Computer-Assisted Retrosynthesis Based on Molecular Similarity.

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.

SUBMITTER: Coley CW 

PROVIDER: S-EPMC5746854 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature