Cheminformatics analysis of organic substituents: identification of the most common substituents, calculation of substituent properties, and automatic identification of drug-like bioisosteric groups

被引:218
作者
Ertl, P [1 ]
机构
[1] Novartis Pharma AG, Mol Simulat Grp, CH-4002 Basel, Switzerland
来源
JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES | 2003年 / 43卷 / 02期
关键词
D O I
10.1021/ci0255782
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A large set of more than 3 million molecules was processed to find all the organic substituents contained in the set and to identify the most common ones. During the analysis, 849 574 unique substituents were found. Extrapolated to the number of known organic molecules, this result suggests that about 3.1 million substituents are known. Based on these findings the size of virtual organic chemistry space accessible using currently known synthetic methods is estimated to be between 10(20) and 10(21) molecules. The extracted substituents were characterized by calculated electronic, hydrophobic, steric, and hydrogen bonding properties as well as by the drug-likeness index. Various possible applications of such a large database of drug-like substituents characterized by calculated properties are discussed and illustrated by reference to a Web-based tool for automatic identification of bioisosteric groups.
引用
收藏
页码:374 / 380
页数:7
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