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Stereogroup lost when importing chiral sulfoxide from v3000 molfile #7983

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spparel opened this issue Nov 4, 2024 · 0 comments
Open

Stereogroup lost when importing chiral sulfoxide from v3000 molfile #7983

spparel opened this issue Nov 4, 2024 · 0 comments
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@spparel
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spparel commented Nov 4, 2024

Hello,

We came across the following issue.

When I import a compound containing a chiral sulfoxide with the corresponding stereogroup, the behavior is different when I import from cxsmiles vs when I import from v3000 molfile.

from rdkit import Chem
smilesParserParams = Chem.SmilesParserParams()
smilesParserParams.allowCXSMILES = True

source_smi = 'Cc1ccc(NC(=O)OCc2ccccc2[S@](C)=O)cc1 |a:16|'
mol: Chem.Mol = Chem.MolFromSmiles(source_smi, smilesParserParams)
mol.Debug()

Result:
...
16 16 S chg: 0 deg: 3 exp: 4 imp: 0 hyb: SP3 chi: CCW nbrs:[15 17 18]
Stereo Groups:
0 ABS rId: 0 wId: 0 atoms: { 16 }

m3k = '''
  Mrv2317 11042416102D          

  0  0  0     0  0            999 V3000
M  V30 BEGIN CTAB
M  V30 COUNTS 21 22 0 0 0
M  V30 BEGIN ATOM
M  V30 1 C -4.001 -2.31 0 0
M  V30 2 C -2.6674 -3.08 0 0
M  V30 3 C -1.3337 -2.31 0 0
M  V30 4 C 0 -3.08 0 0
M  V30 5 C 0 -4.6199 0 0
M  V30 6 N 1.3337 -5.3899 0 0
M  V30 7 C 2.6674 -4.6199 0 0
M  V30 8 O 2.6674 -3.08 0 0
M  V30 9 O 4.001 -5.3899 0 0
M  V30 10 C 5.3346 -4.6199 0 0
M  V30 11 C 6.6683 -5.3899 0 0
M  V30 12 C 8.002 -4.6199 0 0
M  V30 13 C 9.3357 -5.3899 0 0
M  V30 14 C 9.3357 -6.9299 0 0
M  V30 15 C 8.002 -7.6999 0 0
M  V30 16 C 6.6683 -6.9299 0 0
M  V30 17 C 5.3346 -7.6999 0 0 CFG=2
M  V30 18 C 4.001 -6.9299 0 0
M  V30 19 O 5.3346 -9.2399 0 0
M  V30 20 C -1.3337 -5.3899 0 0
M  V30 21 C -2.6674 -4.6199 0 0
M  V30 END ATOM
M  V30 BEGIN BOND
M  V30 1 1 1 2
M  V30 2 4 2 3
M  V30 3 4 3 4
M  V30 4 4 4 5
M  V30 5 1 5 6
M  V30 6 1 6 7
M  V30 7 2 7 8
M  V30 8 1 7 9
M  V30 9 1 9 10
M  V30 10 1 10 11
M  V30 11 4 11 12
M  V30 12 4 12 13
M  V30 13 4 13 14
M  V30 14 4 14 15
M  V30 15 4 15 16
M  V30 16 4 11 16
M  V30 17 1 17 16
M  V30 18 1 17 18 CFG=1
M  V30 19 4 5 20
M  V30 20 4 20 21
M  V30 21 4 2 21
M  V30 22 1 17 19
M  V30 END BOND
M  V30 BEGIN COLLECTION
M  V30 MDLV30/STEABS ATOMS=(1 17)
M  V30 END COLLECTION
M  V30 END CTAB
M  END
'''
m3 = Chem.MolFromMolBlock(m3k)
m3.Debug()

Result:
16 16 S chg: 0 deg: 3 exp: 4 imp: 0 hyb: SP3 chi: CCW nbrs:[15 17 18]

But no stereogroup included.

This seems specific to sulfoxides.

The issue can be reproduced in:
RDKit:2024.03.5
RDKit:2024.09.2

Configuration (please complete the following information):

  • OS: windows 11
  • Python version (if relevant): 3.11
  • Are you using conda? Yes
  • If you are using conda, which channel did you install the rdkit from? Conda-forge
  • If you are not using conda: how did you install the RDKit?
@spparel spparel added the bug label Nov 4, 2024
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