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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, (-)-

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(O)=C4)C(O)=C1

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
Molecular Formula C22H18O11
Molecular Weight 458.3717
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

(-)-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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Apoptosis regulator Bcl-2
19
Target ID: P10415
Gene ID: 596.0
Gene Symbol: BCL2
Target Organism: Homo sapiens (Human)
Inhibitor
8504
 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)
Inhibitor
8504
 315.0 nM [Ki]
Inhibitor
8504
 2.4 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Preventing
Preclinical
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The evaluation of catechins that contain a galloyl moiety as potential HIV-1 integrase inhibitors.
2010-12
Tea catechins inhibit hepatocyte growth factor receptor (MET kinase) activity in human colon cancer cells: kinetic and molecular docking studies.
2009-11-12
Theaflavin derivatives in black tea and catechin derivatives in green tea inhibit HIV-1 entry by targeting gp41.
2005-05-25
Cancer prevention by tea polyphenols is linked to their direct inhibition of antiapoptotic Bcl-2-family proteins.
2003-12-01
Inhibition of proliferation of human cancer cells and cyclooxygenase enzymes by anthocyanidins and catechins.
2003
Tea catechins and related polyphenols as anti-cancer agents.
2000
Patents

Patents

WO2008004774 A1
1

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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:45:35 GMT 2025
Edited
by admin
on Mon Mar 31 21:45:35 GMT 2025
Record UNII
IRW3C4Y31Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NVP-XAA 225
Preferred Name English
GALLOCATECHIN GALLATE, (-)-
Common Name English
(-)-GALLOCATECHIN 3-GALLATE
Common Name English
L-GCG
Common Name English
(-)-GALLOCATECHIN GALLATE
Common Name 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
Created by admin on Mon Mar 31 21:45:35 GMT 2025 , Edited by admin on Mon Mar 31 21:45:35 GMT 2025
PRIMARY
FDA UNII
IRW3C4Y31Q
Created by admin on Mon Mar 31 21:45:35 GMT 2025 , Edited by admin on Mon Mar 31 21:45:35 GMT 2025
PRIMARY
EPA CompTox
DTXSID20195144
Created by admin on Mon Mar 31 21:45:35 GMT 2025 , Edited by admin on Mon Mar 31 21:45:35 GMT 2025
PRIMARY
CAS
4233-96-9
Created by admin on Mon Mar 31 21:45:35 GMT 2025 , Edited by admin on Mon Mar 31 21:45:35 GMT 2025
PRIMARY
PUBCHEM
199472
Created by admin on Mon Mar 31 21:45:35 GMT 2025 , Edited by admin on Mon Mar 31 21:45:35 GMT 2025
PRIMARY
NIH
NCATS
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