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

• ChemBase ID: 172098
• Molecular Formular: C22H22O9
• Molecular Mass: 430.40468
• Monoisotopic Mass: 430.12638228
• SMILES: c1c(cc(cc1)C(=O)c1ccccc1)[C@@H](C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C
• Canonical SMILES: O=C([C@H](c1cccc(c1)C(=O)c1ccccc1)C)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C22H22O9/c1-11(13-8-5-9-14(10-13)15(23)12-6-3-2-4-7-12)21(29)31-22-18(26)16(24)17(25)19(30-22)20(27)28/h2-11,16-19,22,24-26H,1H3,(H,27,28)/t11-,16-,17-,18+,19-,22-/m0/s1
• InChIKey: PBTXSZZKPHBHMA-QVTYPLGRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[(2S)-2-(3-benzoylphenyl)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[(2S)-2-(3-benzoylphenyl)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[(αS)-3-Benzoyl-α-methylbenzeneacetate]-β-D-glucopyranuronic Αcid; (S)-Ketoprofen Glucuronide; (S)-Ketoprofen Acyl-β-D-glucuronide

Database IDs

• CAS Number: 140148-26-1
• PubChem SID: 164228008
• PubChem CID: 71749694

CALCULATED PROPERTIES

• Acid pKa: 3.2414277
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.5727478
• LogD (pH = 7.4): -1.7723304
• Log P: 1.6655399
• Molar Refractivity: 104.8142 cm^3
• Polarizability: 41.780273 Å^3
• Polar Surface Area: 150.59 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 138-140°C

Safety Information

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

DETAILS

Toronto Research Chemicals - K200816

A metabolite of (S)-Ketoprofen (K200808).

REFERENCES

• Smith, P., et al.: Drug Metab. Dispos., 1990, 18, 639 (1990)
• Skordi, E., et al.: Xenobiotica, 34, 1075 (1990)