Papers › Computer-Assisted Retrosynthesis Based on Molecular Similarity

Computer-Assisted Retrosynthesis Based on Molecular Similarity

16 Nov 2017ACS Cent. Sci. 2017 11archive 2025-07-28

Connor W. Coley, Luke Rogers, William H. Green, and Klavs F. Jensen

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.

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RetrosynthesisSingle-step retrosynthesis

Results from the paper archive 2025-07-28

TaskDatasetModelMetricValueRank at snapshotLeaderboardReport
Single-step retrosynthesis USPTO-50k RetroSim (reaction class as prior) Top-1 accuracy 52.9 #25 of 35 Archive leaderboard report
Single-step retrosynthesis USPTO-50k RetroSim (reaction class as prior) Top-10 accuracy 88.1 #25 of 35 Archive leaderboard report
Single-step retrosynthesis USPTO-50k RetroSim (reaction class as prior) Top-3 accuracy 73.8 #25 of 35 Archive leaderboard report
Single-step retrosynthesis USPTO-50k RetroSim (reaction class as prior) Top-5 accuracy 81.2 #25 of 35 Archive leaderboard report
Single-step retrosynthesis USPTO-50k RetroSim (reaction class unknown) Top-1 accuracy 37.3 #34 of 35 Archive leaderboard report
Single-step retrosynthesis USPTO-50k RetroSim (reaction class unknown) Top-10 accuracy 74.1 #34 of 35 Archive leaderboard report
Single-step retrosynthesis USPTO-50k RetroSim (reaction class unknown) Top-3 accuracy 54.7 #34 of 35 Archive leaderboard report
Single-step retrosynthesis USPTO-50k RetroSim (reaction class unknown) Top-5 accuracy 63.3 #34 of 35 Archive leaderboard report

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