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Journal of Computer-Aided Molecular Design

, Volume 30, Issue 11, pp 959–967 | Cite as

Prediction of cyclohexane-water distribution coefficients with COSMO-RS on the SAMPL5 data set

  • Andreas Klamt
  • Frank Eckert
  • Jens Reinisch
  • Karin Wichmann
Article

Abstract

The Conductor-Like-Screening-Model for Real Solvents (COSMO-RS) method has been used for the blind prediction of cyclohexane-water distribution coefficients logD within the SAMPL challenge. The partition coefficient logP of the neutral species was calculated first and then corrected for dissociation or protonation, as appropriate for acidic or basic solutes, to obtain the cyclohexane-water logD. Using the latest version of the COSMOtherm implementation, this approach in combination with a rigorous conformational sampling yielded a predictive accuracy of 2.11 log units (RMSD) for the 53 compounds of the blind prediction dataset. By that it was the most accurate of all contest submissions and it also achieved the best rank order. The RMSD mainly arises from a group of outliers in the negative logD range, which at least partly may arise from dimerization or other experimental problems coming up for very polar molecules in very non-polar solvents.

Keywords

Solvation Distribution coefficients COSMO-RS SAMPL5 Molecular modeling Molecular simulation 

Supplementary material

10822_2016_9927_MOESM1_ESM.pdf (630 kb)
Supplementary material 1 (PDF 630 kb)

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Copyright information

© Springer International Publishing Switzerland 2016

Authors and Affiliations

  • Andreas Klamt
    • 1
    • 2
  • Frank Eckert
    • 1
  • Jens Reinisch
    • 1
  • Karin Wichmann
    • 1
  1. 1.COSMOlogic GmbH&CoKGLeverkusenGermany
  2. 2.Institute of Physical and Theoretical ChemistryUniversity of RegensburgRegensburgGermany

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