Epigallocatechin gallate

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Epigallocatechin gallate
Accession Number
DB12116
Type
Small Molecule
Groups
Investigational
Description

Epigallocatechin gallate has been investigated for the treatment of Hypertension and Diabetic Nephropathy.

Structure
Thumb
Synonyms
  • EGCG
  • Epigallocatechin gallate
External IDs
NVP-XAA 723 / PF-EGCG 90
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
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
Categories
UNII
BQM438CTEL
CAS number
989-51-5
Weight
Average: 458.3717
Monoisotopic: 458.084911418
Chemical Formula
C22H18O11
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAryl hydrocarbon receptorNot AvailableHuman
UDNA (cytosine-5)-methyltransferase 1
inhibitor
Human
UDihydrofolate reductase, mitochondrialNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Epigallocatechin Gallate.
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Epigallocatechin Gallate.
AncestimThe risk or severity of cytotoxicity can be increased when Ancestim is combined with Epigallocatechin Gallate.
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Epigallocatechin Gallate.
CymarinCymarin may decrease the cardiotoxic activities of Epigallocatechin Gallate.
DeslanosideDeslanoside may decrease the cardiotoxic activities of Epigallocatechin Gallate.
DigitoxinDigitoxin may decrease the cardiotoxic activities of Epigallocatechin Gallate.
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Epigallocatechin Gallate.
GitoformateGitoformate may decrease the cardiotoxic activities of Epigallocatechin Gallate.
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Epigallocatechin Gallate.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0003153
KEGG Compound
C09731
PubChem Compound
65064
PubChem Substance
347828417
ChemSpider
58575
BindingDB
50070942
ChEBI
4806
ChEMBL
CHEMBL297453
HET
KDH
Wikipedia
Epigallocatechin_gallate
PDB Entries
2kdh / 3ng5 / 3oob / 4awm

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingPreventionMalignant Neoplasm of Colon1
1CompletedTreatmentDisseminated Sclerosis1
1Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1, 2Enrolling by InvitationPreventionEpigallocatechin Gallate / Radiation Mucositis / Radio Dermatitis1
2CompletedBasic ScienceProstate Cancer1
2CompletedTreatmentCardiac Involvement / Light Chain (AL) Amyloidosis1
2CompletedTreatmentDiabetic Nephropathies / High Blood Pressure (Hypertension)1
2Enrolling by InvitationTreatmentEpigallocatechin Gallate / Esophagitis / Neoplasms, Lung / Prevention & Control1
2Enrolling by InvitationTreatmentEpigallocatechin Gallate / Neoplasms, Breast / Prevention & Control / Skin Inflammation1
2TerminatedTreatmentDisseminated Sclerosis1
2WithdrawnTreatmentBMI >30 kg/m2 / High Blood Pressure (Hypertension) / Insulin Resistance / Type 2 Diabetes Mellitus1
2, 3Active Not RecruitingTreatmentDuchenne's Muscular Dystrophy (DMD)1
2, 3Unknown StatusTreatmentDiabetes Mellitus (DM) / Hyperlipidemias1

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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
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

Taxonomy

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
Catechin gallate / Epigallocatechin / 3'-hydroxyflavonoid / 4'-hydroxyflavonoid / 5-hydroxyflavonoid / 7-hydroxyflavonoid / Hydroxyflavonoid / Galloyl ester / Gallic acid or derivatives / P-hydroxybenzoic acid alkyl ester
show 28 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
polyphenol, gallate ester, catechin (CHEBI:4806) / Proanthocyanidins, Flavan 3-ols (C09731) / Proanthocyanidins (LMPK12030005)

Targets

Kind
Protein
Organism
Human
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. [PubMed:11064004]
Kind
Protein
Organism
Human
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. [PubMed:14633667]
Kind
Protein
Organism
Human
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. [PubMed:20054477]

Drug created on October 20, 2016 15:23 / Updated on October 01, 2018 15:09