DrawMorganBit fails by default

[eguidotti]

I'm trying to visualise fingerprints with DrawMorganBit but an error occurs when prepareMolsBeforeDrawing=True (the default) and stereochemistry is not displayed when prepareMolsBeforeDrawing=False. To reproduce:

1. Generate the fingerprints for a molecule and plot the molecule

from rdkit import Chem
from rdkit.Chem import Draw
from rdkit.Chem.rdMolDescriptors import GetMorganFingerprint

smiles = "C[C@]12C[C@H](O)[C@H]3[C@@H](CCC4=CC(=O)C=C[C@@]43C)[C@@H]1CC[C@]2(O)C(=O)CO"
mol = Chem.MolFromSmiles(smiles)

info = {}
GetMorganFingerprint(mol, radius=2, bitInfo=info, useChirality=True)
fingerprint = 1236726849

mol

2. plot the fingerprint setting prepareMolsBeforeDrawing=False -> OK but does not display stereochemistry

drawOptions = Draw.rdMolDraw2D.MolDrawOptions()
drawOptions.prepareMolsBeforeDrawing = False
Draw.DrawMorganBit(mol, fingerprint, info, drawOptions=drawOptions)

3. plot the fingerprint by default -> FAILS

Draw.DrawMorganBit(mol, fingerprint, info)

[23:39:09] 

****
Invariant Violation
no eligible neighbors for chiral center
Violation occurred on line 240 in file /Users/runner/work/rdkit-pypi/rdkit-pypi/build/temp.macosx-11.0-arm64-cpython-39/rdkit/Code/GraphMol/FileParsers/MolFileStereochem.cpp
Failed Expression: nbrScores.size()
****

---------------------------------------------------------------------------
RuntimeError                              Traceback (most recent call last)
Cell In[16], line 1
----> 1 Draw.DrawMorganBit(mol, fingerprint, info)

File ~/Library/Caches/pypoetry/virtualenvs/drugpredictor-wS4XGoJo-py3.9/lib/python3.9/site-packages/rdkit/Chem/Draw/IPythonConsole.py:304, in DrawMorganBit(mol, bitId, bitInfo, drawOptions, **kwargs)
    302 else:
    303   fn = Draw.DrawMorganBit
--> 304 return _DrawBit(fn, mol, bitId, bitInfo, drawOptions=drawOptions, **kwargs)

File ~/Library/Caches/pypoetry/virtualenvs/drugpredictor-wS4XGoJo-py3.9/lib/python3.9/site-packages/rdkit/Chem/Draw/IPythonConsole.py:277, in _DrawBit(fn, *args, **kwargs)
    274 if 'useSVG' not in kwargs:
    275   kwargs['useSVG'] = ipython_useSVG
--> 277 res = fn(*args, **kwargs)
    278 if kwargs['useSVG']:
    279   return SVG(res)

File ~/Library/Caches/pypoetry/virtualenvs/drugpredictor-wS4XGoJo-py3.9/lib/python3.9/site-packages/rdkit/Chem/Draw/__init__.py:701, in DrawMorganBit(mol, bitId, bitInfo, whichExample, **kwargs)
    699 def DrawMorganBit(mol, bitId, bitInfo, whichExample=0, **kwargs):
    700   atomId, radius = bitInfo[bitId][whichExample]
--> 701   return DrawMorganEnv(mol, atomId, radius, **kwargs)

File ~/Library/Caches/pypoetry/virtualenvs/drugpredictor-wS4XGoJo-py3.9/lib/python3.9/site-packages/rdkit/Chem/Draw/__init__.py:865, in DrawMorganEnv(mol, atomId, radius, molSize, baseRad, useSVG, aromaticColor, ringColor, centerColor, extraColor, drawOptions, **kwargs)
    863 drawOptions.includeMetadata = False
    864 drawer.SetDrawOptions(drawOptions)
--> 865 drawer.DrawMolecule(menv.submol, highlightAtoms=menv.highlightAtoms,
    866                     highlightAtomColors=menv.atomColors, highlightBonds=menv.highlightBonds,
    867                     highlightBondColors=menv.bondColors, highlightAtomRadii=menv.highlightRadii,
    868                     **kwargs)
    869 drawer.FinishDrawing()
    870 return drawer.GetDrawingText()

RuntimeError: Invariant Violation
	no eligible neighbors for chiral center
	Violation occurred on line 240 in file Code/GraphMol/FileParsers/MolFileStereochem.cpp
	Failed Expression: nbrScores.size()
	RDKIT: 2022.03.5
	BOOST: 1_75

Expected behavior
The fingerprint should be plotted correctly by default, and preserve the stereochemistry of the parent molecule. From my understanding, DrawMorganBit should plot a zoom of the molecule on the fingerprint environment. But it seems some additional steps happen here that attempt to sanitize or modify the fingerprint environment before plotting

Configuration (please complete the following information):

• RDKit version: 2022.03.5
• OS: macOS
• Python version (if relevant): 3.9
• Are you using conda? No
• If you are using conda, which channel did you install the rdkit from? pipit
• If you are not using conda: how did you install the RDKit? pip install rdkit-pypi

[greglandrum]

Confirmed the problem.