Journal of Computer-Aided Molecular Design

, Volume 21, Issue 4, pp 145–153 | Cite as

3D-QSAR study of hallucinogenic phenylalkylamines by using CoMFA approach

  • Zhuoyong Zhang
  • Liying An
  • Wenxiang Hu
  • Yuhong Xiang
Original Paper


The three-dimensional quantitative structure–activity relationship (3D-QSAR) has been studied on 90 hallucinogenic phenylalkylamines by the comparative molecular field analysis (CoMFA). Two conformations were compared during the modeling. Conformation I referred to the amino group close to ring position 6 and conformation II related to the amino group trans to the phenyl ring. Satisfactory results were obtained by using both conformations. There were still differences between the two models. The model based on conformation I got better statistical results than the one about conformation II. And this may suggest that conformation I be preponderant when the hallucinogenic phenylalkylamines interact with the receptor. To further confirm the predictive capability of the CoMFA model, 18 compounds with conformation I were randomly selected as a test set and the remaining ones as training set. The best CoMFA model based on the training set had a cross-validation coefficient q 2 of 0.549 at five components and non cross-validation coefficient R 2 of 0.835, the standard error of estimation was 0.219. The model showed good predictive ability in the external test with a coefficient R pre 2 of 0.611. The CoMFA coefficient contour maps suggested that both steric and electrostatic interactions play an important role. The contributions from the steric and electrostatic fields were 0.450 and 0.550, respectively.


3D-QSAR Amphetamines CoMFA Hallucinogen Phenylethylamines 



This work is supported by the Science and Technology Program of Beijing Municipal Government and the Scientific Research Common Program of Commission of Education.


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Copyright information

© Springer Science+Business Media, LLC 2006

Authors and Affiliations

  • Zhuoyong Zhang
    • 1
  • Liying An
    • 1
  • Wenxiang Hu
    • 1
  • Yuhong Xiang
    • 1
  1. 1.Department of ChemistryCapital Normal UniversityBeijingP.R. China

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