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
Structure for Epigallocatechin gallate (DB12116)
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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. - 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Completed Treatment Multiple System Atrophy (MSA) 1 3 Recruiting Treatment Uterine Fibroids (Leiomyomas) 1 2 Active Not Recruiting Treatment Papilloma-induced Cervical Lesions 1 2 Completed Supportive Care Frailty / Inflammation 1 2 Completed Treatment Cardiac Involvement / Primary Amyloidosis 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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 212.9112788 predictedDarkChem Lite v0.1.0 [M-H]- 212.6246788 predictedDarkChem Lite v0.1.0 [M-H]- 212.7334788 predictedDarkChem Lite v0.1.0 [M-H]- 212.4155788 predictedDarkChem Lite v0.1.0 [M-H]- 201.71758 predictedDeepCCS 1.0 (2019) [M+H]+ 211.3136788 predictedDarkChem Lite v0.1.0 [M+H]+ 212.1974788 predictedDarkChem Lite v0.1.0 [M+H]+ 211.8704788 predictedDarkChem Lite v0.1.0 [M+H]+ 211.7712788 predictedDarkChem Lite v0.1.0 [M+H]+ 203.65459 predictedDeepCCS 1.0 (2019) [M+Na]+ 212.4030788 predictedDarkChem Lite v0.1.0 [M+Na]+ 212.5098788 predictedDarkChem Lite v0.1.0 [M+Na]+ 212.0844788 predictedDarkChem Lite v0.1.0 [M+Na]+ 212.2262788 predictedDarkChem Lite v0.1.0 [M+Na]+ 209.56772 predictedDeepCCS 1.0 (2019)
Targets
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- 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]
- 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]
- 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