Repository logo
 

A review of molecular representation in the age of machine learning

Published version
Peer-reviewed

Change log

Authors

Abstract

jats:titleAbstract</jats:title>jats:pResearch in chemistry increasingly requires interdisciplinary work prompted by, among other things, advances in computing, machine learning, and artificial intelligence. Everyone working with molecules, whether chemist or not, needs an understanding of the representation of molecules in a machine‐readable format, as this is central to computational chemistry. Four classes of representations are introduced: string, connection table, feature‐based, and computer‐learned representations. Three of the most significant representations are simplified molecular‐input line‐entry system (SMILES), International Chemical Identifier (InChI), and the MDL molfile, of which SMILES was the first to successfully be used in conjunction with a variational autoencoder (VAE) to yield a continuous representation of molecules. This is noteworthy because a continuous representation allows for efficient navigation of the immensely large chemical space of possible molecules. Since 2018, when the first model of this type was published, considerable effort has been put into developing novel and improved methodologies. Most, if not all, researchers in the community make their work easily accessible on GitHub, though discussion of computation time and domain of applicability is often overlooked. Herein, we present questions for consideration in future work which we believe will make chemical VAEs even more accessible.</jats:p>jats:pThis article is categorized under:<jats:list list-type="simple"> jats:list-itemjats:pData Science > Chemoinformatics</jats:p></jats:list-item> </jats:list></jats:p>

Description

Keywords

Chemoinformatics, Advanced Review, Advanced Reviews, chemoinformatics, fingerprints, machine learning, molecular representation, variational autoencoder

Journal Title

WIREs Computational Molecular Science

Conference Name

Journal ISSN

1759-0876
1759-0884

Volume Title

Publisher

Wiley
Sponsorship
Engineering and Physical Sciences Research Council (EP/S024220/1)