Canonicalization and Enumeration of Tautomers

10/15/99


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Table of Contents

Canonicalization and Enumeration of Tautomers

Introduction

Tautomerism

Example of Tautomerism

Donor & Acceptor Atom Types

sp2 Hybridized Atom Types

Properties of Atom Types

Interconversion of Atom Types

Valence Tautomerism

Case Study: Guanine (G)

Reduced Representation

Case Study: Guanine

Canonical Node Ordering

Node Ordering Properties

Case Study: Guanine

Tautomer Enumeration Algorithm 1

Tautomer Enumeration Algorithm 2

Assignment Propagation 1

Assignment Propagation 2

Case Study: Guanine

Case Study: Guanine

Case Study: Guanine

Canonicalization vs. Enumeration

Case Study: Guanine

Symmetry Related Tautomers

Keto/Enol Atom Types

Keto/Enol Node Ordering

Case Study: Guanine (G)

Frequency of Tautomers

Comparison with ACD/Tautomers

Application 1: Registration

Application 2: Clustering/Diversity

Application 3: Ligand Docking

Application 4: Property Calculation

Ring Chain Tautomerism 1

Baldwin’s Rules for Ring Closure

Ring-Chain Tautomerism 2

Resonance Form Canonicalization

Bibliography

Acknowledgements

Author: Roger Sayle