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Ligand trans-4-coumaric acid

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

BRENDA

phenylpropanoid biosynthesis, suberin monomers biosynthesis, tyrosine metabolism

KEGG

Biosynthesis of phenylpropanoids, Biosynthesis of secondary metabolites, Degradation of aromatic compounds, Isoquinoline alkaloid biosynthesis, Phenylpropanoid biosynthesis, Tyrosine metabolism, Ubiquinone and other terpenoid-quinone biosynthesis more

MetaCyc

4-coumarate degradation (aerobic), 4-coumarate degradation (anaerobic), 4-hydroxybenzoate biosynthesis I (eukaryotes), 4-hydroxybenzoate biosynthesis III (plants), 4-hydroxybenzoate biosynthesis IV (plants), 6-gingerol analog biosynthesis (engineered), Amaryllidacea alkaloids biosynthesis, avenanthramide biosynthesis, coumarins biosynthesis (engineered), curcuminoid biosynthesis, flavonoid biosynthesis, flavonoid di-C-glucosylation, free phenylpropanoid acid biosynthesis, L-tyrosine degradation V (reductive Stickland reaction), naringenin biosynthesis (engineered), phaselate biosynthesis, phenylpropanoid biosynthesis, phenylpropanoid biosynthesis, initial reactions, rosmarinic acid biosynthesis I, suberin monomers biosynthesis, superpathway of scopolin and esculin biosynthesis, umbelliferone biosynthesis, vanillin biosynthesis I, xanthohumol biosynthesis more

Show all BRENDA pathways known for trans-4-coumaric acid

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (6 results)

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Show Natural Substrate (6 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.126

UDP-alpha-D-glucose + 4-hydroxycinnamate = UDP + 4-O-(beta-D-glucopyranosyl)-4-hydroxycinnamate

706373

-

2.4.1.177

UDP-glucose + 4-coumarate = UDP + 4-coumaroyl beta-D-glucoside

759563

-

2.4.1.209

UDP-glucose + cis-p-coumarate + H2O = 4'-O-beta-D-glucosyl-cis-p-coumarate + UDP

288689

-

4.1.1.102

4-coumarate = 4-vinylphenol + CO2

733069

-

6.2.1.12

ATP + 4-coumarate + CoA = ?

621, 603, 620, 615, 599, 597, 595, 600

-

6.2.1.12

ATP + 4-coumarate + CoA = AMP + diphosphate + 4-coumaroyl-CoA

745743, 728481, 745107, 675650, 727643, 745872, 746109, 746513, 672870, 726875, 728512, 728464, 727118, 728204, 746098, 744736, 745004, 746036, 653527, 652422, 651262, 653481, 653597, 653015, 653496, 651117, 652146, 653536, 653477, 676288, 676302, 676305, 746000

-

6.2.1.12

2 entries

In Vivo Product in Enzyme-catalyzed Reactions (16 results)

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Show Natural Product (16 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.91

trans-cinnamate + [reduced NADPH-hemoprotein reductase] + O2 = 4-coumaric acid + [oxidized NADPH-hemoprotein reductase] + H2O

0

-

1.14.14.91

trans-cinnamate + [reduced NADPH-hemoprotein reductase] + O2 = 4-hydroxycinnamate + [oxidized NADPH-hemoprotein reductase] + H2O

0

-

1.14.14.91

2 entries

1.3.8.15

phloretate + electron-transfer flavoprotein EtfA-EtfB = 4-coumarate + reduced electron-transfer flavoprotein EtfA-EtfB

0

-

2.4.1.B70

1-O-(4-coumaroyl)-beta-D-glucose + cyanidin 3-O-[2-O-(2-O-(sinapoyl)-beta-D-xylosyl)-6-O-(6-(4-coumaroyl))-beta-D-glucoside] 5-O-[6-O-(malonyl)-beta-D-glucoside] = 4-coumarate + cyanidin 3-O-[2-O-(2-O-(sinapoyl)-beta-D-xylosyl)-6-O-(6-(4-O-beta-D-glucosyl)-4-coumaroyl)-beta-D-glucoside] 5-O-[6-O-(malonyl)-beta-D-glucoside]

0

-

3.1.1.73

methyl 4-coumarate + H2O = 4-coumaric acid + methanol

0

-

3.1.1.73

brewers spent grain + H2O = ferulic acid + p-coumaric acid + 5,5'-diferulate + ?

0

-

3.1.1.73

brewers spent grain + H2O = ferulic acid + p-coumaric acid + ?

0

-

3.1.1.73

feruloyl polysaccharide + H2O = ferulic acid + p-coumaric acid + ?

0

-

3.1.1.73

italian rye gras cell walls + H2O = ferulic acid + p-coumaric acid + ?

0

-

3.1.1.73

maize internodes + H2O = ferulic acid + p-coumaric acid + ?

0

-

3.1.1.73

oat straw + H2O = ferulic acid + p-coumaric acid + ?

0

-

3.1.1.73

spent grain + H2O = ferulic acid + p-coumaric acid + ?

0

-

3.1.1.73

wheat bran + H2O = ferulic acid + p-coumaric acid + 5,5'-diferulate + ?

0

-

3.1.1.73

wheat bran + H2O = ferulic acid + p-coumaric acid + ?

