Molecular Hypergraph Grammar with Its Application to Molecular Optimization



  • Hiroshi Kajino

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Molecular optimization aims to discover novel molecules with desirable properties, and its two fundamental challenges are: (i) it is not trivial to generate valid molecules in a controllable way due to hard chemical constraints such as the valency conditions, and (ii) it is often costly to evaluate a property of a novel molecule, and therefore, the number of property evaluations is limited. These challenges are to some extent alleviated by a combination of a variational autoencoder (VAE) and Bayesian optimization (BO), where VAE converts a molecule into/from its latent continuous vector, and BO optimizes a latent continuous vector (and its corresponding molecule) within a limited number of property evaluations. While the most recent work, for the first time, achieved 100% validity, its architecture is rather complex due to auxiliary neural networks other than VAE, making it difficult to train. This paper presents a molecular hypergraph grammar variational autoencoder (MHG-VAE), which uses a single VAE to achieve 100% validity. Our idea is to develop a graph grammar encoding the hard chemical constraints, called molecular hypergraph grammar (MHG), which guides VAE to always generate valid molecules. We also present an algorithm to construct MHG from a set of molecules.

Please cite our work using the BibTeX below.

  title = 	 {Molecular Hypergraph Grammar with Its Application to Molecular Optimization},
  author =       {Kajino, Hiroshi},
  booktitle = 	 {Proceedings of the 36th International Conference on Machine Learning},
  pages = 	 {3183--3191},
  year = 	 {2019},
  editor = 	 {Chaudhuri, Kamalika and Salakhutdinov, Ruslan},
  volume = 	 {97},
  series = 	 {Proceedings of Machine Learning Research},
  month = 	 {09--15 Jun},
  publisher =    {PMLR},
  pdf = 	 {},
  url = 	 {}
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