"""
Classifies: CHEBI:26244 prenols
"""
from rdkit import Chem

def is_prenols(smiles: str):
    """
    Determines if a molecule is a prenol based on its SMILES string.
    A prenol contains one or more isoprene units and an alcohol (OH) group
    or a phosphate group.

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

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

    # Refined isoprene unit patterns
    # Common isoprene configurations - linear or terminal methyl as seen in prenol forms
    isoprene_unit_1 = Chem.MolFromSmarts("C(=C)C(C)C")  # Example pattern for typical isoprene
    isoprene_unit_2 = Chem.MolFromSmarts("CC(=CC)C")    # Alternate pattern
    
    # Searching both isoprene patterns 
    num_isoprene_units = len(mol.GetSubstructMatches(isoprene_unit_1)) + len(mol.GetSubstructMatches(isoprene_unit_2))

    # Check for isoprene units
    if num_isoprene_units == 0:
        return False, "No isoprene units found"

    # Check for alcohol group
    oh_group = Chem.MolFromSmarts("[OX2H]")
    has_oh_group = mol.HasSubstructMatch(oh_group)
    
    # Check for phosphate groups
    phosphate_group = Chem.MolFromSmarts("P(=O)(O)[O-]")    # Refine to reflect divalent portrayal and deoxidized forms
    has_phosphate_group = mol.HasSubstructMatch(phosphate_group)

    # Ensure at least one of the groups (OH/phosphate) is present
    if has_oh_group:
        return True, f"Contains {num_isoprene_units} isoprene unit(s) and an alcohol group (OH)"
    elif has_phosphate_group:
        return True, f"Contains {num_isoprene_units} isoprene unit(s) and a phosphate group"
    
    return False, "No alcohol (OH) or phosphate group found"


