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Volumn 46, Issue 17, 2003, Pages 3572-3580

Prediction of aqueous solubility of a diverse set of compounds using quantitative structure-property relationships

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL STRUCTURE; DRUG INDUSTRY; DRUG SCREENING; DRUG SOLUBILITY; GENETIC ALGORITHM; PREDICTION; QUANTITATIVE STRUCTURE PROPERTY RELATION;

EID: 0041731599     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020266b     Document Type: Article
Times cited : (228)

References (48)
  • 1
    • 0003941956 scopus 로고    scopus 로고
    • American Chemical Society and Oxford University Press: Washington, DC, New York, Oxford
    • Yalkowsky, S. H. Solubility and Solubilization in Aqueous Media; American Chemical Society and Oxford University Press: Washington, DC, New York, Oxford, 1999.
    • (1999) Solubility and Solubilization in Aqueous Media
    • Yalkowsky, S.H.1
  • 3
    • 0029128834 scopus 로고
    • Success rates for new drugs entering clinical testing in the United States
    • DiMasi, J. A. Success Rates for New Drugs Entering Clinical Testing in the United States. Clin. Pharmacol. Ther. 1995, 58, 1-14.
    • (1995) Clin. Pharmacol. Ther. , vol.58 , pp. 1-14
    • DiMasi, J.A.1
  • 4
    • 0023947965 scopus 로고
    • Pharmaceutical innovation by the seven UK-owned pharmaceutical companies (1964-1985)
    • Prentis, R. A.; Lis, Y.; Walker, S. R. Pharmaceutical Innovation by the Seven UK-owned Pharmaceutical Companies (1964-1985). Br. J. Clin. Pharmacol. 1988, 25, 387-396.
    • (1988) Br. J. Clin. Pharmacol. , vol.25 , pp. 387-396
    • Prentis, R.A.1    Lis, Y.2    Walker, S.R.3
  • 5
    • 0034461768 scopus 로고    scopus 로고
    • Drug-like properties and the causes of poor solubility and poor permeability
    • Lipinski, C. A. Drug-like Properties and the Causes of Poor Solubility and Poor Permeability. J. Pharmacol. Toxicol. Methods 2001, 44, 235-249.
    • (2001) J. Pharmacol. Toxicol. Methods , vol.44 , pp. 235-249
    • Lipinski, C.A.1
  • 6
    • 0035289779 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and Computational Approaches to Estimate Solubility and Permeability in Drug Discovery and Development Settings. Adv. Drug Delivery Rev. 2001, 46, 3-26.
    • (2001) Adv. Drug Delivery Rev. , vol.46 , pp. 3-26
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 7
    • 84956773910 scopus 로고    scopus 로고
    • Library filtering systems and prediction of drug-like properties
    • Walters, W. P.; Murcko, M. A. Library Filtering Systems and Prediction of Drug-like Properties. Methods Principles Med. Chem. 2000, 10, 15-32.
    • (2000) Methods Principles Med. Chem. , vol.10 , pp. 15-32
    • Walters, W.P.1    Murcko, M.A.2
  • 8
    • 0035953319 scopus 로고    scopus 로고
    • Property-based design: Optimization of drug absorption and pharmacokinetics
    • van de Waterbeemd, H.; Smith, D. A.; Beaumont, K.; Walker, D. K. Property-Based Design: Optimization of Drug Absorption and Pharmacokinetics. J. Med. Chem. 2001, 44, 1313-1333.
    • (2001) J. Med. Chem. , vol.44 , pp. 1313-1333
    • Van de Waterbeemd, H.1    Smith, D.A.2    Beaumont, K.3    Walker, D.K.4
  • 9
    • 0033981358 scopus 로고    scopus 로고
    • Computational methods for the prediction of "drug-likeness"
    • Clark, D. E.; Pickett, S. D. Computational methods for the prediction of "drug-likeness". Drug Discovery Today 2000, 5, 49-58.
    • (2000) Drug Discovery Today , vol.5 , pp. 49-58
    • Clark, D.E.1    Pickett, S.D.2
  • 10
    • 0035829402 scopus 로고    scopus 로고
    • One-dimensional molecular representations and similarity calculations: Methodology and validation
    • Dixon, S. L.; Merz, K. M., Jr. One-Dimensional Molecular Representations and Similarity Calculations: Methodology and Validation. J. Med. Chem. 2001, 44, 3795-3809.
