Date Severity Status Feedback
Sep 21 2011 7:28PM Normal Acknowledged I have tried entering both the SMILES and InChI for quinine (obtained from Chemspider) into the SciFinder structure editor. (It does not accept the InChIKey.) Each time I received this error (paraphrased): "angles between attachments to a chiral node don't provide unambiguous stereo representation. Redraw attachments to remove ambiguity." I am not a chemist. I am sending this to you because I think it is a structure issue rather than a SciFinder issue. So, why is this error occurring? I would like to understand because I am a librarian trying to learn.
There are lots of points for discussion here. 1. Unlike InChI or SMILES - InChIKey does not encode the structural information, but must be "looked-up" (see: http://en.wikipedia.org/wiki/InChI) 2. The structure in this record is valid and has fully defined unambiguous stereochemistry, which in this case is correct for quinine. 3. SciFinder is a product of CAS and they would be best placed to explain the error to you. Based on your error message my best guess would be that when the SMILES or InChI is converted to a structure in the editor the layout (which is presumably something done by the editor itself) is not generated in a way that the software can capture the stereochemical information. It is possible that minor tweaks to the layout would fix this issue. If there is a chemical information specialist in your organisation they may also be able to provide more insight.