Structure via PubChem · Public domain (PubChem)
Epicatechin gallate
Sign in to saveAlso known as 3-gallate(-)-epicatechol, (-)-cis-3,3',4',5,7-pentahydroxyflavane 3-gallate, ECG, Teatannin, 3-O-galloylepicatechin
chemical compound
Chemical data
- Formula
- C22H18O10
- Molecular weight
- 442.4 g/mol
- IUPAC name
- [(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
- SMILES
- C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O
- InChIKey
- LSHVYAFMTMFKBA-TZIWHRDSSA-N
- XLogP
- 1.5
- Polar surface area
- 177 Ų
- H-bond donors
- 7
- H-bond acceptors
- 10
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,283 papers- Epicatechin gallate promotes vascularization in co-culture of human osteoblasts and outgrowth endothelial cells.Experimental biology and medicine (Maywood, N.J.) · 2023
- Epicatechin-3-Gallate Signaling and Protection against Cardiac Ischemia/Reperfusion Injury.The Journal of pharmacology and experimental therapeutics · 2019
- (-)-Epicatechin gallate prevents inflammatory response in hypoxia-activated microglia and cerebral edema by inhibiting NF-κB signaling.Archives of biochemistry and biophysics · 2022
- (-)-Epicatechin gallate ameliorates cyprodinil-induced cardiac developmental defects through inhibiting aryl hydrocarbon receptor in zebrafish.Birth defects research · 2024
- Epicatechin gallate prevents the de novo synthesis of fatty acid and the migration of prostate cancer cells.Acta biochimica et biophysica Sinica · 2021
via PubMed
Wikidata facts
- Mass
- 442.09
Show 7 more facts
- found in taxon
- Senegalia chundra
- chemical formula
- C₂₂H₁₈O₁₀
- canonical SMILES
- C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O
- isomeric SMILES
- C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O
- subject has role
- protease inhibitor
- has characteristic
- bitterness
- Commons category
- Epicatechin gallate
via Wikidata · CC0