(2S,3S,4S,5R,6R)-6-{1-[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: 171131
• Molecular Formular: C25H28N2O10S
• Molecular Mass: 548.56222
• Monoisotopic Mass: 548.14646611
• SMILES: n1cc(ccc1CCOc1ccc(cc1)CC1C(=O)NC(=O)S1)C(C)O[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)C(O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C25H28N2O10S/c1-12(36-24-20(30)18(28)19(29)21(37-24)23(32)33)14-4-5-15(26-11-14)8-9-35-16-6-2-13(3-7-16)10-17-22(31)27-25(34)38-17/h2-7,11-12,17-21,24,28-30H,8-10H2,1H3,(H,32,33)(H,27,31,34)/t12?,17?,18-,19-,20+,21-,24+/m0/s1
• InChIKey: FYVRNHIXJROHRR-ICPRVBMASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{1-[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-{1-[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: 1-[6-[2-[4-[(2,4-Dioxo-5-thiazolidinyl)methyl]phenoxy]ethyl]-3-pyridinyl]ethyl β-D-Glucopyranosiduronic Acid; Hydroxy Pioglitazone (M-IV) β-D-Glucuronide

Database IDs

• CAS Number: 625853-76-1
• PubChem SID: 164227041
• PubChem CID: 71749271

CALCULATED PROPERTIES

• Acid pKa: 3.2259986
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -1.2926779
• LogD (pH = 7.4): -3.3863385
• Log P: -0.59750116
• Molar Refractivity: 131.264 cm^3
• Polarizability: 52.31568 Å^3
• Polar Surface Area: 184.74 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H952070

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)