Comparing the chemical spaces of metabolites and available chemicals: models of metabolite-likeness

Mol Divers. 2007 Feb;11(1):23-36. doi: 10.1007/s11030-006-9054-0. Epub 2007 Feb 16.

Abstract

The chemical space covered by compounds involved in metabolic reactions was compared with that of a random dataset of purchasable compounds by chemoinformatics techniques. The comparison was based on 3D structure, 2D structure, or descriptors of global properties, by means of self-organizing maps, random forests, and classification trees. The overlap between metabolites and non-metabolites was observed to be the least in the space defined by the global descriptors, the most discriminatory features being the number of OH groups, presence of aromatic systems, and molecular weight. Discrimination between the two datasets was achieved with accuracy up to 97%. Models were built to produce a metabolite-likeness parameter. A relationship between metabolite-likeness and ready biodegradability was observed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biodegradation, Environmental
  • Computer Simulation*
  • Databases, Factual
  • Metabolism*
  • Models, Chemical*
  • Molecular Conformation
  • Organic Chemicals / classification*
  • Organic Chemicals / metabolism
  • Quantitative Structure-Activity Relationship*

Substances

  • Organic Chemicals