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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H18O11
Molecular Weight 458.3726
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPIGALLOCATECHIN GALLATE

SMILES

c1c(cc(c(c1O)O)O)[C@]2([H])[C@@]([H])(Cc3c(cc(cc3O2)O)O)OC(=O)c4cc(c(c(c4)O)O)O

InChI

InChIKey=WMBWREPUVVBILR-WIYYLYMNSA-N
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

HIDE SMILES / InChI

Molecular Formula C22H18O11
Molecular Weight 458.3726
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Epigallocatechin-3-gallate (EGCG), the major polyphenol from green tea, has the potential to impact a variety of human diseases. EGCG functions as a powerful antioxidant, preventing oxidative damage in healthy cells, but also as an antiangiogenic and antitumor agent and as a modulator of tumor cell response to chemotherapy. It was shown, that EGCG can inhibit 5-cytosine DNA methyltransferase (DNMT) activity and reactivate methylation-silenced genes in cancer cells and another of the probable mechanisms by EGCG exercise their anti-tumor property is through the suppression of the NFκB signaling pathway. EGCG has emerged as a potential neuroprotective agent for the treatment of neurological disorders associated with harmful effects of reactive oxygen species. The neuroprotective mechanism of action is probably based on several factors, including EGCG's modulation of several signal transduction pathways, its influence on the expression of genes regulating cell survival or programmed cell death, as well as its modulation of mitochondrial function. A phase II/III trial of oral Sunphenon epigallocatechin-3-gallate in patients with progressive multiple sclerosis has been completed. In addition, EGCG was in phase III clinical trials for the treatment of multiple system atrophy and for patients with Duchenne Muscular Dystrophy ((DMD). DMD is the most frequent neuromuscular condition to occur in childhood and youth.

