Ligand apigenin

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Basic Ligand Information

Molecular Structure
Picture of apigenin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C15H10O5
apigenin
KZNIFHPLKGYRTM-UHFFFAOYSA-N
Synonyms:
4',5,7-trihydroxy-flavone, 4',5,7-trihydroxyflavone, 5,7,4'-trihydroxyflavone, 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one, chamomile

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
apigenin + [reduced NADPH-hemoprotein reductase] + O2 = ?
show the reaction diagram
-
apigenin + [reduced NADPH-hemoprotein reductase] + O2 = luteolin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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S-adenosyl-L-methionine + 5,7,4'-trihydroxyflavone = S-adenosyl-L-homocysteine + 4'-methoxy-5,7-dihydroxyflavone
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
naringenin + [reduced NADPH-hemoprotein reductase] + O2 = apigenin + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
-
apigenin-7-beta-glucopyranoside + H2O = apigenin + beta-D-glucose
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (38 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
apigenin + [reduced NADPH-hemoprotein reductase] + O2 = 3',8-dihydroxyapigenin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
apigenin + [reduced NADPH-hemoprotein reductase] + O2 = luteolin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
S-adenosyl-L-methionine + apigenin = S-adenosyl-L-homocysteine + 7-O-methylapigenin
show the reaction diagram
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S-adenosyl-L-methionine + apigenin = S-adenosyl-L-homocysteine + acacetin
show the reaction diagram
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S-adenosyl-L-methionine + 5,7,4'-trihydroxyflavone = S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyflavone
show the reaction diagram
-
S-adenosyl-L-methionine + 5,7,4'-trihydroxyflavone = S-adenosyl-L-homocysteine + 4'-methoxy-5,7-dihydroxyflavone
show the reaction diagram
-
S-adenosyl-L-methionine + 5,7,4'-trihydroxyflavone = S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyflavone
show the reaction diagram
-
S-adenosyl-L-methionine + 5,7,4'-trihydroxyflavone = S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyflavone
show the reaction diagram
-
UDP-glucose + apigenin = UDP + apigenin 7-O-beta-D-glucoside
show the reaction diagram
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UDPglucose + apigenin = UDP + apigenin 7-O-glucoside
show the reaction diagram
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UDPglucuronic acid + apigenin = UDP + apigenin 7-O-glucuronide
show the reaction diagram
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UDP-glucose + apigenin = UDP + ?
show the reaction diagram
-
UDP-glucose + apigenin = UDP + apigenin 7-O-beta-D-glucoside
show the reaction diagram
-
UDP-alpha-D-glucose + apigenin = UDP + ?
show the reaction diagram
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dimethylallyl diphosphate + apigenin = diphosphate + 3'-C-dimethylallyl apigenin
show the reaction diagram
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3,3-dimethylallyl diphosphate + apigenin = diphosphate + ?
show the reaction diagram
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dimethylallyl diphosphate + apigenin = diphosphate + ?
show the reaction diagram
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3'-phosphoadenylyl sulfate + apigenin = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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adenosine 3'-phosphate 5'-phosphosulfate + apigenin = adenosine 3',5'-bisphosphate + apigenin 7-sulfate
show the reaction diagram
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3'-phosphoadenylyl sulfate + apigenin = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (20 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
naringenin + [reduced NADPH-hemoprotein reductase] + O2 = apigenin + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
-
(2S)-naringenin + 2-oxoglutarate + O2 = (2R,3S)-cis-dihydrokaempferol + (2R,3R)-trans-dihydrokaempferol + apigenin + kaempferol + succinate + CO2 + H2O
show the reaction diagram
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-
apigenin 7-O-beta-D-glucopyranoside + H2O = apigenin + beta-D-glucopyranose
show the reaction diagram
-
-
apigenin 7-O-beta-D-glucopyranoside + H2O = apigenin + D-glucose
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
increases liver xanthine oxidase activities significantly, but has no effect on serum xanthine oxidase activities
-
apigenin reduces cell viability, and induces apoptotic cell death in a dose-dependent manner. In addition, it evokes a dose-related elevation of intracellular reactive oxygen species level. Treatment with various inhibitors of the NADPH oxidase significantly blunts both the generation of reactive oxygen species and induction of apoptosis induced by apigenin
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0.05 mM, 5fold increase in DNA-cleavage activity for isoform II beta, 2fold increase for isoform II alpha
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nearly 2fold induction of the heavy subunit gene promotor and heavy subunit expression
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Inhibitor in Enzyme-catalyzed Reactions (65 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.02 mM inhibits by ca. 50%
-
IC50: 0.0003 mM
-
uncompetitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
-
tyrosinase inhibitors from Marrubium velutinum, flavones/flavonols
-
IC50: 50 microM
-
complete inhibition at 0.01 mM
-
0.01 mM, 61% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
-
flavonone, non-competitive with both NADPH and GSSG, influence on glutathione recognition
-
IC50: 0.0176 mM
-
inhibition of p56lck
-
IC50: 0.023 mM
-
a flavonoid inhibitor of CDK6, CDK5, and CDK1
-
antagonizes aminoflavone by inhibiting SULT1A1
-
IC50: 0.0105 mM, PDB3; IC50: 0.0167 mM, PDB2; IC50: 0.0254 mM, PDB1
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weak, but still statistically significant inhibition of PDE5A1
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26% inhibition at 0.1 mM, 42% at 0.3 mM
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i.e. apigenin, inhibits isomerization of 4,2',4'-trihydroxychalcone
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inhibition of enzyme-mediated religation of DNA
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3D Structure of Enzyme-Ligand-Complex (PDB) (5 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (4 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
13.4
-
pH 7.0, 25°C

KM Value (23 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0058
-
pH 7.0, 25°C
0.0033
-
pH 7, 25°C
0.0033
-
pH 7.0, 25°C
0.05
-
-
0.0046
-
pH 7.8, 20°C
0.0027
-
-
0.0053
-
pH 6.5, 37°C, recombinant SULT1E1; pH 6.5, 37°C, SULT1E1

Ki Value (11 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0012
-
-
3.4
-
-
0.002
-
-
0.00028
-
pH 7.5, 25°C
0.0004
-
-
0.00074
-
-
0.0374
-
-

IC50 Value (38 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0218
-
-
0.0003
-
IC50: 0.0003 mM
0.00043
-
IC50: 430 nM
0.0166
-
pH 7.0, 23°C
0.05
-
IC50: 50 microM
0.036
-
pH 7.5, 22°C
0.00113
-
pH and temperature not specified in the publication
0.0176
-
IC50: 0.0176 mM
0.0008
-
-
0.023
-
IC50: 0.023 mM
0.022
-
in 0.1 M sodium phosphate buffer, pH 7.0, at 30°C
0.0357
-
at pH 7.0 and 25°C
0.0041
-
-
0.2
-
above, pH 6.8, 30°C
0.18
-
pH and temperature not specified in the publication
0.04
-
pH 7.4, 37°C

References & Links

Links to other databases for apigenin

ChEBI
PubChem
ChEBI
PubChem