    • (2001) J. Med. Chem. , vol.44 , pp. 3795-3809
    • Dixon, S.L.1    Merz K.M., Jr.2
  • 11
    • 0034687231 scopus 로고    scopus 로고
    • Prediction of drug absorption using multivariate statistics
    • Egan, W. J.; Merz, K. M., Jr.; Baldwin, J. J. Prediction of Drug Absorption Using Multivariate Statistics. J. Med. Chem. 2000, 43, 3867-3877.
    • (2000) J. Med. Chem. , vol.43 , pp. 3867-3877
    • Egan, W.J.1    Merz K.M., Jr.2    Baldwin, J.J.3
  • 13
    • 0000445633 scopus 로고    scopus 로고
    • Prediction of aqueous solubility of organic compounds from molecular structure
    • Mitchel, B. E.; Jurs, P. C. Prediction of Aqueous Solubility of Organic Compounds from Molecular Structure. J. Chem. Inf. Comput. Sci. 1998, 38, 489-496.
    • (1998) J. Chem. Inf. Comput. Sci. , vol.38 , pp. 489-496
    • Mitchel, B.E.1    Jurs, P.C.2
  • 14
    • 0028429968 scopus 로고
    • Prediction of aqueous solubility of organic compounds
    • Nelson, T. M.; Jurs, P. C. Prediction of Aqueous Solubility of Organic Compounds. J. Chem. Inf. Comput. Sci. 1994, 34, 601-609.
    • (1994) J. Chem. Inf. Comput. Sci. , vol.34 , pp. 601-609
    • Nelson, T.M.1    Jurs, P.C.2
  • 15
    • 0002615508 scopus 로고    scopus 로고
    • Prediction of aqueous solubility for a diverse set of heteroatom-containing organic compounds using a quantitative structure-property relationship
    • Sutter, J. M.; Jurs, P. C. Prediction of Aqueous Solubility for a Diverse Set of Heteroatom-Containing Organic Compounds using a Quantitative Structure-property Relationship. J. Chem. Inf. Comput. Sci. 1996, 36, 100-107.
    • (1996) J. Chem. Inf. Comput. Sci. , vol.36 , pp. 100-107
    • Sutter, J.M.1    Jurs, P.C.2
  • 16
    • 0035470268 scopus 로고    scopus 로고
    • Prediction of aqueous solubility of heteroatom-containing organic compounds from molecular structure
    • McElroy, N. R.; Jurs, P. C. Prediction of Aqueous Solubility of Heteroatom-Containing Organic Compounds from Molecular Structure. J. Chem. Inf. Comput. Sci. 2001, 41, 1237-1247.
    • (2001) J. Chem. Inf. Comput. Sci. , vol.41 , pp. 1237-1247
    • McElroy, N.R.1    Jurs, P.C.2
  • 17
    • 0027078680 scopus 로고
    • A new method for the estimation of the aqueous solubility of organic compounds
    • Bodor, N.; Huang, M.-J. A New Method for the Estimation of the Aqueous Solubility of Organic Compounds. J. Pharm. Sci. 1992, 81, 954-960.
    • (1992) J. Pharm. Sci. , vol.81 , pp. 954-960
    • Bodor, N.1    Huang, M.-J.2
  • 18
    • 0001515707 scopus 로고    scopus 로고
    • Correlation of the aqueous solubility of hydrocarbons and halogenated hydrocarbons with molecular structure
    • Huibers, P. D.; Katritzky, A. R. Correlation of the Aqueous Solubility of Hydrocarbons and Halogenated Hydrocarbons with Molecular Structure. J. Chem. Inf. Comput. Sci. 1998, 38, 283-292.
    • (1998) J. Chem. Inf. Comput. Sci. , vol.38 , pp. 283-292
    • Huibers, P.D.1    Katritzky, A.R.2
  • 19
    • 0020599769 scopus 로고
    • Solubility partitioning VI: Octanol solubility and octanol-water partition coefficients
    • Yalkowsky, S. H.; Valvani, S. C.; Roseman, T. J. Solubility and Partitioning VI: Octanol Solubility and Octanol-Water Partition Coefficients. J. Pharm. Sci. 1983, 72, 866-870.
