Hydrophobic similarity between molecules: A MST-based hydrophobic similarity index

✍ Scribed by J. Muñoz; X. Barril; B. Hernández; Modesto Orozco; F. Javier Luque

• Book ID: 102304998
• Publisher: John Wiley and Sons
• Year: 2002
• Tongue: English
• Weight: 184 KB
• Volume: 23
• Category: Article
• ISSN: 0192-8651
• DOI: 10.1002/jcc.10055

✦ Synopsis

Abstract

A similarity index based on the hydrophilic/hydrophobic properties of molecules is presented. Such an index is defined based on the fractional partition of the free energy of solvation developed within the framework of the self‐consistent reaction field MST model, which divides the free energy of solvation or the free energy of transfer into contributions assigned to the surface elements defining the solute/solvent interface. These surface contributions can be integrated to derive atomic or group contributions. The suitability of the index to compute the molecular similarity based on hydrophobic/hydrophilic properties is examined by considering their application in a variety of test systems, including structure‐activity relationships, absorption properties, and molecular recognition. The similarity index is expected to be a very powerful tool in molecular similarity studies for compounds of chemical, biochemical, and pharmaceutical interest. © 2002 Wiley Periodicals, Inc. J Comput Chem 23: 554–563, 2002; DOI 10.1002/jcc.10055