A Generative Model For Electron Paths
Authors: John Bradshaw, Matt J. Kusner, Brooks Paige, Marwin H. S. Segler, José Miguel Hernández-Lobato
Keywords: Molecules, Reaction Prediction, Graph Neural Networks, Deep Generative Models
TL;DR: A generative model for reaction prediction that learns the mechanistic electron steps of a reaction directly from raw reaction data.
Abstract: Chemical reactions can be described as the stepwise redistribution of electrons in molecules. As such, reactions are often depicted using "arrow-pushing" diagrams which show this movement as a sequence of arrows. We propose an electron path prediction model (ELECTRO) to learn these sequences directly from raw reaction data. Instead of predicting product molecules directly from reactant molecules in one shot, learning a model of electron movement has the benefits of (a) being easy for chemists to interpret, (b) incorporating constraints of chemistry, such as balanced atom counts before and after the reaction, and (c) naturally encoding the sparsity of chemical reactions, which usually involve changes in only a small number of atoms in the reactants. We design a method to extract approximate reaction paths from any dataset of atom-mapped reaction SMILES strings. Our model achieves excellent performance on an important subset of the USPTO reaction dataset, comparing favorably to the strongest baselines. Furthermore, we show that our model recovers a basic knowledge of chemistry without being explicitly trained to do so.