EPICATECHIN GALLATE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H18O10
Molecular Weight	442.3723
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC2=C(C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O2)C4=CC(O)=C(O)C=C4)C(O)=C1

InChI

InChIKey=LSHVYAFMTMFKBA-TZIWHRDSSA-N

InChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C22H18O10
Molecular Weight	442.3723
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29191128 | https://www.ncbi.nlm.nih.gov/pubmed/17685652

Epicatechin gallate is one of the flavonoids, found in green tea and it acts as an antagonist of the mu/kappa/delta opioid receptors. Recently was studied the effect of epicatechin gallate on fructose uptake in human intestinal epithelia. Based on the result was made a conclusion, that epicatechin gallate could be a good candidate for preventing diseases caused by excessive fructose intake.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Opioid receptors; mu/kappa/delta 33 Target ID: CHEMBL2095181 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17685652	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Inhibition of human immunodeficiency viral replication by tannins and related compounds.	1992 May	1416904
Inhibition of HIV infection by flavanoids.	1993 Oct	8279812
Inhibition of 12-O-tetradecanoylphorbol-13-acetate and other skin tumor-promoter-caused induction of epidermal interleukin-1 alpha mRNA and protein expression in SENCAR mice by green tea polyphenols.	1995 Sep	7665919
Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures.	2001	11962253
Simplified catechin-gallate inhibitors of HIV-1 reverse transcriptase.	2001 Oct 22	11591519
Inhibition of adenovirus infection and adenain by green tea catechins.	2003 Apr	12742577
Epigallocatechin gallate modulates CYP450 isoforms in the female Swiss-Webster mouse.	2003 Dec	14600287
Epigallocatechin gallate, the main component of tea polyphenol, binds to CD4 and interferes with gp120 binding.	2003 Nov	14610487
Copper complexes of (-)-epicatechin gallate and (-)-epigallocatechin gallate act as inhibitors of Ribonuclease A.	2006 Aug 21	16884715
Green tea catechins upregulate superoxide dismutase and catalase in fruit flies.	2007 May	17440995
Flavonoids inhibit the AU-rich element binding of HuC.	2009 Jan 31	19192392
Tea polyphenols can restrict benzo[a]pyrene-induced lung carcinogenesis by altered expression of p53-associated genes and H-ras, c-myc and cyclin D1.	2009 May	18656336
The evaluation of catechins that contain a galloyl moiety as potential HIV-1 integrase inhibitors.	2010 Dec	20832370
Intervention of human breast cell carcinogenesis chronically induced by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine.	2012 Apr	22307971
A tea catechin, epigallocatechin-3-gallate, is a unique modulator of the farnesoid X receptor.	2012 Jan 15	22178739
(-)-Epigallocatechin-3-gallate is a new inhibitor of hepatitis C virus entry.	2012 Mar	22105803
Bioactivity-guided fractionation of Phyllanthus orbicularis and identification of the principal anti HSV-2 compounds.	2012 Oct	22318977
Green tea catechins alone or in combination alter functional parameters of human neutrophils via suppressing the activation of TLR-4/NFκB p65 signal pathway.	2015 Oct	26187476

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Epigallocatechin gallate (EGCG) and epicatechin gallate (ECG) are green tea catechins which are known as powerful antioxidants. There was examined the possible protective effects of ECG and EGCG on the neurotoxicity of acrylamide (ACR) neurotoxicity in-vitro model. PC12 cells were exposed to different concentrations of ECG and EGCG. Both ECG and EGCG (20 μM) showed inhibitory effects on ACR cytotoxicity. ACR significantly induced gait abnormalities decreased GSH level and increased lipid peroxidation in the cerebral cortex.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:01:56 UTC 2023` Edited by `admin` on `Fri Dec 15 16:01:56 UTC 2023`
Record UNII	92587OVD8Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPICATECHIN GALLATE

Common Name

English

EPICATECHOL 3-GALLATE

Common Name

English

(-)-EPICATECHIN-3-O-GALLATE (CONSTITUENT OF GRAPE SEEDS OLIGOMERIC PROANTHOCYANIDINS) [DSC]

Common Name

English

EPICATECHIN 3-O-GALLATE

Common Name

English

EPICATECHINGALLATE, L-

Common Name

English

(-)-EPI CATECHIN-3-O-GALLATE

Common Name

English

(-)-EPICATECHIN-3-O-GALLATE(EGC) (CONSTITUENT OF POWDERED DECAFFEINATED GREEN TEA EXTRACT) [DSC]

Common Name

English

(-)-EPICATECHIN GALLATE

Common Name

English

L-ECG

Common Name

English

NSC-636594

Code

English

BENZOIC ACID, 3,4,5-TRIHYDROXY-, (2R,3R)-2-(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-5,7-DIHYDROXY-2H-1-BENZOPYRAN-3-YL ESTER

Common Name

English

ECG

Common Name

English

Classification Tree Code System Code

DSLD

4085 (Number of products:1)