Assessing the reliability of a QSAR model's predictions

Journal of Molecular Graphics and Modelling - Tập 23 Số 6 - Trang 503-523 - 2005
Linnan He1, Peter C. Jurs1
1Department of Chemistry , The Pennsylvania State University , 104 Chemistry Building , University Park , PA 16802 , USA .

Tóm tắt

Từ khóa


Tài liệu tham khảo

Borman, 1990, New QSAR techniques eyed for environmental assessments, Chem. Eng. News, 68, 20, 10.1021/cen-v068n050.p020

Nendza, 1991, QSAR modeling of the ERL-D fathead minnow acute toxicity database, Xenobiotica, 21, 147, 10.3109/00498259109039458

Russom, 1997, Predicting modes of toxic action from chemical structure: acute toxicity in the fathead minnow (Pimephales Promelas), Environ. Toxicol. Chem., 16, 948, 10.1897/1551-5028(1997)016<0948:PMOTAF>2.3.CO;2

Eldred, 1999, Prediction of fathead minnow acute toxicity of organic compounds from molecular structure, Chem. Res. Toxicol., 12, 670, 10.1021/tx980273w

Kaiser, 1999, Using probabilistic neural networks to model the toxicity of chemicals to the fathead minnow (Pimephales Promelas): a study based on 965 compounds, Chemosphere, 38, 3237, 10.1016/S0045-6535(99)00553-6

U.S. Environmental Protection Agency, AQUIRE database http://www.epa.gov/ecotox/, 2001.

Newsome, 1991, A QSAR study of the toxicity of amines to the fathead minnow, Sci. Total Environ., 109/110, 537, 10.1016/0048-9697(91)90207-U

Hall, 1989, Structure–activity relationship studies on the toxicity of benzene derivatives: III. Predictions and extensions to new substituents, Environ. Toxicol. Chem., 8, 431, 10.1002/etc.5620080509

1984, 1–5

Jurs, 1979

Tuper, 1979

MATLAB, http://www.mathworks.com.

Han, 2000

Stewart, 1990, MOPAC: a semiempirical molecular orbital program, J. Comput. Aided Mol. Des., 4, 1, 10.1007/BF00128336

J.P.P., Stewart, MOPAC 6.0, Quantum Chemistry Program Exchange, Indiana University, Bloominton, 1990, Program 455.

Dewar, 1985, AM1: a new general purpose quantum mechanical molecular model, J. Am. Chem. Soc., 107, 3902, 10.1021/ja00299a024

Kier, 1986

Balaban, 1982, Highly discriminating distance-based topological index, Chem. Phys. Lett., 89, 399, 10.1016/0009-2614(82)80009-2

Madan, 1999, Superpendentic index: a novel highly discriminating topological descriptor for predicting biological activity, J. Chem. Inf. Comput. Sci., 39, 9, 10.1021/ci990485e

Kier, 2000, Intermolecular accessibility: the meaning of molecular connectivity, J. Chem. Inf. Comput. Sci., 40, 792, 10.1021/ci990135s

Rohrbaugh, 1987, Molecular shape and the prediction of high-performance liquid chromatographic retention indexes of polycyclic aromatic hydrocarbons, Anal. Chem., 59, 1048, 10.1021/ac00134a025

Goldstein, 1950

Pearlman, 1980

Stouch, 1986, A simple method for the representation, quantification, and comparison of the volumes and shapes of chemical compounds, J. Chem. Inf. Comput. Sci., 26, 4, 10.1021/ci00049a002

Katritzky, 1996, Correlation of boiling pints with molecular structure. 1. A training set of 298 diverse organics and a test set of 9 simple organics, J. Phys. Chem., 100, 10400, 10.1021/jp953224q

Dixo, 1992, Atomic charge calculations for quantitative structure–property relationships, J. Comput. Chem., 18, 492, 10.1002/jcc.540130411

Abraham, 1987, Charge calculations in molecular mechanics IV: a general method for conjugated systems, J. Comput. Chem., 13, 288

Stanton, 1990, Use of charged partial surface area structural descriptors in computer-assisted quantitative structure–property relationship studies, Anal. Chem., 62, 2323, 10.1021/ac00220a013

Vinogradov, 1971

Russell, 1992, Computer assisted study of the relationship between molecular structure and Henry's law constant, Anal. Chem., 64, 1350, 10.1021/ac00037a009

Sutter, 1995, Automated descriptor selection for quantitative structure–activity relationships using generalized simulated annealing, J. Chem. Inf. Comput. Sci., 35, 77, 10.1021/ci00023a011

Sutter, 1995, Selection of molecular descriptors for quantitative structure–activity relationships

Stanton, 1991, Computer-assisted prediction of normal boiling points of furans, tetrahydrofurans, and thiophenes, J. Chem. Inf. Comput. Sci., 31, 301, 10.1021/ci00002a017

Belsey, 1980

Wessel, 1994, Prediction of reduced ion mobility constants from structural information using multiple linear regression analysis and computational neural networks, Anal. Chem., 66, 2480, 10.1021/ac00087a012

Xu, 1994, Quantitative structure–property relationships for toxicity of phenols using regression analysis and computational neural networks, Environ. Toxicol. Chem., 13, 841, 10.1002/etc.5620130520

Kier, 1985, A shape index from molecular graphs, Quant. Struct.-Act. Relat. Pharmacol., Chem. Biol., 4, 109, 10.1002/qsar.19850040303

Kier, 1986

Kier, 1976

Liu, 1998, Approach to estimation and prediction for normal boiling point (nbp) of alkanes based on a novel molecular distance edge (mde) vector, lambda, J. Chem. Inf. Comput. Sci., 38, 387, 10.1021/ci970109z

Randic, 1984, On molecular idenitification numbers, J. Chem. Inf. Comput. Sci., 24, 164, 10.1021/ci00043a009

Randic, 1979, Comput. Chem., 3, 5, 10.1016/0097-8485(79)80002-9

Wiener, 1947, J. Am. Chem. Soc., 69, 17, 10.1021/ja01193a005

Gupta, 1999, Superpendentic index: a novel topological descriptor for predicting biological activity, J. Chem. Inf. Comput. Sci., 39, 272, 10.1021/ci980073q

Kier, 1990, An electrotopological-state index for atoms in molecules, Pharm. Res., 7, 801, 10.1023/A:1015952613760