def _apply_forward_reaction(template_row: pd.Series,
config: Config) -> Optional[pd.DataFrame]:
smarts_fwd = reverse_template(template_row.retro_template)
mols = create_reactants_molecules(template_row.reactants)
try:
ref_mol = Molecule(smiles=template_row.products, sanitize=True)
except MoleculeException as err:
raise _ReactionException(
f"reaction {template_row.reaction_hash} failed with msg {str(err)}"
)
try:
products = Reaction(mols=mols, smarts=smarts_fwd).apply()
except ValueError as err:
raise _ReactionException(
f"reaction {template_row.reaction_hash} failed with msg {str(err)}"
)
new_products = {
product[0]
for product in products if product[0] != ref_mol
}
if not new_products:
return None
correct_products = {
product[0]
for product in products if product[0].basic_compare(ref_mol)
}
if not correct_products:
raise _ReactionException(
f"reaction {template_row.reaction_hash} failed to produce correct product"
)
return _new_dataframe(
template_row,
config,
nrows=len(new_products),
reaction_hash=[
reaction_hash(template_row.reactants, product)
for product in new_products
],
products=[product.smiles for product in new_products],
)
def _sample_library(library: pd.DataFrame, config: Config,
sampler_func: Callable) -> _DfGenerator:
for _, row in library.iterrows():
mols = create_reactants_molecules(row.reactants)
try:
ref_mol = Molecule(smiles=row.products, sanitize=True)
except MoleculeException:
yield None
continue
new_product = None
for template_row in sampler_func(row):
if row.template_hash == template_row.template_hash:
continue
smarts_fwd = reverse_template(template_row.retro_template)
try:
new_product = Reaction(mols=mols,
smarts=smarts_fwd).apply()[0][0]
except (ValueError, IndexError):
continue
if new_product.basic_compare(ref_mol):
continue
break # If we have reached here, we have found a match that fits all criteria
if not new_product:
yield None
continue
# pylint: disable=undefined-loop-variable
yield _new_dataframe(
row,
config,
reaction_hash=[reaction_hash(row.reactants, new_product)],
products=[new_product.smiles],
classification=[""],
retro_template=[template_row.retro_template],
template_hash=[template_row.template_hash],
selectivity=[0],
outcomes=[1],
template_code=[template_row.template_code],
)
def test_reverse_template():
retro_template = "([C:2]-[C:3](=[O;D1;H0:4])-[N;H0;D3;+0:5](-[CH3;D1;+0:1])-[c:6])>>(I-[CH3;D1;+0:1]).([C:2]-[C:3](=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6])" # noqa
expected = "(I-[CH3;D1;+0:1]).([C:2]-[C:3](=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6])>>([C:2]-[C:3](=[O;D1;H0:4])-[N;H0;D3;+0:5](-[CH3;D1;+0:1])-[c:6])" # noqa
assert reverse_template(retro_template) == expected