0

-

3.1.1.73

10 entries

4.3.1.23

L-tyrosine = trans-p-hydroxycinnamate + NH3

0

-

4.3.1.25

L-tyrosine = trans-p-hydroxycinnamate + NH3

0

-

Substrate in Enzyme-catalyzed Reactions (56 results)

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Show Substrate (56 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.10.3.2

p-coumaric acid + O2 = ?

687239

-

1.10.3.2

p-coumaric acid + O2 = ? + H2O

396394, 396353

-

1.11.1.10

trans-4-hydroxycinnamic acid + Br- + H+ + H2O2 = trans-1-bromo-2-(4-hydroxyphenyl)ethylene + H2O

348325

-

1.11.1.10

trans-4-hydroxycinnamic acid + Cl- + H+ + H2O2 = trans-1-chloro-2-(4-hydroxyphenyl)ethylene + H2O

348325

-

1.10.3.2

2 entries

1.11.1.10

2 entries

1.11.1.7

p-coumaric acid + H2O2 = ?

700707, 675644, 439765, 673542, 695687

3uba, 3D-view

1.14.14.9

4-coumarate + NADH + H+ + O2 = ? + NAD+ + H2O

764477

-

1.14.14.9

4-coumaric acid + FADH2 + O2 = caffeic acid + FAD + H2O

727212, 765827

-

1.14.14.9

p-coumaric acid + FADH2 + O2 = caffeic acid + FAD + H2O

744140

-

1.14.18.1

4-coumaric acid + O2 = ?

673560, 744953

-

1.14.18.1

p-coumaric acid + O2 + AH2 = caffeic acid + H2O + A

636382, 636434, 636380, 636450, 636424, 687875

-

1.14.18.1

p-coumaric acid + O2 = ?

712227, 700667

-

1.14.18.1

p-coumaric acid + O2 = caffeic acid + H2O

697659, 699628

-

1.14.14.9

3 entries

1.14.18.1

4 entries

1.14.99.15

4-coumaric acid + AH2 + O2 = caffeic acid + A + H2O

726728

-

1.2.1.30

p-coumaric acid + NADPH + ATP = 3-(4-hydroxphenyl)-2-propen-1-al + NADP+ + AMP + H2O

288180, 288182, 288183

-

1.3.1.11

4-coumarate + NADH = ?

390510

-

1.3.1.31

4-coumaric acid + NAD+ = 3-(4-hydroxyphenyl)propionic acid + NADH + H+

740951

-

1.3.1.31

p-coumaric acid + NADH + H+ = ? + NAD+

763450

-

1.3.1.31

2 entries

2.3.1.152

UDP-glucose + 4-coumaric acid = ?

16328

-

2.4.1.104

UDP-glucose + 4-coumaric acid = UDP + 4-O-glucosylcoumaric acid

488400

-

2.4.1.120

UDP-alpha-D-glucose + 4-coumarate = UDP + 1-O-(4-coumaroyl)-beta-D-glucose

660293, 660175

-

2.4.1.120

UDP-alpha-D-glucose + 4-coumaric acid = UDP + 1-O-(4-coumaroyl)-beta-D-glucose

488516, 488519

-

2.4.1.120

2 entries

2.4.1.121

UDPglucose + p-coumaric acid = UDP + p-coumaroyl-beta-1-D-glucose

488524

-

2.4.1.126

UDP-alpha-D-glucose + 4-hydroxycinnamate = UDP + 4-O-(beta-D-glucopyranosyl)-4-hydroxycinnamate

706373

-

2.4.1.126

UDPglucose + p-coumaric acid = UDP + p-coumaroyl-beta-D-glucose + 4-O-glucosyl-p-coumaric acid

639510

-

2.4.1.126

2 entries

2.4.1.136

UDP-glucose + p-coumarate = UDP + 1-O-p-coumaroyl-beta-D-glucose

488579

-

2.4.1.177

UDP-glucose + 4-coumarate = UDP + 4-coumaroyl beta-D-glucoside

759563

-

2.4.1.177

UDP-glucose + p-coumarate = UDP + p-coumaroyl-D-glucose

637802, 637801

-

2.4.1.177

p-coumaric acid + UDP-glucose = UDP + p-coumaroyl-beta-D-glucoside

676590

-

2.4.1.177

UDP-glucose + p-coumaric acid = UDP + p-coumaroyl beta-D-glucose

660116

-

2.4.1.209

cis-p-coumarate + UDP-glucose + H2O = 4'-O-beta-D-glucosyl-cis-p-coumarate + UDP

288689

-

2.4.1.209

UDP-glucose + cis-p-coumarate + H2O = 4'-O-beta-D-glucosyl-cis-p-coumarate + UDP

288689

-

2.4.1.209

UDP-glucose + cis-p-coumarate = 4'-O-beta-D-glucosyl-cis-p-coumarate + UDP

288689

-

2.4.1.237

UDP-glucose + 4-coumaric acid = UDP + ?

