(2S,3S,4S,5R,6S)-6-{[2-(3-fluoro-4-phenylphenyl)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 169293
• Molecular Formular: C21H21FO8
• Molecular Mass: 420.3850432
• Monoisotopic Mass: 420.12204585
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1C(=O)O)OC(=O)C(c1ccc(c(c1)F)c1ccccc1)C)O)O)O
• Canonical SMILES: O=C(C(c1ccc(c(c1)F)c1ccccc1)C)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H21FO8/c1-10(12-7-8-13(14(22)9-12)11-5-3-2-4-6-11)20(28)30-21-17(25)15(23)16(24)18(29-21)19(26)27/h2-10,15-18,21,23-25H,1H3,(H,26,27)/t10?,15-,16-,17+,18-,21-/m0/s1
• InChIKey: PLPQBSOCUVSKTP-DHOLTFTNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[2-(3-fluoro-4-phenylphenyl)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[2-(3-fluoro-4-phenylphenyl)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-(2-Fluoro-α-methyl[1,1'-biphenyl]-4-acetate)-β-D-glucopyranuronic Acid; Flurbiprofen Glucuronide; Flurbiprofen Acyl-β-D-glucuronide (Mixture of Diastereomers)

Database IDs

• CAS Number: 91683-37-3
• PubChem SID: 162263425
• PubChem CID: 71316898

CALCULATED PROPERTIES

• Acid pKa: 3.1898272
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.29072902
• LogD (pH = 7.4): -1.4511077
• Log P: 1.9961141
• Molar Refractivity: 99.5913 cm^3
• Polarizability: 40.72181 Å^3
• Polar Surface Area: 133.52 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: yellow Solid
• Melting Point: 144-146°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - F598715

Metabolite of Flurbiprofen (F598700).

REFERENCES

• Van Breemen, R., et al.: Drug Metab. Disposition, 14, 197 (1986)
• Spraul, M., et al.: J. Pharm. Biomed. Anal., 11, 1009 (1986)