1-[4-(hydroxymethyl)benzenesulfonyl]-3-{octahydrocyclopenta[c]pyrrol-2-yl}urea

• ChemBase ID: 170613
• Molecular Formular: C15H21N3O4S
• Molecular Mass: 339.40994
• Monoisotopic Mass: 339.12527717
• SMILES: c1cc(ccc1S(=O)(=O)NC(=O)NN1CC2C(C1)CCC2)CO
• Canonical SMILES: OCc1ccc(cc1)S(=O)(=O)NC(=O)NN1CC2C(C1)CCC2
• InChI: InChI=1S/C15H21N3O4S/c19-10-11-4-6-14(7-5-11)23(21,22)17-15(20)16-18-8-12-2-1-3-13(12)9-18/h4-7,12-13,19H,1-3,8-10H2,(H2,16,17,20)
• InChIKey: IHCHVBQHVIUSTM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[4-(hydroxymethyl)benzenesulfonyl]-3-{octahydrocyclopenta[c]pyrrol-2-yl}urea
• IUPAC Traditional name: 3-{hexahydro-1H-cyclopenta[c]pyrrol-2-yl}-1-[4-(hydroxymethyl)benzenesulfonyl]urea
• Synonyms: N-[[(Hexahydrocyclopenta[c]pyrrol-2(1H)-yl)amino]carbonyl]-4-(hydroxymethyl)benzenesulfonamide; Hydroxy Gliclazide

Database IDs

• CAS Number: 87368-00-1
• PubChem SID: 164226523
• PubChem CID: 192219

CALCULATED PROPERTIES

• Acid pKa: 4.0650625
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.3848548
• LogD (pH = 7.4): -0.48852417
• Log P: 0.45286992
• Molar Refractivity: 85.6508 cm^3
• Polarizability: 34.03177 Å^3
• Polar Surface Area: 98.74 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H942545

The major hydroxylated metabolite of Gliclazide (G409875).

REFERENCES

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