    • (1983) J. Pharm. Sci. , vol.72 , pp. 866-870
    • Yalkowsky, S.H.1    Valvani, S.C.2    Roseman, T.J.3
  • 20
    • 0030056288 scopus 로고    scopus 로고
    • Improved method for estimating water solubility from octanol/water partition coefficient
    • Meylan, W. M.; Howard, P. H.; Boethling, R. S. Improved Method for Estimating Water Solubility from Octanol/water Partition Coefficient. Environ. Toxicol. Chem. 1996, 15, 100-106.
    • (1996) Environ. Toxicol. Chem. , vol.15 , pp. 100-106
    • Meylan, W.M.1    Howard, P.H.2    Boethling, R.S.3
  • 21
    • 0022889696 scopus 로고
    • A Method for calculation of the aquous solubility of organic compounds by using new fragment solubility constants
    • Wakita, K.; Yoshimoto, M.; Miyamoto, S.; Watanabe, H. A Method for Calculation of the Aquous Solubility of Organic Compounds by Using New Fragment Solubility Constants. Chem. Pharm. Bull. 1986, 34, 4663-4681.
    • (1986) Chem. Pharm. Bull. , vol.34 , pp. 4663-4681
    • Wakita, K.1    Yoshimoto, M.2    Miyamoto, S.3    Watanabe, H.4
  • 22
    • 0026147366 scopus 로고
    • Develpment of an automatic estimation system for both the partition coefficient and aqueous solubility
    • Suzuki, T. Develpment of an Automatic Estimation System for Both the Partition Coefficient and Aqueous Solubility. J. Comput.-Aided Mol. Design 1991, 5, 149-166.
    • (1991) J. Comput.-Aided Mol. Design , vol.5 , pp. 149-166
    • Suzuki, T.1
  • 23
    • 0035273557 scopus 로고    scopus 로고
    • Estimation of the aqueous solubility of organic molecules by the group contribution approach
    • Klopman, G.; Zhu, H. Estimation of the Aqueous Solubility of Organic Molecules by the Group Contribution Approach. J. Chem. Inf. Comput. Sci. 2001, 41, 439-445.
    • (2001) J. Chem. Inf. Comput. Sci. , vol.41 , pp. 439-445
    • Klopman, G.1    Zhu, H.2
  • 24
    • 0028990049 scopus 로고
    • Group contribution methods to estimate water solubility of organic chemicals
    • Kuhne, R.; Ebert, R.-U.; Kleint, F., Schmidt, G.; Schuurmann, G. Group Contribution Methods to Estimate Water Solubility of Organic Chemicals. Chemosphere 1995, 30, 2061-2077.
    • (1995) Chemosphere , vol.30 , pp. 2061-2077
    • Kuhne, R.1    Ebert, R.-U.2    Kleint, F.3    Schmidt, G.4    Schuurmann, G.5
  • 25
    • 0032841864 scopus 로고    scopus 로고
    • The correlation and prediction of the solubility of compounds in water using an amended solvation energy relationship
    • Abraham, M. H.; Le, J. The Correlation and Prediction of the Solubility of Compounds in Water Using an Amended Solvation Energy Relationship. J. Pharm. Sci. 1999, 88, 868-880.
    • (1999) J. Pharm. Sci. , vol.88 , pp. 868-880
    • Abraham, M.H.1    Le, J.2
  • 26
    • 0031054880 scopus 로고    scopus 로고
    • Aqueous solubility prediction of environmentally important chemicals from the mobil order thermodynamics
    • Ruelle, P.; Kesselring, U. W. Aqueous Solubility Prediction of Environmentally Important Chemicals from the Mobil Order Thermodynamics. Chemosphere 1997, 34, 275-298.
    • (1997) Chemosphere , vol.34 , pp. 275-298
    • Ruelle, P.1    Kesselring, U.W.2
  • 27
    • 0032061266 scopus 로고    scopus 로고
    • Aqueous solubility prediction of drugs based on molecular topology and neural network modeling
    • Huuskonen, J.; Salo, M.; Taskinen, J. Aqueous Solubility Prediction of Drugs Based on Molecular Topology and Neural Network Modeling. J. Chem. Inf. Comput. Sci. 1998, 38, 450-456.
