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

• ChemBase ID: 171130
• Molecular Formular: C25H28N2O10S
• Molecular Mass: 548.56222
• Monoisotopic Mass: 548.14646611
• SMILES: n1cc(ccc1CCOc1ccc(cc1)CC1C(=O)NC(=O)S1)CCO[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: O=C1NC(=O)C(S1)Cc1ccc(cc1)OCCc1ccc(cn1)CCO[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C25H28N2O10S/c28-18-19(29)21(23(32)33)37-24(20(18)30)36-9-7-14-1-4-15(26-12-14)8-10-35-16-5-2-13(3-6-16)11-17-22(31)27-25(34)38-17/h1-6,12,17-21,24,28-30H,7-11H2,(H,32,33)(H,27,31,34)/t17?,18-,19-,20+,21-,24+/m0/s1
• InChIKey: XFRAGOPCVGUPPM-UMIGEIBGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{2-[6-(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)pyridin-3-yl]ethoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{2-[6-(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)pyridin-3-yl]ethoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 2-[6-[2-[4-[(2,4-Dioxo-5-thiazolidinyl)methyl]phenoxy]ethyl]-3-pyridinyl]ethyl β-D-Glucopyranosiduronic Acid; Hydroxy Pioglitazone (M-VII) β-D-Glucuronide

Database IDs

• CAS Number: 625853-75-0
• PubChem SID: 164227040
• PubChem CID: 71749270

CALCULATED PROPERTIES

• Acid pKa: 3.2916
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -1.2014177
• LogD (pH = 7.4): -3.3272529
• Log P: -0.87880605
• Molar Refractivity: 131.6002 cm^3
• Polarizability: 52.24746 Å^3
• Polar Surface Area: 184.74 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H952065

A novel metabolite of Pioglitazone (P471000).

REFERENCES

• Krieter, P., et al.: Drug Metab. Dispos., 22, 625 (1994)
• Chilcott, J., et al.: Clin. Ther., 23, 1792 (1994)