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Conformer Generation Fails for three-coordinate Ns with specified stereo #5883

Description

@gncs

Describe the bug
RDKit doesn't seem to be able to generate conformers for a three-membered ring with two nitrogen atoms if stereocenters are specified.

To Reproduce

from rdkit.Chem import AllChem

mol = AllChem.AddHs(AllChem.MolFromSmiles("N1NC1"))

c1 = AllChem.Mol(mol, quickCopy=False)
AllChem.AssignStereochemistry(c1, flagPossibleStereoCenters=False)

for isomer in AllChem.EnumerateStereoisomers(c1):
    AllChem.EmbedMolecule(isomer)
    assert isomer.GetNumConformers() == 1

c2 = AllChem.Mol(mol, quickCopy=False)
AllChem.AssignStereochemistry(c2, flagPossibleStereoCenters=True)  # flagPossibleStereoCenters

for isomer in AllChem.EnumerateStereoisomers(c2):
    AllChem.EmbedMolecule(isomer)
    assert isomer.GetNumConformers() == 1  # Fails

Configuration

  • RDKit version: 2022.09.1, py38h5acb366_1, conda-forge
  • OS: Ubuntu 20.04

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