Graph theoretical similarity approach to compare molecular electrostatic potentials.
In this work we introduce a graph theoretical method to compare MEPs, which is independent of molecular alignment. It is based on the edit distance of weighted rooted trees, which encode the geometrical and topological information of Negative Molecular Isopotential Surfaces. A meaningful chemical classification of a set of 46 molecules with different functional groups was achieved. Structure--activity relationships for the corticosteroid binding affinity (CBG) of 31 steroids by means of hierarchical clustering resulted in a clear partitioning in high, intermediate, and low activity groups, whereas the results from quantitative structure--activity relationships, obtained from a partial least-squares analysis, showed comparable or better cross-validated correlation coefficients than the ones reported for previous methods based solely in the MEP.
Marín
Ray M
RM
Grupo de Química Teórica, Universidad Nacional de Colombia, BogotA D. C., Colombia.
Aguirre
Nestor F
NF
Daza
Edgar E
EE
D016000:Cluster Analysis; D016018:Least-Squares Analysis; D008958:Models, Molecular; D009930:Organic Chemicals / Q000737:chemistry* / Q000145:classification; D021281:Quantitative Structure-Activity Relationship; D015203:Reproducibility of Results; D055672:Static Electricity; D013256:Steroids / Q000145:classification; D013499:Surface Properties; D014156:Transcortin / Q000145:classification / Q000378:metabolism
D009930:Organic Chemicals; D013256:Steroids; D014156:Transcortin