(3S,5S,6S)-3,4,5-trihydroxy-6-[(2-{3-[hydroxy(phenyl)methyl]phenyl}propanoyl)oxy]oxane-2-carboxylic acid

• ChemBase ID: 167644
• Molecular Formular: C22H24O9
• Molecular Mass: 432.42056
• Monoisotopic Mass: 432.14203235
• SMILES: O1[C@H]([C@H](O)C([C@@H](C1C(=O)O)O)O)OC(=O)C(C)c1cccc(c1)C(O)c1ccccc1
• Canonical SMILES: O=C(C(c1cccc(c1)C(c1ccccc1)O)C)O[C@@H]1OC(C(=O)O)[C@H](C([C@H]1O)O)O
• InChI: InChI=1S/C22H24O9/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/h2-11,15-19,22-26H,1H3,(H,27,28)/t11?,15?,16?,17-,18-,19?,22-/m0/s1
• InChIKey: MBJCDFJNDKPDMW-JSZZOKOSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,5S,6S)-3,4,5-trihydroxy-6-[(2-{3-[hydroxy(phenyl)methyl]phenyl}propanoyl)oxy]oxane-2-carboxylic acid
• IUPAC Traditional name: (3S,5S,6S)-3,4,5-trihydroxy-6-[(2-{3-[hydroxy(phenyl)methyl]phenyl}propanoyl)oxy]oxane-2-carboxylic acid
• Synonyms: 1-[3-(Hydroxyphenylmethyl)-α-methylbenzeneacetate]-β-D-glucopyranuronic Acid; Dihydro Ketoprofen β-D-Glucuronide (Mixture of Diastereomers)

Database IDs

• CAS Number: 849104-47-8
• PubChem SID: 162261777
• PubChem CID: 46781312

CALCULATED PROPERTIES

• Acid pKa: 3.3350282
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -0.92648655
• LogD (pH = 7.4): -2.1953723
• Log P: 1.2230773
• Molar Refractivity: 105.3374 cm^3
• Polarizability: 42.17589 Å^3
• Polar Surface Area: 153.75 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 88-90°C

Safety Information

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

DETAILS

Toronto Research Chemicals - D449180

A metabolite of racemic Ketoprofen.

REFERENCES

• Lindon, J., et al.: Drug Metab. Reviews, 29, 705 (1997)
• Akira, K., et al.: Drug Metab. Dispos., 26, 457 (1998).