methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[2-(acetyloxy)-5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]phenoxy]oxane-2-carboxylate

• ChemBase ID: 159187
• Molecular Formular: C25H28O14
• Molecular Mass: 552.48142
• Monoisotopic Mass: 552.14790558
• SMILES: c1(c(ccc(c1)/C=C/C(=O)OC)OC(=O)C)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC
• Canonical SMILES: COC(=O)/C=C/c1ccc(c(c1)O[C@@H]1O[C@@H](C(=O)OC)[C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C25H28O14/c1-12(26)34-17-9-7-16(8-10-19(30)32-5)11-18(17)38-25-23(37-15(4)29)21(36-14(3)28)20(35-13(2)27)22(39-25)24(31)33-6/h7-11,20-23,25H,1-6H3/b10-8+/t20-,21-,22-,23+,25+/m0/s1
• InChIKey: NESIOVKSSASDQU-LBUMYLFRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[2-(acetyloxy)-5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]phenoxy]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[2-(acetyloxy)-5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]phenoxy]oxane-2-carboxylate
• Synonyms: Methyl {2’-Acetoxy-4’-[3’’-(methylprop-2’’(E)-enoate)]phenyl 2,3,4-Tri-O-acetyl-β-D-glucopyranoside}uronate; 4-O-Acetyl Caffeic Acid Methyl Ester 3-O-(Tri-O-acetyl-β-D-glucuronic Acid Methyl Ester)

Database IDs

• PubChem SID: 162253322
• PubChem CID: 71312849

CALCULATED PROPERTIES

• H Acceptors: 8
• H Donor: 0
• LogD (pH = 5.5): 1.340486
• LogD (pH = 7.4): 1.340486
• Log P: 1.340486
• Molar Refractivity: 125.1777 cm^3
• Polarizability: 50.73759 Å^3
• Polar Surface Area: 176.26 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethylformamide Methanol
• Apperance: Pale Brown Solid

DETAILS

Toronto Research Chemicals - A171800

Protected metabolite of Caffeic acid.