660792

-

2.4.1.237

UDP-glucose + p-coumaric acid = UDP + (2E)-3-[4-(beta-D-glucopyranosyloxy)phenyl]prop-2-enoic acid

489572

-

2.4.1.35

UDP-glucose + p-coumaric acid = UDP + p-coumaroyl 3-O-beta-D-glucoside

757325

-

2.4.1.35

UDPglucose + p-coumaric acid = UDP + 4-beta-D-glucopyranosyloxy-trans-cinnamic aicd

489104

-

2.4.1.35

UDPglucose + p-hydroxycinnamic acid = UDP + 4-beta-D-glucopyranosyloxy-trans-cinnamic acid

489108

-

2.4.1.177

4 entries

2.4.1.209

3 entries

2.4.1.237

2 entries

2.4.1.35

3 entries

2.4.1.81

UDP-glucose + 4-coumaric acid = UDP + 1-O-[4-coumaroyl]-beta-D-glucopyranose

759388

-

2.5.1.111

dimethylallyl diphosphate + 4-coumarate = diphosphate + 4-O-dimethylallylcoumarate

722465

-

2.8.2.1

4-nitrophenyl sulfate + 4-coumaric acid = 4-nitrophenol + 4-sulfocinnamic acid

738167

-

2.8.3.23

3,4-dihydroxyphenylpropanoyl-CoA + 4-coumarate = 3,4-dihydroxyphenylpropanoate + 4-coumaroyl-CoA

731177

-

3.1.1.42

p-coumaric acid + 2-phenylethyl bromide = 2-phenylethyl p-coumarate + bromide

663734

-

4.1.1.102

4-coumarate = 4-vinylphenol + CO2

762925, 747388, 733178, 746588, 747102, 733069

-

4.1.1.102

4-hydroxycinnamate = 4-hydroxystyrene + CO2

733069, 734054

-

4.1.1.102

4-hydroxycinnamic acid = 4-hydroxystyrene + CO2

747102

-

4.1.1.102

4-hydroxycinnamic acid = 4-vinylphenol + CO2

747296

-

4.3.1.24

(2E)-4-hydroxycinnamate + NH3 = L-tyrosine

716820

-

4.3.1.24

4-hydroxy-trans-cinnamate + NH3 = 4-hydroxy-L-phenylalanine

748273

-

4.1.1.102

4 entries

4.3.1.24

2 entries

4.3.1.25

4-hydroxy-trans-cinnamate + NH3 = 4-hydroxy-L-phenylalanine

748273

-

6.2.1.12

4-coumarate + MgATP2- + tetrapolyphosphate = adenosine 5'-pentaphosphate + ?

653536

-

6.2.1.12

4-coumarate + MgATP2- + tripolyphosphate = adenosine 5'-tetraphosphate + ?

653536

-

6.2.1.12

ATP + 4-coumarate + CoA = ?

621, 603, 620, 615, 599, 597, 595, 600

-

6.2.1.12

ATP + 4-coumarate + CoA = AMP + diphosphate + 4-coumaroyl-CoA

676288, 618, 612, 595, 596, 597, 609, 598, 605, 653527, 599, 601, 676305, 600, 606, 608, 652422, 602, 694037, 603, 604, 651262, 653481, 653536, 653597, 745743, 607, 610, 611, 621, 613, 615, 616, 617, 619, 620, 389482, 728481, 694662, 653015, 745107, 675650, 688652, 727643, 745872, 653496, 651117, 653477, 746109, 652146, 746513, 672870, 726875, 728512, 694771, 692504, 694735, 728464, 727118, 728204, 746098, 744736, 745004, 746000, 746036, 614, 693420, 694698, 662721, 676302, 694601, 704148, 732001

-

6.2.1.12

4 entries

6.2.1.2

ATP + trans-4-coumaric acid + CoA = AMP + diphosphate + trans-4-coumaroyl-CoA

690837

-

6.2.1.30

ATP + 4-coumarate + CoA = AMP + diphosphate + 4-coumaryl-CoA

727565

-

6.2.1.30

ATP + trans-4-coumaric acid + CoA = AMP + diphosphate + trans-4-coumaroyl-CoA

690837

-

6.2.1.30

2 entries

Product in Enzyme-catalyzed Reactions (70 results)

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Show Product (70 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.91

trans-cinnamate + [reduced NADPH-hemoprotein reductase] + O2 = 4-coumaric acid + [oxidized NADPH-hemoprotein reductase] + H2O

0

-

1.14.14.91

trans-cinnamate + [reduced NADPH-hemoprotein reductase] + O2 = 4-hydroxycinnamate + [oxidized NADPH-hemoprotein reductase] + H2O

348369, 348389, 348391, 348380, 348375, 348386, 0, 348370, 348390, 348387, 348372, 348373, 348378, 348374, 348379, 348381, 348382, 348383, 348385, 348367, 348384, 348371, 348368, 348377, 348388, 348376, 348366

-

1.14.14.91

2 entries

1.14.14.92

cinnamate + [reduced NADPH-hemoprotein reductase] + O2 = 4-coumarate + [oxidized NADPH-hemoprotein reductase] + H2O

440259

-

1.3.8.15

phloretate + electron-transfer flavoprotein EtfA-EtfB = 4-coumarate + reduced electron-transfer flavoprotein EtfA-EtfB

