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Algorithmic Analysis of Cahn-Ingold-Prelog Rules of Stereochemistry: Proposals for Revised Rules and a Guide for Machine Implementation

preprint
submitted on 24.05.2018 and posted on 25.05.2018 by Robert M. Hanson, John Mayfield, Mikko J. Vainio, Andrey Yerin, Dmitry Redkin, Sophia Musacchio

The most recent version of the Cahn-Ingold-Prelog rules for the determination of stereodescriptors as described in Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (the “Blue Book”) were analyzed by an international team of cheminformatics software developers. Algorithms for machine implementation were designed, tested, and cross-validated. Deficiencies in Sequence Rules 1b and 2 were found, and proposed language for their modification is presented. A concise definition of an additional rule (“Rule 6,” below) is proposed, which succinctly covers several cases only tangentially mentioned in the 2013 recommendations. Each rule is discussed from the perspective of machine implementation. The four resultant implementations are supported by validation suites in 2D and 3D SDF format as well as SMILES. The validation suites include all significant examples in Chapter 9 of the Blue Book, as well as several additional structures that highlight more complex aspects of the rules not addressed or not clearly analyzed in that work. These additional structures support a case for the need for modifications of the Sequence Rules.

History

Email Address of Submitting Author

john.mayfield@cantab.net

Email Address(es) for Other Author(s)

hansonr@stolaf.edu, mikko.vainio@abo.fi, erin@acdlabs.ru, redkin@acdlabs.ru, musacc1@stolaf.edu

Institution

NextMove Software

Country

United Kingdom

ORCID For Submitting Author

0000-0001-7730-2646

Declaration of Conflict of Interest

No conflict of interest

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