__metadata__ = {   'chemical_class': {   'id': 'CHEBI:26244',
                          'name': 'prenols',
                          'definition': 'Any alcohol possessing the general '
                                        'formula H-[CH2C(Me)=CHCH2]nOH in '
                                        'which the carbon skeleton is composed '
                                        'of one or more isoprene units '
                                        '(biogenetic precursors of the '
                                        'isoprenoids).',
                          'parents': ['CHEBI:24913', 'CHEBI:30879'],
                          'xrefs': ['PMID:3113948', 'PMID:4207873'],
                          'all_positive_examples': []},
    'config': None,
    'message': '\n'
               'Attempt failed: F1 score of 0.40935672514619886 is too low.\n'
               'Outcomes:\n'
               '------\n'
               '\n'
               'True positives: SMILES: '
               'OC\\C=C(\\CC\\C=C(\\CC/C=C(\\CC/C=C(\\CC/C=C(\\CC\\C=C(\\CCCC(CCCC(CCCC(C)C)C)C)/C)/C)/C)/C)/C)/C '
               'NAME: '
               '(2E,6E,10Z,14Z,18Z,22E)-3,7,11,15,19,23,27,31,35-Nonamethylhexatriaconta-2,6,10,14,18,22-hexaen-1-ol '
               'REASON: CORRECT Contains 11 isoprene unit(s) and an alcohol '
               'group (OH)\n'
               ' * SMILES: '
               'CC(C)=CCC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\COP([O-])(=O)OP([O-])([O-])=O '
               'NAME: all-trans-hexaprenyl diphosphate(3-) REASON: CORRECT '
               'Contains 10 isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: C\\C(CO)=C/CC\\C(C)=C\\C=O NAME: '
               '(6E)-8-hydroxygeranial REASON: CORRECT Contains 2 isoprene '
               'unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'CC(C)=CCC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C/CC\\C(C)=C/CC\\C(C)=C/CC\\C(C)=C/CC\\C(C)=C/CC\\C(C)=C/CC\\C(C)=C/CC\\C(C)=C/COP([O-])(=O)OP([O-])([O-])=O '
               'NAME: ditrans,polycis-undecaprenyl diphosphate(3-) REASON: '
               'CORRECT Contains 20 isoprene unit(s) and an alcohol group '
               '(OH)\n'
               ' * SMILES: '
               'C(/C=C(/CC\\C=C(\\CC/C=C(\\C)/CCC=C(C)C)/C)\\C)C\\C(\\C)=C\\CC\\C(\\C)=C\\CC/C(/C)=C/CC\\C(=C\\CO)\\C '
               'NAME: all-trans-octaprenol REASON: CORRECT Contains 14 '
               'isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'OC(CCC=C(C)C)(CCCC(O)(CCCC(O)(CCCC(O)(CCCC(O)(CCCC(O)(CCCC(O)(CCC/C(=C/CC/C(=C/CO)/C)/C)C)C)C)C)C)C)C '
               'NAME: Bionectin F REASON: CORRECT Contains 4 isoprene unit(s) '
               'and an alcohol group (OH)\n'
               ' * SMILES: CC(C)=CCC\\C(C)=C/CC\\C(C)=C\\CO NAME: '
               '(2-trans,6-cis)-farnesol REASON: CORRECT Contains 4 isoprene '
               'unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'CC(C)=CCC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\COP([O-])(=O)OP([O-])([O-])=O '
               'NAME: all-trans-decaprenyl diphosphate(3-) REASON: CORRECT '
               'Contains 18 isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: C(=C\\CO)(\\CCC=C(C)C)/C NAME: nerol REASON: '
               'CORRECT Contains 2 isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'OC(CCC(O)C(O)(C)C)(CCCC(O)(CCCC(O)(CCCC(O)(CCCC(O)(CCC/C(=C/CC/C(=C/CC/C(=C/CO)/C)/C)/C)C)C)C)C)C '
               'NAME: Glisoprenin F REASON: CORRECT Contains 5 isoprene '
               'unit(s) and an alcohol group (OH)\n'
               ' * SMILES: CC(C)=CCC\\C(C)=C\\CC\\C(C)=C\\CO NAME: '
               '(2-trans,6-trans)-farnesol REASON: CORRECT Contains 4 isoprene '
               'unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'OCC[C@H](CC/C=C(\\CC/C=C(\\CC/C=C(\\CC/C=C(\\CC/C=C(\\CC/C=C(\\CC/C=C(\\CC/C=C(\\CC/C=C(\\CC/C=C(\\CC/C=C(\\CC/C=C(\\CC/C=C(\\CC/C=C(\\CC/C=C(\\CC\\C=C(\\CC/C=C(/CCC=C(C)C)\\C)/C)/C)/C)/C)/C)/C)/C)/C)/C)/C)/C)/C)/C)/C)/C)/C)C '
               'NAME: Dolichol-19 REASON: CORRECT Contains 35 isoprene unit(s) '
               'and an alcohol group (OH)\n'
               ' * SMILES: '
