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3D-LogP: An Alignment-Free 3D Description of Local Lipophilicity for QSAR Studies
| Abstract |
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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.
Affiliation(s): (3) Synt:em, Nimes, France
(4) Aventis Pharmaceuticals, Bridgewater, New Jersey, USA
(5) Institute of Medicinal Chemistry, School of Pharmacy, University of Lausanne, Lausanne, Switzerland
(4) Aventis Pharmaceuticals, Bridgewater, New Jersey, USA
(5) Institute of Medicinal Chemistry, School of Pharmacy, University of Lausanne, Lausanne, Switzerland
Series: Methods in Molecular Biology | Volume: 275 | Pub. Date: May-12-2004 | Page Range: 215-260 | DOI: 10.1385/1-59259-802-1:215
Subject: Bioinformatics
Key Words: 3D-QSAR - hydrophobicity - lipophilicity - 3D-LogP
- conformation-dependent lipophilicity - alignment-independent 3D descriptor - molecular lipophilicity potential (MLP) - ADME-related descriptor
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