Ligand kaempferol

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 kaempferol (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C15H10O6
kaempferol
IYRMWMYZSQPJKC-UHFFFAOYSA-N
Synonyms:
3,4',5,7-tetrahydroxyflavone, 3,5,7,4'-tetrahydroxyflavone, 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one, 5,7,4'-trihydroxyflavonol, kaemferol

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
kaempferol + [reduced NADPH-hemoprotein reductase] + O2 = quercetin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
S-adenosyl-L-methionine + kaempferol = S-adenosyl-L-homocysteine + 7-O-methylkaempferol
show the reaction diagram
-
S-adenosyl-L-methionine + kaempferol = S-adenosyl-L-homocysteine + 7-O-methylkaempferol
show the reaction diagram
-
UDP-galactose + kaempferol = UDP + kaempferol 3-O-beta-D-galactoside
show the reaction diagram
-
UDP-glucose + kaempferol = UDP + kaempferol 7-O-beta-D-glucoside
show the reaction diagram
-
UDP-alpha-D-glucose + kaempferol = UDP + kaempferol 3-O-beta-D-glucoside
show the reaction diagram
UDP-alpha-D-xylose + kaempferol = UDP + kaempferol 3-O-beta-D-xyloside
show the reaction diagram
-

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

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE

Substrate in Enzyme-catalyzed Reactions (57 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
kaempferol + [reduced NADPH-hemoprotein reductase] + O2 = quercetin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
S-adenosyl-L-methionine + kaempferol = S-adenosyl-L-homocysteine + kaempferide
show the reaction diagram
-
S-adenosyl-L-methionine + kaempferol = ?
show the reaction diagram
-
S-adenosyl-L-methionine + kaempferol = 7-O-methylkaempferol
show the reaction diagram
-
UDP-alpha-D-glucose + kaempferol = UDP + kaempferol 7-O-beta-D-glucoside
show the reaction diagram
-
UDPglucose + kaempferol = UDP + 4-O-beta-D-glucosyl-kaempferol
show the reaction diagram
-
UDP-L-rhamnose + kaempferol = kaempferol-3-O-rhamnoside + UDP
show the reaction diagram
-
UDP-D-glucuronate + kaempferol = UDP + kaempferol 7-O-beta-D-glucuronoside
show the reaction diagram
-
UDP-glucose + kaempferol = UDP + kaempferol 7-O-beta-D-glucoside
show the reaction diagram
-
UDP-alpha-D-glucose + kaempferol = UDP + ?
show the reaction diagram
-
UDPglucose + kaempferol = ?
show the reaction diagram
-
UDP-alpha-D-glucose + kaempferol = UDP + astragalin
show the reaction diagram
-
UDP-alpha-D-glucose + kaempferol = UDP + ?
show the reaction diagram
-
UDP-alpha-D-glucose + kaempferol = UDP + kaempferol 4'-O-glucoside
show the reaction diagram
-
UDP-alpha-D-xylose + kaempferol = UDP + kaempferol 3-O-beta-D-xyloside
show the reaction diagram
-
3,3-dimethylallyl diphosphate + kaempferol = diphosphate + ?
show the reaction diagram
-
3'-phosphoadenylylsulfate + kaempferol = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
-
3'-phosphoadenylylsulfate + kaempferol = adenosine 3',5'-bisphosphate + kaempferol 3-sulfate
show the reaction diagram
-
adenosine 3'-phosphate 5'-phosphosulfate + kaempferol = adenosine 3',5'-bisphosphate + kaempferol 7-sulfate
show the reaction diagram
-
3'-phosphoadenylylsulfate + kaempferol = adenosine 3',5'-bisphosphate + kaempferol sulfate
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (15 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
UDP + kaempferol 3-O-beta-D-galactoside = UDP-alpha-D-galactose + kaempferol
show the reaction diagram
-
-
kaempferol 3-O-beta-D-glucuronide + H2O = kaempferol + D-glucuronate
show the reaction diagram
-
-
kaempferol 3-O-rutinoside + H2O = kaempferol + rutinose
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
2fold induction of the heavy subunit gene promotor and heavy subunit expression
-