               'OC(C(O)CC/C(=C/CC/C(=C/CC/C(=C/CO)/C)/C)/C)(CCCC(O)(CCCC(O)(CCCC(O)(CCCC(O)(CCCC(O)(CCCC(O)(CCCC(O)(CCCC(O)(CCCC(O)(CCCC(O)(CCC=C(C)C)C)C)C)C)C)C)C)C)C)C)C '
               'NAME: SCH 66878 REASON: CORRECT Contains 6 isoprene unit(s) '
               'and an alcohol group (OH)\n'
               ' * SMILES: '
               'OC(CCC=C(C)C)(CCCC(O)(CCCC(O)(CCCC(O)(CCCC(=CCCC(=CCCC(=CCCC(=CCO)C)C)C)C)C)C)C)C '
               'NAME: Glisoprenin A REASON: CORRECT Contains 8 isoprene '
               'unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'OC(CCC(O)C(O)(C)C)(CCCC(O)(CCCC(O)(CCCC(O)(CCC/C(=C/CC/C(=C/CC/C(=C/CC/C(=C/CO)/C)/C)/C)/C)C)C)C)C '
               'NAME: Glisoprenin D REASON: CORRECT Contains 7 isoprene '
               'unit(s) and an alcohol group (OH)\n'
               ' * SMILES: CC(C)=CCC\\C(C)=C/CC\\C(C)=C/CO NAME: '
               '(2-cis,6-cis)-farnesol REASON: CORRECT Contains 4 isoprene '
               'unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'CC(C)=CCC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\COP([O-])([O-])=O '
               'NAME: undecaprenyl phosphate(2-) REASON: CORRECT Contains 20 '
               'isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'C(C\\C=C(\\CC\\C=C(\\CC\\C=C(\\CCC=C(C)C)/C)/C)/C)/C(=C\\CO)/C '
               'NAME: (2Z,6E,10E,14E)-geranylfarnesol REASON: CORRECT Contains '
               '8 isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: [H]C(CO)=C(C)CCC([H])=C(C)CCC=C(C)C NAME: farnesol '
               'REASON: CORRECT Contains 4 isoprene unit(s) and an alcohol '
               'group (OH)\n'
               ' * SMILES: '
               'C(C\\C=C(\\CC\\C=C(\\CC\\C=C(\\CCC=C(C)C)/C)/C)/C)/C(=C/CO)/C '
               'NAME: (2E,6E,10E,14E)-geranylfarnesol REASON: CORRECT Contains '
               '8 isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'CC(C)=CCC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CO '
               'NAME: solanesol REASON: CORRECT Contains 16 isoprene unit(s) '
               'and an alcohol group (OH)\n'
               ' * SMILES: '
               'CC(C)=CCC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CC\\C(C)=C\\CO '
               'NAME: all-trans-undecaprenol REASON: CORRECT Contains 20 '
               'isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'C(/C=C(/CCC=C(C)C)\\C)C\\C(\\C)=C\\CC\\C(\\C)=C\\CC/C(/C)=C/CC\\C(=C\\CO)\\C '
               'NAME: all-trans-hexaprenol REASON: CORRECT Contains 10 '
               'isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: CC(C)=CCC\\C(C)=C\\CC\\C(C)=C/CO NAME: '
               '(2-cis,6-trans)-farnesol REASON: CORRECT Contains 4 isoprene '
               'unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'OC(C(O)CO)(CC/C=C(/CC/C=C(/CCCC(O)(CCCC(O)(CCCC(O)(CCCC(O)(CCCC(O)(CCCC(O)(CCC=C(C)C)C)C)C)C)C)C)\\C)\\C)C '
               'NAME: Gymnoprenol A10 REASON: CORRECT Contains 5 isoprene '
               'unit(s) and an alcohol group (OH)\n'
               'False positives: SMILES: '
               'CCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OC[C@@H](O)CO)OC(=O)CCCCCCC\\C=C/CCCCCCCC '
               'NAME: '
               '1-myristoyl-2-oleoyl-sn-glycero-3-phosphatidylglycerol(1-) '
               'REASON: WRONGLY CLASSIFIED Contains 2 isoprene unit(s) and an '
               'alcohol group (OH)\n'
               ' * SMILES: C(=C\\C/C=C\\CCCC(NC)=O)\\C/C=C\\C/C=C\\CCCCC NAME: '
               'N-methyl arachidonoyl amine REASON: WRONGLY CLASSIFIED '
               'Contains 8 isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'C[C@@H]([C@H]1CC[C@H]2[C@@H]3CC=C4C=CC(=O)[C@]4(C)[C@H]3CC[C@]12C)[C@H]1CC(C)=C(CO)C(=O)O1 '
               'NAME: withalongolide F REASON: WRONGLY CLASSIFIED Contains 7 '
               'isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'O(C(=O)CCCCCCCCCCCCCCCCCCC)[C@@H](COC(=O)CCCCCCCCCCCCC)COC(=O)CCCCCCC/C=C\\CCCCCC '
               'NAME: TG(14:0/20:0/16:1(9Z)) REASON: WRONGLY CLASSIFIED '
               'Contains 2 isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: O1C=2CC3(C(CC2C(=C1)C)C(CCC3=O)=C)C NAME: '
               '8,12-Epoxy-4(15),7,11-eudesmatrien-1-one REASON: WRONGLY '
