Heuristic molecular lipophilicity potential (HMLP): Lipophilicity and hydrophilicity of amino acid side chains

Heuristic molecular lipophilicity potential (HMLP) is applied in the study of lipophilicity and hydrphilcity of 20 natural amino acids side chains. The HMLP parameters, surface area Si, lipophilic indices Li, and hydrophilic indices Hi of amino acid side chains are derived from lipophilicity potential L(r). The parameters are correlated with the experimental data of phase‐transferring free energies of vapor‐to‐water, vapor‐to‐cyclohexane, vapor‐to‐octanol, cyclohexane‐to‐water, octanol‐to‐water, and cyclohexane‐to‐octanol through a linear free energy equation ΔG°tr,i = b0 + b1Si+ + b2Si− + b3Li + b4Hi. For all above six phase‐transfer free energies, the HMLP parameters of 20 amino acid side chains give good calculation results using linear free energy equation. HMLP is an ab initio quantum chemical approach and a structure‐based technique. Except for atomic van der Waals radii, there are no other empirical parameters used. The HMLP has clear physical and chemical meaning and provides useful lipophilic and hydrophilic parameters for the studies of proteins and peptides. © 2006 Wiley Periodicals, Inc. J Comput Chem 27: 685–692, 2006

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