def setUp(self):
"""
Set up tests.
"""
self.reader = serial.MolReader()
# generate molecules
smiles = ['CC(=O)OC1=CC=CC=C1C(=O)O', 'CC(C)CC1=CC=C(C=C1)C(C)C(=O)O',
'CC1=CC=C(C=C1)C2=CC(=NN2C3=CC=C(C=C3)S(=O)(=O)N)C(F)(F)F']
names = ['aspirin', 'ibuprofen', 'celecoxib']
self.mols = []
for s, n in zip(smiles, names):
mol = Chem.MolFromSmiles(s)
mol.SetProp('_Name', n)
AllChem.Compute2DCoords(mol)
self.mols.append(mol)
# write molecules to file
self.temp_dir = tempfile.mkdtemp()
writer = serial.MolWriter()
_, self.filename = tempfile.mkstemp(dir=self.temp_dir,
suffix='.sdf.gz')
with writer.open(self.filename) as w:
w.write(self.mols)
self.sharder = DatasetSharder(filename=self.filename,
write_shards=False)
self.reader = serial.MolReader()
def test_not_close_other(self):
"""
Make sure MolIO doesn't close files it didn't open.
"""
_, filename = tempfile.mkstemp(suffix='.sdf', dir=self.temp_dir)
with open(filename) as f:
reader = serial.MolReader(f, mol_format='sdf')
reader.close()
assert not f.closed
# also test the context manager
with open(filename) as g:
with serial.MolReader(g, mol_format='sdf'):
pass
assert not g.closed
def read_data(self):
"""
Read labeled molecules.
"""
with serial.MolReader().open(self.filename) as reader:
mols = list(reader)
return mols
def read_mols_from_file(self):
"""
Read molecules from a file.
"""
with serial.MolReader().open(self.filename) as reader:
for mol in reader.get_mols():
yield mol
def test_is_a_salt(self):
"""
Test that a molecule that _is_ a salt is not returned empty.
"""
smiles = 'C(=CC(=O)O)C(=O)O'
reader = serial.MolReader(StringIO(smiles), 'smi', remove_salts=True)
mols = list(reader.get_mols())
assert len(mols) == 1 and mols[0].GetNumAtoms()
def test_skip_failures(self):
"""
Test skip read failures.
"""
smiles = 'CO(C)C'
reader = serial.MolReader(StringIO(smiles), 'smi')
mols = list(reader.get_mols())
assert len(mols) == 0
def test_no_remove_salts(self):
"""
Test salt retention.
"""
_, filename = tempfile.mkstemp(suffix='.sdf', dir=self.temp_dir)
with open(filename, 'wb') as f:
for mol in [self.aspirin_sodium, self.levalbuterol_hcl]:
f.write(Chem.MolToMolBlock(mol))
f.write('$$$$\n') # molecule delimiter
ref_mols = [self.aspirin_sodium, self.levalbuterol_hcl]
self.reader = serial.MolReader(remove_salts=False)
self.reader.open(filename)
mols = self.reader.get_mols()
mols = list(mols)
assert len(mols) == 2
self.reader = serial.MolReader(remove_salts=True)
for mol, ref_mol in zip(mols, ref_mols):
assert mol.ToBinary() == ref_mol.ToBinary()
desalted = self.reader.clean_mol(ref_mol)
assert mol.GetNumAtoms() > desalted.GetNumAtoms()
def test_remove_hydrogens(self):
"""
Test hydrogen removal.
"""
_, filename = tempfile.mkstemp(suffix='.sdf', dir=self.temp_dir)
with open(filename, 'wb') as f:
f.write(Chem.MolToMolBlock(self.aspirin_h))
reader = serial.MolReader(remove_hydrogens=True)
reader.open(filename)
mols = reader.get_mols()
assert mols.next().ToBinary() == self.aspirin.ToBinary()
def test_read_compressed_file_like(self):
"""
Read from a file-like object using gzip.
"""
_, filename = tempfile.mkstemp(suffix='.sdf.gz', dir=self.temp_dir)
with gzip.open(filename, 'wb') as f:
f.write(Chem.MolToMolBlock(self.aspirin))
with gzip.open(filename) as f:
reader = serial.MolReader(f, mol_format='sdf')
mols = reader.get_mols()
assert mols.next().ToBinary() == self.aspirin.ToBinary()
def test_no_remove_hydrogens(self):
"""
Test hydrogen retention.