               'CLASSIFIED Contains 3 isoprene unit(s) and an alcohol group '
               '(OH)\n'
               ' * SMILES: '
               'O=C1O[C@@H](C[C@H](OC)CCCC=C(C=C[C@H]([C@@H](C=C(C=C(C=C1C)C)C)C)O[C@@H]2O[C@H]([C@H](OC)[C@H]([C@@H]2O)O)C)C)C[C@@]3(O[C@@H]([C@H](C)[C@@H]([C@H]3C)O)C[C@@H](O[C@@H]4O[C@H]([C@H](O[C@@H]5O[C@@H]([C@@H](O)[C@@H](C5)OC)C)[C@](C4)(O)C)C)COC)O '
               'NAME: Apoptolidin C REASON: WRONGLY CLASSIFIED Contains 7 '
               'isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'P(OC1C(O)C(O)C(O)[C@@H](O)C1O)(OC[C@H](OC(=O)CCCCCCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCC/C=C\\CCCCCCCC)(O)=O '
               'NAME: PI(20:1(11Z)/22:0) REASON: WRONGLY CLASSIFIED Contains 2 '
               'isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'O1C([C@@H](O)C[C@@H]1[C@H]([C@@H]2[C@@]3([C@@](C=4C([C@@]5(C(C([C@@H](O)CC5)(C)C)CC4)C)=CC3)(C)CC2)C)C)(C)C '
               'NAME: Ganoderchochlearin A REASON: WRONGLY CLASSIFIED Contains '
               '10 isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'CC[C@@H]1NC(=O)[C@H]([C@H](OS([O-])(=O)=O)[C@H](C)C\\C=C\\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O)C(C)C '
               'NAME: cyclosporin A sulfate REASON: WRONGLY CLASSIFIED '
               'Contains 1 isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: O(CC/C=C\\CCCCCCCC/C=C\\CCCC)C(=O)C NAME: '
               '3Z,13Z-Octadecadienyl acetate REASON: WRONGLY CLASSIFIED '
               'Contains 4 isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: [H]C(CC(=C)C(C)C)=C(C)C(O)=O NAME: '
               '2,6-dimethyl-5-methylenehept-2-enoic acid REASON: WRONGLY '
               'CLASSIFIED Contains 4 isoprene unit(s) and an alcohol group '
               '(OH)\n'
               ' * SMILES: O=C(CCC(C(C)C)/C=C/C(C)=C)C NAME: '
               '8-Methyl-5-isopropyl-6,8-nonadiene-2-one REASON: WRONGLY '
               'CLASSIFIED Contains 3 isoprene unit(s) and an alcohol group '
               '(OH)\n'
               ' * SMILES: '
               'O=C1OCC2=C1C[C@@H](O)[C@@H]3[C@@]2([C@@H](O)CCC3(C)C)C NAME: '
               'Astellolide C REASON: WRONGLY CLASSIFIED Contains 4 isoprene '
               'unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'O=C1C([C@H]2[C@](C3=C([C@]4([C@]([C@@H]([C@@H](CC/C=C(/C(=O)O)\\C)C)CC4)(C)CC3)C)[C@@H](C2)O)(C)CC1)(C)C '
               'NAME: (24E)-7alpha-hydroxy-3-oxolanosta-8,24-dien-26-oic acid '
               'REASON: WRONGLY CLASSIFIED Contains 9 isoprene unit(s) and an '
               'alcohol group (OH)\n'
               ' * SMILES: '
               'O=C1C([C@H]2C(=O)C[C@@]3([C@@H](C(=O)OC)[C@@](C(=O)[C@](O)(C(=O)OC)C)(C)C(C[C@H]3[C@]2(C)CC1)=C)C)(C)C '
               'NAME: Asperterpene K REASON: WRONGLY CLASSIFIED Contains 4 '
               'isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'O[C@@H]1[C@H]([C@@H](C(=O)C1)C/C=C\\CCCC(O)=O)/C=C/[C@H](O)CCCCC '
               'NAME: ent-Prostaglandin E2 REASON: WRONGLY CLASSIFIED Contains '
               '5 isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: O=C1[C@H]([C@]2([C@H](C1)C)CC(=O)C(=CC2)C)C(C)C '
               'NAME: Epiacoronene REASON: WRONGLY CLASSIFIED Contains 2 '
               'isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'O=C1O[C@@H]([C@H]([C@@H]2[C@@]3([C@@](C4=C([C@]5([C@H](O)C[C@H](O)C([C@@H]5CC4)(C)C)C)CC3)(C)CC2)C)C)CC=C1C '
               'NAME: Colobetaolactone II REASON: WRONGLY CLASSIFIED Contains '
               '9 isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'P(OCC(OC(=O)CCCCCCCCCCCCCC)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)/15:0) REASON: WRONGLY CLASSIFIED '
               'Contains 6 isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               '[H][C@]12CCN(C[C@]1(OC[C@@]2(C(=O)OC)c1cc2ccccc2[nH]1)C=C)C(=O)OCC '
               'NAME: Alstolobine A, (rel)- REASON: WRONGLY CLASSIFIED '
               'Contains 2 isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'P(OCC(OC(=O)CCCCCCC/C=C\\CCCCCC)COC(=O)CCC/C=C\\C/C=C\\C/C=C\\C/C=C\\CCCCC)(OCCNC)(O)=O '
               'NAME: PE-NMe(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) REASON: WRONGLY '
               'CLASSIFIED Contains 10 isoprene unit(s) and an alcohol group '
