Sulfonamides pharmacophore points

The basic set of Pharmacophore Points includes amine, amide, alcohol, ketone, sulfone, sulfonamide, carboxylic acid, carbamate, guaifidine, amidine, urea, and ester. 

Fig. 5.5 Putative interactions of the cocrystallized selective Cox2 ligand SC-558 with its active site, assuming a neutral sulfonamide group - the state used to assign pharmacophore feature flags by the used software. Dotted lines stand for hydrogen bonds, the other residues being responsible for hydrophobic contacts. From a physicochemical point of view, an ionized SO2 NH involved in a salt bridge with Arg 513 and hydrogen bonding to the other tautomer of His 90 would make more sense.

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