Inhibitor in Enzyme-catalyzed Reactions (85 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
IC50: 380 nM
-
inhibits at lower concentration
-
IC50: 20 microM
-
complete inhibition at 0.01 mM
-
slightly, flavonol, non-competitive with both NADPH and GSSG, influence on glutathione recognition
-
0.1 mM, strong inhibition of N-acetylserotonin methyltransferase activity
-
the formation of ethylglucuronoside is inhibited by the flavonoids for all enzymes except for UGT2B15, mechanism-based inhibition; the formation of ethylglucuronoside is inhibited by the flavonoids for all UGT enzymes except for UGT2B15, mechanism-based inhibition; the formation of ethylglucuronoside is inhibited by the flavonoids for all UGT enzymes except for UGT2B15, mechanism-based inhibition; the formation of ethylglucuronoside is inhibited by the flavonoids for all UGT enzymes except for UGT2B15, mechanism-based inhibition; the formation of ethylglucuronoside is inhibited by the flavonoids for all UGT enzymes except for UGT2B15, mechanism-based inhibition; the formation of ethylglucuronoside is inhibited by the flavonoids for all UGT enzymes except for UGT2B15, mechanism-based inhibition; the formation of ethylglucuronoside is inhibited by the flavonoids for all UGT enzymes except for UGT2B15, mechanism-based inhibition
-
inhibition of p56lck
-
a less potent flavonoid inhibitor of CDK6, CDK5, and CDK1
-
strong binding affinity to the enzyme (RdRp)
-
a flavonol, 0.888 mM, pH 6.0, room temperature, 34.5% maximum inhibition
-
13.7% inhibition at 0.03 mM
-
IC50 for recombinant SrtA(DELTA24): 0.07794 mM, no antibacterial activity against Staphylococcus aureus
-
IC50 for recombinant SrtB(DELTA30): 0.02455 mM, no antibacterial activity against Staphylococcus aureus
-
slight inhibition
-
mixed inhibition
-

3D Structure of Enzyme-Ligand-Complex (PDB) (23 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (21 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
466.7
-
pH 6, 25°C
17
-
pH 7.0, 25°C
1.25
-
recombinant enzyme, at pH 8.0 and 30°C
0.46
-
pH 7.5, 30°C, with UDP-glucose, recombinant enzyme
61.1
-
pH 7.5, 43°C, forward reaction
5.65
-
with UDP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C

KM Value (49 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.013
-
pH 6, 25°C
0.001
-
pH 7.0, 25°C
0.0017
-
pH 7, 25°C
0.0017
-
pH 7.0, 25°C
0.013
-
30°C
0.174
-
recombinant enzyme, at pH 8.0 and 30°C
0.0263
-
-
0.02809
-
pH 7.5, 30°C, with UDP-glucose, recombinant enzyme
0.01
-
-
0.00209
-
with UDP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C
0.0263
-
pH 7.0
0.00083
-
pH 7.5, 30°C

Ki Value (12 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0036
-
-
0.006
-
-
0.043
-
-
0.3
-
pH not specified in the publication, 30°C, value above
0.1514
-
pH 8.0, 25°C, recombinant enzyme
0.021
-
in the presence of increasing amounts of inhibitor at different concentrations of the substrates methylglyoxal and glutathione, Dixon plot analysis, significantly lower inhibition than that with curcumin, competitive inhibition, pH 7.0, 30°C

IC50 Value (46 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0212
-
pH 7.0
0.00011
-
at pH 7.4 and 37°C
0.017
-
pH 6.0
0.02
-
above, pH 7.4, 25°C, recombinant enzyme
0.001
0.005
IC50 between 0.001 and 0.005 mM, reduction of estra-4-en-3,17-dione
0.00038
-
IC50: 380 nM
0.0744
-
pH 7.0, 23°C
0.00208
-
-
0.02
-
IC50: 20 microM
0.0012
-
pH and temperature not specified in the publication
0.001
0.002
pH 7.4, 30°C, purified recombinant isozymes GST M1-1 and M2-2
0.02016
-
pH 7.4, 37°C
0.012
-
pH 6.8, 30°C
0.0329
-
pH 7.4, 37°C
0.109
-
pH and temperature not specified in the publication
0.07794
-
IC50 for recombinant SrtA(DELTA24): 0.07794 mM, no antibacterial activity against Staphylococcus aureus
0.02455
-
IC50 for recombinant SrtB(DELTA30): 0.02455 mM, no antibacterial activity against Staphylococcus aureus
0.0374
-
at pH 2.0 and 37°C
0.031
-
pH 8.0, 25°C, recombinant enzyme
0.035
-
pH 8.0, 25°C, recombinant enzyme
0.0206
-
indicate that the hydroxy groups at the B ring of flavonoids contribute to the human GLO I inhibitory activity of the flavonoid compounds at 25°C, pH 7.0

References & Links

Links to other databases for kaempferol

ChEBI
PubChem
ChEBI
PubChem