               '(OH)\n'
               ' * SMILES: '
               'C[C@@H]1C[C@@H]2OC(=O)[C@]3(C)[C@H]2[C@@H](OC3(C)O)[C@@]2(C)[C@H]1C=CC2=O '
               'NAME: Tenulin REASON: WRONGLY CLASSIFIED Contains 3 isoprene '
               'unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'C[C@H](CCCCCCC/C=C/C(=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)N2C=NC3=C(N)N=CN=C23)O[C@@H]4O[C@@H](C)[C@H](O)C[C@H]4O '
               'NAME: ascr#19-CoA(4-) REASON: WRONGLY CLASSIFIED Contains 1 '
               'isoprene unit(s) and an alcohol group (OH)\n'
               ' * SMILES: '
               'C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)[C@H](O)C=C1C[C@@H](O)CC[C@]31C '
               'NAME: androst-5-ene-3beta,7alpha,17beta-triol REASON: WRONGLY '
               'CLASSIFIED Contains 5 isoprene unit(s) and an alcohol group '
               '(OH)\n'
               ' * SMILES: '
               '[C@@H]1([C@@H](C[C@H]([C@@H](O1)C)O)O)OCCCCCCCCCCCCCCCCC/C=C/C(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)=O '
               'NAME: oscr#35-CoA REASON: WRONGLY CLASSIFIED Contains 1 '
               'isoprene unit(s) and an alcohol group (OH)\n'
               'False negatives: SMILES: CC(C)=CCO NAME: prenol REASON: MISSED '
               'No isoprene units 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=C1C2=C(OC(=C1)C)C3=C(OC)C=C(OC)C=C3C(=C2O)C4=C5OC(=CC(C5=C(O)C=6C4=CC(OC)=CC6OC)=O)C',
                                     'name': 'Isonigerone',
                                     'reason': 'No isoprene units found'},
                                 {   'smiles': 'CCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OC[C@@H](O)CO)OC(=O)CCCCCCC\\C=C/CCCCCCCC',
                                     'name': '1-myristoyl-2-oleoyl-sn-glycero-3-phosphatidylglycerol(1-)',
                                     'reason': 'No isoprene units found'},
                                 {   'smiles': 'C(=C\\C/C=C\\CCCC(NC)=O)\\C/C=C\\C/C=C\\CCCCC',
                                     'name': 'N-methyl arachidonoyl amine',
                                     'reason': 'No isoprene units found'},
                                 {   'smiles': 'OC1(O)[C@]23N(CC1)C(N(O)[C@H]([C@@]3(N=C(N2)N)[H])CO)=N',
                                     'name': 'Decarbamoylneosaxitoxin',
                                     'reason': 'No isoprene units found'},
                                 {   'smiles': 'S([C@H]1N(C(=O)/C(=C\\C2=CC=C(OCC=C(C)C)C=C2)/N(C1=O)C)C)C',
                                     'name': 'Fusaperazine F',
                                     'reason': 'No alcohol (OH) or phosphate '
                                               'group found'},
                                 {   'smiles': 'Oc1ccccc1I',
                                     'name': '2-iodophenol',
                                     'reason': 'No isoprene units found'},
                                 {   'smiles': 'O=C1N(CC(=O)N[C@H](C(=O)O[C@H]([C@@H](C(NC(C=C1)=C)=O)C)C(CCCCCCCCCCCCCC)C)C(O)C(=O)N)C',
                                     'name': 'Rakicidin H',
                                     'reason': 'No isoprene units found'},
                                 {   'smiles': 'O1[C@@H]([C@@H](O)[C@H](O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)CO)[C@@H](O)[C@@H]1OC[C@H]3O[C@@H](OC[C@H]4O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]4O)[C@H](O)[C@@H](O)[C@@H]3O)CO[C@@H]5O[C@@H]([C@@H](O)[C@H](O[C@@H]6O[C@@H]([C@@H](O)[C@H](O)[C@H]6O)CO)[C@H]5O)CO[C@@H]7O[C@@H]([C@@H](O)[C@H](O)[C@H]7O)CO',
                                     'name': '(2R,3R,4S,5S,6R)-6-[[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4S,5R,6R)-6-[[(2R,3R,4S,5R,6R)-3,5-Dihydroxy-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]-3,5-dihydroxy-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol',
                                     'reason': 'No isoprene units found'},
