Prediction of Organic Reaction Outcomes Using Machine Learning
Name
Prediction of organic reaction.pdf
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1.71 MB
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Adobe PDF
Checksum (MD5)
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Author(s)
Coley, Connor W.
Barzilay, Regina
Jaakkola, Tommi S.
Green, William H.
Jensen, Klavs F.
Coley, Connor Wilson
Jaakkola, Tommi S.
Green, William H.
Jensen, Klavs F.
Date Issued
April 2017
Journal
ACS Central Science
Publisher
American Chemical Society (ACS)
Citation
Coley, Connor W.; Barzilay, Regina; Jaakkola, Tommi S. et al. “Prediction of Organic Reaction Outcomes Using Machine Learning.” ACS Central Science 3, 5 (April 2017): 434–443 © 2017 American Chemical Society
Version
Final published version
Abstract
Computer assistance in synthesis design has existed for over 40 years, yet retrosynthesis planning software has struggled to achieve widespread adoption. One critical challenge in developing high-quality pathway suggestions is that proposed reaction steps often fail when attempted in the laboratory, despite initially seeming viable. The true measure of success for any synthesis program is whether the predicted outcome matches what is observed experimentally. We report a model framework for anticipating reaction outcomes that combines the traditional use of reaction templates with the flexibility in pattern recognition afforded by neural networks. Using 15 000 experimental reaction records from granted United States patents, a model is trained to select the major (recorded) product by ranking a self-generated list of candidates where one candidate is known to be the major product. Candidate reactions are represented using a unique edit-based representation that emphasizes the fundamental transformation from reactants to products, rather than the constituent molecules’ overall structures. In a 5-fold cross-validation, the trained model assigns the major product rank 1 in 71.8% of cases, rank ≤3 in 86.7% of cases, and rank ≤5 in 90.8% of cases.
MIT Department
Massachusetts Institute of Technology. Computer Science and Artificial Intelligence Laboratory
Massachusetts Institute of Technology. Department of Chemical Engineering
Massachusetts Institute of Technology. Department of Electrical Engineering and Computer Science
Terms of Use
Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
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DOI of Published Version
https://doi.org/10.1021/acscentsci.7b00064