CNS Activity

Curator's Comment:: A low concentration of epigallocatechin gallate that was suggested from BBB permeability may prevent cognitive dysfunction by increasing brain plasticity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P26358
Gene ID: 1786.0
Gene Symbol: DNMT1
Target Organism: Homo sapiens (Human)
6.89 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Green tea extracts decrease carcinogen-induced mammary tumor burden in rats and rate of breast cancer cell proliferation in culture.
2001
Epigallocatechin gallate protects U937 cells against nitric oxide-induced cell cycle arrest and apoptosis.
2001
Inactivation of parvovirus B19 in coagulation factor concentrates by UVC radiation: assessment by an in vitro infectivity assay using CFU-E derived from peripheral blood CD34+ cells.
2001 Apr
Ester bond-containing tea polyphenols potently inhibit proteasome activity in vitro and in vivo.
2001 Apr 20
Metabolic fate of (-)-[4-(3)H]epigallocatechin gallate in rats after oral administration.
2001 Aug
The molecular interaction of human salivary histatins with polyphenolic compounds.
2001 Aug
Potent antimutagenic activity of white tea in comparison with green tea in the Salmonella assay.
2001 Aug 22
Tea catechin, (-)-epigallocatechin gallate, causes membrane depolarizations of myenteric neurons in the guinea-pig small intestine.
2001 Aug 24
Apoptosis induction by epigallocatechin gallate involves its binding to Fas.
2001 Aug 3
The medicinal action of androgens and green tea epigallocatechin gallate.
2001 Dec
Effects of epigallocatechin-3-gallate on growth, epidermal growth factor receptor signaling pathways, gene expression, and chemosensitivity in human head and neck squamous cell carcinoma cell lines.
2001 Dec
The green tea polyphenol (-)-epigallocatechin gallate attenuates beta-amyloid-induced neurotoxicity in cultured hippocampal neurons.
2001 Dec 21
Apoptosis-inducing activity of high molecular weight fractions of tea extracts.
2001 Feb
Synthesis of (-)-[4-3H]epigallocatechin gallate and its metabolic fate in rats after intravenous administration.
2001 Feb
Green tea polyphenol (-)-epigallocatechin-3-gallate treatment of human skin inhibits ultraviolet radiation-induced oxidative stress.
2001 Feb
Green tea polyphenols as potent enhancers of glucocorticoid-induced mouse mammary tumor virus gene expression.
2001 Feb 16
Inhibitory effect of epigallocatechin-gallate on brain tumor cell lines in vitro.
2001 Jan
Combination cancer chemoprevention with green tea extract and sulindac shown in intestinal tumor formation in Min mice.
2001 Jan
Phase I pharmacokinetic study of tea polyphenols following single-dose administration of epigallocatechin gallate and polyphenon E.
2001 Jan
Degradation of green tea catechins in tea drinks.
2001 Jan
Comparative efficacy as antioxidants between ascorbic acid and epigallocatechin gallate on cells of two human lymphoblastoid lines.
2001 Jan 15
Protective effects of (-)-epigallocatechin-3-gallate on UVA- and UVB-induced skin damage.
2001 Jan-Feb
Production of hydrogen peroxide and methionine sulfoxide by epigallocatechin gallate and antioxidants.
2001 Jul-Aug
Green tea polyphenols: novel irreversible inhibitors of dopa decarboxylase.
2001 Jun 1
Oxygen radical absorbance capacity of the phenolic compounds in plant extracts fractionated by high-performance liquid chromatography.
2001 Jun 15
A simple isolation method for the major catechins in green tea using high-speed countercurrent chromatography.
2001 Mar
Stereospecificity in membrane effects of catechins.
2001 Mar 14
Phase I trial of oral green tea extract in adult patients with solid tumors.
2001 Mar 15
Synthesis of a 3,4,5-trimethoxybenzoyl ester analogue of epigallocatechin-3-gallate (EGCG): a potential route to the natural product green tea catechin, EGCG.
2001 Mar 22
EGCG, a major component of green tea, inhibits tumour growth by inhibiting VEGF induction in human colon carcinoma cells.
2001 Mar 23
Enantioselective synthesis of epigallocatechin-3-gallate (EGCG), the active polyphenol component from green tea.
2001 Mar 8
Combination effect of lignin F and natural products.
2001 Mar-Apr
Green tea polyphenol (-)-epigallocatechin-3-gallate treatment to mouse skin prevents UVB-induced infiltration of leukocytes, depletion of antigen-presenting cells, and oxidative stress.
2001 May
Anti-interferon gamma action of epigallocatechin-3-gallate mediated by specific inhibition of STAT1 activation.
2001 May
Inhibitory effect of epigallocatechin gallate on adhesion of murine melanoma cells to laminin.
2001 Nov 8
Simplified catechin-gallate inhibitors of HIV-1 reverse transcriptase.
2001 Oct 22
Inhibition by epigallocatechin gallate (EGCg) of conjugative R plasmid transfer in Escherichia coli.
2001 Sep
A novel method of measuring hydroxyl radical-scavenging activity of antioxidants using gamma-irradiation.
2001 Sep
Inhibitory activities of (-)-epigallocatechin-3-O-gallate against topoisomerases I and II.
2001 Sep
Epigallocatechin gallate synergy with ampicillin/sulbactam against 28 clinical isolates of methicillin-resistant Staphylococcus aureus.
2001 Sep
Antioxidant activity and inhibitory effect of Gamazumi (Viburnum dilatatum THUNB.) on oxidative damage induced by water immersion restraint stress in rats.
2001 Sep
The green tea polyphenol (-)-epigallocatechin-3-gallate blocks nuclear factor-kappa B activation by inhibiting I kappa B kinase activity in the intestinal epithelial cell line IEC-6.
2001 Sep
Effects of (-)-epigallocatechin-3-gallate, the main component of green tea, on the cloned rat brain Kv1.5 potassium channels.
2001 Sep 1
Molecular mechanisms underlying chemopreventive activities of anti-inflammatory phytochemicals: down-regulation of COX-2 and iNOS through suppression of NF-kappa B activation.
2001 Sep 1
Reduction of spontaneous mutagenesis in mismatch repair-deficient and proficient cells by dietary antioxidants.
2001 Sep 1
Epigallocatechin-3-gallate inhibits basic fibroblast growth factor-induced intracellular signaling transduction pathway in rat aortic smooth muscle cells.
2002 Feb
Inhibitory effects of (-)-epigallocatechin gallate on the life cycle of human immunodeficiency virus type 1 (HIV-1).
2002 Jan
Hamamelitannin from Hamamelis virginiana inhibits the tumour necrosis factor-alpha (TNF)-induced endothelial cell death in vitro.
2002 Jan
Potentiometric and (1)H NMR studies of complexation of Al(3+) with (-)-epigallocatechin gallate, a major active constituent of green tea.
2002 Jan 1
Green tea polyphenol stimulates a Ras, MEKK1, MEK3, and p38 cascade to increase activator protein 1 factor-dependent involucrin gene expression in normal human keratinocytes.
2002 Jan 18
Patents

