handle for clashing embedding and minimisation

pyproject.toml

@@ -1,7 +1,7 @@
 [tool.poetry]
 name = "jazzy"
-version = "0.1.1"
-description = "Jazzy"
+version = "0.1.2"
+description = "Jazzy allows calculating a set of atomic/molecular descriptors including the Gibbs free energy of hydration (kJ/mol), its polar/apolar components, and the hydrogen-bond strength of donor and acceptor atoms."
 authors = ["Gian Marco Ghiandoni <[email protected]>", "Eike Caldeweyher <[email protected]>"]
 license = "Apache-2.0"
 readme = "README.rst"

src/jazzy/config.py

@@ -4,6 +4,7 @@
 MINIMISATION_METHOD = None
 ROUNDING_DIGITS = 4
 ANNOTATION_FONT_SCALE = 0.7
+EMBEDDING_TYPES = ("2D", "3D")
 
 
 class Config(object):

src/jazzy/core.py

@@ -17,6 +17,7 @@
 from rdkit.Chem import rdMolDescriptors
 from rdkit.Chem.rdchem import Mol
 
+from jazzy.config import EMBEDDING_TYPES
 from jazzy.config import ROUNDING_DIGITS
 from jazzy.exception import EmbeddingError
 from jazzy.exception import KallistoError
@@ -47,10 +48,6 @@ def rdkit_molecule_from_smiles(
     Returns:
         An RDKit molecule (rdkit.Chem.rdchem.Mol) or None if the process fails
 
-    Raises:
-        ValueError: If 'minimisation_method' does not correspond to one of the
-            available methods.
-
     """
     # create molecule, add hydrogens
     m = Chem.MolFromSmiles(smiles)
@@ -66,29 +63,19 @@ def rdkit_molecule_from_smiles(
         return None
 
     # energy minimisation
-    valid_methods = [None, "MMFF94", "MMFF94s", "UFF"]
-    if minimisation_method is not None:
-        if minimisation_method not in valid_methods:
-            raise ValueError(f"Select a valid minimisation method {valid_methods}")
-        if minimisation_method == valid_methods[1]:
-            AllChem.MMFFOptimizeMolecule(mh)
-        if minimisation_method == valid_methods[2]:
-            AllChem.MMFFOptimizeMolecule(mh, mmffVariant="MMFF94s")
-        if minimisation_method == valid_methods[3]:
-            AllChem.UFFOptimizeMolecule(mh)
+    _minimise_molecule(mh, minimisation_method, **kwargs)
     return mh
 
 
-def _embed_molecule(rdkit_molecule: Chem.rdchem.Mol, **kwargs) -> None:
+def _embed_molecule(rdkit_molecule: Mol, **kwargs) -> None:
     """Molecule embedding using either the 2D or 3D method."""
     embedding_type = kwargs.get("embedding_type", "3D")
     embedding_seed = kwargs.get("embedding_seed", 11)
-    valid_types = ["2D", "3D"]
-    if embedding_type not in valid_types:
-        raise ValueError(f"Select a valid embedding type {valid_types}")
-    if embedding_type == valid_types[0]:
+    if embedding_type not in EMBEDDING_TYPES:
+        raise ValueError(f"Select a valid embedding type {EMBEDDING_TYPES}")
+    if embedding_type == EMBEDDING_TYPES[0]:
         AllChem.Compute2DCoords(rdkit_molecule, sampleSeed=embedding_seed)
-    if embedding_type == valid_types[1]:
+    if embedding_type == EMBEDDING_TYPES[1]:
         params = (
             rdDistGeom.ETDG()
         )  # ETDG over others as it seems produce fewer failures
@@ -105,7 +92,26 @@ def _embed_molecule(rdkit_molecule: Chem.rdchem.Mol, **kwargs) -> None:
             raise EmbeddingError(error_msg)
 
