GALLOCATECHIN GALLATE, (-)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H18O11
Molecular Weight	458.3717
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of GALLOCATECHIN GALLATE, (-)-

Structure Search

SMILES

OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@@H](OC2=C1)C4=CC(O)=C(O)C(O)=C4

InChI

InChIKey=WMBWREPUVVBILR-NQIIRXRSSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12925310 | https://www.ncbi.nlm.nih.gov/pubmed/14640575

(-)-Gallocatechin gallate is a polyphenol, which occurs naturally in various plants, including green tea leaves. The compound was shown to have anti-cancer activity in vitro, with breast cancer, lung cancer, and colon cancer cells. It is supposed that the drug may act by inhibiting Bcl family of proteins. It has been reported to inhibit HIV-1 replication by targeting several steps in HIV-1 life cycle. (-)-Gallocatechin gallate (in combination with other catechins) caused the hypocholesterolemic effect in rats.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Apoptosis regulator Bcl-2 19 Target ID: P10415 Gene ID: 596.0 Gene Symbol: BCL2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14678963	Inhibitor 8297	235.0 nM [Ki]
Bcl-2-like protein 1 3 Target ID: Q07817 Gene ID: 598.0 Gene Symbol: BCL2L1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14678963	Inhibitor 8297	315.0 nM [Ki]
Human immunodeficiency virus type 1 integrase 19 Target ID: CHEMBL3471 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20832370	Inhibitor 8297	2.4 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12925310	Primary	Basic research	Unknown Approved Use Unknown
Atherosclerosis 74 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14640575	Preventing	Preclinical	Unknown Approved Use Unknown
HIV-1 infection 151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20832370	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Theaflavin derivatives in black tea and catechin derivatives in green tea inhibit HIV-1 entry by targeting gp41.	2005 May 25	15823507
The evaluation of catechins that contain a galloyl moiety as potential HIV-1 integrase inhibitors.	2010 Dec	20832370

Patents

Sample Use Guides

In Vivo Use Guide

Rats were administered the emulsion of heat-epimerized catechins at the concentration of 120 mg in 3 ml (the mixture contains 7.7% (-)-catechin gallate, 7.29% (-)-epicatechin gallate, 24.1% (-)-gallocatechin gallate and 20.9% (-)-epigallocatechin gallate).

Route of Administration: Other

In Vitro Use Guide

In a cell growth assay, human tumor cell lines MCF-7, SF-268, HCT-116 and NCI-H460 were treated with 100, 50, 25, 12.5, and 6.25 uM of (-)-gallocatechin gallate for 48 h. The drug gave 97% inhibition of growth of breast cells, at 50-uM concentration. At 50-uM concentrations, it was the most effective against colon cells and inhibited proliferation at 93%. It gave 67% inhibition of the growth of the lung cells, at 50-uM concentrations. At 100-uM concentrations, total growth inhibition of SF-268 cells was obtained with (-)-gallocatechin gallate.

Name

Type

Language

GALLOCATECHIN GALLATE, (-)-

Common Name

English

(-)-GALLOCATECHIN 3-GALLATE

Common Name

English

L-GCG

Common Name

English

(-)-GALLOCATECHIN GALLATE

Common Name

English

NVP-XAA 225

Code

English

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

Systematic Name

English

(-)-GALLOCATECHOL GALLATE

Common Name

English

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

Common Name

English

(-)-GALLOCATECHIN 3-O-GALLATE

Common Name

English

Code System Code Type Description

CHEBI

156271