def test_different_forcefield_constraints(self, toolkit):
"""Test that the --constrained argument produces different results"""
from openff.cli.tests.utils import get_data_file_path
registry = make_registry(toolkit)
mol = get_data_file_path("molecules/azidoazide.smi")
constrained = generate_conformers(
molecule=mol,
forcefield="openff-1.0.0",
prefix="parsley100",
registry=registry,
constrained=True,
)
unconstrained = generate_conformers(
molecule=mol,
forcefield="openff-1.0.0",
prefix="parsley100",
registry=registry,
constrained=False,
)
assert not np.allclose(
constrained[0].conformers[0],
unconstrained[0].conformers[0],
)
def test_load_one_mol_mol2_with_charge(self, toolkit):
"""
Test loading one molecule from a .mol2 file WITHOUT charges
.. note :: This file was generated via the one-liner below and has nan
charges, which may or may not be valid.
```
Molecule.from_smiles('CCO').to_file(
'ethanol_no_charges.mol2',
file_format='mol2',
)
```
"""
registry = make_registry(toolkit)
ethanol_partial_charges = get_data_file_path(
"molecules/ethanol_no_charges.mol2")
charges_in = Molecule.from_file(
ethanol_partial_charges).partial_charges
mols_out = generate_conformers(
molecule=ethanol_partial_charges,
forcefield="openff-1.0.0.offxml",
registry=registry,
)
assert len(mols_out) == 1
assert not charges_in
assert not mols_out[0].partial_charges
def test_load_multi_mol_sdf(self, toolkit):
"""Test the case of an SDF file with multiple molecules"""
registry = make_registry(toolkit)
butane_multi = get_data_file_path("molecules/butane_multi.sdf")
generate_conformers(
molecule=butane_multi,
forcefield="openff-1.0.0.offxml",
registry=registry,
)
def test_preserve_stereo_smi(self, toolkit):
"""Test loading a molecule with defined stereo from SMILES and preserving that stereochemistry"""
registry = make_registry(toolkit)
mol = get_data_file_path("molecules/dichloroethene_stereo.smi")
mols_out = generate_conformers(
molecule=mol,
forcefield="openff-1.0.0.offxml",
registry=registry,
)
assert Molecule(mol).is_isomorphic_with(mols_out[0])
def test_load_multi_mol_smi(self, toolkit):
"""Test loading multiple molecules from SMILES in a .smi file"""
registry = make_registry(toolkit)
dyes = get_data_file_path("molecules/multi_mols.smi")
mols_out = generate_conformers(
molecule=dyes,
forcefield="openff-1.0.0.offxml",
registry=registry,
)
assert len(mols_out) > 3
def test_load_one_mol_smi(self, toolkit):
"""Test loading one molecule from SMILES in a .smi file"""
registry = make_registry(toolkit)
hexane = get_data_file_path("molecules/hexane.smi")
mols_out = generate_conformers(
molecule=hexane,
forcefield="openff-1.0.0.offxml",
registry=registry,
)
assert len(mols_out) > 1
def test_available_forcefields(self, toolkit, ff_name):
"""Test that all forcefields available through get_available_forcefields
can at least do a basic conformer generaiton"""
# TODO: Possibly ensure this produces non-garbage output,
# instead of only "doesn't raise an error we know of"
registry = make_registry(toolkit)
mol = get_data_file_path("molecules/ethanol.sdf")
generate_conformers(
molecule=mol,
forcefield=ff_name,
registry=registry,
)
def test_load_ambiguous_stereo_smi(self, toolkit):
"""Test loading a molecule with ambiguous stereo from SMILES and enumerating stereoisomers"""