    • (1998) J. Chem. Inf. Comput. Sci. , vol.38 , pp. 450-456
    • Huuskonen, J.1    Salo, M.2    Taskinen, J.3
  • 28
    • 0001645890 scopus 로고    scopus 로고
    • Estimation of aqueous solubility for a diverse set of organic compounds based on molecular topology
    • Huuskonen, J. Estimation of Aqueous Solubility for a Diverse Set of Organic Compounds Based on Molecular Topology. J. Chem. Inf. Comput. Sci. 2000, 40, 773-777.
    • (2000) J. Chem. Inf. Comput. Sci. , vol.40 , pp. 773-777
    • Huuskonen, J.1
  • 29
    • 0035526162 scopus 로고    scopus 로고
    • Estimation of aqueous solubility of chemical compounds using E-state indices
    • Tetko, I. V.; Tanchuk, V. Y.; Kasheva, T. N.; Villa, A. E. P. Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices. J. Chem. Inf. Comput. Sci. 2001, 41, 1488-1493.
    • (2001) J. Chem. Inf. Comput. Sci. , vol.41 , pp. 1488-1493
    • Tetko, I.V.1    Tanchuk, V.Y.2    Kasheva, T.N.3    Villa, A.E.P.4
  • 30
    • 0035498340 scopus 로고    scopus 로고
    • Development of quantitative structure-property relationship models for early ADME evaluation in drug discovery. 1. Aqueous solubility
    • Liu, R.; So, S.-S. Development of Quantitative Structure-Property Relationship Models for Early ADME Evaluation in Drug Discovery. 1. Aqueous Solubility. J. Chem. Inf. Comput. Sci. 2001, 41, 1633-1639.
    • (2001) Chem. Inf. Comput. Sci. , vol.41 , pp. 1633-1639
    • Liu, R.1    So, S.-S.2
  • 31
    • 0034608316 scopus 로고    scopus 로고
    • Prediction of drug solubility from Monte Carlo simulations
    • Jorgensen, W. L.; Duffy, E. M. Prediction of Drug Solubility from Monte Carlo Simulations. Bioorg. Med. Chem. Lett. 2000, 10, 1155-1158.
    • (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 1155-1158
    • Jorgensen, W.L.1    Duffy, E.M.2
  • 32
    • 0035263415 scopus 로고    scopus 로고
    • Prediction of drug solubility by the general solubility equation (GSE)
    • Ran, Y.; Yalkowsky, S. H. Prediction of Drug Solubility by the General Solubility Equation (GSE). J. Chem. Inf. Comput. Sci. 2001, 41, 354-357.
    • (2001) J. Chem. Inf. Comput. Sci. , vol.41 , pp. 354-357
    • Ran, Y.1    Yalkowsky, S.H.2
  • 34
    • 0041388761 scopus 로고    scopus 로고
    • Yalkowsky, S. H., College of Pharmacy, University of Arizona, Tucson, AZ
    • Adb, the AROZONA dATAbASE of Aqueous Solubility, Yalkowsky, S. H., College of Pharmacy, University of Arizona, Tucson, AZ, 1997.
    • (1997) Adb, the AROZONA dATAbASE of Aqueous Solubility
  • 35
    • 0003505236 scopus 로고    scopus 로고
    • Syracuse Research Corporation, SRC Environmental Research Center, Syrucuse, NY
    • Physical/Chemical Property Database (PHYSPROP), Syracuse Research Corporation, SRC Environmental Research Center, Syrucuse, NY, 1999.
    • (1999) Physical/Chemical Property Database (PHYSPROP)
  • 37
    • 0004305176 scopus 로고    scopus 로고
    • MDL Information Systems, Inc.: San Leandro, CA
    • Comprehensive Medicinal Chemistry; MDL Information Systems, Inc.: San Leandro, CA, 1999.