Sample Use Guides

Sunphenon EGCG (Epigallo Catechin Gallate) 200-800mg (1-4 capsules)
Route of Administration: Oral
Epigallocatechin gallate (EGCG) could inhibit the viability and invasion, and induce the apoptosis, of bladder cancer T24 cells. The apoptosis of bladder cancer cells was notably increased by 20 µm EGCG. In addition, 20 µm EGCG inhibited bladder cancer cell viability. However, 10 µm EGCG did not exhibit any significant inhibitory effect on T24 cell viability. The effect of EGCG on the invasive ability of the bladder cancer cells was then investigated, which demonstrated that 10 µm and 20 µm of EGCG significantly inhibited invasion compared with the control group.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:27:39 UTC 2021
Edited
by admin
on Fri Jun 25 21:27:39 UTC 2021
Record UNII
BQM438CTEL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPIGALLOCATECHIN GALLATE
INCI  
INCI  
Official Name English
(-)-EPIGALLOCATECHIN-3-O-GALLATE (EGCG) (CONSTITUENT OF POWDERED DECAFFEINATED GREEN TEA EXTRACT) [DSC]
Common Name English
(-)-EPIGALLOCATECHIN-3-O-GALLATE [USP-RS]
Common Name English
PF-EGCG 90
Code English
EGCG [WHO-DD]
Common Name English
EGCG [MI]
Common Name English
TEAVIGO
Brand Name English
(-)-EPIGALLOCATECHIN-3-O-GALLATE
USP-RS  
Common Name English
EPIGALLOCATECHIN-GALLATE
Common Name English
EGCG
MI   WHO-DD  
Common Name English
EPIGALLOCATECHIN GALLATE [INCI]
Common Name English
NVP-XAA 723
Code English
3-O-GALLOYL-(-)-EPIGALLOCATECHIN
Common Name English
(-)-EPIGALLOCATECHIN GALLATE
Common Name English
BENZOIC ACID, 3,4,5-TRIHYDROXY-, (2R,3R)-3,4-DIHYDRO-5,7-DIHYDROXY-2-(3,4,5-TRIHYDROXYPHENYL)-2H-1-BENZOPYRAN-3-YL ESTER
Common Name English
EPIGALLOCATECHIN 3-O-GALLATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C68454
Created by admin on Fri Jun 25 21:27:39 UTC 2021 , Edited by admin on Fri Jun 25 21:27:39 UTC 2021
DSLD 2960 (Number of products:2)
Created by admin on Fri Jun 25 21:27:39 UTC 2021 , Edited by admin on Fri Jun 25 21:27:39 UTC 2021
DSLD 1193 (Number of products:210)
Created by admin on Fri Jun 25 21:27:39 UTC 2021 , Edited by admin on Fri Jun 25 21:27:39 UTC 2021
Code System Code Type Description
USP_CATALOG
1236700
Created by admin on Fri Jun 25 21:27:39 UTC 2021 , Edited by admin on Fri Jun 25 21:27:39 UTC 2021
PRIMARY USP-RS
PUBCHEM
65064
Created by admin on Fri Jun 25 21:27:39 UTC 2021 , Edited by admin on Fri Jun 25 21:27:39 UTC 2021
PRIMARY
NCI_THESAURUS
C1088
Created by admin on Fri Jun 25 21:27:39 UTC 2021 , Edited by admin on Fri Jun 25 21:27:39 UTC 2021
PRIMARY
DRUG BANK
DB12116
Created by admin on Fri Jun 25 21:27:39 UTC 2021 , Edited by admin on Fri Jun 25 21:27:39 UTC 2021
PRIMARY
WIKIPEDIA
EPIGALLOCATECHIN GALLATE
Created by admin on Fri Jun 25 21:27:39 UTC 2021 , Edited by admin on Fri Jun 25 21:27:39 UTC 2021
PRIMARY
EPA CompTox
989-51-5
Created by admin on Fri Jun 25 21:27:39 UTC 2021 , Edited by admin on Fri Jun 25 21:27:39 UTC 2021
PRIMARY
FDA UNII
BQM438CTEL
Created by admin on Fri Jun 25 21:27:39 UTC 2021 , Edited by admin on Fri Jun 25 21:27:39 UTC 2021
PRIMARY
EVMPD
SUB33667
Created by admin on Fri Jun 25 21:27:39 UTC 2021 , Edited by admin on Fri Jun 25 21:27:39 UTC 2021
PRIMARY
MERCK INDEX
M4843
Created by admin on Fri Jun 25 21:27:39 UTC 2021 , Edited by admin on Fri Jun 25 21:27:39 UTC 2021
PRIMARY Merck Index
MESH
C045651
Created by admin on Fri Jun 25 21:27:39 UTC 2021 , Edited by admin on Fri Jun 25 21:27:39 UTC 2021
PRIMARY
CAS
989-51-5
Created by admin on Fri Jun 25 21:27:39 UTC 2021 , Edited by admin on Fri Jun 25 21:27:39 UTC 2021
PRIMARY
RXCUI
24246
Created by admin on Fri Jun 25 21:27:39 UTC 2021 , Edited by admin on Fri Jun 25 21:27:39 UTC 2021
PRIMARY RxNorm
Related Record Type Details
PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT
TRANSPORTER -> INHIBITOR
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ACTIVE MOIETY