                                 {   'smiles': 'O([C@H]1[C@H](O)[C@@H](NC(=O)C)[C@@H](O[C@@H]1CO)O[C@H]2[C@H](O)[C@@H](NC(=O)C)[C@@H](O[C@@H]2CO[C@@H]3O[C@H]([C@@H](O)[C@@H](O)[C@@H]3O)C)O)[C@@H]4O[C@@H]([C@@H](O)[C@H](O[C@H]5O[C@@H]([C@@H](O)[C@H](O)[C@@H]5O[C@@H]6O[C@@H]([C@@H](O[C@@H]7O[C@@H]([C@H](O)[C@H](O)[C@H]7O)CO)[C@H](O)[C@@H]6NC(=O)C)CO)CO)[C@@H]4O)CO[C@H]8O[C@@H]([C@@H](O)[C@H](O)[C@@H]8O[C@@H]9O[C@@H]([C@@H](O[C@@H]%10O[C@@H]([C@H](O)[C@H](O)[C@H]%10O)CO)[C@H](O)[C@H]9NC(=O)C)CO)CO',
                                     'name': 'Gal2GlcNAc2Man3GlcNAcFucGlcNAc',
                                     'reason': 'No isoprene units found'},
                                 {   'smiles': 'CN1CC2(CCN(CC2)S(=O)(=O)C3=CN(C=N3)C)C4=C([C@@H]1CO)NC5=C4C=CC(=C5)OC',
                                     'name': "[(1R)-7-methoxy-2-methyl-1'-[(1-methyl-4-imidazolyl)sulfonyl]-1-spiro[3,9-dihydro-1H-pyrido[3,4-b]indole-4,4'-piperidine]yl]methanol",
                                     'reason': 'No isoprene units found'}],
    'sample_false_negatives': [],
    'attempt': 3,
    'reasoning': 'The previous implementation aimed to classify chemical '
                 'entities as prenols by checking for the presence of isoprene '
                 'units and either an alcohol (OH) or phosphate group. '
                 'However, the results showed a low F1 score, indicating that '
                 "it's not performing as expected. Let's analyze the possible "
                 'causes of failure and suggest improvements:\n'
                 '\n'
                 '### Observations & Hypotheses:\n'
                 '\n'
                 '1. **Isoprene Unit Detection**:\n'
                 '   - The SMARTS pattern used (`"[C](=C)[C][C]"`) for '
                 'detecting isoprene units may not be comprehensive enough, as '
                 'it missed correctly identifying isoprene units in some of '
                 'the "true positives" and "false negatives."\n'
                 '   - Isoprene units have a common structure but may appear '
                 'in various configurations; the SMARTS pattern might need '
                 'refinement or the addition of more patterns to account for '
                 'all possible configurations seen in SMILES involving '
                 'isoprene.\n'
                 '\n'
                 '2. **Missing Validation**:\n'
                 '   - The function missed identifying some molecules despite '
                 'their valid structures (e.g., prenol). This may be due to '
                 'simplistic pattern matching or edge case skipping.\n'
                 '\n'
                 '3. **Alcohol or Phosphate Group**:\n'
                 '   - The function should account for variations in how OH '
                 'and phosphate groups are represented in different '
                 'chemistries.\n'
                 '\n'
                 '### Improvement Strategy:\n'
                 '\n'
                 '1. **Refine Isoprene Unit Pattern**:\n'
                 '   - Expand the pattern to capture more structural nuances, '
                 'specifically for cases of chained isoprene units.\n'
                 '   - Consider backbone variations encountered in typical '
                 'isoprene repeats.\n'
                 '\n'
                 '2. **Improve Functional Group Checks**:\n'
                 '   - For alcohol detection, ensure to account for hydroxyl '
                 'attachments in potentially corner cases.\n'
                 '   - Expand phosphates and check for potential derivative '
                 'forms or related groups that function similarly.\n'
                 '\n'
                 '3. **Threshold and Parsing**:\n'
                 '   - Examine structures to better capture the intrinsic '
                 'complexities of formulae and resolve discrepancies while '
                 'ensuring no false identification.\n'
                 '\n'
                 "Let's try to improve the function using these suggestions:",
    'success': True,
    'best': True,
    'error': '',
    'stdout': None,
    'num_true_positives': 36,
    'num_false_positives': 100,
    'num_true_negatives': 626,
    'num_false_negatives': 0,
    'num_negatives': None,
    'precision': 0.2647058823529412,
    'recall': 1.0,
    'f1': 0.4186046511627907,
    'accuracy': 0.868766404199475,
    'negative_predictive_value': 1.0}