Search Menu
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information
Search Scholarly Publications

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

Journal Article · · Chemical Science
DOI: https://doi.org/10.1039/D1SC06515G · OSTI ID:1841025
ORCiD logo [1];  [1]; ORCiD logo [2];  [3]; ORCiD logo [4]
  1. Energy Technologies Area, Lawrence Berkeley National Laboratory, Berkeley, CA 94720, USA
  2. College of Chemistry, University of California, Berkeley, CA 94720, USA, Materials Science Division, Lawrence Berkeley National Laboratory, Berkeley, CA 94720, USA
  3. Luxembourg Institute of Science and Technology, Luxembourg
  4. Department of Materials Science and Engineering, University of California, Berkeley, CA 94720, USA, Molecular Foundry, Lawrence Berkeley National Laboratory, Berkeley, CA 94720, USA
+ Show Author Affiliations

Contrastive pretraining of chemical reactions by matching augmented reaction representations to improve machine learning performance on small reaction datasets.

Sponsoring Organization:
USDOE
Grant/Contract Number:
AC02-05CH11231; AC02-05CH11231
OSTI ID:
1841025
Journal Information:
Chemical Science, Journal Name: Chemical Science Journal Issue: 5 Vol. 13; ISSN 2041-6520; ISSN CSHCBM
Publisher:
Royal Society of Chemistry (RSC)Copyright Statement
Country of Publication:
United Kingdom
Language:
English

References (42)

Neural-Symbolic Machine Learning for Retrosynthesis and Reaction Prediction journal February 2017
A Short Review of Chemical Reaction Database Systems, Computer-Aided Synthesis Design, Reaction Prediction and Synthetic Feasibility journal June 2014
Atom‐to‐atom Mapping: A Benchmarking Study of Popular Mapping Algorithms and Consensus Strategies journal November 2021
Molecular graph convolutions: moving beyond fingerprints journal August 2016
Navigating through the Maze of Homogeneous Catalyst Design with Machine Learning journal February 2021
Multilabel Classification Models for the Prediction of Cross-Coupling Reaction Conditions journal January 2021
Reaction Mechanism Generator v3.0: Advances in Automatic Mechanism Generation journal May 2021
Development and Application of a Data-Driven Reaction Classification Model: Comparison of an Electronic Lab Notebook and Medicinal Chemistry Literature journal September 2019
Deep Learning of Activation Energies journal March 2020
Neural Networks for the Prediction of Organic Chemistry Reactions journal October 2016
Prediction of Organic Reaction Outcomes Using Machine Learning journal April 2017
Computer-Assisted Retrosynthesis Based on Molecular Similarity journal November 2017
Using Machine Learning To Predict Suitable Conditions for Organic Reactions journal November 2018
Atom pairs as molecular features in structure-activity studies: definition and applications journal May 1985
SMILES, a chemical language and information system. 1. Introduction to methodology and encoding rules journal February 1988
Extended-Connectivity Fingerprints journal April 2010
Stereochemically Consistent Reaction Mapping and Identification of Multiple Reaction Mechanisms through Integer Linear Optimization
  • First, Eric L.; Gounaris, Chrysanthos E.; Floudas, Christodoulos A.
  • Journal of Chemical Information and Modeling, Vol. 52, Issue 1 https://doi.org/10.1021/ci200351b
journal December 2011
Algorithm for Reaction Classification journal October 2013
Development of a Novel Fingerprint for Chemical Reactions and Its Application to Large-Scale Reaction Classification and Similarity journal December 2014
Stereochemistry of Electrocyclic Reactions journal January 1965
Data-Driven Prediction of Formation Mechanisms of Lithium Ethylene Monocarbonate with an Automated Reaction Network journal August 2021
The Open Reaction Database journal November 2021
Rapid and Accurate Prediction of p K a Values of C–H Acids Using Graph Convolutional Neural Networks journal October 2019
Transfer learning enables the molecular transformer to predict regio- and stereoselective reactions on carbohydrates journal September 2020
Machine learning in chemical reaction space journal October 2020
Understanding the physical metallurgy of the CoCrFeMnNi high-entropy alloy: an atomistic simulation study journal January 2018
Uncertainty quantification in molecular simulations with dropout neural network potentials journal August 2020
Exploring chemical compound space with quantum-based machine learning journal June 2020
Reactants, products, and transition states of elementary chemical reactions based on quantum chemistry journal May 2020
Quantum chemical calculations of lithium-ion battery electrolyte and interphase species journal August 2021
Mapping the space of chemical reactions using attention-based neural networks journal January 2021
“Found in Translation”: predicting outcomes of complex organic chemistry reactions using neural sequence-to-sequence models journal January 2018
Data augmentation and transfer learning strategies for reaction prediction in low chemical data regimes journal January 2021
Machine learning dihydrogen activation in the chemical space surrounding Vaska's complex journal January 2020
BonDNet: a graph neural network for the prediction of bond dissociation energies for charged molecules journal January 2021
Reaction-based machine learning representations for predicting the enantioselectivity of organocatalysts journal January 2021
Predicting enzymatic reactions with a molecular transformer journal January 2021
Further considerations on the thermodynamics of chemical equilibria and reaction rates journal January 1936
Momentum Contrast for Unsupervised Visual Representation Learning conference June 2020
Extraction of organic chemistry grammar from unsupervised learning of chemical reactions journal April 2021
Deep learning for AI journal July 2021
Visualization of very large high-dimensional data sets as minimum spanning trees journal February 2020

Similar Records

Related Subjects