Any feedback?
Please rate this page
(ligand.php)
(0/150)

BRENDA support

Ligand genistein

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.

Basic Ligand Information

Molecular Structure
Picture of genistein (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C15H10O5
genistein
TZBJGXHYKVUXJN-UHFFFAOYSA-N
Synonyms:
4',5,7-trihydroxy-isoflavone, 5,7,4'-trihydroxyisoflavone, 5,7,4'trihydroxyisoflavone, 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one, baichanin A, genistein[side 1], genistein[side 2], genisteol, genisterin, prunetol, sophoricol

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
genistein + [reduced NADPH-hemoprotein reductase] + O2 = 2'-hydroxygenistein + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
genistein + [reduced NADPH-hemoprotein reductase] + O2 = 2'-hydroxygenistein + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
S-adenosyl-L-methionine + genistein = S-adenosyl-L-homocysteine + biochanin A
show the reaction diagram
-
UDP-glucuronate + genistein = UDP + genistein beta-D-glucuronoside
show the reaction diagram
-
UDP-glucose + genistein = UDP + genistein 7-O-beta-D-glucoside
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
genistin + H2O = genistein + beta-D-glucopyranose
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (57 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
genistein + [reduced NADPH-hemoprotein reductase] + O2 = 3',8-dihydroxygenistein + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
genistein + NADPH + O2 = ?
show the reaction diagram
-
genistein + [reduced NADPH-hemoprotein reductase] + O2 = 2'-hydroxygenistein + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
genistein + [reduced NADPH-hemoprotein reductase] + O2 = 2'-hydroxygenistein + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
S-adenosyl-L-methionine + 5,7,4'-trihydroxyisoflavone = S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyisoflavone
show the reaction diagram
-
S-adenosyl-L-methionine + genistein = S-adenosyl-L-homocysteine + biochanin A
show the reaction diagram
-
S-adenosyl-L-methionine + genistein = S-adenosyl-L-homocysteine + O-methoxy-genistein
show the reaction diagram
-
S-adenosyl-L-methionine + genistein = ?
show the reaction diagram
-
S-adenosyl-L-methionine + genistein = ?
show the reaction diagram
-
S-adenosyl-L-methionine + genistein = S-adenosyl-L-homocysteine + O-methoxy-genistein
show the reaction diagram
-
UDP-glucose + genistein = UDP + genistein 7-O-beta-D-glucoside
show the reaction diagram
-
UDP-glucose + genistein = UDP + ?
show the reaction diagram
-
dimethylallyl diphosphate + genistein = ?
show the reaction diagram
-
dimethylallyl diphosphate + genistein = diphosphate + ?
show the reaction diagram
-
dimethylallyl diphosphate + genistein = diphosphate + wighteone
show the reaction diagram
-
3'-phosphoadenylylsulfate + genistein = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
-
adenosine 3'-phosphate 5'-phosphosulfate + genistein = adenosine 3',5'-bisphosphate + genistein 7-sulfate
show the reaction diagram
-
3'-phosphoadenylylsulfate + genistein = adenosine 3',5'-bisphosphate + genistein 7-sulfate + genistein 4'-sulfate
show the reaction diagram
-
ATP + H2O + genistein[side 1] = ADP + phosphate + genistein[side 2]
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (21 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(2S)-naringenin + O2 + [reduced NADPH-hemoprotein reductase] = genistein + 2 H2O + [oxidized NADPH-hemoprotein reductase]
show the reaction diagram
-
genistein-7-glucoside + H2O = genistein + D-glucose
show the reaction diagram
-
genistin + H2O = genistein + beta-D-glucopyranose
show the reaction diagram
-
genistin + H2O = beta-D-glucose + genistein
show the reaction diagram
-
2,5,7,4'-tetrahydroxyisoflavanone = genistein + H2O
show the reaction diagram
-
ATP + H2O + genistein[side 1] = ADP + phosphate + genistein[side 2]
show the reaction diagram
-

Activator in Enzyme-catalyzed Reactions (8 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.05 mM, 8fold increase in DNA-cleavage activity for isoform II beta, 5fold increase for isoform II alpha
-

