Publications

Journal of Chemical Information and Modeling · 2024

BartSmiles: Generative Masked Language Models for Molecular Representations

Gayane Chilingaryan*, Hovhannes Tamoyan*, Ani Tevosyan*, Nelly Babayan, Karen Hambardzumyan, Zaven Navoyan, Armen Aghajanyan, Hrant Khachatrian, and Lusine Khondkaryan

* Equal contribution.

Abstract

We discover a robust self-supervised strategy tailored towards molecular representations for generative masked language models through a series of tailored, in-depth ablations. Using this pre-training strategy, we train BARTSmiles, a BART-like model with an order of magnitude more compute than previous self-supervised molecular representations. In-depth evaluations show that BARTSmiles consistently outperforms other self-supervised representations across classification, regression, and generation tasks setting a new state-of-the-art on 11 tasks. We then quantitatively show that when applied to the molecular domain, the BART objective learns representations that implicitly encode our downstream tasks of interest. For example, by selecting seven neurons from a frozen BARTSmiles, we can obtain a model having performance within two percentage points of the full fine-tuned model on task Clintox. Lastly, we show that standard attribution interpretability methods, when applied to BARTSmiles, highlight certain substructures that chemists use to explain specific properties of molecules. The code and the pretrained model are publicly available.

Citation

@article{chilingaryan2024bartsmiles,
  title     = {BartSmiles: Generative Masked Language Models for Molecular
               Representations},
  author    = {Chilingaryan, Gayane and Tamoyan, Hovhannes and Tevosyan, Ani
               and Babayan, Nelly and Hambardzumyan, Karen and Navoyan, Zaven
               and Aghajanyan, Armen and Khachatrian, Hrant
               and Khondkaryan, Lusine},
  journal   = {Journal of Chemical Information and Modeling},
  volume    = {64},
  number    = {15},
  pages     = {5832--5843},
  year      = {2024},
  publisher = {American Chemical Society},
  doi       = {10.1021/acs.jcim.4c00512}
}