Tautomerism in large databases.
Tautomerism in large databases.
复制标题
DOI：
10.1007/s10822-010-9346-4
复制
发表时间：
2010-06
影响因子：
3.5
通讯作者：
Nicklaus, Marc C.
中科院分区：
文献类型：
--
作者：
Sitzmann, Markus;Ihlenfeldt, Wolf-Dietrich;Nicklaus, Marc C.
我们使用 NCI CADD Group 的化学结构数据库 (CSDB)（汇集了 150 多个小分子数据库，总计 1.035 亿条结构记录）对当前最大的真实（即非计算机生成）化合物集之一进行互变异构分析。该分析是使用 NCI CADD Group 开发的可计算化学结构标识符进行的，基于化学信息学工具包 CACTVS 中提供的哈希码和新开发的评分方案，用于定义任何遇到的结构的规范互变异构体。使用了 CACTVS 的互变异构定义，即一组以 SMIRKS 线符号表示的 21 条变换规则，它对所包括的互变异构互变的可能类型采取了全面的立场。发现 CSDB 中超过 2/3 的独特结构可能存在互变异构。根据原始结构记录（包括原始结构记录）计算出总共 6.8 亿个互变异构体。同一数据库中的互变异构重叠（即至少存在一个其他条目，实际上只是同一化合物的不同互变异构表示），原始结构记录的平均比例为 0.3%，CSDB 中的一些数据库的值高达近 2%。投射到一组独特的结构（通过 FICuS 标识符）上，这种情况仍然发生在大约 1.5% 的病例中。在 CSDB 的所有组成数据库中，发现集合中近 10% 的记录存在互变异构重叠。
We have used the Chemical Structure DataBase (CSDB) of the NCI CADD Group, an aggregated collection of over 150 small-molecule databases totaling 103.5 million structure records, to conduct tautomerism analyses on one of the largest currently existing sets of real (i.e. not computer-generated) compounds. This analysis was carried out using calculable chemical structure identifiers developed by the NCI CADD Group, based on hash codes available in the chemoinformatics toolkit CACTVS and a newly developed scoring scheme to define a canonical tautomer for any encountered structure. CACTVS’s tautomerism definition, a set of 21 transform rules expressed in SMIRKS line notation, was used, which takes a comprehensive stance as to the possible types of tautomeric interconversion included. Tautomerism was found to be possible for more than 2/3 of the unique structures in the CSDB. A total of 680 million tautomers were calculated from, and including, the original structure records. Tautomerism overlap within the same individual database (i.e. at least one other entry was present that was really only a different tautomeric representation of the same compound) was found at an average rate of 0.3% of the original structure records, with values as high as nearly 2% for some of the databases in CSDB. Projected onto the set of unique structures (by FICuS identifier), this still occurred in about 1.5% of the cases. Tautomeric overlap across all constituent databases in CSDB was found for nearly 10% of the records in the collection.
登录
查看更多内容
影响因子：
3
作者：
IHLENFELDT, WD;GASTEIGER, J
通讯作者：
GASTEIGER, J
影响因子：
--
作者：
Rogers, D;Brown, RD;Hahn, M
通讯作者：
Hahn, M
影响因子：
3.5
作者：
Shelley, John C.;Cholleti, Anuradha;Uchimaya, Makoto
通讯作者：
Uchimaya, Makoto
影响因子：
3
作者：
Sitzmann, M.;Filippov, I. V.;Nicklaus, M. C.
通讯作者：
Nicklaus, M. C.
DOI：
10.1021/ci025582d
发表时间：
2003-05-01
期刊：
JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES
影响因子：
--
作者：
Trepalin, SV;Skorenko, AV;Savchuk, NP
通讯作者：
Savchuk, NP