Abstract
The chemical structure of a compound has a direct influence on its physical, chemical, and biological properties. The present study describes data pertaining to calculations and statistical analysis of the physicochemical parameters of drugs obtained directly or indirectly from nature. The study projects various physiochemical parameters required for their druggability. The study reveals that most of these drugs fall close to Lipinski’s rule of five. Among the reported physicochemical parameters, the number of aromatic rings is most interesting. Illustrations regarding the same are reported, along with their statistical trends.
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References
Ajay A, Walters WP, Murko MA (1998) Can we learn to distinguish between drug-like and ‘nondrug-like’ molecules? J Med Chem 41:3314–3324
Babine RE, Bender SL (1997) Molecular recognition of proteinminus signligand complexes: applications to drug design. Chem Rev 97(5):1359–1472
Bajorath J (2002) Chemoinformatics methods for systematic comparison of molecules from natural and synthetic sources and design of hybrid libraries. Mol Divers 5(4):305–313
Balunas MJ, Kinghorn AD (2005) Drug discovery from medicinal plants. Life Sci 78(5):431–441
Bemis GW, Murcko MA (1999) Properties of known drugs. 2. Side chains. J Med Chem 42(25):5095–5099
British Pharmacopeia Commission (2005) British pharmacopoeia, vols I–IV. Stationery Office Books, London
Clardy J, Walsh C (2004) Lessons from natural molecules. Nature 432(7019):829–837
Clark DE, Pickett SD (2000) Computational methods for the prediction of ‘drug-likeness’. Drug Discov Today 5(2):49–58
Cragg GM, Newman D (2001) Natural product drug discovery in the next millennium. Pharm Biol 39:8–17
Deschamps JD, Gautschi JT, Whitman S, Johnson TA, Gassner NC, Crews P, Holman TR (2007) Discovery of platelet-type 12-human lipoxygenase selective inhibitors by high-throughput screening of structurally diverse libraries. Bioorg Med Chem 15(22):6900–6908
Ertl P, Rohde B, Selzer P (2000) Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties. J Med Chem 43(20):3714–3717
Faller B, Ertl P (2007) Computational approaches to determine drug solubility. Adv Drug Deliv Rev 59(7):533–545
Ganesan A (2008) The impact of natural products upon modern drug discovery. Curr Opin Chem Biol 12(3):306–317
Gurib-Fakim A (2006) Medicinal plants: traditions of yesterday and drugs of tomorrow. Mol Aspects Med 27(1):1–93
Kola I, Landis J (2004) Can the pharmaceutical industry reduce attrition rates? Nature Rev Drug Discov 3(8):711–715
Larsson J, Gottfries J, Bohlin L, Backlund A (2005) Expanding the ChemGPS chemical space with natural products. J Nat Prod 68(7):985–991
Lipinski CA (2000) Drug-like properties and the causes of poor solubility and poor permeability. J Pharmacol Toxicol Methods 44(1):235–249
Lipinski CA (2004) Lead- and drug-like compounds: the rule-of-five revolution. Drug Discov Today Technol 1(4):337–341
Lipinski CA, Lombardo F, Dominy BW, Feeney PJ (1997) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 23:3–25
Molinspiration Cheminformatics. Nova ulica 61, SK-900 26. Available at: http://www.molinspiration.com/cgi-bin/properties
Merck (2001) Merck index, chemicals, drugs and biological, 13th edn. Merck, White House Station
Muegge I, Heald SL, Britelli D (2001) Simple selection criteria for drug-like chemical matter. J Med Chem 44(12):1841–1846
Newman DJ, Cragg GM, Sander KM (2003) Natural products as sources of new drugs over the period 1981–2002. J Nat Prod 66:1022–1037
Proudfoot JR (2002) Drugs, leads, and drug-likeness: an analysis of some recently launched drugs. Bioorg Med Chem Lett 12(12):1647–1650
Sadowski J, Kubinyi H (1998) A scoring scheme for discriminating between drugs and nondrugs. J Med Chem 41(18):3325–3329
Swarna VM, Undem BJ, Korlipara VL (2007) Design and synthesis of 3,5-disubstituted benzamide analogues of DNK333 as dual NK1/NK2 receptor probes. Bioorg Med Chem Lett 17(4):890–894
Tan DS (2005) Diversity-oriented synthesis: exploring the intersections between chemistry and biology. Nat Chem Biol 1(2):74–84
Tan NC, Yu P, Kwon YU, Kodadek T (2008) High-throughput evaluation of relative cell permeability between peptoids and peptides. Bioorg Med Chem 16(11):5853–5861
U.S. Pharmacopeia (2006) United States pharmacopeia. 29th rev. USP Convention, Rockville
Zhang M, Wilkinson B (2007) Drug discovery beyond the rule-of-five. Curr Opin Biotechnol 18(6):478–488
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Kumar, B.R.P., Soni, M., Bhikhalal, U.B. et al. Analysis of physicochemical properties for drugs from nature. Med Chem Res 19, 984–992 (2010). https://doi.org/10.1007/s00044-009-9244-2
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DOI: https://doi.org/10.1007/s00044-009-9244-2