Epigallocatechin gallate
Star1
This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Epigallocatechin gallate
- DrugBank Accession Number
- DB12116
- Background
Epigallocatechin gallate has been investigated for the treatment of Hypertension and Diabetic Nephropathy.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 458.3717
Monoisotopic: 458.084911418 - Chemical Formula
- C22H18O11
- Synonyms
- EGCG
- Epigallocatechin gallate
- Epigallocatechin-3-gallate
- External IDs
- NVP-XAA 723
- PF-EGCG 90
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UAryl hydrocarbon receptor Not Available Humans UDNA (cytosine-5)-methyltransferase 1 inhibitorHumans UDihydrofolate reductase, mitochondrial Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareEtrasimod The risk or severity of immunosuppression can be increased when Epigallocatechin gallate is combined with Etrasimod. Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Antiscar Epigallocatechin gallate (.3 g/100g) + 13-cis-12-(3'-Carboxyphenyl)retinoic acid (2 g/100g) + Allantoin (2 g/100g) + Onion (.5 g/100g) + Petrolatum (3 g/100g) Patch Topical Basiem 2015-04-01 2015-04-20 US
Categories
- Drug Categories
- Anticarcinogenic Agents
- Antimutagenic Agents
- Antineoplastic Agents
- Antioxidants
- Benzopyrans
- Biological Factors
- Central Nervous System Agents
- Chromans
- Chromones
- Compounds used in a research, industrial, or household setting
- Flavonoids
- Heterocyclic Compounds, Fused-Ring
- Neuroprotective Agents
- Protective Agents
- Pyrans
- Urokinase-Type Plasminogen Activator, antagonists & inhibitors
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Flavonoids
- Sub Class
- Flavans
- Direct Parent
- Catechin gallates
- Alternative Parents
- Epigallocatechins / 3'-hydroxyflavonoids / 4'-hydroxyflavonoids / 5-hydroxyflavonoids / 7-hydroxyflavonoids / Galloyl esters / p-Hydroxybenzoic acid alkyl esters / m-Hydroxybenzoic acid esters / 1-benzopyrans / Pyrogallols and derivatives show 10 more
- Substituents
- 1-benzopyran / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 3'-hydroxyflavonoid / 4'-hydroxyflavonoid / 5-hydroxyflavonoid / 7-hydroxyflavonoid / Alkyl aryl ether / Aromatic heteropolycyclic compound / Benzenetriol show 28 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- polyphenol, gallate ester, catechin (CHEBI:4806) / Proanthocyanidins, Flavan 3-ols (C09731) / Proanthocyanidins (LMPK12030005)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- BQM438CTEL
- CAS number
- 989-51-5
- InChI Key
- WMBWREPUVVBILR-WIYYLYMNSA-N
- InChI
- 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
- IUPAC Name
- (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
- SMILES
- OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C1=CC(O)=C(O)C(O)=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0003153
- KEGG Compound
- C09731
- PubChem Compound
- 65064
- PubChem Substance
- 347828417
- ChemSpider
- 58575
- BindingDB
- 50070942
- 24246
- ChEBI
- 4806
- ChEMBL
- CHEMBL297453
- ZINC
- ZINC000003870412
- PDBe Ligand
- KDH
- Wikipedia
- Epigallocatechin_gallate
- PDB Entries
- 2kdh / 3ng5 / 3oob / 4awm / 6s2g / 7upg
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Multiple System Atrophy (MSA) 1 3 Recruiting Treatment Uterine Fibroids (Leiomyomas) 1 2 Completed Supportive Care Frailty / Inflammation 1 2 Completed Treatment Cardiac Involvement / Primary Amyloidosis 1 2 Completed Treatment Diabetic Nephropathy / Hypertension 1 2 Completed Treatment Endometriosis 1 2 Enrolling by Invitation Treatment Papilloma-induced Cervical Lesions 1 2 Not Yet Recruiting Prevention Cirrhosis of the Liver 1 2 Not Yet Recruiting Supportive Care Frailty / Inflammation 1 2 Terminated Treatment Multiple Sclerosis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Patch Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0728 mg/mL ALOGPS logP 2.38 ALOGPS logP 3.08 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 7.99 Chemaxon pKa (Strongest Basic) -5.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 8 Chemaxon Polar Surface Area 197.37 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 111.75 m3·mol-1 Chemaxon Polarizability 43.27 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets

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1. DetailsAryl hydrocarbon receptor
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transcription regulatory region dna binding
- Specific Function
- Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes...
- Gene Name
- AHR
- Uniprot ID
- P35869
- Uniprot Name
- Aryl hydrocarbon receptor
- Molecular Weight
- 96146.705 Da
References
- Williams SN, Shih H, Guenette DK, Brackney W, Denison MS, Pickwell GV, Quattrochi LC: Comparative studies on the effects of green tea extracts and individual tea catechins on human CYP1A gene expression. Chem Biol Interact. 2000 Nov 1;128(3):211-29. [Article]
2. DetailsDNA (cytosine-5)-methyltransferase 1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Zinc ion binding
- Specific Function
- Methylates CpG residues. Preferentially methylates hemimethylated DNA. Associates with DNA replication sites in S phase maintaining the methylation pattern in the newly synthesized strand, that is ...
- Gene Name
- DNMT1
- Uniprot ID
- P26358
- Uniprot Name
- DNA (cytosine-5)-methyltransferase 1
- Molecular Weight
- 183163.635 Da
References
- Fang MZ, Wang Y, Ai N, Hou Z, Sun Y, Lu H, Welsh W, Yang CS: Tea polyphenol (-)-epigallocatechin-3-gallate inhibits DNA methyltransferase and reactivates methylation-silenced genes in cancer cell lines. Cancer Res. 2003 Nov 15;63(22):7563-70. [Article]
3. DetailsDihydrofolate reductase, mitochondrial
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Nadp binding
- Specific Function
- Key enzyme in folate metabolism. Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Required to prevent uracil accumulation in mtDNA. Binds its own mRNA and that of DHFR.
- Gene Name
- DHFRL1
- Uniprot ID
- Q86XF0
- Uniprot Name
- Dihydrofolate reductase, mitochondrial
- Molecular Weight
- 21619.88 Da
References
- Sanchez-del-Campo L, Saez-Ayala M, Chazarra S, Cabezas-Herrera J, Rodriguez-Lopez JN: Binding of natural and synthetic polyphenols to human dihydrofolate reductase. Int J Mol Sci. 2009 Dec 18;10(12):5398-410. doi: 10.3390/ijms10125398. [Article]
Drug created at October 20, 2016 21:23 / Updated at February 18, 2022 00:37