# TODO: Should the CLI accept both paths and SMILES as strings, or only files?
registry = make_registry(toolkit)
mol = get_data_file_path(
"molecules/dichloroethene_ambiguous_stereo.smi")
mols_out = generate_conformers(
molecule=mol,
forcefield="openff-1.0.0.offxml",
registry=registry,
)
assert len(mols_out) == 4
def test_load_one_mol_sdf_without_charge(self, toolkit):
"""Test loading one molecule from a .sdf file WITHOUT charges"""
registry = make_registry(toolkit)
ethanol = get_data_file_path("molecules/ethanol.sdf")
assert Molecule.from_file(ethanol).partial_charges is None
mols_out = generate_conformers(
molecule=ethanol,
forcefield="openff-1.0.0.offxml",
registry=registry,
)
assert len(mols_out) > 1
assert mols_out[0].partial_charges is not None
def test_load_one_mol_sdf_with_charge(self, toolkit):
"""Test loading one molecule from a .sdf file WITH charges"""
registry = make_registry(toolkit)
ethanol_partial_charges = get_data_file_path(
"molecules/ethanol_partial_charges.sdf")
charges_in = Molecule.from_file(
ethanol_partial_charges).partial_charges
assert charges_in is not None
mols_out = generate_conformers(
molecule=ethanol_partial_charges,
forcefield="openff-1.0.0.offxml",
registry=registry,
)
assert len(mols_out) > 1
assert np.allclose(mols_out[0].partial_charges, charges_in)
def test_get_conformer_energies(self, toolkit):
registry = make_registry(toolkit)
mols = get_conformer_energies(
molecule=get_data_file_path(
"molecules/ruxolitinib_conformers.sdf"),
registry=registry,
forcefield="openff-1.0.0",
constrained=False,
)
for mol in mols:
for conformer_idx in range(mol.n_conformers):
original = mol.properties[
"original conformer energies (kcal/mol)"]
minimized = mol.properties[
"minimized conformer energies (kcal/mol)"]
assert minimized < original
def test_load_one_mol_mol2_without_charge(self, toolkit):
"""Test loading one molecule from a .mol2 file WITH charges"""
if toolkit != "openeye":
pytest.skip("Test requires OpenEye toolkit")
registry = make_registry(toolkit)
ethanol_partial_charges = get_data_file_path(
"molecules/ethanol_partial_charges.mol2")
charges_in = Molecule.from_file(
ethanol_partial_charges).partial_charges
mols_out = generate_conformers(
molecule=ethanol_partial_charges,
forcefield="openff-1.0.0.offxml",
registry=registry,
)
assert len(mols_out) > 1
assert np.allclose(mols_out[0].partial_charges, charges_in)
def test_parsing_error():
"""Ensure that failed molecule parsing is caught"""
from openff.cli.utils.exceptions import MoleculeParsingError
# Ensure the exception can be raised with no keyword arguments
exec_msg = "Failed to parse a molecule file."
with pytest.raises(MoleculeParsingError, match=exec_msg):
raise MoleculeParsingError
# Try to parse a MOL2 file with RDKit
registry = make_registry("rdkit")
mol = get_data_file_path("molecules/ethanol_no_charges.mol2")
exec_msg = (
r"Failed to parse a molecule file. Attempted to parse file "
".*ethanol_no_charges.mol2 using toolkit registry containing+.*RDKit")
with pytest.raises(MoleculeParsingError, match=exec_msg):
generate_conformers(
molecule=mol,
forcefield="openff-1.0.0.offxml",
registry=registry,
)
def test_different_forcefields(self, toolkit):
"""Test that different --forcefield arguments produce different results"""
from openff.cli.tests.utils import get_data_file_path
registry = make_registry(toolkit)
mol = get_data_file_path("molecules/azidoazide.smi")
parsley_1_0_0 = generate_conformers(
molecule=mol,
forcefield="openff-1.0.0",
prefix="parsley100",
registry=registry,
)
parsley_1_2_0 = generate_conformers(
molecule=mol,
forcefield="openff-1.2.0",
prefix="parsley120",
registry=registry,
)
assert not np.allclose(
parsley_1_0_0[0].conformers[0],
parsley_1_2_0[0].conformers[0],
)
def test_p_prefix(self, toolkit):
"""Ensure the output file has the -p prefix"""
registry = make_registry(toolkit)
ethanol = get_data_file_path("molecules/ethanol.sdf")
mols_out = generate_conformers(
molecule=ethanol,
forcefield="openff-1.0.0.offxml",
registry=registry,
prefix="test_ethanol",
)
with tempfile.TemporaryDirectory() as tmp_dir:
with temporary_cd(tmp_dir):
write_mols(
mols=mols_out,
toolkit_registry=registry,
molecule=ethanol,
prefix="test_ethanol",
)
assert pathlib.Path("test_ethanol_0.sdf").is_file()
def test_different_toolkits():
"""Test that different --toolkit argumnents produce different results"""
from openff.cli.tests.utils import get_data_file_path
rdkit = make_registry("rdkit")
openeye = make_registry("openeye")
mol = get_data_file_path("molecules/azidoazide.smi")
rdkit_results = generate_conformers(
molecule=mol,
forcefield="openff-1.0.0",
prefix="rdkit",
registry=rdkit,
)
openeye_results = generate_conformers(
molecule=mol,
forcefield="openff-1.0.0",
prefix="openeye",
registry=openeye,
)
assert not np.allclose(
rdkit_results[0].conformers[0],
openeye_results[0].conformers[0],
)
