methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{4-[(1E,6E)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxohepta-1,6-dien-1-yl]-2-methoxyphenoxy}oxane-2-carboxylate

• ChemBase ID: 165050
• Molecular Formular: C34H36O15
• Molecular Mass: 684.64064
• Monoisotopic Mass: 684.20542045
• SMILES: c1(c(ccc(c1)/C=C/C(=O)CC(=O)/C=C/c1ccc(c(c1)OC)O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC)OC
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2ccc(cc2OC)/C=C/C(=O)CC(=O)/C=C/c2ccc(c(c2)OC)O)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C34H36O15/c1-18(35)45-29-30(46-19(2)36)32(47-20(3)37)34(49-31(29)33(41)44-6)48-26-14-10-22(16-28(26)43-5)8-12-24(39)17-23(38)11-7-21-9-13-25(40)27(15-21)42-4/h7-16,29-32,34,40H,17H2,1-6H3/b11-7+,12-8+/t29-,30-,31-,32+,34+/m0/s1
• InChIKey: HRLLMEXRAURVBG-IMLTWFSPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{4-[(1E,6E)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxohepta-1,6-dien-1-yl]-2-methoxyphenoxy}oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{4-[(1E,6E)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxohepta-1,6-dien-1-yl]-2-methoxyphenoxy}oxane-2-carboxylate
• Synonyms: 4-[(1E,6E)-7-(4-Hydroxy-3-methoxyphenyl)-3,5-dioxo-1,6-heptadien-1-yl]-2-methoxyphenyl β-D-Glucopyranosiduronic Acid Triacetate Methyl Ester; Curcumin β-D-Glucuronide Triacetate Methyl Ester

Database IDs

• PubChem SID: 162259183
• PubChem CID: 71315014

CALCULATED PROPERTIES

• Acid pKa: 9.2486315
• H Acceptors: 11
• H Donor: 1
• LogD (pH = 5.5): 3.645924
• LogD (pH = 7.4): 3.6398964
• Log P: 3.6460013
• Molar Refractivity: 168.046 cm^3
• Polarizability: 66.14356 Å^3
• Polar Surface Area: 196.49 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichlormehane; Dimethyl Formamide; Ethyl Acetate; Methanol
• Apperance: Brown Foam

Safety Information

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

DETAILS

Toronto Research Chemicals - C838515

A protected metabolite of Curcumin (C838510) in hepatic tissue and portal blood.

REFERENCES

• Sharma, O., et al.: Biochem. Pharmacol., 25, 1811 (1976)
• Colletti, L., et al.: J. Clin. Invest., 85, 1936 (1976)
• Sharma, R., et al.: Clin. Cancer Res., 7, 1894 (1976)