0

-

2.4.1.299

1-O-4-coumaroyl-beta-D-glucose + cyanidin 3-O-beta-D-glucoside = 4-coumarate + cyanidin 3,5-di-O-beta-D-glucoside

0

-

2.4.1.300

1-O-4-coumaroyl-beta-D-glucose + cyanidin 3-O-beta-D-glucoside = 4-coumarate + cyanidin 3,7-di-O-beta-D-glucoside

0

-

2.4.1.300

p-coumaroyl-beta-D-glucose + cyanidin 3-O-rutinoside = p-coumarate + cyanidin 3-O-rutinoside-7-O-beta-D-glucoside

0

-

2.4.1.300

2 entries

2.4.1.B70

1-O-(4-coumaroyl)-beta-D-glucose + cyanidin 3-O-[2-O-(2-O-(sinapoyl)-beta-D-xylosyl)-6-O-(6-(4-coumaroyl))-beta-D-glucoside] 5-O-[6-O-(malonyl)-beta-D-glucoside] = 4-coumarate + cyanidin 3-O-[2-O-(2-O-(sinapoyl)-beta-D-xylosyl)-6-O-(6-(4-O-beta-D-glucosyl)-4-coumaroyl)-beta-D-glucoside] 5-O-[6-O-(malonyl)-beta-D-glucoside]

0

-

3.1.1.42

methyl p-coumarate + H2O = methanol + p-coumarate

0

-

3.1.1.49

p-coumaroylcholine = p-coumaric acid + choline

0, 80961

-

3.1.1.73

methyl 4-coumarate + H2O = 4-coumarate + methanol

0

-

3.1.1.73

methyl 4-coumarate + H2O = 4-coumaric acid + methanol

0

-

3.1.1.73

methyl 4-coumarate + H2O = methanol + 4-coumaric acid

0

-

3.1.1.73

methyl p-coumarate + H2O = 4-coumaric acid + methanol

0

-

3.1.1.73

methyl 4-hydroxycinnamate + H2O = methanol + 4-hydroxycinnamate

0

-

3.1.1.73

methyl 4-hydroxy cinnamate + H2O = methanol + 4-hydroxycinnamic acid

0

-

3.1.1.73

methyl 4-hydroxycinnamate + H2O = 4-hydroxycinnamic acid + methanol

0

-

3.1.1.73

wood meal + H2O = ferulic acid + hydroxycinnamic acid + ?

0

-

3.1.1.73

bagasse + H2O = ? + ferulate + p-coumarate

0

-

3.1.1.73

coffee pulp + H2O = caffeate + ferulate + p-coumarate + ?

0

-

3.1.1.73

destarched wheat bran + H2O = caffeate + ferulate + p-coumarate + ?

0

-

3.1.1.73

methyl p-coumarate + H2O = methanol + p-coumarate

0

-

3.1.1.73

methyl p-coumarate + H2O = p-coumarate + methanol

0

-

3.1.1.73

rice husk + H2O = ? + ferulate + p-coumarate

0

-

3.1.1.73

sugar beet pectin + H2O = caffeate + ferulate + p-coumarate + ?

0

-

3.1.1.73

5-O-p-coumaroylquinic acid + H2O = p-coumaric acid + quinic acid

0

-

3.1.1.73

brewers spent grain + H2O = ferulic acid + p-coumaric acid + 5,5'-diferulate + ?

0

-

3.1.1.73

brewers spent grain + H2O = ferulic acid + p-coumaric acid + ?

0

-

3.1.1.73

coffee pulp + H2O = ferulic acid + caffeic acid + p-coumaric acid + ?

0

-

3.1.1.73

coniferyl p-coumarate + H2O = p-coumaric acid + coniferol

0

-

3.1.1.73

ethyl p-coumarate + H2O = p-coumaric acid + ethanol

0

-

3.1.1.73

feruloyl polysaccharide + H2O = ferulic acid + p-coumaric acid + ?

0

-

3.1.1.73

italian rye gras cell walls + H2O = ferulic acid + p-coumaric acid + ?

0

-

3.1.1.73

maize internodes + H2O = ferulic acid + p-coumaric acid + ?

0

-

3.1.1.73

methyl p-coumarate + H2O = methanol + p-coumaric acid

0

-

3.1.1.73

methyl p-coumarate + H2O = p-coumaric acid + methanol

0

-

3.1.1.73

O-5-O-(trans-p-coumaroyl)-alpha-L-arabinofuranosyl-(1-3)-O-beta-D-xylopyranosyl-(1-4)-D-xylopyranose + H2O = p-coumaric acid + alpha-L-arabinofuranosyl-(1-3)-O-beta-D-xylopyranosyl-(1-4)-D-xylopyranose

0

-

3.1.1.73

O-5-O-[(E)-p-coumaroyl]-alpha-L-arabinofuranosyl-(1-3)-O-beta-D-xylopyranosyl-(1-4)-D-xylopyranose + H2O = p-coumaric acid + alpha-L-arabinofuranosyl-(1-3)-O-beta-D-xylopyranosyl-(1-4)-D-xylopyranose

0

-

3.1.1.73

oat straw + H2O = ferulic acid + p-coumaric acid + ?

0

-

3.1.1.73

p-coumaric acid methyl ester + H2O = p-coumaric acid + methanol

0

-

3.1.1.73

rye grass + H2O = ferulic acid + p-coumaric acid + ?

