Dear Andrew, the reason why Chem.CanonSmiles("CN[S@@](=O)C1=CC=CC=C1") returns
'CN[S@@](=O)c1ccccc1' and Chem.CanonSmiles("CN1.[S@@]1(=O)C1=CC=CC=C1") returns 'CN[S@](=O)c1ccccc1' is that there is a "ghost" atom involved in determining the sulfur chirality, which is a lone pair, which is the sulfur lone pair, which concurs in determining the atom parity. Even if this is not in the Daylight specs, the lone-pair is usually treated as an implicit nitrogen, and therefore considered as the first atom in the clockwise or anticlockwise accounting: http://sourceforge.net/p/cdk/mailman/message/34650435/ http://www.opensmiles.org/opensmiles.html#chirality Therefore, the sulfoxide case is equivalent to the following: Chem.CanonSmiles("CN[C@@H](O)C1=CC=CC=C1") 'CN[C@@H](O)c1ccccc1' Chem.CanonSmiles("CN1.[C@@H]1(O)C1=CC=CC=C1") 'CN[C@H](O)c1ccccc1' Best, Paolo On 02/08/16 15:30, Andrew Dalke wrote: > Thanks Paolo and Hannes for pointing me to sulfoxide. I am enlightened! > > I assume this is something that every chemist knows, but it's not mentioned > in the Daylight SMILES documentation (or the OpenSMILES documentation), so I > had no clue. I wonder how many more cases there are like that. > > Any idea then on why the following two have inverted chiralities? > > >>> Chem.CanonSmiles("CN[S@@](=O)C1=CC=CC=C1") > 'CN[S@@](=O)c1ccccc1' > > >>> Chem.CanonSmiles("C2.N23.[S@@]3(=O)C1=CC=CC=C1") > 'CN[S@](=O)c1ccccc1' > > > > > Andrew > da...@dalkescientific.com > > > > ------------------------------------------------------------------------------ > Site24x7 APM Insight: Get Deep Visibility into Application Performance > APM + Mobile APM + RUM: Monitor 3 App instances at just $35/Month > Monitor end-to-end web transactions and take corrective actions now > Troubleshoot faster and improve end-user experience. Signup Now! > http://pubads.g.doubleclick.net/gampad/clk?id=272487151&iu=/4140 > _______________________________________________ > Rdkit-discuss mailing list > Rdkit-discuss@lists.sourceforge.net > https://lists.sourceforge.net/lists/listinfo/rdkit-discuss ------------------------------------------------------------------------------ Site24x7 APM Insight: Get Deep Visibility into Application Performance APM + Mobile APM + RUM: Monitor 3 App instances at just $35/Month Monitor end-to-end web transactions and take corrective actions now Troubleshoot faster and improve end-user experience. Signup Now! http://pubads.g.doubleclick.net/gampad/clk?id=272487151&iu=/4140 _______________________________________________ Rdkit-discuss mailing list Rdkit-discuss@lists.sourceforge.net https://lists.sourceforge.net/lists/listinfo/rdkit-discuss