Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H18O11 |
| Molecular Weight | 458.3717 |
| Optical Activity | ( - ) |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C4=CC(O)=C(O)C(O)=C4
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
| Molecular Formula | C22H18O11 |
| Molecular Weight | 458.3717 |
| 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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P26358 Gene ID: 1786.0 Gene Symbol: DNMT1 Target Organism: Homo sapiens (Human) |
6.89 µM [Ki] | ||
Target ID: map04064 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
73.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11205489/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPIGALLOCATECHIN GALLATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
438.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11205489/ |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPIGALLOCATECHIN GALLATE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
169.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11205489/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPIGALLOCATECHIN GALLATE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
111.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11205489/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPIGALLOCATECHIN GALLATE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
22.5 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11205489/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPIGALLOCATECHIN GALLATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
161.4 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11205489/ |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPIGALLOCATECHIN GALLATE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
101.9 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11205489/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPIGALLOCATECHIN GALLATE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
35.4 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11205489/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPIGALLOCATECHIN GALLATE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
118 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11205489/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPIGALLOCATECHIN GALLATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
114 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11205489/ |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPIGALLOCATECHIN GALLATE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
183.7 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11205489/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPIGALLOCATECHIN GALLATE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
162.3 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11205489/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPIGALLOCATECHIN GALLATE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1600 mg single, oral Highest studied dose Dose: 1600 mg Route: oral Route: single Dose: 1600 mg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: |
|
800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FED Sources: |
Other AEs: Headache, Stomach ache... Other AEs: Headache (25%) Sources: Stomach ache (grade 1, 12.5%) Abdominal pain (grade 1, 25%) Nausea (grade 1, 25%) Dizziness (grade 1, 12.5%) Muscle pain (grade 1, 12.5%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Headache | 25% | 800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FED Sources: |
| Dizziness | grade 1, 12.5% | 800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FED Sources: |
| Muscle pain | grade 1, 12.5% | 800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FED Sources: |
| Stomach ache | grade 1, 12.5% | 800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FED Sources: |
| Abdominal pain | grade 1, 25% | 800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FED Sources: |
| Nausea | grade 1, 25% | 800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FED Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Synergistic effects of (-)-epigallocatechin gallate with sulindac against colon carcinogenesis of rats treated with azoxymethane. | 2002-03-08 |
|
| Epigallocatechin-3-gallate inhibits basic fibroblast growth factor-induced intracellular signaling transduction pathway in rat aortic smooth muscle cells. | 2002-02 |
|
| 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. | 2002-01-18 |
|
| The role of inducible nitric oxide synthase in cocaine-induced locomotor sensitization. | 2002-01-16 |
|
| Green tea catechins inhibit vascular endothelial growth factor receptor phosphorylation. | 2002-01-15 |
|
| In vitro therapeutic effect of epigallocatechin gallate on nicotine-induced impairment of resistance to Legionella pneumophila infection of established MH-S alveolar macrophages. | 2002-01-15 |
|
| Potentiometric and (1)H NMR studies of complexation of Al(3+) with (-)-epigallocatechin gallate, a major active constituent of green tea. | 2002-01-01 |
|
| Preformulation study of epigallocatechin gallate, a promising antioxidant for topical skin cancer prevention. | 2002-01 |
|
| (-)Epigallocatechin-3-gallate inhibits leukocyte elastase: potential of the phyto-factor in hindering inflammation, emphysema, and invasion. | 2002-01 |
|
| Angioprevention': angiogenesis is a common and key target for cancer chemopreventive agents. | 2002-01 |
|
| Inhibitory effects of (-)-epigallocatechin gallate on the life cycle of human immunodeficiency virus type 1 (HIV-1). | 2002-01 |
|
| Hamamelitannin from Hamamelis virginiana inhibits the tumour necrosis factor-alpha (TNF)-induced endothelial cell death in vitro. | 2002-01 |
|
| The green tea polyphenol (-)-epigallocatechin gallate attenuates beta-amyloid-induced neurotoxicity in cultured hippocampal neurons. | 2001-12-21 |
|
