Hi,

(Open Babel 2.2.3)

The following smiles
O=C1COC=C1
has a charge of -5 when ionized as follow:
babel -p 7.4 file.smi out.smi
The smiles output is:
[O-][C-]1=[C-][C-]=[O-]C1

With babel 2.2.99 I just build:
[O-]C1=CC=[O]C1
better but not OK, IMHO.


I found this with
C[C@@]1(C(=O)C=C(O1)C(=O)[O-])c1ccccc1     ZINC00000010
which gives with -p 7.4
C[C@@]1([C-](=[C-][C-](=[O-]1)C(=O)[O-])[O-])c1ccccc1

More than 400 molecules seems to be problematic, out of my test set of
20 thousands, like
COC1=CC(=O)O[C@@H](C1)/C=C/c2ccccc2 ZINC00001102
CC1(N=C(N=C(N1c2ccc(cc2)Cl)N)N)C ZINC00001233
CC1([NH+]=C(N=C(N1c2ccc(cc2)Cl)N)N)C ZINC00001233

ionized (2.2.3, didn't try with 2.2.99):
C[O-]=[C-]1[C-]=[C-]([O-])O[C@@H](C1)/C=C/c1ccccc1      ZINC00001102
CC1(N=[C+](N=[C+](N1c1ccc(cc1)Cl)N)N)C  ZINC00001233
CC1([N+]=[C+](N=[C+](N1c1ccc(cc1)Cl)N)N)C       ZINC00001233

Is it a bug?

Regards,
Pascal

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