(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[(1E,6E)-7-[4-hydroxy-3-(2H3)methoxyphenyl]-3,5-dioxohepta-1,6-dien-1-yl]-2-methoxyphenoxy}oxane-2-carboxylic acid

• ChemBase ID: 165049
• Molecular Formular: C27H28O12
• Molecular Mass: 544.50402
• Monoisotopic Mass: 544.15807634
• 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]1O)O)O)C(=O)O)OC
• Canonical SMILES: COc1cc(/C=C/C(=O)CC(=O)/C=C/c2ccc(c(c2)OC)O)ccc1O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C27H28O12/c1-36-20-11-14(5-9-18(20)30)3-7-16(28)13-17(29)8-4-15-6-10-19(21(12-15)37-2)38-27-24(33)22(31)23(32)25(39-27)26(34)35/h3-12,22-25,27,30-33H,13H2,1-2H3,(H,34,35)/b7-3+,8-4+/t22-,23-,24+,25-,27+/m0/s1
• InChIKey: BNSAVBGHRVFVNN-XSCLDSQRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[(1E,6E)-7-[4-hydroxy-3-(^2H₃)methoxyphenyl]-3,5-dioxohepta-1,6-dien-1-yl]-2-methoxyphenoxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[(1E,6E)-7-[4-hydroxy-3-(^2H₃)methoxyphenyl]-3,5-dioxohepta-1,6-dien-1-yl]-2-methoxyphenoxy}oxane-2-carboxylic acid
• Synonyms: 4-[(1E,6E)-7-(4-Hydroxy-3-methoxy-d3-phenyl)-3,5-dioxo-1,6-heptadien-1-yl]-2-methoxyphenyl β-D-Glucopyranosiduronic Acid; Curcumin β-D-Glucuronide-d3

Database IDs

• PubChem SID: 162259182
• PubChem CID: 71315013

CALCULATED PROPERTIES

• Acid pKa: 3.149048
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): -0.1483517
• LogD (pH = 7.4): -1.2833633
• Log P: 2.176731
• Molar Refractivity: 135.8224 cm^3
• Polarizability: 52.51349 Å^3
• Polar Surface Area: 189.28 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C838512

Labelled analogue of Curcumin β-D-Glucuronide, a 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)