Cheminformatics analysis of organic substituents: Identification of the most common substituents, calculation of substituent properties, and automatic identification of drug-like bioisosteric groups

Journal of Chemical Information and Computer Sciences

Volumn 43, Issue 2, 2003, Pages 374-380

  Ertl, Peter ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMINFORMATICS ANALYSIS;

DATABASE SYSTEMS; DRUG DOSAGE; EXTRAPOLATION;

INFORMATION SCIENCE;

EID: 0037362041     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci0255782     Document Type: Conference Paper

References (17)

1. Hansch, C.; Leo, A. Exploring QSAR: Fundamentals and Applications in Chemistry and Biology; American Chemical Society: Washington, DC, 1995.
2. Craig, P. N. Interdependence between Physical Parameters and Selection of Substituent Groups for Correlation Studies. J. Med. Chem. 1971, 14, 680-684.
3. Topliss, J. G. Utilization of Operational Schemes for Analogue Synthesis in Drug Design. J. Med. Chem. 1972, 75, 1006-1011.
4. Lewell, X. Q.; Judd, D. B.; Watson, S. P.; Hann, M. N. RECAP - Retrosynthetic Combinatorial Analysis Procedure: A Powerful New Technique for Identifying Privileged Molecular Fragments with Useful Applications in Combinatorial Chemistry. J. Chem. Inf. Comput. Sci. 1998, 38, 511-522.
5. Rohde, B. Reaction type informetrics of chemical reaction databases: How "large" is chemistry? In Further Advances in Chemical Information; Royal Soc. Chem.: 1994; pp 109-127.
6. 6).
7. Viswanadhan, V. N.; Ghose, A. K.; Revankar, G. R.; Robins, R. K. Atomic physicochemical parameters for three-dimensional structure directed quantitative structure - activity relationships. 4. J. Chem. Inf. Comput. Sci. 1989, 29, 163-172.
8. Ertl, P. Simple Quantum Chemical Parameters as an Alternative to the Hammett Sigma Constants in QSAR Studies. Quant. Struct.-Act. Relat. 1997, 16, 377-382.
9. Derwent World Drug Index WDI 2001.2, published by Derwent Information.
10. Bemis, G. W.; Murcko, M. A. Properties of Known Drugs. 2. Side Chains. J. Med. Chem. 1999, 42, 5095-5099.
11. Ormerod, A.; Willett, P.; Bawden, D. Comparison of Fragment Weighting Schemes for Substructural Analysis. Quant. Struct.-Act. Relat. 1989, 5, 115-129.
12. Ertl, P.; Jacob, O. WWW-based Chemical Information System. J. Mol. Struct. (THEOCHEM) 1997, 419, 113-120.
13. Ertl, P. QSAR Analysis through the World-Wide Web. Chimia 1998, 52, 673-677.
14. Ertl, P.; Miltz, W.; Rohde, B.; Selzer, P. Web-based Cheminformatics for Bench Chemists. Drug Discovery World Fall 2000, 45-50.
15. Patani, G. A.; LaVoie, E. J. Bioisosterism: A Rational Approach in Drug Design. Chem. Rev. 1996, 95, 3147-3176.
16. Ertl, P. World Wide Web-based System for the Calculation of Substituent Parameters and Substituent Similarity Searches. J. Mol. Graph. Mod. 1998, 75, 11-13.
17. JME molecular editor applet allowing creation or editing of molecules may be obtained directly from the author; see also the JME HomePage at www.molinspiration.com/jme/.