(2S,3S,4S,5R,6S)-6-{2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carbonyloxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 168873
• Molecular Formular: C22H24N2O9S
• Molecular Mass: 492.49896
• Monoisotopic Mass: 492.12025136
• SMILES: c1(c(cc(cc1)c1sc(c(n1)C)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C#N)OCC(C)C
• Canonical SMILES: N#Cc1cc(ccc1OCC(C)C)c1nc(c(s1)C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C22H24N2O9S/c1-9(2)8-31-13-5-4-11(6-12(13)7-23)19-24-10(3)18(34-19)21(30)33-22-16(27)14(25)15(26)17(32-22)20(28)29/h4-6,9,14-17,22,25-27H,8H2,1-3H3,(H,28,29)/t14-,15-,16+,17-,22-/m0/s1
• InChIKey: ZRXRMGPMLDOOKN-FVMGUFKOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carbonyloxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carbonyloxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 2-[3-Cyano-4-(2-methylpropoxy)phenyl]-4-methyl-5-thiazolecarboxylate β-D-Glucopyranuronic Acid; 2-(3-Cyano-4-isobutyloxyphenyl)-4-methyl-5-thiazolecarboxylate β-D-Glucopyranuronic Acid; Febuxostat Acyl-β-D-glucuronide

Database IDs

• CAS Number: 1351692-92-6
• PubChem SID: 162263005
• PubChem CID: 71316713

CALCULATED PROPERTIES

• Acid pKa: 3.5654547
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -0.15601844
• LogD (pH = 7.4): -1.5818214
• Log P: 1.7731359
• Molar Refractivity: 126.2274 cm^3
• Polarizability: 46.2474 Å^3
• Polar Surface Area: 179.43 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 172-175°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - F229030

A metabolite of Febuxostat (F229000), a novel nonpurine selective inhibitor of Xanthin Oxidase.

REFERENCES

• Grabowski, B., et al.: J. Clin. Pharmacol., 51, 189 (2011)
• Osada, Y., et al.: Eur. J. Pharmacol., 241, 183 (2011)
• Okamoto, K., et al.: J. Biol. Chem., 278, 1848 (2011)
• Mayer, M.D., et al.: Am. J. Therap., 12, 22 (2011)
• Tomlinson, B., et al.: Curr. Opi