Hydrophobic similarity between molecules: a MST-based hydrophobic similarity index.
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.
Muñoz
J
J
Departament de Fisicoquímica, Facultat de Farmàcia, Universitat de Barcelona, Avgda. Diagonal s/n, Barcelona 08028, Spain.
Barril
X
X
Hernández
B
B
Orozco
Modesto
M
Luque
F Javier
FJ
D000465:Algorithms; D000818:Animals; D019295:Computational Biology / Q000379:methods; D004247:DNA / Q000737:chemistry; D004735:Energy Transfer; D006146:Guanidines / Q000737:chemistry*; D006635:Histamine H2 Antagonists / Q000737:chemistry* / Q000493:pharmacokinetics; D006860:Hydrogen Bonding; D007422:Intestines; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D051381:Rats; D012997:Solvents / Q000737:chemistry; D013329:Structure-Activity Relationship; D013816:Thermodynamics; D014867:Water / Q000737:chemistry*
D006146:Guanidines; D006635:Histamine H2 Antagonists; D012997:Solvents; D014867:Water; D004247:DNA; C004711:dicyandiamido