Algorithmic Analysis of Cahn-IngoId-Prelog Rules of Stereochemistry: Proposals for Revised Rules and a Guide for Machine Implementation
Algorithmic Analysis of Cahn-IngoId-Prelog Rules of Stereochemistry: Proposals for Revised Rules and a Guide for Machine Implementation
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DOI：
10.1021/acs.jcim.8b00324
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发表时间：
2018-09-01
影响因子：
5.6
通讯作者：
Redkin, Dmitry
中科院分区：
文献类型：
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作者：
Hanson, Robert M.;Musacchi, Sophia;Redkin, Dmitry
Cahn Ingold Prelog规则的最新版本，用于确定立体描述符，如《有机化学命名法：IUPAC建议和首选名称2013》（“蓝皮书”）中所述；Favre和Powell。英国皇家化学学会，2014；http://dx.doi.org/10.1039/9781849733069)，由一个国际化学信息学软件开发团队进行分析。设计、测试和交叉验证了机器实现的算法。发现了序列规则1b和2的不足，并提出了修改它们的建议语言。建议对一项附加规则（下文“规则6”）作出简明定义，其中简明地涵盖了2013年建议中只略微提及的几种情况。每条规则都是从机器实现的角度来讨论的。这四种最终实现由300个复合验证套件以2D和3D结构数据文件（SDF）格式以及SMILES （https://cipvalidationsuite.github.io/ValidationSuite）支持。验证套件包括蓝皮书第9章中所有重要的示例，以及一些额外的结构，这些结构突出了在该工作中未处理或未明确分析的规则的更复杂方面。这些额外的结构支持需要修改序列规则的情况。
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 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 a 300-compound validation suite in both 2D and 3D structure data file (SDF) format as well as SMILES (https://cipvalidationsuite.github.io/ValidationSuite). 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 to the Sequence Rules.