Compound: Epicatechin gallate
SMILES: O=C(O[C@H]1[C@H](Oc2cc(O)cc(c2C1)O)c3cc(O)c(O)cc3)c4cc(O)c(O)c(c4)O
InChIKey: LSHVYAFMTMFKBA-TZIWHRDSSA-N
Synonyms: Epicatechin gallate, 92587OVD8Z, Epicatechin-3-galloyl ester, DTXSID70925231, NSC-636594, RefChem:590910, DTXCID101354061, 863-03-6, (-)-Epicatechin gallate, 1257-08-5, (-)-Epicatechin-3-O-gallate, (-)-epicatechingallate, (-)-Epicatechin-3-gallate, L-Epicatechin gallate, epicatechin monogallate, Teatannin, ECG, (-)-Epicatechin 3-O-gallate, Epicatechol, gallate, 3-O-Galloylepicatechin, MFCD00075936, [(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate, 3-Gallate(-)-Epicatechol, (-)-cis-3,3',4',5,7-Pentahydroxyflavane 3-gallate, CHEMBL36327, C22H18O10, (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate, epicatechin-3-O-gallate, Benzoic acid, 3,4,5-trihydroxy-, (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl ester, epi-Catechin 3-O-gallate, (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3-yl 3,4,5-trihydroxybenzoate, NSC 636594, (-)-Epicatechin 3-gallate, 3-Galloyl-(-)-epicatechin, UNII-92587OVD8Z, EPICATECHIN 3-O-GALLATE, NSC636594, (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate, Epicatechol, 3-gallate, (-)-, epicatechin gallate, (2R-cis)-isomer, (-)epicatechingallate, Spectrum_000314, L-ECG, SpecPlus_000275, (-) epicatechin gallate, epicatechin-gallate-(-), Spectrum2_000165, Spectrum3_000246, Spectrum4_001540, Spectrum5_000080, SCHEMBL39047, BSPBio_001632, EPICATECHOL 3-GALLATE, KBioGR_001980, KBioSS_000794, SPECTRUM210238, Benzoic acid, 3,4,5-trihydroxy-, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl ester, (2R-cis)-, DivK1c_006371, EPICATECHINGALLATE, L-, SPBio_000029, (-)EPICATECHIN GALLATE, MEGxp0_000810, orb1305097, orb3139507, SCHEMBL29355754, SCHEMBL30977096, SCHEMBL31297152, CHEBI:70255, GTPL12462, HY-N0002R, KBio1_001315, KBio2_000794, KBio2_003362, KBio2_005930, KBio3_001132, 3,4,5-Trihydroxy-benzoic acid 2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-chroman-3-yl ester, HY-N0002, MSK40120, (-)-Epicatechin gallate (Standard), BDBM50153015, CCG-38376, LMPK12020090, s3925, AKOS015965216, AC-6037, CS-3761, EBC-445043, FE22721, SDCCGMLS-0066549.P001, (-)-EPI CATECHIN-3-O-GALLATE, NCGC00179135-01, NCGC00179135-02, NCGC00179135-07, AS-15722, SY071164, E0890, NS00094557, C22594, SR-05000002675, Q5382492, SR-05000002675-1, BRD-K50660797-001-01-0, BRD-K50660797-001-03-6, BRD-K50660797-001-04-4, BRD-K50660797-001-05-1, (-)-cis-3,3',4',5, 7-Pentahydroxyflavane 3-gallate, (-)-Epicatechin gallate, >=98% (HPLC), from green tea, Epicatechin gallate, primary pharmaceutical reference standard, 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxychroman-3-yl (2R,3R)-3,4,5-Trihydroxybenzoate, rel-(2R,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxychroman-3-yl 3,4,5-trihydroxybenzoate, 3,4,5-Trihydroxy-benzoic acid (2R,3R)-2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-chroman-3-yl ester, Benzoic acid, 3,4,5-trihydroxy-, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7- dihydroxy-2H-1-benzopyran-3-yl ester, (-)-cis-
Theoretical properties:
molecular_formula: C22H18O10
molecular_weight: 442.4 g/mol
exact_mass: 442.08999677 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 7
hydrogen_bond_acceptor_count: 10
rotatable_bond_count: 4
heavy_atom_count: 32
topological_polar_surface_area: 177 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 257 - 258 °C
Descriptions:
pubchem: (-)-epicatechin-3-O-gallate is a gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida. It has a role as a metabolite, an EC 3.2.1.1 (alpha-amylase) inhibitor and an EC 3.2.1.20 (alpha-glucosidase) inhibitor. It is a catechin, a polyphenol and a gallate ester. It is functionally related to a gallic acid and a (-)-epicatechin.
chebi: A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3<i>R</i>)-hydroxy group of epicatechin. A natural product found in <em>Parapiptadenia rigida</em>.
chembl: EPICATECHIN GALLATE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Epicatechin gallate (ECG, (−)-epicatechin-3-gallate) is a flavan-3-ol, a type of flavonoid, primarily found in green tea (Camellia sinensis), with smaller amounts in cocoa, grapes, and other plants. It is also reported in buckwheat and in grape.
As a polyphenolic catechin, ECG is formed by the esterification of epicatechin with gallic acid, contributing to antioxidant, antimicrobial, and potential anticancer properties. ECG is studied for its ability to reverse methicillin resistance in Staphylococcus aureus and inhibit inflammatory pathways, but its clinical use is limited by poor bioavailability and thermal instability in boiling water. Recent research highlights its potential in modulating SARS-CoV-2-related inflammation and bacterial virulence factors.
Epicatechin, as well as many other flavonoids, has been found to act as a nonselective antagonist of the opioid receptors, albeit with somewhat low affinity.