Property distributions: Differences between drugs, natural products, and molecules from combinatorial chemistry

Journal of Chemical Information and Computer Sciences

Volumn 43, Issue 1, 2003, Pages 218-227

  Feher, Miklos ^a   Schmidt, Jonathan M ^a  

^a Signalgene Inc Canada   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL CENTERS; COMBINATORIAL CHEMISTRY; COMBINATORIAL COMPOUNDS; DRUG MOLECULES; NATURAL PRODUCTS;

CHEMICAL BONDS; DRUG PRODUCTS; MOLECULAR WEIGHT DISTRIBUTION; MOLECULES; PRINCIPAL COMPONENT ANALYSIS; PROBABILITY DISTRIBUTIONS; STRUCTURE (COMPOSITION); SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

BIOLOGICAL PRODUCT; DRUG;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; COMBINATORIAL CHEMISTRY; COMPARATIVE STUDY; DRUG DESIGN; FACTUAL DATABASE; MOLECULAR WEIGHT; STEREOISOMERISM;

BIOLOGICAL PRODUCTS; COMBINATORIAL CHEMISTRY TECHNIQUES; DATABASES, FACTUAL; DRUG DESIGN; MODELS, CHEMICAL; MOLECULAR WEIGHT; PHARMACEUTICAL PREPARATIONS; STEREOISOMERISM;

EID: 0037208308     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci0200467     Document Type: Article

References (35)

1. Szostak, J. W. Introduction: Combinatorial Chemistry. Chem. Rev. 1997, 97, 347-348.
2. Leach, A. R.; Hann, M. M. The in silico world of virtual libraries. Drug Discovery Today 2000, 5, 326-336.
3. 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 Del. Rev. 1997, 23, 3-25.
4. Bemis, G. W.; Murcko, M. A. The Properties of Known Drugs. I. Molecular Frameworks. J. Med. Chem. 1996, 39, 2887-2993.
5. Bemis, G. W.; Murcko, M. A. The Properties of Known Drugs. 2. Side Chains. J. Med. Chem. 1999, 42, 5095-5099.
6. Oprea, T. I. Property Distribution of Drug-Related Chemical Databases. J. Comput.-Aided Mol. Des. 2000, 14, 251-264.
7. 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.
8. Sadowski, J.; Kubinyi, H. A Scoring Scheme for Discriminating between Drugs and Nondrugs. J. Med. Chem. 1998, 41, 3325-3329.
9. Frimurer, T. M.; Bywater, R.; Naerum, L.; Lauritsen, L. N.; Brunak, S. Improving the Odds in Discriminating Drug-like from Non Drug-like Compounds. J. Chem. Inf. Comput. Sci. 2000, 40, 1315-1324.
10. Xu, J.; Stevenson, J.; Drug-like Index: a New Approach to Measure Drug-like Compounds and Their Diversity. J. Chem. Inf. Comput. Sci. 2000, 40, 1177-1187.
11. Kingston, D. G. I. Natural Products as Pharmaceuticals and Sources for Lead Structures. In The Practice of Medicinal Chemistry; Wermuth, C. G., Ed.; Academic Press: London, 1996.
12. Verdine, G. L. The Combinatorial Chemistry of Nature. Nature, 1996, 384, 11-13.
13. Stahura, F. L.; Godden, J. W.; Xue, L.; Bajorath, J. Distinguishing between Natural Products and Synthetic Molecules by Descriptor Shannon Entropy Analysis and Binary QSAR Calculations. J. Chem. Inf. Comput. Sci. 2000, 40, 1245-1252.
14. Henkel, T.; Brunne, R. M.; Müller, H.; Reichel, F. Statistical Investigation of Structural Complementarity of Natural Products and Synthetic Compounds. Angew. Chem., Int. Ed. Engl. 1999, 38, 643-647.
15. Lee, M. L.; Schneider, G. Scaffold Architecture and Pharmacophoric Properties of Natural Products and Trade Drugs: Application in the Design of Natural Product-Based Combinatorial Libraries. J. Comb. Chem. 2001, 3, 284-289.
16. Chapman and Hall Dictionary of Drugs for PC; Chemical Design Ltd., Chipping Norton: Oxfordshire, U.K., 1996.
17. The Merck Index, Twelfth Edition on CD-ROM, Version 12:1; Chapman and Hall Electronic Publishing Division: London, 1996.
18. Maybridge HTS database, June 2000, Maybridge Chemical Co. Ltd.: Tintagel, Cornwall, U.K.
19. ChemBridge EXPRESS-Pick database, February 2001, ChemBridge Corporation: San Diego, CA.
20. ComGenex stock databases, March 2001, ComGenex International: San Francisco, CA.
21. ChemDiv Small Molecule Compound Collections, ChemDiv Inc.: San Diego, CA.
22. SPECS and BioSPECS databases, April 2001, SPECS and BioSPECS B. V., Rijswijk: The Netherlands.
23. Interbioscreen databases, February 2001, Interbioscreen Ltd.: Moscow, Russia.
24. Molecular Operating Environment, Version 2000.02, Chemical Computing Group Inc.: Montreal, Quebec, Canada.
25. Badertscher, M.; Bischofberger, K.; Munk, M. E.; Pretsch, E. A Novel Formalism to Characterize the Degree of Unsaturation of Organic Molecules. J. Chem. Inf. Comput. Sci. 2001, 41, 889-893.
26. Wildman, S. A.; Crippen, G. M. Prediction of Physicochemical Parameters by Atomic Contributions. J. Chem. Inf. Comput. Sci. 1999, 39, 868-873.
27. Sokal, R. F.; Rohlf, F. J. Biometry, 2nd ed.; W. H. Freeman: New York, 1981; pp 43-46.
28. Klebe, G.; Böhm, H.-J. Energetic and Entropic Factors Determining Binding Affinity in Protein-Ligand Complexes. J. Receptor Signal Transduction Res. 1997, 17, 459-473.
29. Triggle, D. J. The Transaction from Agonist to Antagonist Activity: Symmetry and Other Considerations. In The Practice of Medicinal Chemistry; Wermuth, C. G., Ed.; Academic Press: London, pp 547-570.
30. Mann, J. Secondary Metabolism, 2nd ed.; Clarendon Press: Oxford, 1987.
31. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click Chemistry: Chemical Function from a Few Good Reactions. Angew. Chem. Int. Ed. Engl. 2001, 40, 2004-2021.
32. Tute, M. S. Lipophilicity: A History. In Lipophilicity in Drug Action and Toxicology; Pliska, V., Testa, B., van de Waterbeemd, H., Eds.; VCH: Weinheim, 1996; pp 7-26.
33. Böhm, H.-J.; Klebe, G.; Kubinyi, H. Wirkstoffdesign; Spektrum Akademischer Verlag: Heidelberg, 1996; p 153.
34. Zaks, A.; Dodds, D. R. Application of biocatalysis and biotransformations to the synthesis of pharmaceuticals. Drug Design Discovery 1997, 2, 513-531.
35. Hall, D. G.; Manku, S.; Wang, F. Solution and Solid-Phase Strategies for Design, Synthesis and Screening of Libraries Based on Natural Product Templates: A Comprehensive Survey. J. Comb. Chem. 2001, 3, 125-150.