Toward a Comprehensive Treatment of Tautomerism in Chemoinformatics Including in InChI V2.
Toward a Comprehensive Treatment of Tautomerism in Chemoinformatics Including in InChI V2.
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DOI：
10.1021/acs.jcim.9b01080
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发表时间：
2020-03-23
影响因子：
5.6
通讯作者：
Nicklaus MC
中科院分区：
文献类型：
--
作者：
Dhaked DK;Ihlenfeldt WD;Patel H;Delannée V;Nicklaus MC
我们收集了 86 种不同的互变异构体相互转化。其中，54 个为原位（非环链）互变异构，21 个为环链互变异构，11 个为化合价互变异构。这些规则大部分是从实验文献中提取的。二十条规则涵盖了最著名的互变异构类型，例如酮-烯醇互变异构，取自化学信息学工具包 CACTVS 对互变异构的默认处理。这些规则针对总共超过 4 亿个（非唯一）结构的 9 个不同数据库进行了分析，包括其出现率、覆盖范围的相互重叠以及 InChI V.1.05 对规则列举的互变异构体集的概括，包括 InChI 的标准版本和非标准版本，并打开了增加的互变异构体处理选项 15T 和 KET。这些结果和本研究的背景是在 IUPAC InChI 项目的背景下讨论的，该项目的任务是重新设计 InChI 版本 2 的互变异构处理。应用本文中提出的规则将使典型小分子数据库中受 InChI V2 互变异构互变影响的化合物数量大约增加三倍。已经创建了一个网络工具来测试这些规则，网址为 https://cactus.nci.nih.gov/tautomerizer。
We have collected 86 different transforms of tautomeric interconversions. Out of those, 54 are for prototropic (non-ring–chain) tautomerism, 21 for ring–chain tautomerism, and 11 for valence tautomerism. The majority of these rules have been extracted from experimental literature. Twenty rules, covering the most well-known types of tautomerism such as keto–enol tautomerism, were taken from the default handling of tautomerism by the chemoinformatics toolkit CACTVS. The rules were analyzed against nine differerent databases totaling over 400 million (non-unique) structures as to their occurrence rates, mutual overlap in coverage, and recapitulation of the rules’ enumerated tautomer sets by InChI V.1.05, both in InChI’s Standard and a Nonstandard version with the increased tautomer-handling options 15T and KET turned on. These results and the background of this study are discussed in the context of the IUPAC InChI Project tasked with the redesign of handling of tautomerism for an InChI version 2. Applying the rules presented in this paper would approximately triple the number of compounds in typical small-molecule databases that would be affected by tautomeric interconversion by InChI V2. A web tool has been created to test these rules at https://cactus.nci.nih.gov/tautomerizer.
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影响因子：
3.5
作者：
Sitzmann, Markus;Ihlenfeldt, Wolf-Dietrich;Nicklaus, Marc C.
通讯作者：
Nicklaus, Marc C.
影响因子：
8.6
作者：
Heller SR;McNaught A;Pletnev I;Stein S;Tchekhovskoi D
通讯作者：
Tchekhovskoi D
影响因子：
3.5
作者：
Martin, Yvonne Connolly
通讯作者：
Martin, Yvonne Connolly
影响因子：
14.9
作者：
Kim S;Thiessen PA;Bolton EE;Chen J;Fu G;Gindulyte A;Han L;He J;He S;Shoemaker BA;Wang J;Yu B;Zhang J;Bryant SH
通讯作者：
Bryant SH
影响因子：
5.6
作者：
Wahl, Oya;Sander, Thomas
通讯作者：
Sander, Thomas