Do medicinal chemists learn from activity cliffs? A systematic evaluation of cliff progression in evolving compound data sets

Journal of Medicinal Chemistry

Volumn 56, Issue 8, 2013, Pages 3339-3345

  Dimova, Dilyana ^a   Heikamp, Kathrin ^a   Stumpfe, Dagmar ^a   Bajorath, Jürgen ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVITY CLIFF; CHEMICAL AGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG DISTRIBUTION; DRUG POTENCY; REACTION OPTIMIZATION; SCIENTIST; STRUCTURE ACTIVITY RELATION;

CHEMISTRY, PHARMACEUTICAL; DATABASES, FACTUAL; DRUG DESIGN; HUMANS; PHARMACEUTICAL PREPARATIONS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84876847879     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm400147j     Document Type: Article

References (10)

1. Maggiora, G. M. On Outliers and Activity Cliffs-Why QSAR Often Disappoints J. Chem. Inf. Model. 2006, 46, 1535-1535
2. Stumpfe, D.; Bajorath, J. Exploring Activity Cliffs in Medicinal Chemistry J. Med. Chem. 2012, 55, 2932-2942
3. Wassermann, A. M.; Wawer, M.; Bajorath, J. Activity Landscape Representations for Structure-Activity Relationship Analysis J. Med. Chem. 2010, 53, 8209-8223
4. Wassermann, A. M.; Dimova, D.; Bajorath, J. Comprehensive Analysis of Single- and Multi-Target Activity Cliffs Formed by Currently Available Bioactive Compounds Chem. Biol. Drug Des. 2011, 78, 224-228
5. Stumpfe, D.; Bajorath, J. Frequency of Occurrence and Potency Range Distribution of Activity Cliffs in Bioactive Compounds J. Chem. Inf. Model. 2012, 52, 2348-2353
6. Gaulton, A.; Bellis, L. J.; Bento, A. P.; Chambers, J.; Davies, M.; Hersey, A.; Light, Y.; McGlinchey, S.; Michalovich, D.; Al-Lazikani, B.; Overington, J. P. ChEMBL: A Large-Scale Bioactivity Database for Drug Discovery Nucleic Acids Res. 2012, 40, D1100-D1107
7. Kenny, P. W.; Sadowski, J. Structure Modification in Chemical Databases. In Chemoinformatics in Drug Discovery; Oprea, T. I., Ed.; Wiley-VCH: Weinheim, Germany, 2004; pp 271-285.
8. Hussain, J.; Rea, C. Computationally Efficient Algorithm To Identify Matched Molecular Pairs (MMPs) in Large Data Sets J. Chem. Inf. Model. 2010, 50, 339-348
9. Hu, X.; Hu, Y.; Vogt, M.; Stumpfe, D.; Bajorath, J. MMP-Cliffs: Systematic Identification of Activity Cliffs on the Basis of Matched Molecular Pairs J. Chem. Inf. Model. 2012, 52, 1138-1145
10. Tiwaria, A.; Sekhar, A. K. T. Workflow Based Framework for Life Science Informatics Comput. Biol. Chem. 2007, 31, 305-319