(2R,3R)-5,7-dihydroxy-2-[trihydroxy(2H2)phenyl]-3,4-dihydro(6,8-2H2)-2H-1-benzopyran-3-yl 3,4,5-trihydroxy(2H2)benzoate

• ChemBase ID: 168048
• Molecular Formular: C22H18O11
• Molecular Mass: 458.37172
• Monoisotopic Mass: 458.0849114
• SMILES: c1(cc(c2c(c1)O[C@@H]([C@@H](C2)OC(=O)c1cc(c(c(c1)O)O)O)c1cc(c(c(c1)O)O)O)O)O
• Canonical SMILES: Oc1cc(O)c2c(c1)O[C@@H]([C@@H](C2)OC(=O)c1cc(O)c(c(c1)O)O)c1cc(O)c(c(c1)O)O
• InChI: InChI=1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1
• InChIKey: WMBWREPUVVBILR-WIYYLYMNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-5,7-dihydroxy-2-[trihydroxy(^2H₂)phenyl]-3,4-dihydro(6,8-^2H₂)-2H-1-benzopyran-3-yl 3,4,5-trihydroxy(^2H₂)benzoate
• IUPAC Traditional name: (2R,3R)-5,7-dihydroxy-2-[trihydroxy(^2H₂)phenyl]-3,4-dihydro(6,8-^2H₂)-2H-1-benzopyran-3-yl 3,4,5-trihydroxy(^2H₂)benzoate
• Synonyms: Teavigo-d3; epi-Gallocatechin 3-O-Gallate-d3; epi-Gallocatechin Gallate-d3; EGCG-d3; Epigallocatechin-3-monogallate-d3; L-Epigallocatechin Gallate-d3; 3-O-Galloyl-(-)-epigallocatechin-d3; (-)-Epigallocatechin Gallate-d3/d4

Database IDs

• PubChem SID: 162262180
• PubChem CID: 71316355

CALCULATED PROPERTIES

• Acid pKa: 7.9929934
• H Acceptors: 10
• H Donor: 8
• LogD (pH = 5.5): 3.0747623
• LogD (pH = 7.4): 2.9740098
• Log P: 3.0761456
• Molar Refractivity: 111.7453 cm^3
• Polarizability: 42.675007 Å^3
• Polar Surface Area: 197.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E588502

Labelled (-)-Epigallocatechin Gallate, a tumor-inhibiting constituent of green tea. (-)-Epigallocatechin Gallate alters the cleavage of amyloid precursor protein, decreasing production of amaloid-β and amaloid plaques in mice.

REFERENCES

• Yamane, T. et al.: Cancer Res., 55, 2081 (1995)
• Tan, J. et al.: J. Neurosci. 25, 8807 (1995)