(2S,3S,4S,5R,6S)-6-{[2-(3-benzoylphenyl)(3-13C,3,3,3-2H3)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 172096
• Molecular Formular: C22H22O9
• Molecular Mass: 431.39733484
• Monoisotopic Mass: 431.12973712
• SMILES: O1[C@H]([C@@H](O)[C@H]([C@@H]([C@@H]1C(=O)O)O)O)OC(=O)C(c1cccc(c1)C(=O)c1ccccc1)[13CH3]
• Canonical SMILES: O=C(C(c1cccc(c1)C(=O)c1ccccc1)[13CH3])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/i1+1
• InChIKey: PBTXSZZKPHBHMA-PJBLVYQPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[2-(3-benzoylphenyl)(3-^1^3C,3,3,3-^2H₃)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[2-(3-benzoylphenyl)(3-^1^3C,3,3,3-^2H₃)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[3-Benzoly-α-(methyl-13C,d3)benzeneacetate]-β-D-glucopyranuronic Acid; Ketoprofen-13C,d3 Glucuronide; dl-Ketoprofen-13C,d3 Glucuronide; rac Ketoprofen-13C,d3 Acyl-β-D-glucuronide

Database IDs

• PubChem SID: 164228006
• PubChem CID: 71749692

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: 41.780468 Å^3
• Polar Surface Area: 150.59 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetonitrile; DMSO
• Apperance: Off-White Solid
• Melting Point: 83-90°C

Safety Information

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

DETAILS

Toronto Research Chemicals - K200812

A labelled metabolite of Ketoprofen (K200800).

REFERENCES

• Skordi, E., et al.: Xenobiotica, 34, 1075 (2004)