U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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
Inhibition of melanoma growth and metastasis by combination with (-)-epigallocatechin-3-gallate and dacarbazine in mice.
2001
The 'pivotal antioxidant' hypothesis for the role of flavonoids in their reduction of HO* radical-induced damage on DNA.
2001
Green tea extracts decrease carcinogen-induced mammary tumor burden in rats and rate of breast cancer cell proliferation in culture.
2001
A new function of green tea: prevention of lifestyle-related diseases.
2001 Apr
Prolyl endopeptidase inhibitors from green tea.
2001 Aug
Metabolic fate of (-)-[4-(3)H]epigallocatechin gallate in rats after oral administration.
2001 Aug
Modulation of gene expression by (-)-epigallocatechin gallate in PC-9 cells using a cDNA expression array.
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
Apoptosis induction by epigallocatechin gallate involves its binding to Fas.
2001 Aug 3
Involvement of ERK and protein tyrosine phosphatase signaling pathways in EGCG-induced cyclooxygenase-2 expression in Raw 264.7 cells.
2001 Aug 31
Inhibition by green tea catechins of metabolic activation of procarcinogens by human cytochrome P450.
2001 Aug 8
Anticarcinogenic antioxidants as inhibitors against intracellular oxidative stress.
2001 Dec
Rapid conversion of tea catechins to monomethylated products by rat liver cytosolic catechol-O-methyltransferase.
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
Production of hydrogen peroxide and methionine sulfoxide by epigallocatechin gallate and antioxidants.
2001 Jul-Aug
Changes in amino acid pool and utilization during apoptosis in HL-60 cells induced by epigallocatechin gallate or gallic acid.
2001 Jul-Aug
Simultaneous determination of twelve tea catechins by high-performance liquid chromatography with electrochemical detection.
2001 Jun
Development of an androgen reporter gene assay (AR-LUX) utilizing a human cell line with an endogenously regulated androgen receptor.
2001 Nov 1
Green tea epigallocatechin gallate: a natural inhibitor of fatty-acid synthase.
2001 Nov 16
Liquid chromatography with multi-channel electrochemical detection for the determination of epigallocatechin gallate in rat plasma utilizing an automated blood sampling device.
2001 Nov 5
Inhibitory effect of epigallocatechin gallate on adhesion of murine melanoma cells to laminin.
2001 Nov 8
The role of inducible nitric oxide synthase in cocaine-induced locomotor sensitization.
2001 Nov-Dec
Inhibition of UVB-induced oxidative stress-mediated phosphorylation of mitogen-activated protein kinase signaling pathways in cultured human epidermal keratinocytes by green tea polyphenol (-)-epigallocatechin-3-gallate.
2001 Oct 15
Green tea constituent (--)-epigallocatechin-3-gallate inhibits topoisomerase I activity in human colon carcinoma cells.
2001 Oct 19
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 (EGCG) inhibits the sulfation of 1-naphthol in a human colon carcinoma cell line, Caco-2.
2001 Sep
Green tea polyphenol (-)-epigallocatechin-3-gallate prevents N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced dopaminergic neurodegeneration.
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
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
Effects of (-)-epigallocatechin-3-gallate, the main component of green tea, on the cloned rat brain Kv1.5 potassium channels.
2001 Sep 1
Cancer prevention with green tea and monitoring by a new biomarker, hnRNP B1.
2001 Sep 1
Epigallocatechin-3-gallate inhibits basic fibroblast growth factor-induced intracellular signaling transduction pathway in rat aortic smooth muscle cells.
2002 Feb
Preformulation study of epigallocatechin gallate, a promising antioxidant for topical skin cancer prevention.
2002 Jan
(-)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
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 catechins inhibit vascular endothelial growth factor receptor phosphorylation.
2002 Jan 15
In vitro therapeutic effect of epigallocatechin gallate on nicotine-induced impairment of resistance to Legionella pneumophila infection of established MH-S alveolar macrophages.
2002 Jan 15
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
Synergistic effects of (-)-epigallocatechin gallate with sulindac against colon carcinogenesis of rats treated with azoxymethane.
2002 Mar 8
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