0

-

3.1.1.73

spent grain + H2O = ferulic acid + p-coumaric acid + ?

0

-

3.1.1.73

wheat bran + H2O = ferulic acid + p-coumaric acid + 5,5'-diferulate + ?

0

-

3.1.1.73

wheat bran + H2O = ferulic acid + p-coumaric acid + ?

0

-

3.1.1.73

wheat straw + H2O = ferulic acid + p-coumaric acid + ?

0

-

3.1.1.73

xylan polysaccharide + H2O = ferulic acid + p-coumaric acid

0

-

3.1.1.B10

beta-D-xylopyranosyl-(1->2)-5-O-[(E)-p-coumaroyl]-alpha-L-arabinofuranosyl-(1->3)-beta-D-xylopyranosyl-(1->4)-D-xylopyranose + H2O = beta-D-xylopyranosyl-(1->2)-alpha-L-arabinofuranosyl-(1->3)-beta-D-xylopyranosyl-(1->4)-D-xylopyranose + (2E)-4-hydroxycinnamate

0

-

3.1.1.B10

O-beta-D-xylopyranosyl-(1->4)-O-[5-O-((E)-p-coumaroyl)-alpha-L-arabinofuranosyl(1->3)]-O-beta-D-xylopyranosyl-(1->4)-D-xylopyranose + H2O = O-beta-D-xylopyranosyl-(1->4)-O-(alpha-L-arabinofuranosyl(1->3))-O-beta-D-xylopyranosyl-(1->4)-D-xylopyranose + (2E)-4-hydroxycinnamate

0

-

3.1.1.B10

[5-O-((E)-p-coumaroyl)-alpha-L-arabinofuranosyl]-(1->3)-beta-D-xylopyranosyl-(1->4)-D-xylopyranose + H2O = alpha-L-arabinofuranosyl-(1->3)-O-beta-D-xylopyranosyl-(1->4)-D-xylopyranose + (2E)-4-hydroxycinnamate

0

-

3.1.1.B10

cell wall ((E)-4-coumaroyl)-polysaccharide + H2O = (E)-4-coumarate + a cell wall polysaccharide

0

-

3.1.1.73

36 entries

3.1.1.B10

4 entries

3.1.2.4

p-coumaroyl-CoA + H2O = p-coumaric acid + CoA

0

-

3.1.6.1

p-coumaric acid sulfate + H2O = p-coumaric acid + sulfate

0

-

3.2.1.126

p-coumaryl beta-D-glucoside = p-coumaric acid + beta-D-glucose

0

-

3.5.1.71

N-p-coumaroylglycine + H2O = p-coumarate + glycine

0

-

3.5.5.5

4-hydroxycinnamonitrile + H2O = 4-hydroxycinnamic acid + NH3

0

-

4.3.1.23

L-tyrosine = p-hydroxycinnamic acid + NH3

651293

-

4.3.1.23

L-tyrosine = trans-p-hydroxycinnamate + NH3

0

-

4.3.1.24

L-Tyr = (2E)-4-hydroxycinnamate + NH3

0

-

4.3.1.24

L-tyrosine = (2E)-4-hydroxycinnamate + NH3

0

-

4.3.1.24

L-Tyr = p-coumarate + NH3

0

-

4.3.1.24

L-tyrosine = p-coumarate + NH3

0

-

4.3.1.24

L-tyrosine = trans-p-hydroxycinnamate + NH3

0

-

4.3.1.25

L-Tyr = 4-coumarate + NH3

0

-

4.3.1.25

L-Tyr = p-coumarate + NH3

0

-

4.3.1.25

L-tyrosine = p-coumarate + NH3

0, 34344, 34341

-

4.3.1.25

L-tyrosine = p-hydroxycinnamic acid + NH3

0

-

4.3.1.25

L-tyrosine = trans-p-hydroxycinnamate + NH3

0

-

4.3.1.23

2 entries

4.3.1.24

5 entries

4.3.1.25

5 entries

4.3.1.31

L-tyrosine = trans-p-hydroxycinnamate + NH3

0

-

5.4.3.6

L-tyrosine = (4-hydroxyphenyl)prop-2-enoate + NH3

650190

-

5.4.3.6

L-tyrosine = 4-hydroxycinnamic acid + NH3

0

-

5.4.3.6

2 entries

Activator in Enzyme-catalyzed Reactions (6 results)

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Show Activating Compound (6 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.11.1.1

1.6 mM, significant enhancement of activity

676593

-

1.11.1.1

enhances NADH-peroxidase activity in the presence of Mn2+

699261

-

1.11.1.1

2 entries

1.11.1.7

at 3 mM

439733

3uba, 3D-view

2.8.2.1

activation of P-PST

645686

-

3.2.1.21

118% activity at 2.5 mM with cellobioside as substrate

749779

-

4.99.1.10

-

743514

-

Inhibitor in Enzyme-catalyzed Reactions (59 results)

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Show Inhibitors (59 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.21

