Computer-Assisted Retrosynthesis Based on Molecular Similarity
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acscentsci.7b00355.pdf
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1.48 MB
Format
Adobe PDF
Checksum (MD5)
189090103f4512f56a346bcbde0f2342
Author(s)
Coley, Connor Wilson
Rogers, Luke
Green Jr, William H
Jensen, Klavs F
Date Issued
December 2017
Journal
ACS Central Science
Publisher
American Chemical Society (ACS)
Citation
Coley, Connor W. et al. “Computer-Assisted Retrosynthesis Based on Molecular Similarity.” ACS Central Science 3, 12 (November 2017): 1237–1245 © 2017 American Chemical Society
Version
Final published version
Abstract
We demonstrate molecular similarity to be a surprisingly effective metric for proposing and ranking one-step retrosynthetic disconnections based on analogy to precedent reactions. The developed approach mimics the retrosynthetic strategy defined implicitly by a corpus of known reactions without the need to encode any chemical knowledge. Using 40 000 reactions from the patent literature as a knowledge base, the recorded reactants are among the top 10 proposed precursors in 74.1% of 5000 test reactions, providing strong quantitative support for our methodology. Extension of the one-step strategy to multistep pathway planning is demonstrated and discussed for two exemplary drug products.
MIT Department
Massachusetts Institute of Technology. Department of Chemical Engineering
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.7B00355
