(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-[4-(2-methylpropyl)phenyl]butanoyl}oxy)oxane-2-carboxylic acid

• ChemBase ID: 163120
• Molecular Formular: C20H28O8
• Molecular Mass: 396.43152
• Monoisotopic Mass: 396.17841786
• SMILES: c1c(ccc(c1)C(CC)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)CC(C)C
• Canonical SMILES: CCC(c1ccc(cc1)CC(C)C)C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C20H28O8/c1-4-13(12-7-5-11(6-8-12)9-10(2)3)19(26)28-20-16(23)14(21)15(22)17(27-20)18(24)25/h5-8,10,13-17,20-23H,4,9H2,1-3H3,(H,24,25)/t13?,14-,15-,16+,17-,20-/m0/s1
• InChIKey: QOBZSCBWONUETE-HMCJVFJUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-[4-(2-methylpropyl)phenyl]butanoyl}oxy)oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-[4-(2-methylpropyl)phenyl]butanoyl}oxy)oxane-2-carboxylic acid
• Synonyms: α-Ethyl-4-(2-methylpropyl)benzeneacetate β-D-Glucopyranuronic Acid; Butibufen Acyl-β-D-glucuronide(Mixture of Diastereomers)

Database IDs

• PubChem SID: 162257255
• PubChem CID: 71314318

CALCULATED PROPERTIES

• Acid pKa: 3.4703622
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 0.32018387
• LogD (pH = 7.4): -1.0437001
• Log P: 2.3403332
• Molar Refractivity: 97.6315 cm^3
• Polarizability: 39.25078 Å^3
• Polar Surface Area: 133.52 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B689965

A glucuronide metabolite of Butibufen (B689960).