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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
Mechanisms of cancer prevention by tea polyphenols based on inhibition of TNF-alpha expression.
2000
A new concept of tumor promotion by tumor necrosis factor-alpha, and cancer preventive agents (-)-epigallocatechin gallate and green tea--a review.
2000
Correlation of chemopreventive efficacy data from the human epidermal cell assay with in vivo data.
2000 Jan-Feb
Developing a dynamic pharmacophore model for HIV-1 integrase.
2000 Jun 1
Preventive effect of antioxidant on ultraviolet-induced skin cancer in mice.
2000 Mar
Anti-herpes simplex virus type-1 flavonoids and a new flavanone from the root of Limonium sinense.
2000 May
Differential responses of skin cancer-chemopreventive agents silibinin, quercetin, and epigallocatechin 3-gallate on mitogenic signaling and cell cycle regulators in human epidermoid carcinoma A431 cells.
2001
Ester bond-containing tea polyphenols potently inhibit proteasome activity in vitro and in vivo.
2001 Apr 20
The molecular interaction of human salivary histatins with polyphenolic compounds.
2001 Aug
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
Plasma concentrations of individual tea catechins after a single oral dose in humans.
2001 Dec
Rapid conversion of tea catechins to monomethylated products by rat liver cytosolic catechol-O-methyltransferase.
2001 Dec
The medicinal action of androgens and green tea epigallocatechin gallate.
2001 Dec
Effect of polyphenols on calcium content and alkaline phosphatase activity in rat femoral tissues in vitro.
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
Evaluation of antioxidant activity of epigallocatechin gallate in biphasic model systems in vitro.
2001 Feb
Green tea polyphenol (-)-epigallocatechin-3-gallate treatment of human skin inhibits ultraviolet radiation-induced oxidative stress.
2001 Feb
Tumor gelatinases and invasion inhibited by the green tea flavanol epigallocatechin-3-gallate.
2001 Feb 15
Phase I pharmacokinetic study of tea polyphenols following single-dose administration of epigallocatechin gallate and polyphenon E.
2001 Jan
Protective effects of (-)-epigallocatechin-3-gallate on UVA- and UVB-induced skin damage.
2001 Jan-Feb
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
Antimutagenic activity of green tea and black tea extracts studied in a dynamic in vitro gastrointestinal model.
2001 Mar 1
Stereospecificity in membrane effects of catechins.
2001 Mar 14
Enantioselective synthesis of epigallocatechin-3-gallate (EGCG), the active polyphenol component from green tea.
2001 Mar 8
Anti-interferon gamma action of epigallocatechin-3-gallate mediated by specific inhibition of STAT1 activation.
2001 May
Mechanisms of inhibition of the Ras-MAP kinase signaling pathway in 30.7b Ras 12 cells by tea polyphenols (-)-epigallocatechin-3-gallate and theaflavin-3,3'-digallate.
2001 Sep
Cancer prevention with green tea and monitoring by a new biomarker, hnRNP B1.
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
(-)Epigallocatechin-3-gallate inhibits leukocyte elastase: potential of the phyto-factor in hindering inflammation, emphysema, and invasion.
2002 Jan
Angioprevention': angiogenesis is a common and key target for cancer chemopreventive agents.
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
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
Related Record Type Details
ACTIVE MOIETY