Incorrect stereo label

Hi ChemAxon,

We recently encountered a situation where Marvin/JChem appear to assign the incorrect stereo label.

As an example, for the following CXSMILES, from this paper: 

OCCC1=CC=C(C=C1)N(C[C@@H](O)CN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1)S(=O)(=O)C1CCC(Cl)CC1 |c:5,7,25,27,32,34,t:3,23,30|

The ChemAxon tools assign the S label, but Chemdraw assigns the R label, which we think is correct based on the literature.

We are using JChem/Marvin 6.1.4.

 

Thanks,

Krishna

Hi Krishna,

Unfortunately, I cannot reproduce the problem you reported. I imported that SMILES to Marvin and ChemDraw, and I found that in both cases the stereocentre is (S). Also, in daylight's depict, it is imported as (S).

Can you specify the problem in more detail?

Thanks,
Peter

Hi Peter,

Thank you for looking into this.

Unfortunately the structure that does exhibit this problem is proprietary, and the chemist who reported it has not been able to come up with a non-proprietary structure that reproduces the issue. He thought this one did (I didn't have access to ChemDraw to verify), but as you demonstrated it does not.

You can consider this issue closed for now; thank you again for your assistance.

Krishna