D-LogP: an alignment-free 3D description of local lipophilicity for QSAR studies

Methods Mol Biol. 2004:275:215-60. doi: 10.1385/1-59259-802-1:215.

Abstract

The major hurdle to overcome in the development of 3D-QSAR models using steric, electrostatic, or lipophilic "fields" is related to both conformation selection and subsequent suitable overlay (alignment) of compounds. Therefore, it is of some interest to provide a conformationally sensitive lipophilicity descriptor that is alignment-independent. In this chapter we describe the derivation and parametrization of a new descriptor called 3D-LogP and demonstrate both its conformational sensitivity and its effectiveness in QSAR analysis. The 3D-LogP descriptor provides such a representation in the form of a rapidly computable description of the local lipophilicity at points on a user-defined molecular surface.

MeSH terms

  • Computers
  • Molecular Conformation
  • Quantitative Structure-Activity Relationship*
  • Software