I always refer back to this graphic in Alberto Gobbi's "Handling of Tautomerism and Stereochemistry in Compound Registration" paper: https://pubs.acs.org/doi/10.1021/ci200330x
[image: image.png] @Greg Landrum <greg.land...@gmail.com>, I would interpret "para stereochemistry" as #3 in the above image. And "dependent stereochemistry" as #2 in the above plot since the stereochemistry depends on the stereochemistry of other centers. Alberto's paper defines the above as: 1. steroegenic atom/chiral: typical right/left; R/S 2. pseudo-chiral (referencing an IUPAC paper and the gold book); note, the same thing can happen with cis/trans double bond stereo, not depicted above 3. symmetric stereogenic centers 4. stereogenic bond: typical cis/trans; E/Z 5. atropisomers TLDR: english is so imprecise, show me the SMILES. :-) -Brian On Thu, May 27, 2021 at 5:32 AM Greg Landrum <greg.land...@gmail.com> wrote: > > I first heard the term "para stereochemistry" from Salome Rieder (a PhD > student at the ETH Zurich), who pointed me to this paper as a source for > term: > https://pubs.acs.org/doi/pdf/10.1021/ci00016a003 > > I tend to call this "dependent stereochemistry" since I think it's clear, > but that's definitely something I just made up. :-) > > -greg > > > On Wed, May 26, 2021 at 10:54 PM Jean-Marc Nuzillard < > jm.nuzill...@univ-reims.fr> wrote: > >> Dear Paolo, >> >> According to https://goldbook.iupac.org/terms/view/P04921 >> your interpretation is certainly the correct one. >> I still have to find how this r/s assignment is determined. >> >> Many thanks again, >> >> Jean-Marc >> >> >> Le 26/05/2021 à 22:40, Paolo Tosco a écrit : >> > Dear Jean-Marc, >> > >> > I believe it indicates what the IUPAC Gold Book refers to as >> pseudoasymmetry. >> > Let’s see if others agree with my interpretation. >> > >> > Cheers, >> > P. >> > >> >> On 26 May 2021, at 22:28, Jean-Marc Nuzillard < >> jm.nuzill...@univ-reims.fr> wrote: >> >> >> >> I believed I sent a message with the same title a few minutes ago, >> but apparently something went wrong. >> >> >> >> Reading the RDKit book about function FindMolChiralCenters(), >> >> I saw that it provides a better handling of para-stereochemisry. >> >> This concept is not familiar to me. >> >> Google did not help and sent me back to the RDKit Book. >> >> So, what is para-stereochemistry? >> >> >> >> Best regards, >> >> >> >> Jean-Marc >> >> >> >> -- >> >> Jean-Marc Nuzillard >> >> Directeur de Recherches au CNRS >> >> >> >> Institut de Chimie Moléculaire de Reims >> >> CNRS UMR 7312 >> >> Moulin de la Housse >> >> CPCBAI, Bâtiment 18 >> >> BP 1039 >> >> 51687 REIMS Cedex 2 >> >> France >> >> >> >> Tel : 03 26 91 82 10 >> >> Fax : 03 26 91 31 66 >> >> http://www.univ-reims.fr/icmr >> >> http://eos.univ-reims.fr/LSD/CSNteam.html >> >> >> >> http://www.univ-reims.fr/LSD/ >> >> http://www.univ-reims.fr/LSD/JmnSoft/ >> >> >> >> >> >> >> >> _______________________________________________ >> >> Rdkit-discuss mailing list >> >> Rdkit-discuss@lists.sourceforge.net >> >> https://lists.sourceforge.net/lists/listinfo/rdkit-discuss >> >> >> -- >> Jean-Marc Nuzillard >> Directeur de Recherches au CNRS >> >> Institut de Chimie Moléculaire de Reims >> CNRS UMR 7312 >> Moulin de la Housse >> CPCBAI, Bâtiment 18 >> BP 1039 >> 51687 REIMS Cedex 2 >> France >> >> Tel : 03 26 91 82 10 >> Fax : 03 26 91 31 66 >> http://www.univ-reims.fr/icmr >> http://eos.univ-reims.fr/LSD/CSNteam.html >> >> http://www.univ-reims.fr/LSD/ >> http://www.univ-reims.fr/LSD/JmnSoft/ >> >> >> >> _______________________________________________ >> Rdkit-discuss mailing list >> Rdkit-discuss@lists.sourceforge.net >> https://lists.sourceforge.net/lists/listinfo/rdkit-discuss >> > _______________________________________________ > Rdkit-discuss mailing list > Rdkit-discuss@lists.sourceforge.net > https://lists.sourceforge.net/lists/listinfo/rdkit-discuss >
_______________________________________________ Rdkit-discuss mailing list Rdkit-discuss@lists.sourceforge.net https://lists.sourceforge.net/lists/listinfo/rdkit-discuss
