(2S,3S,4S,5R,6R)-6-({[(1-carboxy-2-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}ethyl)sulfanyl]carbonyl}amino)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 176747
• Molecular Formular: C25H30N2O10S
• Molecular Mass: 550.5781
• Monoisotopic Mass: 550.16211617
• SMILES: n1cc(ccc1CCOc1ccc(cc1)CC(SC(=O)N[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C(=O)O)CC
• Canonical SMILES: CCc1ccc(nc1)CCOc1ccc(cc1)CC(C(=O)O)SC(=O)N[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C25H30N2O10S/c1-2-13-3-6-15(26-12-13)9-10-36-16-7-4-14(5-8-16)11-17(23(31)32)38-25(35)27-22-20(30)18(28)19(29)21(37-22)24(33)34/h3-8,12,17-22,28-30H,2,9-11H2,1H3,(H,27,35)(H,31,32)(H,33,34)/t17?,18-,19-,20+,21-,22+/m0/s1
• InChIKey: GQCWGHHINCKKGE-DVGPLREDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-({[(1-carboxy-2-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}ethyl)sulfanyl]carbonyl}amino)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-({[(1-carboxy-2-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}ethyl)sulfanyl]carbonyl}amino)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[[[[1-Carboxy-2-[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]ethyl]thio]carbonyl]amino]-1-deoxy-β-D-glucopyranuronic Acid; Pioglitazone Thiazolidinedione Ring-opened N-β-D-Glucuronide

Database IDs

• CAS Number: 1296832-76-2
• PubChem SID: 164232657
• PubChem CID: 71751677

CALCULATED PROPERTIES

• Acid pKa: 2.9439218
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -2.1794283
• LogD (pH = 7.4): -4.993518
• Log P: -0.09546171
• Molar Refractivity: 132.8948 cm^3
• Polarizability: 52.716232 Å^3
• Polar Surface Area: 195.74 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P471020

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

REFERENCES

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