prop-2-en-1-yl (2S,3S,4S,5R,6S)-6-{[2-(3-benzoylphenyl)(3-13C,3,3,3-2H3)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate

• ChemBase ID: 172105
• Molecular Formular: C25H26O9
• Molecular Mass: 471.46119484
• Monoisotopic Mass: 471.16103725
• SMILES: O1[C@H]([C@@H](O)[C@H]([C@@H]([C@@H]1C(=O)OCC=C)O)O)OC(=O)C(c1cccc(c1)C(=O)c1ccccc1)[13CH3]
• Canonical SMILES: C=CCOC(=O)[C@@H]1O[C@@H](OC(=O)C(c2cccc(c2)C(=O)c2ccccc2)[13CH3])[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C25H26O9/c1-3-12-32-24(31)22-20(28)19(27)21(29)25(33-22)34-23(30)14(2)16-10-7-11-17(13-16)18(26)15-8-5-4-6-9-15/h3-11,13-14,19-22,25,27-29H,1,12H2,2H3/t14?,19-,20-,21+,22-,25-/m0/s1/i2+1
• InChIKey: OZBPANSTJDBACD-UZZAXMJFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: prop-2-en-1-yl (2S,3S,4S,5R,6S)-6-{[2-(3-benzoylphenyl)(3-^1^3C,3,3,3-^2H₃)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate
• IUPAC Traditional name: prop-2-en-1-yl (2S,3S,4S,5R,6S)-6-{[2-(3-benzoylphenyl)(3-^1^3C,3,3,3-^2H₃)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate
• Synonyms: 1-(3-Benzoly-α-methylbenzeneacetate)-β-D-glucopyranuronic Acid Allyl Ester-13CD3; dl-Ketoprofen Glucuronide Allyl Ester-13CD3; Ketoprofen Allyl Glucuronate-13CD3; rac Ketoprofen Glucuronide Allyl Ester-13CD3

Database IDs

• PubChem SID: 164228015
• PubChem CID: 71749696

CALCULATED PROPERTIES

• Acid pKa: 12.1619835
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 2.5426836
• LogD (pH = 7.4): 2.5426762
• Log P: 2.5426838
• Molar Refractivity: 118.746 cm^3
• Polarizability: 47.26242 Å^3
• Polar Surface Area: 139.59 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - K200832

Intermediate in the production of labelled Ketoprofen metabolites