    • (1999) Comprehensive Medicinal Chemistry
  • 39
  • 41
    • 0027692921 scopus 로고
    • Traditional topological indices vs electronic, geometrical, and combined molecular descriptors in QSAR/QSPR research
    • Katritzky, A. R.; Gordeeva, E. V. Traditional Topological Indices vs Electronic, Geometrical, and Combined Molecular Descriptors in QSAR/QSPR Research. J. Chem. Inf. Comput. Sci. 1993, 33, 835-857.
    • (1993) J. Chem. Inf. Comput. Sci. , vol.33 , pp. 835-857
    • Katritzky, A.R.1    Gordeeva, E.V.2
  • 42
    • 9444296174 scopus 로고
    • Highly discriminating distance-based topological index
    • Balaban, A. T. Highly Discriminating Distance-Based Topological Index. Chem. Phys. Lett. 1982, 89, 399-404.
    • (1982) Chem. Phys. Lett. , vol.89 , pp. 399-404
    • Balaban, A.T.1
  • 43
    • 0029404240 scopus 로고
    • Electrotopological state indices for atom Types: A novel combination of electronic, topological, and valence state information
    • Hall, L. H.; Kier, L. B. Electrotopological State Indices for Atom Types: A Novel Combination of Electronic, Topological, and Valence State Information. J. Chem. Inf. Comput. Sci. 1995, 35, 1039-1045.
    • (1995) J. Chem. Inf. Comput. Sci. , vol.35 , pp. 1039-1045
    • Hall, L.H.1    Kier, L.B.2
  • 44
    • 45949120296 scopus 로고
    • Descriptions of molecular shape applied in studies of structure/activity and structure/property relationships
    • Rohrbaugh, R. H.; Jurs, P. C. Descriptions of Molecular Shape Applied in Studies of Structure/activity and Structure/property Relationships. Anal. Chim. Acta 1987, 199, 99-109.
    • (1987) Anal. Chim. Acta , vol.199 , pp. 99-109
    • Rohrbaugh, R.H.1    Jurs, P.C.2
  • 45
    • 10344253046 scopus 로고
    • Development and use of charged partial surface area structural descriptors in computer-assisted quantitative structure-property relationship studies
    • Stanton, D. T.; Jurs, P. C. Development and Use of Charged Partial Surface Area Structural Descriptors in Computer-Assisted Quantitative Structure-Property Relationship Studies. Anal. Chem. 1990, 62, 2323-2329.
    • (1990) Anal. Chem. , vol.62 , pp. 2323-2329
    • Stanton, D.T.1    Jurs, P.C.2
  • 46
    • 0000381930 scopus 로고    scopus 로고
    • Prediction of hydrophobic (lipophilic) properties of small organic molecules using fragmental methods: An analysis of ALOGP adn CLOGP methods
    • Ghose, A. K.; Viswanadhan, V. N.; Wendoloski, J. J. Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragmental Methods: An Analysis of ALOGP adn CLOGP methods. J. Phys. Chem. A 1998, 102, 3762-3772.
    • (1998) J. Phys. Chem. A , vol.102 , pp. 3762-3772
    • Ghose, A.K.1    Viswanadhan, V.N.2    Wendoloski, J.J.3
  • 47
    • 0001085722 scopus 로고
    • The linear free-energy relationship between partition coefficients and the aqueous solubility of organic liquids
    • Hansch, C.; Quinlan, J. E.; Lawrence, G. L. The Linear Free-Energy Relationship between Partition Coefficients and the Aqueous Solubility of Organic Liquids. J. Org. Chem. 1968, 33, 347-350.
    • (1968) J. Org. Chem. , vol.33 , pp. 347-350
    • Hansch, C.1    Quinlan, J.E.2    Lawrence, G.L.3
  • 48
    • 0019470712 scopus 로고
    • Solubility partitioning aqueous solubility and octanol-water partition coefficients of liquid nonelectrolytes
    • Valvani, S. C.; Yalkowsky, S. H.; Roseman, T. J. Solubility and Partitioning IV: aqueous Solubility and Octanol-Water Partition Coefficients of Liquid Nonelectrolytes. J. Pharm. Sci. 1981, 70, 502-507.
    • (1981) J. Pharm. Sci. , vol.70 , pp. 502-507
    • Valvani, S.C.1    Yalkowsky, S.H.2    Roseman T.J. IV3


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