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高等学校化学研究 ›› 2006, Vol. 22 ›› Issue (4): 439-442.

• Articles • 上一篇    下一篇

Application of Density Functional Theoretic Descriptors to Quantitative Structure-Activity Relationships with Temperature Constrained Cascade Correlation Network Models of Nitrobenzene Derivatives

CUI Xiu-jun1, ZHANG Zhuo-yong1,2, YUAN Xing3, ZHANG Jing-ping1, LIU Si-dong1, GUO Li-ping1, Peter de B. HARRINGTON4   

  1. 1. Faculty of Chemistry, Northeast Normal University, Changchun 130024, P. R. China;

    2. Department of Chemistry, Capital Normal University, Beijing 100037, P. R. China;

    3. College of Urban and Environmental Science, Northeast Normal University, Changchun 130024, P. R. China;

    4. Center for Intelligent Chemical Instrumentation, Clippinger Laboratories, Department of Chemistry and Biochemistry, Ohio University, Athens OH 45701-2979, USA
  • 收稿日期:2006-01-09 出版日期:2006-08-24 发布日期:2011-08-06
  • 基金资助:

    Supported by the Science and Technology Program, Beijing Municipal Education Commission(No. KM200310028105).

Application of Density Functional Theoretic Descriptors to Quantitative Structure-Activity Relationships with Temperature Constrained Cascade Correlation Network Models of Nitrobenzene Derivatives

CUI Xiu-jun1, ZHANG Zhuo-yong1,2, YUAN Xing3, ZHANG Jing-ping1, LIU Si-dong1, GUO Li-ping1, Peter de B. HARRINGTON4   

  1. 1. Faculty of Chemistry, Northeast Normal University, Changchun 130024, P. R. China;

    2. Department of Chemistry, Capital Normal University, Beijing 100037, P. R. China;

    3. College of Urban and Environmental Science, Northeast Normal University, Changchun 130024, P. R. China;

    4. Center for Intelligent Chemical Instrumentation, Clippinger Laboratories, Department of Chemistry and Biochemistry, Ohio University, Athens OH 45701-2979, USA
  • Received:2006-01-09 Online:2006-08-24 Published:2011-08-06
  • Supported by:

    Supported by the Science and Technology Program, Beijing Municipal Education Commission(No. KM200310028105).

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摘要： A temperature-constrained cascade correlation network(TCCCN), a back-propagation neural network(BP), and multiple linear regression(MLR) models were applied to quantitative structure-activity relationship(QSAR) modeling, on the basis of a set of 35 nitrobenzene derivatives and their acute toxicities. These structural quantum-chemical descriptors were obtained from the density functional theory(DFT). Stepwise multiple regression analysis was performed and the model was obtained. The value of the calibration correlation coefficient R is 0.925, and the value of cross-validation correlation coefficient R is 0.87. The standard error S=0.308 and the cross-validated(leave-one-out) standard error Scv=0.381. Principal component analysis(PCA) was carried out for parameter selection. RMS errors for training set via TCCCN and BP are 0.067 and 0.095, respectively, and RMS errors for testing set via TCCCN and BP are 0.090 and 0.111, respectively. The results show that TCCCN performs better than BP and MLR.

关键词: DFT, MLR, PCA, BP, TCCCN, QSAR, Nitrobenzene derivative

Abstract: A temperature-constrained cascade correlation network(TCCCN), a back-propagation neural network(BP), and multiple linear regression(MLR) models were applied to quantitative structure-activity relationship(QSAR) modeling, on the basis of a set of 35 nitrobenzene derivatives and their acute toxicities. These structural quantum-chemical descriptors were obtained from the density functional theory(DFT). Stepwise multiple regression analysis was performed and the model was obtained. The value of the calibration correlation coefficient R is 0.925, and the value of cross-validation correlation coefficient R is 0.87. The standard error S=0.308 and the cross-validated(leave-one-out) standard error Scv=0.381. Principal component analysis(PCA) was carried out for parameter selection. RMS errors for training set via TCCCN and BP are 0.067 and 0.095, respectively, and RMS errors for testing set via TCCCN and BP are 0.090 and 0.111, respectively. The results show that TCCCN performs better than BP and MLR.

Key words: DFT, MLR, PCA, BP, TCCCN, QSAR, Nitrobenzene derivative