No Electron Left Behind: A Rule-Based Expert System To Predict Chemical Reactions and Reaction Mechanisms

被引:51
作者
Chen, Jonathan H. [2 ,3 ]
Baldi, Pierre [1 ,2 ,3 ]
机构
[1] Univ Calif Irvine, Dept Biol Chem, Irvine, CA 92697 USA
[2] Univ Calif Irvine, Inst Genom & Bioinformat, Sch Informat & Comp Sci, Irvine, CA 92697 USA
[3] Univ Calif Irvine, Dept Comp Sci, Sch Informat & Comp Sci, Irvine, CA 92697 USA
基金
美国国家科学基金会;
关键词
D O I
10.1021/ci900157k
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Predicting the course and major products of arbitrary reactions is a fundamental problem in chemistry, one that chemists must address in a variety of tasks ranging from synthesis design to reaction discovery. Described here is an expert system to predict organic chemical reactions based on a knowledge base of over 1500 manually composed reaction transformation rules. Novel rule extensions are introduced to enable robust predictions and describe detailed reaction mechanisms at the level of electron flows in elementary reaction steps, ensuring that. all reactions are properly balanced and atom-mapped. The core reaction prediction functionalities of this expert system are illustrated with applications including: (1) prediction of detailed reaction mechanisms; (2) computer-based learning in organic chemistry; (3) retrosynthetic analysis; and (4) combinatorial library design. Select applications are available via http://cdb.ics.uci.edu.
引用
收藏
页码:2034 / 2043
页数:10
相关论文
共 30 条
  • [21] Loudon M., 2001, ORGANIC CHEM, V4th
  • [22] Miller A., 1992, WRITING REACTION MEC
  • [23] *OPENEYE, OECHEM TOOLKIT 1 4 2
  • [24] A novel method for characterization of three-dimensional reaction fields based on electrostatic and steric interactions toward the goal of quantitative analysis and understanding of organic reactions
    Satoh, H
    Itono, S
    Funatsu, K
    Takano, K
    Nakata, T
    [J]. JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES, 1999, 39 (04): : 671 - 678
  • [25] Schnur DM, 2008, CURR OPIN DRUG DISC, V11, P375
  • [26] REACTION PREDICTION - THE SUGGESTIONS OF THE BEPPE PROGRAM
    SELLO, G
    [J]. JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES, 1992, 32 (06): : 713 - 717
  • [27] Smith J.G., 2006, ORGANIC CHEM, V1st
  • [28] ROBIA: A reaction prediction program
    Socorro, IM
    Taylor, K
    Goodman, JM
    [J]. ORGANIC LETTERS, 2005, 7 (16) : 3541 - 3544
  • [29] Computer-aided organic synthesis
    Todd, MH
    [J]. CHEMICAL SOCIETY REVIEWS, 2005, 34 (03) : 247 - 266
  • [30] Issues in computer supported inquiry learning in science
    van Joolingen, W. R.
    de Jong, T.
    Dimitrakopoulou, A.
    [J]. JOURNAL OF COMPUTER ASSISTED LEARNING, 2007, 23 (02) : 111 - 119