2018
DOI: 10.1021/acs.jcim.8b00324
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Algorithmic Analysis of Cahn–Ingold–Prelog Rules of Stereochemistry: Proposals for Revised Rules and a Guide for Machine Implementation

Abstract: 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"; Favre and Powell. Royal Society of Chemistry, 2014; http://dx.doi.org/10.1039/9781849733069 ) 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 … Show more

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Cited by 16 publications
(19 citation statements)
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“…A chiral molecule usually has at least one chiral center and the Cahn-Ingold-Prelog (CIP) priority rules determine the chiral configuration (R/S) without calculations: [1,2] these rules have recently been updated. [3] There are however, optical isomers of coordination compounds used as stereoselectivity catalysts for which the chirality cannot be assigned from the CIP rules. The existence of chirality has important implications [4][5][6] and the origin of chiral asymmetry [7] in molecular biology is one of the great mysteries in the understanding of the origin of life.…”
Section: Introductionmentioning
confidence: 99%
“…A chiral molecule usually has at least one chiral center and the Cahn-Ingold-Prelog (CIP) priority rules determine the chiral configuration (R/S) without calculations: [1,2] these rules have recently been updated. [3] There are however, optical isomers of coordination compounds used as stereoselectivity catalysts for which the chirality cannot be assigned from the CIP rules. The existence of chirality has important implications [4][5][6] and the origin of chiral asymmetry [7] in molecular biology is one of the great mysteries in the understanding of the origin of life.…”
Section: Introductionmentioning
confidence: 99%
“…To codify chirality aspects, the concept of correction factor is employed. A correction factor is a number‐pair used to assign a quantitative meaning to the atoms categorized as rectus (R) or sinister (S) according to the Cahn‐Ingold‐Prelog rules, being the pair 1 and −1 the one most commonly employed. In this software, different from the other ones, real values other than to 1 and − 1 can be selected as the correction factors for the atoms labeled as R or S. The usefulness of using different correction factors have been evidenced in QSAR modeling (see tables 3–5 in ref.…”
Section: Novel Implementations and Resultsmentioning
confidence: 99%
“…If that parameter is less than 0, then the L mδ ‐measure satisfies the subadditivity property (low synergism); if it is equal to 0, then the L mδ ‐measure is additive; and if it is greater than 0, then the L mδ ‐measure satisfies the superadditivity property (high synergism). It is important to remark that, in this work, the sorting of the atom‐level descriptors in ascending order was built into the software for the calculation of the Choquet integral . In this way, the b j value (see Schema ) will be j th smallest value of the atom‐level descriptors.…”
Section: Novel Implementations and Resultsmentioning
confidence: 99%
“…Momen Dipol (11) Nama IUPAC (28) Trihidrooksidoboron Asam Borat (15) Nama Lain (10) Sumber (26) Struktur (12) Nama (9) Kegunaan (14) Sifat (1) Asam Boraks (4) Sasolit Asam Ortoborat (27) Borofaks…”
Section: Analisis Gapunclassified