Stigmata: an algorithm to determine structural commonalities in diverse datasets.
An algorithm, Stigmata, is described, which extracts structural commonalities from chemical datasets. It is discussed using several illustrative examples and a pharmaceutically interesting set of dopamine D2 agonists. The commonalities are determined using two-dimensional topological chemical descriptions and are incorporated into the key feature of the algorithm, the modal fingerprint. Flexibility is built into the algorithm by means of a user-defined threshold value, which affects the information content of the modal fingerprint. The use of the modal fingerprint as a diversity assessment tool, as a database similarity query, and as a basis for color mapping the determined commonalities back onto the chemical structures is demonstrated.
Shemetulskis
N E
NE
Parke-Davis Pharmaceutical Research Division, Warner-Lambert Company, Ann Arbor, Michigan 48105, USA.
Weininger
D
D
Blankley
C J
CJ
Yang
J J
JJ
Humblet
C
C
D000465:Algorithms; D016208:Databases, Factual; D018491:Dopamine Agonists / Q000737:chemistry; D007211:Indoles / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D004364:Pharmaceutical Preparations / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry; D000077489:Piperazine; D010879:Piperazines / Q000737:chemistry
D018491:Dopamine Agonists; D007211:Indoles; D008024:Ligands; D004364:Pharmaceutical Preparations; D010636:Phenols; D010879:Piperazines; D000077489:Piperazine