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

• ChemBase ID: 171294
• Molecular Formular: C24H27N3O10S
• Molecular Mass: 549.55028
• Monoisotopic Mass: 549.14171508
• SMILES: c1cc(cnc1N(CCOc1ccc(cc1)CC1C(=O)NC(=O)S1)C)O[C@@H]1O[C@H]([C@H]([C@H](O)[C@@H]1O)O)C(=O)O
• Canonical SMILES: O=C1NC(=O)C(S1)Cc1ccc(cc1)OCCN(c1ccc(cn1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C24H27N3O10S/c1-27(8-9-35-13-4-2-12(3-5-13)10-15-21(31)26-24(34)38-15)16-7-6-14(11-25-16)36-23-19(30)17(28)18(29)20(37-23)22(32)33/h2-7,11,15,17-20,23,28-30H,8-10H2,1H3,(H,32,33)(H,26,31,34)/t15?,17-,18-,19+,20-,23+/m0/s1
• InChIKey: QGESYIGEZXWVIN-LXSPYKISSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-({6-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)(methyl)amino]pyridin-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-({6-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)(methyl)amino]pyridin-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 6-[6-({2-[4-(2,4-Dioxo-thiazolidin-5-ylmethyl)-phenoxy]ethyl}-methyl-amino)-pyridin-3-yloxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic Acid; 5-Hydroxy Rosiglitazone β-D-Glucuronide (mixture of diastereomers)

Database IDs

• CAS Number: 288853-59-8
• PubChem SID: 164227204
• PubChem CID: 71749335

CALCULATED PROPERTIES

• Acid pKa: 2.9688265
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): -1.1035817
• LogD (pH = 7.4): -3.1694236
• Log P: -0.8425
• Molar Refractivity: 131.7826 cm^3
• Polarizability: 51.72232 Å^3
• Polar Surface Area: 187.98 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 155-158°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H953445

A metabolite of Rosiglitazone.The ratio of the diastereomers will be quite variable due to the acidic proton at one chiral centre.

REFERENCES

• Balton, G.C., et al.: Xenobiotica, 26, 6, 627 (1996)