Chemical information based scaling of molecular descriptors: A universal chemical scale for library design and analysis

Journal of Chemical Information and Computer Sciences

Volumn 42, Issue 4, 2002, Pages 879-884

  Tounge, Brett A ^a   Pfahler, Lori B ^b   Reynolds, Charles H ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR DESCRIPTORS;

COMPUTER SOFTWARE; DATA REDUCTION; DATABASE SYSTEMS; MOLECULAR WEIGHT; TOPOLOGY;

DRUG PRODUCTS;

ARTICLE; CHEMICAL MODEL; COMBINATORIAL CHEMISTRY; COMPUTER SIMULATION; DRUG DESIGN; FACTUAL DATABASE;

COMBINATORIAL CHEMISTRY TECHNIQUES; COMPUTER SIMULATION; DATABASES, FACTUAL; DRUG DESIGN; MODELS, CHEMICAL;

EID: 0036628554     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci025503y     Document Type: Article

References (27)

1. Kubinyi, H. Combinatorial and computational approaches in structure-based drug design. Curr. Opin. Drug Discovery Dev. 1998, 1, 16-27.
2. Pearlman, R.S.; Smith, K.M. Novel software tools for chemical diversity. Perspect. Drug Discovery Des. 1998, 9, 339-353.
3. Willett, P. Chemoinformatics - similarity and diversity in chemical libraries. Curr. Opin. Drug Discovery Dev. 2000, 11, 85-88.
4. Van Drie, J.H.; Lajiness, M.S. Approaches to virtual library design. Drug Discovery Today 1998, 3, 274-283.
5. Mitchell, T.; Showell, G.A. Design strategies for building drug-like chemical libraries. Curr. Opin. Drug Discovery Dev. 2001, 4, 314-318.
6. Lewis, R.A.; Pickett, S.D.; Clark, D.E. Computer-aided molecular diversity analysis and combinatorial library design. In Reviews in Computational Chemistry; Lipkowitz, K.B., Boyd, D.B., Ed.; VCH Publishers: New York, 2000; Vol. 16, pp 1-51.
7. Gorse, D.; Lahana, R. Functional diversity of compound libraries. Curr. Opin. Chem. Biol. 2000, 4, 287-294.
8. Sadowski, J. Optimization of chemical libraries by neural networks. Curr. Opin. Chem. Biol. 2000, 4, 280-282.
9. Sadowski, J.; Kubinyi, H. A scoring scheme for discriminating between drugs and nondrugs. J. Med. Chem. 1998, 41, 3325-3329.
10. Ajay; Walters, W.P.; Murcko, M.A. Can We Learn to Distinguish between "Drug-like" and "Nondrug-like" Molecules? J. Med. Chem. 1998, 41, 3314-3324.
11. MDL Information Systems, Inc., http://www.mdli.com.
12. National Cancer Institute, http://cactus.nci.nih.gov/ncidb2/download.html.
13. Prous Science, http://www.prous.com.
14. Bemis, G.W.; Murcko, M.A. Properties of Known Drugs. 1. Molecular Frameworks. J. Med. Chem. 1996, 39, 2887-2893.
15. Holloway, M.K.; Wai, J.M.; Halgren, T.A.; Fitzgerald, P.M.D.; Vacca, J.P.; Dorsey, B.D.; Levin, R.B.; Thompson, W.J.; Chen, L.J.; et al. A priori prediction of activity for HIV-1 protease inhibitors employing energy minimization in the active site. J. Med. Chem. 1995, 38, 305-317.
16. 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 and CLOGP Methods. J. Phys. Chem. A 1998, 102, 3762-3772.
17. Cummins, D.J.; Andrews, C.W.; Bentley, J.A.; Cory, M. Molecular Diversity in Chemical Databases: Comparison of Medicinal Chemistry Knowledge Bases and Databases of Commercially Available Compounds. J. Chem. Inf. Comput. Sci. 1996, 36, 750-763.
18. Menard, P.R.; Mason, J.S.; Morize, I.; Bauerschmidt, S. Chemistry Space Metrics in Diversity Analysis, Library Design, and Compound Selection. J. Chem. Inf. Comput. Sci. 1998, 38, 1204-1213.
19. Voigt, J.H.; Bienfait, B.; Wang, S.; Nicklaus, M.C. Comparison of the NCI open database with seven large chemical structural databases. J. Chem. Inf. Comput. Sci. 2001, 41, 702-712.
20. Oprea, T.I. Property distribution of drug-related chemical databases. J. Comput.-Aided Mol. Des. 2000, 14, 251-264.
21. Hall, L.H.; Kier, L.B. The electrotopological state: An atomic index for QSAR. Quant. Structure-Activity Relat. 1991, 10, 43-48.
22. Hall, L.H.; Kier, L.B. The electrotopological state: Structure information at the atomic level for molecular graphs. J. Chem. Inf. Comput. Sci. 1991, 31, 76-83.
23. Rogers, D.; Hopfinger, A.J. Application of Genetic Function Approximation to Quantitative Structure-Activity Relationships and Quantitative Structure-Property Relationships. J. Chem. Inf. Comput. Sci. 1994, 34, 854-866.
24. Topliss, J.G.; Edwards, R.P. Chance Factors in Studies of Quantitative Structure-Activity Relationships. J. Med. Chem. 1979, 22, 2.
25. Lipinsld, 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.
26. Lipinski, C.A. Drug-like properties and the causes of poor solubility and poor permeability. J. Pharmacol. Toxicol. Methods 2001, 44, 235-249.
27. Arup, K.G.; Viswandahan, V.N.; Wendoloski, J.J. A Knowledge-Based Approach in Designing Combinatorial or Medicinal Chemistry Libraries for Drug Discovery. 1. A Qualitative and Quantitative Characterization of Known Drug Databases. J. Comb. Chem. 1999, 1, 55-68.