Direct prediction of linear free energy substituent effects from 3D structures using comparative molecular field analysis. 1. Electronic effects of substituted benzoic acids

1991 ◽  
Vol 56 (8) ◽  
pp. 2723-2729 ◽  
Author(s):  
Ki H. Kim ◽  
Yvonne C. Martin
Keyword(s):  
Free Energy ◽  
Substituent Effects ◽  
Field Analysis ◽  
Molecular Field ◽  
Benzoic Acids ◽  
Comparative Molecular Field Analysis ◽  
Electronic Effects ◽  
3D Structures ◽  
Linear Free Energy ◽  
Substituted Benzoic Acids

The transmission of polar effects. Part VI. The ionization of ortho-substituted benzoic acids

1968 ◽  
Vol 46 (18) ◽  
pp. 2941-2944 ◽  
Author(s):  
Keith Bowden ◽  
G. E. Manser
Keyword(s):  
Free Energy ◽  
Benzoic Acid ◽  
Field Effect ◽  
Energy Relation ◽  
Benzoic Acids ◽  
Linear Free Energy ◽  
Free Energy Relation ◽  
Substituted Benzoic Acids ◽  
Reaction Constants

The pKa values of a series of ortho-substituted benzoic acids in 50% ethanol–water have been determined. The effect of ortho-substitution on the ionization of benzoic acid in this and other solvents has been correlated by a linear free energy relation. The reaction constants found are compared with those for the meta/para-substituted benzoic acids. While those for the former system are insensitive to changes in the medium, the latter vary considerably. It is suggested that this is due to transmission by the field effect passing almost entirely through the molecular cavity for ortho-substituents.

Combined Autodock and comparative molecular field analysis study on predicting 5-lipoxygenase inhibitory activity of flavonoids isolated from Spatholobus suberectus Dunn

2015 ◽  
Vol 70 (3-4) ◽  
pp. 103-113 ◽  
Author(s):  
Shiyun Jiang ◽  
Kai Huang ◽  
Wen Liu ◽  
Fengming Fu ◽  
Jie Xu
Keyword(s):  
Free Energy ◽  
Inhibitory Activity ◽  
Binding Free Energy ◽  
Field Analysis ◽  
Molecular Field ◽  
Optimum Number ◽  
Comparative Molecular Field Analysis ◽  
Molecular Field Analysis ◽  
Spatholobus Suberectus ◽  
Autodock 4.2

Abstract 5-Lipoxygenase (5-LOX) plays a key role in the pathway of leukotriene biosynthesis. To predict the inhibitory activity of flavonoid inhibitors against 5-LOX from Spatholobus suberectus Dunn, Autodock 4.2 and comparative molecular field analysis (CoMFA) were employed. For the positive inhibitors (n=7), the value of the coefficient of determination (R2) between the binding free energy, calculated using Autodock 4.2, and the experimental pIC50 is 0.838. In the training set (n=21) of inhibitors against 5-LOX, the R2 of non-cross-validated partial least squares analysis between the actual and predicted pIC50 values, using the no-validation with the optimum number of components set to 6, is 0.997 (p=0.000). For the model generated by CoMFA, the contribution of electrostatic and steric factors are 0.522 and 0.478, respectively. Among the flavonoids of S. suberectus, liquiritigenin, catechin, butin, 3′,4′,7-trihydroxyflavone, plathymenin, and gallocatechin are the more potent inhibitors of 5-LOX based on the calculated binding free energy and the predicted pIC50 value.

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