Fast and General Method To Predict the Physicochemical Properties of Druglike Molecules Using the Integral Equation Theory of Molecular Liquids

Mol Pharm. 2015 Sep 8;12(9):3420-32. doi: 10.1021/acs.molpharmaceut.5b00441. Epub 2015 Aug 6.

Abstract

We report a method to predict physicochemical properties of druglike molecules using a classical statistical mechanics based solvent model combined with machine learning. The RISM-MOL-INF method introduced here provides an accurate technique to characterize solvation and desolvation processes based on solute-solvent correlation functions computed by the 1D reference interaction site model of the integral equation theory of molecular liquids. These functions can be obtained in a matter of minutes for most small organic and druglike molecules using existing software (RISM-MOL) (Sergiievskyi, V. P.; Hackbusch, W.; Fedorov, M. V. J. Comput. Chem. 2011, 32, 1982-1992). Predictions of caco-2 cell permeability and hydration free energy obtained using the RISM-MOL-INF method are shown to be more accurate than the state-of-the-art tools for benchmark data sets. Due to the importance of solvation and desolvation effects in biological systems, it is anticipated that the RISM-MOL-INF approach will find many applications in biophysical and biomedical property prediction.

Keywords: ADME; ADMET; IET; QSAR; QSPR; RISM; Random Forest; bioavailability; caco-2; drug discovery; druglike; hydration free energy; integral equation theory of molecular liquids; permeability; reference interaction site model; solvation free energy; statistical mechanics.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Caco-2 Cells
  • Chemical Phenomena*
  • Chemistry, Pharmaceutical
  • Humans
  • Models, Theoretical*
  • Pharmaceutical Preparations / chemistry*
  • Solvents / chemistry*
  • Thermodynamics
  • Water / chemistry*

Substances

  • Pharmaceutical Preparations
  • Solvents
  • Water