Issue 2, 2019

A graph-convolutional neural network model for the prediction of chemical reactivity

Abstract

We present a supervised learning approach to predict the products of organic reactions given their reactants, reagents, and solvent(s). The prediction task is factored into two stages comparable to manual expert approaches: considering possible sites of reactivity and evaluating their relative likelihoods. By training on hundreds of thousands of reaction precedents covering a broad range of reaction types from the patent literature, the neural model makes informed predictions of chemical reactivity. The model predicts the major product correctly over 85% of the time requiring around 100 ms per example, a significantly higher accuracy than achieved by previous machine learning approaches, and performs on par with expert chemists with years of formal training. We gain additional insight into predictions via the design of the neural model, revealing an understanding of chemistry qualitatively consistent with manual approaches.

Graphical abstract: A graph-convolutional neural network model for the prediction of chemical reactivity

Supplementary files

Article information

Article type
Edge Article
Submitted
22 9 2018
Accepted
23 11 2018
First published
26 11 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 370-377

A graph-convolutional neural network model for the prediction of chemical reactivity

Connor W. Coley, W. Jin, L. Rogers, T. F. Jamison, T. S. Jaakkola, W. H. Green, R. Barzilay and K. F. Jensen, Chem. Sci., 2019, 10, 370 DOI: 10.1039/C8SC04228D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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