# A Transformer Model for Predicting Chemical Products from Generic SMARTS Templates with Data Augmentation

arXiv: https://arxiv.org/abs/2503.05810 · HTML: https://mlsanity.com/paper/2503.05810/

## Key facts

- No citing papers in the map yet (data through 14 Oct 2026).
- Builds on 11 of its 30 references that are in the map.
- First posted on arXiv 4 Mar 2025.

## Builds on (most cited first, 11 of 11)

- [Attention Is All You Need](https://mlsanity.com/paper/1706.03762/) (2017)
- [Exploring the Limits of Transfer Learning with a Unified Text-to-Text Transformer](https://mlsanity.com/paper/1910.10683/) (2019)
- [BART: Denoising Sequence-to-Sequence Pre-training for Natural Language Generation, Translation, and Comprehension](https://mlsanity.com/paper/1910.13461/) (2019)
- [ChemBERTa: Large-Scale Self-Supervised Pretraining for Molecular Property Prediction](https://mlsanity.com/paper/2010.09885/) (2020)
- [Molecular Transformer - A Model for Uncertainty-Calibrated Chemical Reaction Prediction](https://mlsanity.com/paper/1811.02633/) (2018)
- [Large-Scale Chemical Language Representations Capture Molecular Structure and Properties](https://mlsanity.com/paper/2106.09553/) (2021)
- [Predicting Organic Reaction Outcomes with Weisfeiler-Lehman Network](https://mlsanity.com/paper/1709.04555/) (2017)
- [SMILES Enumeration as Data Augmentation for Neural Network Modeling of Molecules](https://mlsanity.com/paper/1703.07076/) (2017)
- [RetroComposer: Composing Templates for Template-Based Retrosynthesis Prediction](https://mlsanity.com/paper/2112.11225/) (2021)
- [LLamol: A Dynamic Multi-Conditional Generative Transformer for De Novo Molecular Design](https://mlsanity.com/paper/2311.14407/) (2023)
- [Surrogate-Based Black-Box Optimization Method for Costly Molecular Properties](https://mlsanity.com/paper/2110.03522/) (2021)

## Abstract (arXiv)

The accurate prediction of chemical reaction outcomes is a major challenge in computational chemistry. Current models rely heavily on either highly specific reaction templates or template-free methods, both of which present limitations. To address these, this work proposes the Broad Reaction Set (BRS), a set featuring 20 generic reaction templates written in SMARTS, a pattern-based notation designed to describe substructures and reactivity. Additionally, we introduce ProPreT5, a T5-based model specifically adapted for chemistry and, to the best of our knowledge, the first language model capable of directly handling and applying SMARTS reaction templates. To further improve generalization, we propose the first augmentation strategy for SMARTS, which injects structural diversity at the pattern level. Trained on augmented templates, ProPreT5 demonstrates strong predictive performance and generalization to unseen reactions. Together, these contributions provide a novel and practical alternative to current methods, advancing the field of template-based reaction prediction.