Evidence map›Paper›PMID 39268059›Full record

ArticleDigital discovery2024

What can attribution methods show us about chemical language models?

Stefan Hödl, Tal Kachman, Yoram Bachrach, Wilhelm T S Huck, William E Robinson

Abstract read
In one paragraph

Article in Digital discovery, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

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2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

1 citing paper in PubMed.

  1. Review
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

5 authors.

Stefan HödlPhysical Organic Chemistry, Radboud University Heyendaalseweg 135 6525AJ Nijmegen The Netherlands william.robinson@ru.nl.ORCID https://orcid.org/0009-0003-8774-7739
Tal KachmanArtificial Intelligence, Donders Institute, Radboud University Thomas Van Aquinostraat 4 6525GD Nijmegen The Netherlands.
Yoram BachrachGoogle Deepmind London UK.
Wilhelm T S HuckPhysical Organic Chemistry, Radboud University Heyendaalseweg 135 6525AJ Nijmegen The Netherlands william.robinson@ru.nl.
William E RobinsonPhysical Organic Chemistry, Radboud University Heyendaalseweg 135 6525AJ Nijmegen The Netherlands william.robinson@ru.nl.ORCID https://orcid.org/0000-0002-7627-0192

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Language models trained on molecular string representations have shown strong performance in predictive and generative tasks. However, practical applications require not only making accurate predictions, but also explainability - the ability to explain the reasons and rationale behind the predictions. In this work, we explore explainability for a chemical language model by adapting a transformer-specific and a model-agnostic input attribution technique. We fine-tune a pretrained model to predict aqueous solubility, compare training and architecture variants, and evaluate visualizations of attributed relevance. The model-agnostic SHAP technique provides sensible attributions, highlighting the positive influence of individual electronegative atoms, but does not explain the model in terms of functional groups or explain how the model represents molecular strings internally to make predictions. In contrast, the adapted transformer-specific explainability technique produces sparse attributions, which cannot be directly attributed to functional groups relevant to solubility. Instead, the attributions are more characteristic of how the model maps molecular strings to its latent space, which seems to represent features relevant to molecular similarity rather than functional groups. These findings provide insight into the representations underpinning chemical language models, which we propose may be leveraged for the design of informative chemical spaces for training more accurate, advanced and explainable models.

Identifiers

PMID39268059
PMCPMC11389796

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.