-

696708

-

1.1.1.239

-

740293

-

1.1.1.37

13.4% inhibition at 0.1 mM

723482

-

1.1.1.44

-

286866

-

1.10.3.2

32.5% residual activity at 1 mM

712084

-

1.10.3.2

0.1 mM, complete inhibition

687338

-

1.10.3.2

-

655375

-

1.10.3.2

1 mM, 25% inhibition

765710

-

1.10.3.2

1 mM, 48% inhibition

743080

-

1.10.3.2

5 mM, 60% inhibition

685393

-

1.10.3.2

6 entries

1.13.11.27

50% inhibition above 10 mM, competitive

395375

-

1.13.11.66

0.2 mM, 97% inhibition; 0.2 mM, 97% inhibition

718555

-

1.13.11.66

0.2 mM, no residual activity

719714

-

1.13.11.66

2 entries

1.14.13.2

-

390019

-

1.14.14.9

substrate inhibition at concentrations higher than 40 mM

744140

-

1.14.18.1

-

699195

-

1.14.18.1

74.4% inhibition at 0.33 mM

713205

-

1.14.18.1

-

636380

-

1.14.18.1

competitive inhibition of tyrosinase by 4-hydroxycinnamic acid is a slow, reversible reaction with fractional remaining activity, has no effects on the proliferation of normal liver L02 cells, delays the mushroom browning. Molecular docking analysis and kinetic modeling, structure-function analysis, detailed overview

745095

-

1.14.18.1

4% inhibition at 0.1 mM

672587

-

1.14.18.1

-

696563

-

1.14.18.1

14% residual activity at 0.5 M

684646

-

1.14.18.1

clinically used tyrosinase inhibitor

744488

-

1.14.18.1

mixed inhibition

689440

-

1.14.18.1

tyrosinase inhibitors from Marrubium cylleneum, phenolic acids

685515

-

1.14.18.1

10 entries

1.17.3.2

competitively inhibits the enzyme by binding to the active site, have a protective effect against reactive oxygen species in cells, structure-function relationship, computational molecular docking, overview

686866

-

2.3.1.172

competitive inhibitor with respect to shisonin, 10 mM, complete inhibition

656032

-

2.3.1.172

dead-end inhibitor, competitive with respect to shisonin, uncompetitive with respect to malonyl-CoA

654691

-

2.3.1.172

2 entries

2.4.1.194

-

636883

-

2.7.1.71

1 mM, 14% inhibition

641902

-

2.7.4.2

1.25 mM, 46% inhibition

645179

-

3.1.1.117

-

761510

-

3.1.4.11

-

694785

-

3.2.1.15

-

730876

-

3.2.1.20

-

709294

-

3.2.1.21

70.5% residual activity at 2.5 mM with 4-nitrophenyl beta-D-glucopyranoside as substrate

749779

-

3.4.15.1

-

731965

-

4.1.1.22

slight inhibition

680301

-

4.1.1.28

-

4221

-

4.1.1.33

-

4376

-

4.2.1.1

-

748811

-

4.2.2.2

33% inhibition at 0.01 mM, 61% inhibition at 0.05 mM

666570

-

4.3.1.24

-

34330, 34332, 34345, 34353, 34358

-

4.3.1.24

0.1 mM, slight

34358

-

4.3.1.24

inhibition of enzyme form PAL116, no inhibition of enzyme form PAL68

34333

-

4.3.1.24

trans-p-coumarate, competitive

34330

-

4.3.1.24

-

34364

-

4.3.1.24

5 entries

4.3.1.25

-

34332, 34341, 34365

-

5.3.2.1

-

703331

-

5.3.2.1

-

2872

-

5.3.2.1

-

649881, 703331

-

5.3.2.1

IC50 ketonase reaction 18.1 microM, pH 6.5, room temperatur, IC50 enolase reaction 103.3 microM, pH 6.2, room temperatur

661889

-

5.3.2.1

4 entries

5.4.3.6

-

3405

-

5.4.99.5

inhibits enzyme form CM1, CM2 and CM3

3538

-

6.2.1.12

-

611

-

6.2.1.12

above 0.1 mM

608

-

6.2.1.12

inhibition above 0.6 mM

620

-

6.2.1.12

strong competitive inhibitor for the other substrates

653527

-

6.2.1.12

4 entries

7.2.2.19

-

689063

-

3D Structure of Enzyme-Ligand-Complex (PDB) (6 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (6 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.11.1.7

3uba, 3D-view

1.3.1.74

2j3j, 3D-view

2.7.11.1

5mov, 3D-view

2.7.11.17

6vzk, 3D-view

2.7.12.2

5j0a, 3D-view

3.1.1.4

4qem, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (55 results)

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Show Turnover Number (55 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.14.14.9