 
-def get_covalent_atom_idxs(rdkit_molecule: Chem.rdchem.Mol) -> list:
+def _minimise_molecule(rdkit_molecule: Mol, minimisation_method: str, **kwargs) -> None:
+    """Minimise the energy of a molecule. Only works for 3D molecules."""
+    valid_methods = (None, "MMFF94", "MMFF94s", "UFF")
+    if not minimisation_method:
+        return
+    embedding_type = kwargs.get("embedding_type", "3D")
+    if embedding_type == EMBEDDING_TYPES[0]:
+        logger.warning("Energy minimisation is not supported for 2D molecules.")
+        return
+    if minimisation_method == valid_methods[1]:
+        AllChem.MMFFOptimizeMolecule(rdkit_molecule)
+    elif minimisation_method == valid_methods[2]:
+        AllChem.MMFFOptimizeMolecule(rdkit_molecule, mmffVariant="MMFF94s")
+    elif minimisation_method == valid_methods[3]:
+        AllChem.UFFOptimizeMolecule(rdkit_molecule)
+    else:
+        raise ValueError(f"Select a valid minimisation method {valid_methods}")
+
+
+def get_covalent_atom_idxs(rdkit_molecule: Mol) -> list:
     """Get covalent indices for atom_idx.
 
     Creates a list of lists, where indices are atom indices and the content
@@ -120,7 +126,7 @@ def get_covalent_atom_idxs(rdkit_molecule: Chem.rdchem.Mol) -> list:
     return atoms_and_idxs
 
 
-def get_all_neighbours(rdkit_molecule: Chem.rdchem.Mol, molecule_covalent_nbrs: list):
+def get_all_neighbours(rdkit_molecule: Mol, molecule_covalent_nbrs: list):
     """Get all alpha, beta, and gamma neighbours.
 
     Create dictionaries for covalent bonding partner (alpha), all nearest
@@ -147,7 +153,7 @@ def get_all_neighbours(rdkit_molecule: Chem.rdchem.Mol, molecule_covalent_nbrs:
     return alpha, beta, gamma
 
 
-def kallisto_molecule_from_rdkit_molecule(rdkit_molecule: Chem.rdchem.Mol) -> Molecule:
+def kallisto_molecule_from_rdkit_molecule(rdkit_molecule: Mol) -> Molecule:
     """Create a kallisto molecule from RDKit molecule.
 
     Args:
@@ -215,7 +221,7 @@ def get_charges_from_kallisto_molecule(
 
 
 def calculate_polar_strength_map(
-    rdkit_molecule: Chem.rdchem.Mol,
+    rdkit_molecule: Mol,
     kallisto_molecule: Molecule,
     atoms_and_nbrs: list,
     charges: list,
@@ -442,7 +448,7 @@ def _calculate_q_delta(q_alpha, q_beta, q_gamma, t):
 
 
 def calculate_delta_apolar(
-    rdkit_molecule: Chem.rdchem.Mol,
+    rdkit_molecule: Mol,
     mol_map: dict,
     g0: float,
     gs: float,
@@ -633,7 +639,7 @@ def interaction_strength(idx: int, mol_map: dict, acceptor_exp: float) -> float:
 
 
 def calculate_delta_interaction(
-    rdkit_molecule: Chem.rdchem.Mol,
+    rdkit_molecule: Mol,
     mol_map: dict,
     atoms_and_nbrs: list,
     gi: float,

tests/test_rdkit.py

@@ -1,5 +1,6 @@
 """Test cases for the rdkit methods."""
 import pytest
+from rdkit.Chem.rdchem import Mol
 
 from jazzy.core import get_all_neighbours
 from jazzy.core import get_covalent_atom_idxs
@@ -62,25 +63,32 @@ def test_minimisation_works_for_valid_method() -> None:
 
 def test_invalid_minimisation_method() -> None:
     """It exits with a ValueError when an invalid method is entered."""
-    with pytest.raises(Exception):
+    with pytest.raises(ValueError):
         smiles = "CC"
         minimisation_method = "MMFF95"
-        m = rdkit_molecule_from_smiles(
+        rdkit_molecule_from_smiles(
             smiles=smiles,
             minimisation_method=minimisation_method,
         )
-        assert m is None
 
 
 def test_invalid_embedding_type() -> None:
     """It exits with a ValueError when an invalid method is entered."""
-    with pytest.raises(Exception):
+    with pytest.raises(ValueError):
         smiles = "CC"
-        m = rdkit_molecule_from_smiles(
+        rdkit_molecule_from_smiles(
             smiles=smiles,
             embedding_type="4d",
         )
-        assert m is None
+
+
+def test_warning_2d_embedding_with_minimisation() -> None:
+    """It ignores the clash between 2D embedding and energy minimisation."""
+    smiles = "CC"
+    m = rdkit_molecule_from_smiles(
+        smiles=smiles, embedding_type="2D", minimisation_method="MMFF94"
+    )
+    assert isinstance(m, Mol)
 
 
 def test_embedding_fails_with_fewer_iterations() -> None: