Ligand epigallocatechin gallate

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Basic Ligand Information

Molecular Structure
Picture of epigallocatechin gallate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C22H18O11
epigallocatechin gallate
WMBWREPUVVBILR-WIYYLYMNSA-N
Synonyms:
(-)-epigallo-3-catechin gallate, (-)-epigallocatechin-3-gallate, (-)-epigallocatechin-3-O-gallate, (-)-epigallocatechin 3-gallate, (-)-epigallocatechin gallate, (-)-gallocatechin-3-O-gallate, (-)epigallocatechin gallate, (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate, epigallocatechin-3-gallate, epigallocatechin-3-monogallate, epigallocatechin-3-O-gallate, epigallocatechin 3-gallate, epigallocatechine-3-gallate, gallocatechin-3-O-gallate, gallocatechin gallate
Pathway Source
Pathways

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
epigallocatechin gallate + O2 = ? + 2 H2O
show the reaction diagram
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(-)-epigallocatechin gallate + H2O = (-)-epigallocatechin + gallic acid
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (20 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(-)-epigallocatechin gallate + O2 = ?
show the reaction diagram
-
S-adenosyl-L-methionine + epigallocatechin-3-O-gallate = S-adenosyl-L-homocysteine + ?
show the reaction diagram
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hydrolyzed potato starch + (-)-epigallocatechin gallate = epigallocatechin gallate 3'-O-alpha-D-glucopyranoside + epigallocatechin gallate 7-O-alpha-D-glucopyranoside
show the reaction diagram
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sucrose + (-)-epigallocatechin gallate = ?
show the reaction diagram
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3'-phosphoadenylyl sulfate + epigallocatechin gallate = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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3'-phosphoadenylylsulfate + epigallocatechin gallate = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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3'-phosphoadenylylsulfate + epigallocatechin gallate = adenosine 3',5'-bisphosphate + epigallocatechin gallate sulfate
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (8 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
enhances COX-2 and isoform mPGES-1 gene expression and production of prostaglandin E2. Induction of mPGES-1 is mediated by active ERK1/2MAP kinases and early growth response gene 1
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Inhibitor in Enzyme-catalyzed Reactions (121 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.012 mM, 50% inhibition
-
0.1 mM, 47% inhibition
-
completely suppresses the activity of DXR at 100 microM, and shows around 50% DXR inhibition at 25 microM
-
NADP+-competitive inhibitor of glucose-6-phosphate dehydrogenase
-
noncompetitive
-
IC50: 0.1 mM
-
non-competitive, binds to the enzyme in the proximity of the FAD binding site via formation of three hydrogen bonds
-
competitive
-
i.e. EGCG, from Thea sativa, slightly inhibits the liver microsomal enzyme
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catechin, non-competitive with both NADPH and GSSG, influence on glutathione recognition
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competitive, the inhibitor can form hydrogen bonds with Pro1223, Glu1265, Cys1225, Ser1229 and Arg1309. Hypermethylation of CpG islands in the promoter regions is an important mechanism to silence the expression of many important genes in cancer. (-)-Epigallocatechin-3-gallate can inhibit DNMT activity and reactivate methylation-silenced genes in cancer cells
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EGCG, non-competitive
-
IC50: 0.046 mM
-
50% inhibition of phosphorylated, active enzyme at 0.0077 mM, 50% inhibition of unphosphorylated, adenosine monophosphate-activated enzyme at 0.0339 mM
-
non-specific
-
time-dependent, irreversible
-
EGCG, inhibits NDPK and suppresses MDA-MB-435S cell growth
-
exposure to (-)-epigallocatechin-3-gallate reduces cellular proliferation and induced apoptosis in both MCF-7 and HL60 cells in vitro, although TERT mRNA expression is decreased only in MCF-7 cells
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inhibition by epigallocatechin-3-gallate of lactase is alleviated about 1.7fold by proline-rich proteins
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EGCG, noncompetitive inhibition
-
noncompetitive
-
inhibits in vitro hydrolysis of lactose by lactase phlorizin hydrolase
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nonpeptide inhibitor of NS3-SP from Rhodiola kirilowii. Methylation and acylation of hydroxyl groups cause a decrease of activity
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IC50: 0.000142 mM, expected to be useful for preventing and curing of Alzheimer‘s disease
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i.e. EGCG, inhibits the proteasomal chymotrypsin-like activity
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most abundant and biologically active ?avonoid present in green tea, strong competitive inhibitory activity
-
polyphenolic compound of green tea with putative anti-cancer activity
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a mixed-type noncompetitive inhibitor, contribution of the gallyl moiety, which forms a hexa-coordination complex with the Mg2+ ion, to enzymatic inhibition
-
10 microM, 55% residual activity
strong inhibition
-
noncompetitive with respect to ATP, reduces the affinity for vanadate, shifts the equilibrium of E1P and E2P toward E1P, and reduces the rate of the E1P to E2P transition
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3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (10 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.184
-
pH 6.8, 35°C

KM Value (16 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.3
-
-
0.101
-
pH 6.8, 35°C

Ki Value (28 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.014
-
-
0.34
-
pH 7.4, 37°C
0.00689
-
substrate: poly(dI-dC)/poly(dI-dC)
0.00165
-
pH 7.5, 25°C
0.0105
-
pH 7.5, 25°C
0.0028
-
pH 7.5, 37°C
0.08124
-
pH 6.0

IC50 Value (64 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.00072
-
in 0.1 M Tris buffer (pH 7.5), 150 mM NaCl, 6 mM MgCl2, at 30°C
0.00025
-
-
0.02
-
pH 7.4, 25°C
0.00033
-
pH 7.0, 23°C
0.1
-
IC50: 0.1 mM
0.0005
-
in 0.1 M sodium phosphate buffer, pH 8.0, using 50 mM sodium glutamate and 0.2 mM NAD+
0.0035
-
25°C, pH 7.4, cell lysate
0.046
-
IC50: 0.046 mM
0.38
-
pH 5.5, 20°C
0.008
0.01
-
0.0038
-
pH and temperature not specified in the publication
0.074
-
in 1.5 mM sodium phosphate buffer (pH 6.8), at 37°C
0.00851
-
-
0.000142
-
IC50: 0.000142 mM, expected to be useful for preventing and curing of Alzheimer‘s disease
0.0128
-
pH 7.5, 37°C
0.014
-
pH 7.5, 25°C
0.000086
0.000194
inhibition of the chymotrypsin-like activity of the proteasome in vitro, pH not specified in the publication, temperature not specified in the publication
0.0424
-
pH 7.5, 37°C
0.00049
-
at pH 8.0 and 25°C
3.78
-
-
0.001
-
pH 7.0, 37°C

References & Links

Links to other databases for epigallocatechin gallate

ChEBI
PubChem
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PubChem