def test_multi_insert_deterministic_and_inverses():
vocab = data_utils.get_vocab()
rng = np.random.RandomState(7)
init_smiles = [
'CCCCCCC1=NN2C(=N)/C(=C\\c3cc(C)n(-c4ccc(C)cc4C)c3C)C(=O)N=C2S1',
'COCC[C@@H](C)C(=O)N(C)Cc1ccc(O)cc1',
'C=CCn1c(S[C@H](C)c2nc3sc(C)c(C)c3c(=O)[nH]2)nnc1C1CC1',
'C[NH+](C/C=C/c1ccco1)CCC(F)(F)F',
'COc1ccc(N2C(=O)C(=O)N(CN3CCC(c4nc5ccccc5s4)CC3)C2=O)cc1',
'Cc1ccc([C@@H](C)[NH2+][C@H](C)C(=O)Nc2ccccc2F)cc1',
'O=c1cc(C[NH2+]Cc2cccc(Cl)c2)nc(N2CCCC2)[nH]1',
'O=C(Cn1nc(C(=O)[O-])c2ccccc2c1=O)Nc1ccc2c(c1)C(=O)c1ccccc1C2=O',
'O=C(Nc1cccc(S(=O)(=O)N2CCCCC2)c1)c1cc(F)c(F)cc1Cl',
'CC(C)Cc1nnc(NC(=O)C(=O)NCCC2CCCCC2)s1',
'C[C@H](NC(=O)[C@@H](O)c1ccccc1)c1nnc2ccccn12',
'O=S(=O)(Nc1cc(F)ccc1F)c1ccc(Cl)cc1F',
'CSc1cc(C(=O)N2c3ccccc3NC(=O)C[C@@H]2C)ccn1',
'CCCN1C(=O)c2[nH]nc(-c3cc(Cl)ccc3O)c2[C@H]1c1ccc(C)cc1',
'CC[S@@](=O)[C@@H]1CCC[C@H](NC(=O)N(Cc2cccs2)C2CC2)C1',
'C[C@@H](c1ccco1)[NH+](Cc1ncc(-c2ccccc2)o1)C1CC1',
'COc1ccc(Cc2nnc(SCC(=O)N3CCC[C@@H](C)C3)o2)cc1',
'O=C(/C=C/c1ccc2c(c1)OCO2)NC[C@@H]1C[NH+]2CCN1CC2',
'COc1ccccc1/C=C/C=C(\\C#N)C(=O)Nc1ccc(C(=O)N(C)C)cc1',
'Cc1cccc(NC(=S)N2CC[NH+](C)CC2)c1C'
]
for idx, smiles in enumerate(init_smiles):
mol = me.get_mol(smiles)
result, act, inverse = me.insert_random_node(mol,
vocab,
rng=rng,
return_action=True,
return_inverse=True)
result_deterministic = me.compute_insert(mol, act, vocab)
assert me.comp_mols(result, result_deterministic)
mol_roundtrip = me.delete_random_leaf(result, act=inverse)
assert me.comp_mols(mol, mol_roundtrip)
# 2nd insertion
result2, act2, inverse2 = me.insert_random_node(result,
vocab,
rng=rng,
return_action=True,
return_inverse=True)
result2_deterministic = me.compute_insert(result, act2, vocab)
assert me.comp_mols(result2, result2_deterministic)
mol_roundtrip2 = me.delete_random_leaf(result2, act=inverse2)
assert me.comp_mols(result, mol_roundtrip2)
def test_deterministic_deletion():
init_smiles = ['CC1=CC(C2=C(C#N)N3N=C(C4CC4)SC3=N2)=CC=C1Cl']
leaf_idxs = [3]
test_targets = ['CC1=NN2C(C#N)=C(C3=CC=C(Cl)C(C)=C3)N=C2S1']
for smiles, leaf_idx, target in zip(init_smiles, leaf_idxs, test_targets):
mol = me.get_mol(smiles)
new_mol = me.delete_random_leaf(mol, act=action.Delete(leaf_idx))
target_mol = me.get_mol(target)
assert me.comp_mols(target_mol, new_mol)
def test_delete_inverse_bond():
smile = 'C1=CC(=CC=C1)C3=C(C#N)[N]2N=CSC2=N3'
vocab = data_utils.get_vocab()
act = action.Delete(leaf_idx=2)
mol = me.get_mol(smile)
result, inverse = me.compute_deletion(mol, act, return_inverse=True)
mol_roundtrip = me.compute_insert(result, inverse, vocab)
assert me.comp_mols(mol, mol_roundtrip)
def test_delete_inverse_kekulize():
smile = 'C1=CC(=CC=C1)C4=C(C#N)[N]3N=C(C2CC2)SC3=N4'
vocab = data_utils.get_vocab()
act = action.Delete(leaf_idx=1)
mol = me.get_mol(smile)
result, inverse = me.compute_deletion(mol, act, return_inverse=True)
mol_roundtrip = me.compute_insert(result, inverse, vocab)
assert me.comp_mols(mol, mol_roundtrip)
def test_deletion():
initial_smile = 'CCC(NC(=O)c1scnc1C1CC1)C(=O)N1CCOCC1'
test_targets = [
'CCC(NC(=O)c1c(C2CC2)ncs1)C(N)=O', 'CCC(CN)NC(=O)c1c(C2CC2)ncs1',
'CC(CN)NC(=O)c1c(C2CC2)ncs1', 'CC(CN)NCc1c(C2CC2)ncs1'
]
mol = me.get_mol(initial_smile)
for i in range(4):
target_mol = me.get_mol(test_targets[i])
rng = np.random.RandomState(i)
mol = me.delete_random_leaf(mol, rng)
assert me.comp_mols(target_mol, mol)
def test_delete_inverse():
smile = 'CC1=CC(C2=C(C#N)N3N=C(C4CC4)SC3=N2)=CC=C1Cl'
vocab = data_utils.get_vocab()
rng = np.random.RandomState(7)
mol = me.get_mol(smile)
result, act, inverse = me.delete_random_leaf(mol,
rng=rng,
return_action=True,
return_inverse=True)
mol_roundtrip = me.insert_random_node(result, vocab, act=inverse)
assert me.comp_mols(mol, mol_roundtrip)
def test_insert_atom_inverse():
smile = 'CC1=CC(C2=C(C#N)N3N=C(C4CC4)SC3=N2)=CC=C1Cl'
vocab = data_utils.get_vocab()
rng = np.random.RandomState(7)
mol = me.get_mol(smile)
atom = mol.GetAtomWithIdx(13)
result, act, inverse = me.insert_at_atom(mol,
atom,
vocab,
rng=rng,
return_action=True,
return_inverse=True)
result = chemutils.sanitize(result)
mol_roundtrip = me.compute_deletion(result, inverse)
assert me.comp_mols(mol, mol_roundtrip)