(2S,3S,4S,5R,6R)-6-[5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-2,4-dioxo-1,3-thiazolidin-3-yl]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 176745
• Molecular Formular: C25H28N2O9S
• Molecular Mass: 532.56282
• Monoisotopic Mass: 532.15155149
• SMILES: n1cc(ccc1CCOc1ccc(cc1)CC1C(=O)N(C(=O)S1)[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)CC
• Canonical SMILES: CCc1ccc(nc1)CCOc1ccc(cc1)CC1SC(=O)N(C1=O)[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C25H28N2O9S/c1-2-13-3-6-15(26-12-13)9-10-35-16-7-4-14(5-8-16)11-17-22(31)27(25(34)37-17)23-20(30)18(28)19(29)21(36-23)24(32)33/h3-8,12,17-21,23,28-30H,2,9-11H2,1H3,(H,32,33)/t17?,18-,19-,20+,21-,23+/m0/s1
• InChIKey: JWBSAEQQNCGUFV-ABCFDMLSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-[5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-2,4-dioxo-1,3-thiazolidin-3-yl]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-[5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-2,4-dioxo-1,3-thiazolidin-3-yl]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-Deoxy-1-[5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-dioxo-3-thiazolidinyl] β-D-Glucopyranuronic Acid; Pioglitazone N-β-D-Glucuronide

Database IDs

• CAS Number: 1296832-75-1
• PubChem SID: 164232655
• PubChem CID: 71751675

CALCULATED PROPERTIES

• Acid pKa: 3.1147904
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -0.15081306
• LogD (pH = 7.4): -1.4522488
• Log P: 0.09421193
• Molar Refractivity: 129.817 cm^3
• Polarizability: 51.50601 Å^3
• Polar Surface Area: 166.72 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P471015

A metabolite of Pioglitazone (P471015) formed via N-glucuronidation of thiazolidinedione ring.

REFERENCES

• Uchiyama, M. et al.: Drug Metab. Disp., 38, 946 (2010)