The scaffold tree: an efficient navigation in the scaffold universe.
The Scaffold Tree algorithm (J Chem Inf Model 47:47-58, 2007) allows to organize large molecular data sets by arranging sets of molecules into a unique tree hierarchy based on their scaffolds, with scaffolds forming leaf nodes of such tree. The hierarchy is created by iterative removal of rings from more complex scaffolds using chemically meaningful set of rules, until a single, root ring is obtained. The classification is deterministic, data set independent, and scales linearly with the number of compounds included in the data set. In this review we summarize the basic principles of the Scaffold Tree methodology and review its applications, which appeared in recent medicinal chemistry literature, including the use of Scaffold Trees for visualization of large chemical data sets, compound clustering, and the identification of novel bioactive molecules. References to several computer programs, including also free tools available on the Internet, allowing to perform classification and visualization of molecules based on their scaffolds are also provided.
Ertl
Peter
P
Novartis Institutes for BioMedical Research, Basel, Switzerland.
Schuffenhauer
Ansgar
A
Renner
Steffen
S
D000465:Algorithms; D002626:Chemistry, Pharmaceutical / Q000379:methods; D016000:Cluster Analysis; D003198:Computer Simulation; D016208:Databases, Factual; D020407:Internet; D008958:Models, Molecular; D015394:Molecular Structure; D004364:Pharmaceutical Preparations / Q000737:chemistry; D012984:Software
D004364:Pharmaceutical Preparations