Epigallocatechin gallate

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

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAryl hydrocarbon receptorNot AvailableHumans
UDNA (cytosine-5)-methyltransferase 1
inhibitor
Humans
UDihydrofolate reductase, mitochondrialNot AvailableHumans
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 outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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.
DrugInteraction
EtrasimodThe 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 regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AntiscarEpigallocatechin 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)PatchTopicalBasiem2015-04-012015-04-20US flag

Categories

Drug Categories
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
Human Metabolome Database
HMDB0003153
KEGG Compound
C09731
PubChem Compound
65064
PubChem Substance
347828417
ChemSpider
58575
BindingDB
50070942
RxNav
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
PhaseStatusPurposeConditionsCount
3CompletedTreatmentMultiple System Atrophy (MSA)1
3RecruitingTreatmentUterine Fibroids (Leiomyomas)1
2Active Not RecruitingTreatmentPapilloma-induced Cervical Lesions1
2CompletedSupportive CareInflammation / Senescence1
2CompletedTreatmentCardiac Involvement / Primary Amyloidosis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
PatchTopical
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0728 mg/mLALOGPS
logP2.38ALOGPS
logP3.08Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)7.99Chemaxon
pKa (Strongest Basic)-5.4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count8Chemaxon
Polar Surface Area197.37 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity111.75 m3·mol-1Chemaxon
Polarizability43.27 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0ug0-0930000000-f01263ac8498e09a9b96
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-0a4i-0301900000-306bcb88a9db3b631447
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSsplash10-00or-0900000000-2209ff009c5d9cffaf40
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSsplash10-0aor-0000900008-24e0bb519bd4a4f909f0
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-014i-0912000000-3adc2bfa8656374fadff
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSsplash10-004i-0900000000-421d0afdbaa8c277f57a
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSsplash10-014i-0911000000-8cd4fb88571a263c38ab
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-0a4i-0301900000-306bcb88a9db3b631447
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSsplash10-00or-0900000000-2209ff009c5d9cffaf40
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSsplash10-0aor-0000900008-24e0bb519bd4a4f909f0
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-014i-0912000000-3adc2bfa8656374fadff
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSsplash10-004i-0900000000-421d0afdbaa8c277f57a
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSsplash10-014i-0911000000-8cd4fb88571a263c38ab
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-000i-0910000000-3ca87cd7e5536628266a
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0159-0917000000-0d7d5d2e8b3cd65a6134
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0159-0917000000-b1f0fb994ee815d3bc77
MS/MS Spectrum - , negativeLC-MS/MSsplash10-014i-0900000000-d3719d6cc341aafdd5ca
MS/MS Spectrum - , negativeLC-MS/MSsplash10-014i-0901000000-bbef161918123e6de6a9
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0691000000-bf8635f20994642ca769
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0690000000-46717d45926c7c5d1a6d
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-03di-0009300000-33f74fa3064539d6bd1e
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-03di-0009300000-b77a4e8b4af2beac67d1
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0910000000-3ca87cd7e5536628266a
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0900000000-0dc849889323d70068fb
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-052o-0030900000-544dab4efa77c783b88e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0900300000-0079e744734f306efb37
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-0010900000-1661904898994895f1e3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fbi-0900100000-c5fac9da6cf66c7530dc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-1918300000-b6dd618222fbc5b5b0fa
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00b9-1904300000-fce79d3896a4e4190722
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-212.9112788
predicted
DarkChem Lite v0.1.0
[M-H]-212.6246788
predicted
DarkChem Lite v0.1.0
[M-H]-212.7334788
predicted
DarkChem Lite v0.1.0
[M-H]-212.4155788
predicted
DarkChem Lite v0.1.0
[M-H]-201.71758
predicted
DeepCCS 1.0 (2019)
[M+H]+211.3136788
predicted
DarkChem Lite v0.1.0
[M+H]+212.1974788
predicted
DarkChem Lite v0.1.0
[M+H]+211.8704788
predicted
DarkChem Lite v0.1.0
[M+H]+211.7712788
predicted
DarkChem Lite v0.1.0
[M+H]+203.65459
predicted
DeepCCS 1.0 (2019)
[M+Na]+212.4030788
predicted
DarkChem Lite v0.1.0
[M+Na]+212.5098788
predicted
DarkChem Lite v0.1.0
[M+Na]+212.0844788
predicted
DarkChem Lite v0.1.0
[M+Na]+212.2262788
predicted
DarkChem Lite v0.1.0
[M+Na]+209.56772
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
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
  1. 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
  1. 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
  1. 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