"""
_, filename = tempfile.mkstemp(suffix='.sdf', dir=self.temp_dir)
with open(filename, 'wb') as f:
f.write(Chem.MolToMolBlock(self.aspirin_h))
reader = serial.MolReader(remove_hydrogens=False, remove_salts=False)
reader.open(filename)
mols = reader.get_mols()
# FIXME get ToBinary test to work
# assert mols.next().ToBinary() == self.aspirin_h.ToBinary()
assert Chem.MolToMolBlock(mols.next()) == Chem.MolToMolBlock(
self.aspirin_h)
def get_smiles(filename, assign_stereo_from_3d=False):
"""
Get SMILES for molecules.
Parameters
----------
filename : str
Input molecule filename.
assign_stereo_from_3d : bool, optional (default False)
Assign stereochemistry from 3D coordinates.
"""
database = MoleculeDatabase(assign_stereo_from_3d=assign_stereo_from_3d)
with serial.MolReader().open(filename) as reader:
for mol in reader:
database.add_mol(mol)
return list(database.smiles)
def _ionize_3d(self, mol):
"""
Ionize a molecule while preserving conformers.
Parameters
----------
mol : RDMol
Molecule.
"""
assert mol.GetNumConformers() > 0
sdf = ''
for conf in mol.GetConformers():
sdf += Chem.MolToMolBlock(mol, confId=conf.GetId(),
includeStereo=True)
sdf += '$$$$\n'
args = ['obabel', '-i', 'sdf', '-o', 'sdf', '-p', str(self.pH)]
p = subprocess.Popen(args, stdin=subprocess.PIPE,
stdout=subprocess.PIPE,
stderr=subprocess.PIPE)
ionized_sdf, _ = p.communicate(sdf)
reader = serial.MolReader(StringIO(ionized_sdf), mol_format='sdf',
remove_salts=False) # no changes
try:
mols = list(reader.get_mols())
except RuntimeError as e: # catch pre-condition violations
raise IonizerError(e.message)
# catch ionizer failure
if len(mols) == 0:
raise IonizerError(mol)
# detection of stereochemistry based on 3D coordinates might result
# in issues when attempting to recombine ionized conformers, but we
# merge them anyway
if len(mols) == 1:
ionized_mol, = mols
else:
ionized_mol = mols[0]
for other in mols[1:]:
for conf in other.GetConformers():
ionized_mol.AddConformer(conf, assignId=True)
return ionized_mol
def setUp(self):
"""
Write SDF and SMILES molecules to temporary files.
"""
self.temp_dir = tempfile.mkdtemp()
# aspirin
self.aspirin = self._get_mol_from_smiles('CC(=O)OC1=CC=CC=C1C(=O)O',
'aspirin')
self.aspirin_h = Chem.AddHs(self.aspirin)
self.aspirin_sodium = self._get_mol_from_smiles(
'CC(=O)OC1=CC=CC=C1C(=O)[O-].[Na+]', 'aspirin sodium')
# levalbuterol (chiral)
self.levalbuterol = self._get_mol_from_smiles(
'CC(C)(C)NC[C@@H](C1=CC(=C(C=C1)O)CO)O', 'levalbuterol')
self.levalbuterol_hcl = self._get_mol_from_smiles(
'CC(C)(C)NC[C@@H](C1=CC(=C(C=C1)O)CO)O.Cl',
'levalbuterol hydrochloride')
self.ref_mols = [self.aspirin, self.levalbuterol]
self.reader = serial.MolReader(compute_2d_coords=False)
def main(input_filenames,
output_filename,
database_filename=None,
assign_stereo_from_3d=False):
"""
Update or create a molecule database.
Parameters
----------
input_filenames : list
Input molecule filename(s).
output_filename : str
Output filename.
database_filename : str, optional
Existing database to update.
assign_stereo_from_3d : bool, optional (default False)
Whether to assign stereochemistry from 3D coordinates.
"""
database = MoleculeDatabase(assign_stereo_from_3d=assign_stereo_from_3d)
if database_filename is not None:
database.load(database_filename)
initial_size = len(database)
for filename in input_filenames:
print filename
with serial.MolReader().open(filename) as reader:
for mol in reader:
try:
database.add_mol(mol)
except ValueError:
if mol.HasProp('_Name'):
print 'Skipping {}'.format(mol.GetProp('_Name'))
else:
print 'Skipping {}'.format(
Chem.MolToSmiles(mol, isomericSmiles=True))
final_size = len(database)
print '{} molecules added to the database'.format(final_size -
initial_size)
database.save(output_filename)
def read_mols(input_filename):
"""
Read molecules from an input file and extract names.
Parameters
----------
input_filename : str
Filename containing molecules.
"""
print "Reading molecules..."
reader = serial.MolReader()
reader.open(input_filename)
mols = []
names = []
for mol in reader.get_mols():
mols.append(mol)
if mol.HasProp('_Name'):
names.append(mol.GetProp('_Name'))
else:
names.append(None)
reader.close()
mols = np.asarray(mols)
names = np.asarray(names)
return mols, names