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

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

KEGG

Biosynthesis of phenylpropanoids, Biosynthesis of secondary metabolites, Flavone and flavonol biosynthesis, Flavonoid biosynthesis

MetaCyc

flavonoid biosynthesis (in equisetum), flavonol acylglucoside biosynthesis I - kaempferol derivatives, flavonol biosynthesis, kaempferide triglycoside biosynthesis, kaempferol diglycoside biosynthesis (pollen-specific)

more

close all tables

open all tables

Roles as Enzyme Ligand

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

top print hide

1.14.14.82

kaempferol + [reduced NADPH-hemoprotein reductase] + O2 = quercetin + [oxidized NADPH-hemoprotein reductase] + H2O

688651, 713316

2.1.1.B75

S-adenosyl-L-methionine + kaempferol = S-adenosyl-L-homocysteine + 7-O-methylkaempferol

713037

2.1.1.B76

S-adenosyl-L-methionine + kaempferol = S-adenosyl-L-homocysteine + 7-O-methylkaempferol

UDP-galactose + kaempferol = UDP + kaempferol 3-O-beta-D-galactoside

654156, 654154

2.4.1.237

UDP-glucose + kaempferol = UDP + kaempferol 7-O-beta-D-glucoside

723498

2.4.1.91

UDP-alpha-D-glucose + kaempferol = UDP + kaempferol 3-O-beta-D-glucoside

674953, 674117, 673320, 688092

2c1z, 3D-view

2.4.2.56

UDP-alpha-D-xylose + kaempferol = UDP + kaempferol 3-O-beta-D-xyloside

723806

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

top print hide

1.14.20.6

2 entries

Substrate in Enzyme-catalyzed Reactions (58 results)

kaempferol + NADPH + H+ + O2 = herbacetin + NADP+ + H2O

kaempferol + [reduced NADPH-hemoprotein reductase] + O2 = quercetin + [oxidized NADPH-hemoprotein reductase] + H2O

439002, 688651, 439004, 439010, 746151, 438999, 439009, 713316, 726210, 742706, 742707, 743169

2.1.1.155

S-adenosyl-L-methionine + kaempferol = S-adenosyl-L-homocysteine + kaempferide

S-adenosyl-L-methionine + kaempferol = ?

S-adenosyl-L-methionine + kaempferol = 7-O-methylkaempferol

UDP-alpha-D-glucose + kaempferol = UDP + kaempferol 7-O-beta-D-glucoside

UDPglucose + kaempferol = UDP + 4-O-beta-D-glucosyl-kaempferol

UDP-L-rhamnose + kaempferol = kaempferol-3-O-rhamnoside + UDP

659272

2.4.1.17

UDP-D-glucuronate + kaempferol = UDP + kaempferol 7-O-beta-D-glucuronoside

692786

2.4.1.170

UDP-glucose + kaempferol = UDP + kaempferol 7-O-beta-D-glucoside

UDP-alpha-D-glucose + kaempferol = UDP + ?

UDPglucose + kaempferol = ?

489108

2.4.1.357

UDP-alpha-D-glucose + kaempferol = UDP + astragalin

749324

2.4.1.358

UDP-alpha-D-glucose + kaempferol = UDP + ?

UDP-alpha-D-glucose + kaempferol = UDP + kaempferol 4'-O-glucoside

759936

2.4.2.56

UDP-alpha-D-xylose + kaempferol = UDP + kaempferol 3-O-beta-D-xyloside

723806

2.5.1.70

3,3-dimethylallyl diphosphate + kaempferol = diphosphate + ?

3'-phosphoadenylylsulfate + kaempferol = adenosine 3',5'-bisphosphate + ?

660901

2.8.2.25

3'-phosphoadenylylsulfate + kaempferol = adenosine 3',5'-bisphosphate + kaempferol 3-sulfate

644307, 644308, 644310, 644311

2.8.2.28

adenosine 3'-phosphate 5'-phosphosulfate + kaempferol = adenosine 3',5'-bisphosphate + kaempferol 7-sulfate

676654

2.8.2.4

3'-phosphoadenylylsulfate + kaempferol = adenosine 3',5'-bisphosphate + kaempferol sulfate

645905

Product in Enzyme-catalyzed Reactions (15 results)

UDP + kaempferol 3-O-beta-D-galactoside = UDP-alpha-D-galactose + kaempferol

3.2.1.31

kaempferol 3-O-beta-D-glucuronide + H2O = kaempferol + D-glucuronate

3.2.1.B31

kaempferol 3-O-rutinoside + H2O = kaempferol + rutinose

Activator in Enzyme-catalyzed Reactions (1 result)

top print hide

6.3.2.2

2fold induction of the heavy subunit gene promotor and heavy subunit expression

651391

Inhibitor in Enzyme-catalyzed Reactions (87 results)

IC50: 380 nM

inhibits at lower concentration

IC50: 20 microM

complete inhibition at 0.01 mM

712711

1.8.1.7

slightly, flavonol, non-competitive with both NADPH and GSSG, influence on glutathione recognition

394769

2.1.1.4

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

665982

2.7.7.48

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

664280

3.4.22.71

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

k_cat Value (Turnover Number) (21 results)

top print hide

1.13.11.24

466.7

pH 6, 25°C

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

759279

2.4.1.234

61.1

pH 7.5, 43°C, forward reaction

655974

2.4.1.357

5.65

with UDP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C

749324

2.4.1.91

3 entries

K_M Value (49 results)

top print hide

1.13.11.24

0.013

pH 6, 25°C

685423

1.14.14.81

0.001

pH 7.0, 25°C

0.0017

pH 7, 25°C

655462

2.1.1.231

0.0017

pH 7.0, 25°C

655462

2.1.1.76

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

723806

K_i Value (12 results)

0.0036

0.006

0.043

0.3

pH not specified in the publication, 30°C, value above

717627

3.5.2.3

0.1514

pH 8.0, 25°C, recombinant enzyme

756119

4.4.1.5

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

694824

IC₅₀ Value (46 results)

top print hide

1.1.1.100

0.0212

pH 7.0

704843

1.1.1.149

0.00011

at pH 7.4 and 37°C

740126

1.1.1.184

0.017

pH 6.0

685454

1.1.1.218

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

670897

1.10.5.1

0.00038

IC50: 380 nM

658434

1.11.1.6

0.0744

pH 7.0, 23°C

0.00208

0.02

IC50: 20 microM

675299

1.6.3.1

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

681559

3.4.14.4

0.0329

pH 7.4, 37°C

0.109

pH and temperature not specified in the publication

718420

3.4.22.70

0.07794

IC50 for recombinant SrtA(DELTA24): 0.07794 mM, no antibacterial activity against Staphylococcus aureus

664280

3.4.22.71

0.02455

IC50 for recombinant SrtB(DELTA30): 0.02455 mM, no antibacterial activity against Staphylococcus aureus

664280

3.4.23.1

0.0374

at pH 2.0 and 37°C

755552

3.5.2.3

0.031

pH 8.0, 25°C, recombinant enzyme

733422

3.5.2.5

0.035

pH 8.0, 25°C, recombinant enzyme

733422

4.4.1.5

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

691217