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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 of CATECHIN 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=C4)C(O)=C1

InChI

InChIKey=LSHVYAFMTMFKBA-CTNGQTDRSA-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

Description

(-)-Catechin 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. (-)-Catechin gallate (in combination with other catechins) caused the hypocholesterolemic effect in rats.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
143.0 nM [Ki]
230.0 nM [Ki]
0.56 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Preventing
Unknown
Primary
Unknown

PubMed

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 (-)-catechin gallate for 48 h. The drug gave about 40% inhibition of growth of breast, colon, and lung cancer cells, at 50-uM concentration.