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
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
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 |
(-)-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 | Condition | Potency |
---|---|---|---|
Target ID: P10415 Gene ID: 596.0 Gene Symbol: BCL2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14678963 |
235.0 nM [Ki] | ||
Target ID: Q07817 Gene ID: 598.0 Gene Symbol: BCL2L1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14678963 |
315.0 nM [Ki] | ||
Target ID: CHEMBL3471 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20832370 |
2.4 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Tea catechins and related polyphenols as anti-cancer agents. | 2000 |
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Inhibition of proliferation of human cancer cells and cyclooxygenase enzymes by anthocyanidins and catechins. | 2003 |
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Cancer prevention by tea polyphenols is linked to their direct inhibition of antiapoptotic Bcl-2-family proteins. | 2003 Dec 1 |
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Theaflavin derivatives in black tea and catechin derivatives in green tea inhibit HIV-1 entry by targeting gp41. | 2005 May 25 |
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Tea catechins inhibit hepatocyte growth factor receptor (MET kinase) activity in human colon cancer cells: kinetic and molecular docking studies. | 2009 Nov 12 |
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The evaluation of catechins that contain a galloyl moiety as potential HIV-1 integrase inhibitors. | 2010 Dec |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14640575
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12925310
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
Edited
Sat Dec 16 07:54:47 GMT 2023
by
admin
on
Sat Dec 16 07:54:47 GMT 2023
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Record UNII |
IRW3C4Y31Q
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Record Status |
Validated (UNII)
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Record Version |
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