Evidence map›Paper›PMID 35222929›Full record

ArticleChemical science2022

Improving machine learning performance on small chemical reaction data with unsupervised contrastive pretraining.

Mingjian Wen, Samuel M Blau, Xiaowei Xie, Shyam Dwaraknath, Kristin A Persson

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In one paragraph

Article in Chemical science, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.

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10citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

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2 · The registry

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3 · Its place in the literature

Who cites it

10 citing papers in PubMed.

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4 · The record

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5 · Who and what money

Authors and funding

5 authors.

Mingjian WenEnergy Technologies Area, Lawrence Berkeley National Laboratory Berkeley CA 94720 USA.ORCID https://orcid.org/0000-0003-0013-575X
Samuel M BlauEnergy Technologies Area, Lawrence Berkeley National Laboratory Berkeley CA 94720 USA.
Xiaowei XieCollege of Chemistry, University of California Berkeley CA 94720 USA.ORCID https://orcid.org/0000-0001-5618-8768
Shyam DwaraknathLuxembourg Institute of Science and Technology Luxembourg.
Kristin A PerssonDepartment of Materials Science and Engineering, University of California Berkeley CA 94720 USA.ORCID https://orcid.org/0000-0003-2495-5509

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Machine learning (ML) methods have great potential to transform chemical discovery by accelerating the exploration of chemical space and drawing scientific insights from data. However, modern chemical reaction ML models, such as those based on graph neural networks (GNNs), must be trained on a large amount of labelled data in order to avoid overfitting the data and thus possessing low accuracy and transferability. In this work, we propose a strategy to leverage unlabelled data to learn accurate ML models for small labelled chemical reaction data. We focus on an old and prominent problem-classifying reactions into distinct families-and build a GNN model for this task. We first pretrain the model on unlabelled reaction data using unsupervised contrastive learning and then fine-tune it on a small number of labelled reactions. The contrastive pretraining learns by making the representations of two augmented versions of a reaction similar to each other but distinct from other reactions. We propose chemically consistent reaction augmentation methods that protect the reaction center and find they are the key for the model to extract relevant information from unlabelled data to aid the reaction classification task. The transfer learned model outperforms a supervised model trained from scratch by a large margin. Further, it consistently performs better than models based on traditional rule-driven reaction fingerprints, which have long been the default choice for small datasets, as well as those based on reaction fingerprints derived from masked language modelling. In addition to reaction classification, the effectiveness of the strategy is tested on regression datasets; the learned GNN-based reaction fingerprints can also be used to navigate the chemical reaction space, which we demonstrate by querying for similar reactions. The strategy can be readily applied to other predictive reaction problems to uncover the power of unlabelled data for learning better models with a limited supply of labels.

Identifiers

PMID35222929
PMCPMC8809395

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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.