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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H18O10
Molecular Weight 442.3732
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPICATECHIN GALLATE

SMILES

c1cc(c(cc1[C@]2([H])[C@@]([H])(Cc3c(cc(cc3O2)O)O)OC(=O)c4cc(c(c(c4)O)O)O)O)O

InChI

InChIKey=LSHVYAFMTMFKBA-TZIWHRDSSA-N
InChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1

HIDE SMILES / InChI

Molecular Formula C22H18O10
Molecular Weight 442.3732
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Epicatechin gallate is one of the flavonoids, found in green tea and it acts as an antagonist of the mu/kappa/delta opioid receptors. Recently was studied the effect of epicatechin gallate on fructose uptake in human intestinal epithelia. Based on the result was made a conclusion, that epicatechin gallate could be a good candidate for preventing diseases caused by excessive fructose intake.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Differential inhibition of HIV-reverse transcriptase and various DNA and RNA polymerases by some catechin derivatives.
1989
Differential inhibitory effects of some catechin derivatives on the activities of human immunodeficiency virus reverse transcriptase and cellular deoxyribonucleic and ribonucleic acid polymerases.
1990 Mar 20
Inhibition of human immunodeficiency viral replication by tannins and related compounds.
1992 May
Inhibition of HIV infection by flavanoids.
1993 Oct
Inhibition of 12-O-tetradecanoylphorbol-13-acetate and other skin tumor-promoter-caused induction of epidermal interleukin-1 alpha mRNA and protein expression in SENCAR mice by green tea polyphenols.
1995 Sep
Prolyl endopeptidase inhibitory activity of fourteen Kampo formulas and inhibitory constituents of Tokaku-joki-to.
2000 Jul
Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures.
2001
Simplified catechin-gallate inhibitors of HIV-1 reverse transcriptase.
2001 Oct 22
Inhibition of adenovirus infection and adenain by green tea catechins.
2003 Apr
Epigallocatechin gallate modulates CYP450 isoforms in the female Swiss-Webster mouse.
2003 Dec
Epigallocatechin gallate, the main component of tea polyphenol, binds to CD4 and interferes with gp120 binding.
2003 Nov
Heteroactivation of cytochrome P450 1A1 by teas and tea polyphenols.
2005 Aug
Theaflavin derivatives in black tea and catechin derivatives in green tea inhibit HIV-1 entry by targeting gp41.
2005 May 25
Antimycobacterial agents from selected Mexican medicinal plants.
2005 Sep
Copper complexes of (-)-epicatechin gallate and (-)-epigallocatechin gallate act as inhibitors of Ribonuclease A.
2006 Aug 21
Catalytic inhibition of human DNA topoisomerase II by interactions of grape cell culture polyphenols.
2006 Mar 22
Flavonoids inhibit the AU-rich element binding of HuC.
2009 Jan 31
Tea polyphenols can restrict benzo[a]pyrene-induced lung carcinogenesis by altered expression of p53-associated genes and H-ras, c-myc and cyclin D1.
2009 May
The evaluation of catechins that contain a galloyl moiety as potential HIV-1 integrase inhibitors.
2010 Dec
Oligomeric proanthocyanidins from Rumex acetosa L. inhibit the attachment of herpes simplex virus type-1.
2011 Jan
Intervention of human breast cell carcinogenesis chronically induced by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine.
2012 Apr
A strategy for designing a concave Pt-Ni alloy through controllable chemical etching.
2012 Dec 7
A tea catechin, epigallocatechin-3-gallate, is a unique modulator of the farnesoid X receptor.
2012 Jan 15
(-)-Epigallocatechin-3-gallate is a new inhibitor of hepatitis C virus entry.
2012 Mar
Bioactivity-guided fractionation of Phyllanthus orbicularis and identification of the principal anti HSV-2 compounds.
2012 Oct
Benzophenone glycosides and epicatechin derivatives from Malania oleifera.
2012 Sep
Green tea catechins alone or in combination alter functional parameters of human neutrophils via suppressing the activation of TLR-4/NFκB p65 signal pathway.
2015 Oct

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Epigallocatechin gallate (EGCG) and epicatechin gallate (ECG) are green tea catechins which are known as powerful antioxidants. There was examined the possible protective effects of ECG and EGCG on the neurotoxicity of acrylamide (ACR) neurotoxicity in-vitro model. PC12 cells were exposed to different concentrations of ECG and EGCG. Both ECG and EGCG (20 μM) showed inhibitory effects on ACR cytotoxicity. ACR significantly induced gait abnormalities decreased GSH level and increased lipid peroxidation in the cerebral cortex.
Substance Class Chemical
Created
by admin
on Sat Jun 26 08:40:46 UTC 2021
Edited
by admin
on Sat Jun 26 08:40:46 UTC 2021
Record UNII
92587OVD8Z
Record Status Validated (UNII)
Record Version
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Name Type Language
EPICATECHIN GALLATE
Common Name English
EPICATECHOL 3-GALLATE
Common Name English
(-)-EPICATECHIN-3-O-GALLATE (CONSTITUENT OF GRAPE SEEDS OLIGOMERIC PROANTHOCYANIDINS) [DSC]
Common Name English
EPICATECHIN 3-O-GALLATE
Common Name English
EPICATECHINGALLATE, L-
Common Name English
(-)-EPI CATECHIN-3-O-GALLATE
Common Name English
(-)-EPICATECHIN-3-O-GALLATE(EGC) (CONSTITUENT OF POWDERED DECAFFEINATED GREEN TEA EXTRACT) [DSC]
Common Name English
(-)-EPICATECHIN GALLATE
Common Name English
L-ECG
Common Name English
NSC-636594
Code English
BENZOIC ACID, 3,4,5-TRIHYDROXY-, (2R,3R)-2-(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-5,7-DIHYDROXY-2H-1-BENZOPYRAN-3-YL ESTER
Common Name English
ECG
Common Name English
Classification Tree Code System Code
DSLD 4085 (Number of products:1)
Created by admin on Sat Jun 26 08:40:46 UTC 2021 , Edited by admin on Sat Jun 26 08:40:46 UTC 2021
Code System Code Type Description
CAS
1257-08-5
Created by admin on Sat Jun 26 08:40:46 UTC 2021 , Edited by admin on Sat Jun 26 08:40:46 UTC 2021
PRIMARY
FDA UNII
92587OVD8Z
Created by admin on Sat Jun 26 08:40:46 UTC 2021 , Edited by admin on Sat Jun 26 08:40:46 UTC 2021
PRIMARY
WIKIPEDIA
EPICATECHIN GALLATE
Created by admin on Sat Jun 26 08:40:46 UTC 2021 , Edited by admin on Sat Jun 26 08:40:46 UTC 2021
PRIMARY
MESH
C062669
Created by admin on Sat Jun 26 08:40:46 UTC 2021 , Edited by admin on Sat Jun 26 08:40:46 UTC 2021
PRIMARY
PUBCHEM
107905
Created by admin on Sat Jun 26 08:40:46 UTC 2021 , Edited by admin on Sat Jun 26 08:40:46 UTC 2021
PRIMARY
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