0.183

-

mutant XS2, pH 7, 30°C

765827

1.14.14.9

0.365

-

mutant XS6, pH 7, 30°C

765827

1.14.14.9

0.375

-

mutant XS5, pH 7, 30°C

765827

1.14.14.9

0.387

-

wild-type, pH 7, 30°C

765827

1.14.14.9

0.497

-

mutant XS3, pH 7, 30°C

765827

1.14.14.9

0.512

-

mutant XS4, pH 7, 30°C

765827

1.14.14.9

0.6

-

pH 7.5, 23°C

764477

2.4.1.81

0.0097

-

pH 6.0, 40°C, recombinant enzyme

759388

2.4.1.81

0.0125

-

pH 6.0, 40°C, recombinant enzyme

759388

2.4.1.81

0.0147

-

pH 6.0, 40°C, recombinant enzyme

759388

2.4.1.81

0.0332

-

pH 6.0, 40°C, recombinant enzyme

759388

2.4.1.81

0.0338

-

pH 6.0, 40°C, recombinant enzyme

759388

2.4.1.81

0.0505

-

pH 6.0, 40°C, recombinant enzyme

759388

4.1.1.102

0.19

-

pH 5, 30°C

747296

4.1.1.102

0.96

-

pH 5, 30°C

747296

4.1.1.102

4.6

-

pH 7.0, 25°C

746588

4.1.1.102

14.1

-

pH 5, 30°C

747296

6.2.1.12

0.0082

-

pH 7.5, temperature not specified in the publication, recombinant isozyme Os4Cl1

728512

6.2.1.12

0.0395

-

pH 7.5, temperature not specified in the publication, recombinant isozyme Os4Cl2

728512

6.2.1.12

0.047

-

pH 7.5, temperature not specified in the publication, recombinant isozyme Os4Cl4

728512

6.2.1.12

0.048

-

pH 7.5, temperature not specified in the publication, recombinant isozyme Os4Cl5

728512

6.2.1.12

0.123

-

mutant enzyme M247Y/A251S, at pH 7.5 and 30°C

746000

6.2.1.12

0.19

-

isoform 4CL3, pH and temperature not specified in the publication

746036

6.2.1.12

0.216

-

wild type enzyme, at pH 7.5 and 30°C

746000

6.2.1.12

0.221

-

mutant enzyme A251S, at pH 7.5 and 30°C

746000

6.2.1.12

0.282

-

mutant enzyme T336A, at pH 7.5 and 25°C

746513

6.2.1.12

0.285

-

pH 7.5, temperature not specified in the publication, recombinant isozyme Os4Cl3

728512

6.2.1.12

0.49

-

recombinant V186I/V187L, pH 7.8, 30°C

728481

6.2.1.12

0.58

-

pH 7.5, 22°C

728204

6.2.1.12

0.66

-

recombinant wild-type enzyme, pH 7.8, 30°C

728481

6.2.1.12

0.7

1

pH 7.5, 30°C

728464

6.2.1.12

0.742

-

recombinant F269L/K415T, pH 7.8, 30°C

728481

6.2.1.12

0.782

-

mutant enzyme M247Y, at pH 7.5 and 30°C

746000

6.2.1.12

0.96

-

pH 7.5, 22°C

728204

6.2.1.12

0.996

-

mutant enzyme T193A, at pH 7.5 and 25°C

746513

6.2.1.12

0.996

-

mutant enzyme Y239A, at pH 7.5 and 25°C

746513

6.2.1.12

1

-

pH 7.5, 22°C

728204

6.2.1.12

1.02

-

pH 7.8, 22°C

727118

6.2.1.12

1.28

-

pH 7.8, 22°C

727118

6.2.1.12

1.47

-

mutant enzyme K443A, at pH 7.5 and 25°C

746513

6.2.1.12

1.623

-

recombinant V186G, pH 7.8, 30°C

728481

6.2.1.12

1.819

-

recombinant F239S, pH 7.8, 30°C

728481

6.2.1.12

1.98

-

mutant enzyme H237A, at pH 7.5 and 25°C

746513

6.2.1.12

3.036

-

mutant enzyme R435A, at pH 7.5 and 25°C

746513

6.2.1.12

3.71

-

isoform 4CL5, pH and temperature not specified in the publication

746098

6.2.1.12

3.978

-

wild type enzyme, at pH 7.5 and 25°C

746513

6.2.1.12

4.05

-

recombinant Q274H, pH 7.8, 30°C

728481

6.2.1.12

4.15

-

isoform 4CL1, pH and temperature not specified in the publication

746036

6.2.1.12

4.24

-

isoform 4CL1, pH and temperature not specified in the publication

746098

6.2.1.12

4.47

-

mutant enzyme Y239F, at pH 7.5 and 25°C

746513

6.2.1.12

4.55

-

isoform 4CL2, pH and temperature not specified in the publication

746098

6.2.1.12

6.84

-

isoform 4CL3, pH and temperature not specified in the publication

746098

6.2.1.12

7.11

-

mutant enzyme K197A, at pH 7.5 and 25°C

746513

6.2.1.12

9.144

-

mutant enzyme M344A, at pH 7.5 and 25°C

746513

6.2.1.12

88.68

-

isoform 4CL4, pH and temperature not specified in the publication

746098

1.14.14.9

7 entries

2.4.1.81

6 entries

4.1.1.102

4 entries

6.2.1.12

38 entries

K_M Value (106 results)

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Show KM Value (106 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.10.3.2

