 'COc1ccc(\\C=C\\C(=O)N[C@H](CCCNC(N)=N)C(O)=O)cc1Br',
                                     'name': 'subereamine A',
                                     'reason': 'No naphthoquinone core found'}],
    'sample_false_negatives': [   {   'smiles': '[C@H](C)([C@@H]([C@@H]([C@H](\\C=C\\O[C@]1(OC=2C(C1=O)=C3C(C(C(C(=C3[O-])/C=N/N4CCN(CC4)C)=O)=O)=C(C2C)[O-])C)OC)C)OC(=O)C)[C@H](O)[C@@H]([C@@H](O)[C@@H](C)/C=C/C=C(/C)\\C(N)=O)C',
                                      'name': 'rifampicin ortho-naphthoquinone '
                                              'carboxamide(2-)',
                                      'reason': 'Hydroxy group not directly '
                                                'attached to the '
                                                'naphthoquinone core'},
                                  {   'smiles': '[C@H](C)([C@@H]([C@@H]([C@H](\\C=C\\O[C@]1(OC=2C(C1=O)=C3C(C(C(C=C3[O-])=O)=O)=C(C2C)[O-])C)OC)C)OC(=O)C)[C@H](O)[C@@H]([C@@H](O)[C@@H](C)/C=C/C=C(/C)\\C(N)=O)C',
                                      'name': 'rifamycin SV '
                                              'ortho-naphthoquinone '
                                              'carboxamide(2-)',
                                      'reason': 'Hydroxy group not directly '
                                                'attached to the '
                                                'naphthoquinone core'},
                                  {   'smiles': '[C@H](C)([C@@H]([C@@H]([C@H](\\C=C\\O[C@]1(OC=2C(C1=O)=C3C(C(C(=CC3=O)[O-])=O)=C(C2C)[O-])C)OC)C)OC(=O)C)[C@H](O)[C@@H]([C@@H](O)[C@@H](C)/C=C/C=C(/C)\\C(N)=O)C',
                                      'name': 'rifamycin SV '
                                              'para-naphthoquinone '
                                              'carboxamide(2-)',
                                      'reason': 'Hydroxy group not directly '
                                                'attached to the '
                                                'naphthoquinone core'},
                                  {   'smiles': '[C@H](C)([C@@H]([C@@H]([C@H](\\C=C\\O[C@]1(OC=2C(C1=O)=C3C(C(C(=C(C3=O)/C=N/N4CCN(CC4)C)[O-])=O)=C(C2C)[O-])C)OC)C)OC(=O)C)[C@H](O)[C@@H]([C@@H](O)[C@@H](C)/C=C/C=C(/C)\\C(N)=O)C',
                                      'name': 'rifampicin para-naphthoquinone '
                                              'carboxamide(2-)',
                                      'reason': 'Hydroxy group not directly '
                                                'attached to the '
                                                'naphthoquinone core'}],
    'attempt': 1,
    'reasoning': 'The previous code had a few issues that led to incorrect '
                 'classifications:\n'
                 '\n'
                 '1. **Naphthoquinone Core Pattern**: The pattern '
                 '`c1ccc2C(=O)C=CC(=O)c2c1` only matches a specific '
                 'arrangement of the naphthoquinone core, but there are other '
                 'possible arrangements (e.g., 1,2-naphthoquinone vs. '
                 '1,4-naphthoquinone). This led to some false negatives where '
                 'the naphthoquinone core was present but not matched by the '
                 'pattern.\n'
                 '\n'
                 '2. **Hydroxy Group Attachment Check**: The code checked if '
                 'the hydroxy group was attached to any atom in the '
                 "naphthoquinone core, but it didn't account for cases where "
                 'the hydroxy group might be part of a larger substituent that '
                 'is attached to the core. This led to some false positives.\n'
                 '\n'
                 '3. **Complex Structures**: Some of the false positives were '
                 'due to complex structures where the hydroxy group was not '
                 'directly attached to the naphthoquinone core but was part of '
                 'a larger substituent.\n'
                 '\n'
                 'To improve the code, we need to:\n'
                 '- Use a more general pattern for the naphthoquinone core.\n'
                 '- Ensure that the hydroxy group is directly attached to the '
                 'naphthoquinone core.\n'
                 '- Handle complex structures more carefully.\n'
                 '\n'
                 'Here is the improved code:',
    'success': True,
    'best': True,
    'error': '',
    'stdout': None,
    'num_true_positives': 30,
    'num_false_positives': 100,
    'num_true_negatives': 35958,
    'num_false_negatives': 4,
    'num_negatives': None,
    'precision': 0.23076923076923078,
    'recall': 0.8823529411764706,
    'f1': 0.36585365853658536,
    'accuracy': 0.9971184750083121,
    'negative_predictive_value': 0.9998887714810077}