Structure Database (LMSD)
Common Name
Epigallocatechin 3-gallate
Systematic Name
Synonyms
3D model of Epigallocatechin 3-gallate
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
(–)-Epigallocatechin gallate (EGCG) is a phenol that has been found in green and black tea plants and has diverse biological activities.1,2,3,4,5,6,7 It is lytic against T. cruzi amastigotes, with a 50% bactericidal concentration (MBC50) value of 0.53 pM.1 EGCG decreases deoxyguanosine oxidation and tyrosine nitration (IC50s = 0.25 and 0.11 mM, respectively) and inhibits macrophage-mediated LDL oxidation in vitro.2,3 EGCG increases LDL receptor binding activity and lowers cholesterol levels in HepG2 cells via increased cholesterol efflux.4 It inhibits heregulin-β1-induced activation of ErbB2 and ErbB3, as well as migration and invasion of MCF-7 breast cancer cells.5 In vivo, EGCG reduces food intake and body weight, serum levels of insulin, leptin, testosterone, and growth hormone, and the size of the ventral prostate, testis, liver, and spleen in male Sprague Dawley, lean Zucker, and obese Zucker rats when administered at doses of 82, 81, and 92 mg/kg, respectively.6 It also reduces increases in hepatic steatosis, inflammatory cell infiltration, and injury in a mouse model of non-alcoholic steatohepatitis (NASH) induced by a methionine- and choline-deficient diet when administered at doses of 50 and 100 mg/kg.7
This information has been provided by Cayman Chemical
References
String Representations
InChiKey (Click to copy)
WMBWREPUVVBILR-WIYYLYMNSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
C12C=C(O)C=C(O)C=1C[C@@H](OC(=O)C1C=C(O)C(O)=C(O)C=1)[C@@H](C1C=C(O)C(O)=C(O)C=1)O2
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
33
Rings
4
Aromatic Rings
3
Rotatable Bonds
4
Van der Waals Molecular Volume
377.31
Topological Polar Surface Area
199.44
Hydrogen Bond Donors
8
Hydrogen Bond Acceptors
11
logP
2.52
Molar Refractivity
109.43
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Updated at
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