Inhibitor in Enzyme-catalyzed Reactions (89 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
inhibition of isoenzyme BB-ADH, no inhibition of isoenzyme AA-ADH and TT-ADH
-
inhibits by 19%
-
isoflavone, isolated and purified from korean soybean paste, structural analysis
-
noncompetitive
-
i.e. 4',5,7-trihydroxyisoflavone
-
0.5 mM, almost complete inhibition. The inhibition is increased when genistein is preincubated with the enzyme and NADH
-
5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one
-
0.0287 mM
-
0.003 mM, 25.4% inhibition. 0.03 mM, 79.5% inhibition; 0.003 mM, 38.8% inhibition. 0.03 mM, 97.6% inhibition; weak; weak
-
inhibition of isozymes GST M1-1 and M2-2
-
0.2 mM, 20% inhibition
-
partial inhibition
-
decreases Plk1 expression
-
rapid inhibition in vivo
-
competitive versus the DNA primer and non-competitive versus the dNTP substrate, IC50: 0.0287 mM
-
IC50: 0.0025 mM, competitive
-
potent mixed type inhibitor
-
inhibits sPLA(2) enzymes of inflammatory exudates in a concentration dependent manner. Increasing the Ca2+ concentration from 2.5 to 15 mM and substrate concentration up to 0.000120 mM does not alter the level of inhibition
-
65.7% inhibition at 1 mM
-
IC50: 0.0017 mM, PDB2; IC50: 0.0129 mM, PDB3; IC50: 0.0168 mM, PDB1
-
IC50: 0.073 mM, PDB5
-
IC50: 0.0095 mM, PDE4
-
a isoflavone, 0.888 mM, pH 6.0, room temperature, 25.1% maximum inhibition
-
mixed type
-
0.003-0.3 mM genistein decreases the angiotensin-converting enzyme activity in blood plasma in a concentration-dependent manner; the isoflavone inhibits ACE in plasma and alters the vascular responses to angiotensin I and bradykinin, overview
-
broad spectrum tyrosine kinase inhibitor, significantly inhibits BFT-stimulated interleukin-8 production
-
markedly suppresses the VEGF mRNA induction in MT clones without affecting the VEGF expression in control clones
-
weak
-
IC50: 0.0023 mM
-
suppresses binding of proinsulin to PDI, inhibits 66% of PDIs chaperone activity
-
i.e. genistein, inhibits isomerization of 4,2',4'-trihydroxychalcone
-
bindings of genistein and ATP are competitive
-
tyrosine kinase inhibitor, block phosphorylation of alpha-subunit of the Na+,K+-ATPase
-

3D Structure of Enzyme-Ligand-Complex (PDB) (25 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (27 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
1.6
-
at pH 7.0 and 30°C
0.027
-
pH not specified in the publication, 37°C

KM Value (31 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0735
-
pH 7, 25°C
0.0735
-
pH 7.0, 25°C
0.0226
-
at pH 7.0 and 30°C
0.16
-
pH not specified in the publication, 37°C
0.041
-
pH 7.4, 37°C

Ki Value (13 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.00055
-
pH 7.4, 25°C, recombinant enzyme
0.0739
-
-
0.0005
-
-

IC50 Value (26 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0059
-
pH 7.4, 25°C
0.0061
-
pH 6.0
0.0042
-
pH 7.4, 25°C, recombinant enzyme
0.001
-
IC50: 0.001 mM
0.125
-
pH 7.4, 27°C
0.00468
-
pH 7.0 and 37°C
0.71
-
pH not specified in the publication, temperature not specified in the publication
0.045
-
-
0.004
0.005
pH 7.4, 30°C, purified recombinant isozymes GST M1-1 and M2-2
0.0287
-
competitive versus the DNA primer and non-competitive versus the dNTP substrate, IC50: 0.0287 mM
0.0025
-
IC50: 0.0025 mM, competitive
0.0209
-
at pH 7.0 and 25°C
0.073
-
IC50: 0.073 mM, PDB5
0.0095
-
IC50: 0.0095 mM, PDE4
0.007
-
pH 6.8, 30°C
0.0366
-
pH 7.4, 37°C
0.0981
-
at pH 2.0 and 37°C
0.0023
-
IC50: 0.0023 mM

References & Links

Links to other databases for genistein

ChEBI
PubChem
ChEBI
PubChem