4-{[({octahydrocyclopenta[c]pyrrol-2-yl}carbamoyl)amino]sulfonyl}benzoic acid

• ChemBase ID: 163750
• Molecular Formular: C15H19N3O5S
• Molecular Mass: 353.39346
• Monoisotopic Mass: 353.10454172
• SMILES: c1cc(ccc1S(=O)(=O)NC(=O)NN1CC2C(C1)CCC2)C(=O)O
• Canonical SMILES: O=C(NS(=O)(=O)c1ccc(cc1)C(=O)O)NN1CC2C(C1)CCC2
• InChI: InChI=1S/C15H19N3O5S/c19-14(20)10-4-6-13(7-5-10)24(22,23)17-15(21)16-18-8-11-2-1-3-12(11)9-18/h4-7,11-12H,1-3,8-9H2,(H,19,20)(H2,16,17,21)
• InChIKey: DSNDPTBTZSQWJS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[({octahydrocyclopenta[c]pyrrol-2-yl}carbamoyl)amino]sulfonyl}benzoic acid
• IUPAC Traditional name: 4-[({hexahydro-1H-cyclopenta[c]pyrrol-2-yl}carbamoyl)aminosulfonyl]benzoic acid
• Synonyms: 4-[[[[(Hexahydrocyclopenta[c]pyrrol-2(1H)-yl)amino]carbonyl]amino]sulfonyl]benzoic Acid; S 2574; Carboxy Gliclazide

Database IDs

• CAS Number: 38173-52-3
• PubChem SID: 162257885
• PubChem CID: 53776869

CALCULATED PROPERTIES

• Acid pKa: 3.409406
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.9206614
• LogD (pH = 7.4): -3.4281898
• Log P: 0.8778026
• Molar Refractivity: 86.0911 cm^3
• Polarizability: 33.968197 Å^3
• Polar Surface Area: 115.81 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C178440

A metabolite of Gliclazide (G409875).

REFERENCES

• Miyazaki, H., et al.: Eur. J. Drug Metab. Pharmacokinet., 8, 117 (1983)
• Rieutord, A., et al.: Xenobiotica, 25, 1345 (1983)