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Retrosynthesis Prediction with Conditional Graph Logic Network (2001.01408v1)

Published 6 Jan 2020 in cs.LG and stat.ML

Abstract: Retrosynthesis is one of the fundamental problems in organic chemistry. The task is to identify reactants that can be used to synthesize a specified product molecule. Recently, computer-aided retrosynthesis is finding renewed interest from both chemistry and computer science communities. Most existing approaches rely on template-based models that define subgraph matching rules, but whether or not a chemical reaction can proceed is not defined by hard decision rules. In this work, we propose a new approach to this task using the Conditional Graph Logic Network, a conditional graphical model built upon graph neural networks that learns when rules from reaction templates should be applied, implicitly considering whether the resulting reaction would be both chemically feasible and strategic. We also propose an efficient hierarchical sampling to alleviate the computation cost. While achieving a significant improvement of $8.1\%$ over current state-of-the-art methods on the benchmark dataset, our model also offers interpretations for the prediction.

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Authors (5)
  1. Hanjun Dai (63 papers)
  2. Chengtao Li (16 papers)
  3. Connor W. Coley (59 papers)
  4. Bo Dai (245 papers)
  5. Le Song (140 papers)
Citations (164)

Summary

Retrosynthesis Prediction with Conditional Graph Logic Network

The paper "Retrosynthesis Prediction with Conditional Graph Logic Network" addresses one of the pivotal challenges within organic chemistry—retrosynthesis planning. This task involves deducing the potential reactants required to synthesize a given target molecule. Traditionally, retrosynthesis requires expert chemists to navigate a vast search space of possible transformations, a process demanding extensive skill and intuition. The advent of computer-aided solutions has dramatically enhanced efficiency, but current approaches predominantly rely on template-based models. These models employ rigid subgraph matching rules to suggest reactants without adequately accounting for chemical viability or strategic considerations.

The authors propose a novel framework, the Conditional Graph Logic Network (CGLN), designed to overcome the limitations of existing methodologies. This model introduces a probabilistic graphical model built upon Graph Neural Networks (GNNs) to suggest reaction templates. It interprets chemical knowledge as logical rules and flexibly applies them by conditioning on subgraph patterns—essentially discerning when a template's rule should be invoked, thereby implicitly considering chemical plausibility.

A critical component of the proposed approach is hierarchical sampling, which efficiently mitigates the computational overload associated with exhaustive template searches. This mechanism leads to an impressive improvement of 8.1% in top-1 accuracy over existing state-of-the-art methods when tested on a benchmark dataset.

Model Design and Implementation

The Conditional Graph Logic Network is characterized by its structural reasoning method, decomposed into two stages:

  1. Template Matching: This step leverages reaction core subgraphs and computes compatibility scores between these cores and the target molecules using GNN-derived embeddings.
  2. Reactants Matching: The task subsequently addresses matching the subgraph patterns in the template to a valid set of reactant molecules.

To enhance computational efficiency for the inference task, the model incorporates hierarchical sampling. This permits the system to prioritize and sample templates and reactants based on their confidence scores—a vast improvement over exhaustive combinatorial methods.

Experimentation and Results

The evaluation using the USPTO-50k benchmark demonstrated the model’s robustness. Notably, the CGLN outperformed several established models including neural sequence-to-sequence approaches and similarity-based template ranking algorithms. Notably, the CGLN achieved competitive top-kk accuracy even when the model did not have access to the reaction type a priori.

Interpretability and Recommendation Potential

One of the core advantages of the Conditional Graph Logic Network is its interpretability. The model not only predicts reactants but also provides insights into the underlying reasoning process, showcasing which portions of molecular graphs contribute to decision-making—a feature absent in many purely neural methodologies.

Implications and Speculative Future Directions

The implications of this research extend into areas of strategic synthesis planning, potentially reducing reliance on expert-defined rules by learning chemically relevant patterns dynamically. The work could be extended by integrating novel template creation or using machine learning to refine template specificity dynamically.

Further explorations might include hybrid models that combine the interpretability benefits of logic-based systems with the richness and flexibility inherent in neural approaches—an avenue especially promising in the burgeoning field of synthetic chemistry automation.

Overall, the framework bridges a gap between rigid template-based techniques and flexible neural models, offering enhanced efficiency and interpretability in synthesis planning—an exciting development in computational chemistry.