| Anticarcinogenic antioxidants as inhibitors against intracellular oxidative stress. | 2001-12 |
|
| Plasma concentrations of individual tea catechins after a single oral dose in humans. | 2001-12 |
|
| Rapid conversion of tea catechins to monomethylated products by rat liver cytosolic catechol-O-methyltransferase. | 2001-12 |
|
| The medicinal action of androgens and green tea epigallocatechin gallate. | 2001-12 |
|
| Effect of polyphenols on calcium content and alkaline phosphatase activity in rat femoral tissues in vitro. | 2001-12 |
|
| 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. | 2001-12 |
|
| Production of hydrogen peroxide and methionine sulfoxide by epigallocatechin gallate and antioxidants. | 2001-11-29 |
|
| Changes in amino acid pool and utilization during apoptosis in HL-60 cells induced by epigallocatechin gallate or gallic acid. | 2001-11-29 |
|
| Green tea epigallocatechin gallate: a natural inhibitor of fatty-acid synthase. | 2001-11-16 |
|
| Inhibitory effect of epigallocatechin gallate on adhesion of murine melanoma cells to laminin. | 2001-11-08 |
|
| Liquid chromatography with multi-channel electrochemical detection for the determination of epigallocatechin gallate in rat plasma utilizing an automated blood sampling device. | 2001-11-05 |
|
| Development of an androgen reporter gene assay (AR-LUX) utilizing a human cell line with an endogenously regulated androgen receptor. | 2001-11-01 |
|
| Simplified catechin-gallate inhibitors of HIV-1 reverse transcriptase. | 2001-10-22 |
|
| Green tea constituent (--)-epigallocatechin-3-gallate inhibits topoisomerase I activity in human colon carcinoma cells. | 2001-10-19 |
|
| 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. | 2001-10-15 |
|
| Effects of (-)-epigallocatechin-3-gallate, the main component of green tea, on the cloned rat brain Kv1.5 potassium channels. | 2001-09-01 |
|
| Cancer prevention with green tea and monitoring by a new biomarker, hnRNP B1. | 2001-09-01 |
|
| Molecular mechanisms underlying chemopreventive activities of anti-inflammatory phytochemicals: down-regulation of COX-2 and iNOS through suppression of NF-kappa B activation. | 2001-09-01 |
|
| Reduction of spontaneous mutagenesis in mismatch repair-deficient and proficient cells by dietary antioxidants. | 2001-09-01 |
|
| Inhibition by epigallocatechin gallate (EGCg) of conjugative R plasmid transfer in Escherichia coli. | 2001-09 |
|
| A novel method of measuring hydroxyl radical-scavenging activity of antioxidants using gamma-irradiation. | 2001-09 |
|
| Inhibitory activities of (-)-epigallocatechin-3-O-gallate against topoisomerases I and II. | 2001-09 |
|
| Epigallocatechin gallate (EGCG) inhibits the sulfation of 1-naphthol in a human colon carcinoma cell line, Caco-2. | 2001-09 |
|
| Green tea polyphenol (-)-epigallocatechin-3-gallate prevents N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced dopaminergic neurodegeneration. | 2001-09 |
|
| Epigallocatechin gallate synergy with ampicillin/sulbactam against 28 clinical isolates of methicillin-resistant Staphylococcus aureus. | 2001-09 |
|
| Antioxidant activity and inhibitory effect of Gamazumi (Viburnum dilatatum THUNB.) on oxidative damage induced by water immersion restraint stress in rats. | 2001-09 |
|
| 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. | 2001-09 |
|
| 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. | 2001-09 |
|
| Involvement of ERK and protein tyrosine phosphatase signaling pathways in EGCG-induced cyclooxygenase-2 expression in Raw 264.7 cells. | 2001-08-31 |
|
| Tea catechin, (-)-epigallocatechin gallate, causes membrane depolarizations of myenteric neurons in the guinea-pig small intestine. | 2001-08-24 |
|
| Prolyl endopeptidase inhibitors from green tea. | 2001-08 |
|
| Metabolic fate of (-)-[4-(3)H]epigallocatechin gallate in rats after oral administration. | 2001-08 |
|
| Modulation of gene expression by (-)-epigallocatechin gallate in PC-9 cells using a cDNA expression array. | 2001-08 |
|
| A new function of green tea: prevention of lifestyle-related diseases. | 2001-04 |
|
| 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 |
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
Edited
Mon Mar 31 18:03:38 GMT 2025
by
admin
on
Mon Mar 31 18:03:38 GMT 2025
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| Record UNII |
BQM438CTEL
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C68454
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DSLD |
2960 (Number of products:2)
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DSLD |
1193 (Number of products:210)
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1236700
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65064
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C1088
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4806
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DB12116
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EPIGALLOCATECHIN GALLATE
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DTXSID1029889
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BQM438CTEL
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SUB33667
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m4843
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C045651
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989-51-5
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24246
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100000127611
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BQM438CTEL
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PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT |
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TRANSPORTER -> INHIBITOR |
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ACTIVE MOIETY |
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