Holistic chemical evaluation reveals pitfalls in reaction prediction models
Not on the map. Why?
Abstract (arXiv)
The prediction of chemical reactions has gained significant interest within the machine learning community in recent years, owing to its complexity and crucial applications in chemistry. However, model evaluation for this task has been mostly limited to simple metrics like top-k accuracy, which obfuscates fine details of a model's limitations. Inspired by progress in other fields, we propose a new assessment scheme that builds on top of current approaches, steering towards a more holistic evaluation. We introduce the following key components for this goal: CHORISO, a curated dataset along with multiple tailored splits to recreate chemically relevant scenarios, and a collection of metrics that provide a holistic view of a model's advantages and limitations. Application of this method to state-of-the-art models reveals important differences on sensitive fronts, especially stereoselectivity and chemical out-of-distribution generalization. Our work paves the way towards robust prediction models that can ultimately accelerate chemical discovery.
Key facts. Cited by 4 papers in the map (data through 7 Oct 2026). Builds on 26 of its 70 references that are in the map. First posted on arXiv 14 Dec 2023.
Builds on
26 of 70 references.
References · 26
- 2017Attention Is All You Needcited by 59,932
- 2023LLaMA: Open and Efficient Foundation Language Modelscited by 13,958
- 2021Evaluating Large Language Models Trained on Codecited by 8,053
- 2014Neural Machine Translation by Jointly Learning to Align and Translatecited by 4,530
- 2019Benchmarking Neural Network Robustness to Common Corruptions and Perturbationscited by 2,857
- 2022Beyond the Imitation Game: Quantifying and extrapolating the capabilities of language modelscited by 1,970
- 2021Train Short, Test Long: Attention with Linear Biases Enables Input Length Extrapolationcited by 1,085
- 2017MoleculeNet: A Benchmark for Molecular Machine Learningcited by 1,037
- 2016Automatic chemical design using a data-driven continuous representation of moleculescited by 762
- 2015Convolutional Networks on Graphs for Learning Molecular Fingerprintscited by 751
- 2023ChemCrow: Augmenting large-language models with chemistry toolscited by 609
- 2021Towards Out-Of-Distribution Generalization: A Surveycited by 431
14 more
- 2020The Open Catalyst 2020 (OC20) Dataset and Community Challengescited by 246
- 2018Molecular Transformer - A Model for Uncertainty-Calibrated Chemical Reaction Predictioncited by 225
- 2017Learning to Plan Chemical Synthesescited by 175
- 2019MNIST-C: A Robustness Benchmark for Computer Visioncited by 137
- 2022A Length-Extrapolatable Transformercited by 123
- 2017Predicting Organic Reaction Outcomes with Weisfeiler-Lehman Networkcited by 102
- 2020On the Value of Out-of-Distribution Testing: An Example of Goodhart's Lawcited by 74
- 2021Permutation invariant graph-to-sequence model for template-free retrosynthesis and reaction predictioncited by 66
- 2022Eco2AI: carbon emissions tracking of machine learning models as the first step towards sustainable AIcited by 58
- 2017"Found in Translation": Predicting Outcomes of Complex Organic Chemistry Reactions using Neural Sequence-to-Sequence Modelscited by 54
- 2022Differentiable Top-k Classification Learningcited by 21
- 2023Bayesian Optimization of Catalysis With In-Context Learningcited by 20
- 2021Understanding and Testing Generalization of Deep Networks on Out-of-Distribution Datacited by 5
- 2022ImDrug: A Benchmark for Deep Imbalanced Learning in AI-aided Drug Discoverycited by 3
Built on by
Citing papers per year: 2025: 1; 2026: 3.
4 papers.
- 2025Challenging reaction prediction models to generalize to novel chemistrycited by 6
- 2026Agentic generation of verifiable rules for deterministic, self-expanding reaction classificationcited by 1
- 2026Self-Driving Datasets: From 20 Million Papers to Nuanced Biomedical Knowledge at Scalecited by 0
- 2026Mechanistic Reaction Prediction via Discrete Flow Matching on Graph-Structured Electron Occupationcited by 0
- 2026Mechanistic Reaction Prediction via Discrete Flow Matching on Graph-Structured Electron Occupation27 Aug 2026
- 2026Agentic generation of verifiable rules for deterministic, self-expanding reaction classification1 Jul 2026
- 2026Self-Driving Datasets: From 20 Million Papers to Nuanced Biomedical Knowledge at Scale7 May 2026
- 2025Challenging reaction prediction models to generalize to novel chemistry11 Jan 2025