prop-2-en-1-yl (3S,5S,6S)-6-({2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylate

• ChemBase ID: 168901
• Molecular Formular: C26H27ClO10
• Molecular Mass: 534.93958
• Monoisotopic Mass: 534.12927474
• SMILES: c1c(ccc(c1)OC(C(=O)O[C@@H]1OC([C@H](C([C@H]1O)O)O)C(=O)OCC=C)(C)C)C(=O)c1ccc(cc1)Cl
• Canonical SMILES: C=CCOC(=O)C1O[C@@H](OC(=O)C(Oc2ccc(cc2)C(=O)c2ccc(cc2)Cl)(C)C)[C@@H](C([C@@H]1O)O)O
• InChI: InChI=1S/C26H27ClO10/c1-4-13-34-23(32)22-20(30)19(29)21(31)24(35-22)36-25(33)26(2,3)37-17-11-7-15(8-12-17)18(28)14-5-9-16(27)10-6-14/h4-12,19-22,24,29-31H,1,13H2,2-3H3/t19?,20-,21-,22?,24-/m0/s1
• InChIKey: ZRQRPEQSPFAAFS-OKPZMGIJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: prop-2-en-1-yl (3S,5S,6S)-6-({2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylate
• IUPAC Traditional name: prop-2-en-1-yl (3S,5S,6S)-6-({2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylate
• Synonyms: 1-[2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropanoate] β-D-Glucopyranuronic Acid Allyl Ester; Fenofibric Acid Acyl-β-D-glucuronide Allyl Ester

Database IDs

• PubChem SID: 162263033
• PubChem CID: 71316724

CALCULATED PROPERTIES

• Acid pKa: 12.161902
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 3.2878358
• LogD (pH = 7.4): 3.2878284
• Log P: 3.287836
• Molar Refractivity: 129.4237 cm^3
• Polarizability: 51.739346 Å^3
• Polar Surface Area: 148.82 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Light Orange Solid

DETAILS

Toronto Research Chemicals - F248665

Protected Fenofibric Acid metabolite.