0.24

-

-

396394

1.14.14.9

0.054

-

pH 7.5, 23°C

764477

1.14.14.9

0.132

-

mutant XS6, pH 7, 30°C

765827

1.14.14.9

0.138

-

wild-type, pH 7, 30°C

765827

1.14.14.9

0.211

-

mutant XS4, pH 7, 30°C

765827

1.14.14.9

0.235

-

mutant XS5, pH 7, 30°C

765827

1.14.14.9

0.236

-

mutant XS3, pH 7, 30°C

765827

1.14.14.9

0.388

-

mutant XS2, pH 7, 30°C

765827

1.14.18.1

0.268

-

electron donor ascorbic acid

636424

1.14.18.1

0.42

-

-

636450

1.14.18.1

1.5

-

in 0.1M sodium phosphate buffer (pH 7.0) at 25°C

697659

1.14.18.1

4

-

-

636382

1.14.14.9

7 entries

1.14.18.1

4 entries

2.4.1.120

3.6

-

-

660175

2.4.1.126

0.0008

-

-

639510

2.4.1.177

0.6035

-

-

676590

2.4.1.209

0.044

-

-

288689

2.4.1.81

0.0699

-

pH 6.0, 40°C, recombinant enzyme

759388

2.4.1.81

0.088

-

pH 6.0, 40°C, recombinant enzyme

759388

2.4.1.81

0.1288

-

pH 6.0, 40°C, recombinant enzyme

759388

2.4.1.81

0.2208

-

pH 6.0, 40°C, recombinant enzyme

759388

2.4.1.81

0.254

-

pH 6.0, 40°C, recombinant enzyme

759388

2.4.1.81

0.329

-

pH 6.0, 40°C, recombinant enzyme

759388

4.1.1.102

0.18

-

pH 7.0, 25°C

746588

4.1.1.102

0.54

-

pH 5, 30°C

747296

4.1.1.102

0.74

-

pH 5, 30°C

747296

4.1.1.102

0.79

-

pH 6.5, 30°C

733178

4.1.1.102

1.07

-

pH 5, 30°C

747296

4.3.1.24

5.9

-

mutant F137V, pH 10, 30°C

716820

4.3.1.24

12.6

-

wild-type, pH 10, 30°C

716820

6.2.1.12

0.0009

-

mutant enzyme K443A, at pH 7.5 and 25°C

746513

6.2.1.12

0.0015

-

wild type enzyme, at pH 7.5 and 25°C

746513

6.2.1.12

0.00166

-

pH 7.5, 30°C

728464

6.2.1.12

0.0025

-

pH 7.5, 22°C

728204

6.2.1.12

0.0029

-

mutant enzyme T193A, at pH 7.5 and 25°C

746513

6.2.1.12

0.0031

-

isozyme 4CL2, at pH 7.8 and 32°C

694698

6.2.1.12

0.0035

-

pH 7.8, 22°C

727118

6.2.1.12

0.0036

-

4CL2, pH 7.5, 30°C

653527

6.2.1.12

0.0036

-

recombinant F269L/K415T, pH 7.8, 30°C

728481

6.2.1.12

0.0039

-

pH 7.5, temperature not specified in the publication, recombinant isozyme Os4Cl4

728512

6.2.1.12

0.004

-

recombinant isozyme 4CL1

694601

6.2.1.12

0.0049

-

pH 7.5, temperature not specified in the publication, recombinant isozyme Os4Cl3

728512

6.2.1.12

0.0049

-

recombinant V186I/V187L, pH 7.8, 30°C

728481

6.2.1.12

0.0051

-

mutant enzyme T336A, at pH 7.5 and 25°C

746513

6.2.1.12

0.0051

-

recombinant V186G, pH 7.8, 30°C

728481

6.2.1.12

0.0055

-

isozyme 4CL1, pH 7.8, 32°C

694698

6.2.1.12

0.0062

-

-

609

6.2.1.12

0.0069

-

mutant enzyme Y239F, at pH 7.5 and 25°C

746513

6.2.1.12

0.0073

-

pH 7.5, 22°C

728204

6.2.1.12

0.00747

-

recombinant wild-type enzyme, pH 7.8, 30°C

728481

6.2.1.12

0.009

-

-

651117

6.2.1.12

0.009

-

4CL3

652422

6.2.1.12

0.009

-

pH 7.5, 22°C

728204

6.2.1.12

0.0091

-

pH 7.8, 22°C

727118

6.2.1.12

0.01

-

-

651117

6.2.1.12

0.01

-

isoenzyme II

615

6.2.1.12

0.0103

-

pH 7.5, temperature not specified in the publication, recombinant isozyme Os4Cl5

728512

6.2.1.12

0.0104

-

recombinant F239S, pH 7.8, 30°C

728481

6.2.1.12

0.01097

-

isoform 4CL3, pH and temperature not specified in the publication

746036

6.2.1.12

0.0119

-

pH 7.5, temperature not specified in the publication, recombinant isozyme Os4Cl1

728512

6.2.1.12

0.01271

-

isoform 4CL2, pH and temperature not specified in the publication

746098

6.2.1.12

0.013

-

isoenzyme III

615

6.2.1.12

0.0139

-

mutant enzyme K197A, at pH 7.5 and 25°C

746513

6.2.1.12

0.016

-

recombinant isozyme 4CL2

694601

6.2.1.12

0.0168

-

pH 7.5, temperature not specified in the publication, recombinant isozyme Os4Cl2

728512

6.2.1.12

0.017

-

5-hydroxyferulate

615

6.2.1.12

0.017

-

isoenzyme 2

608

6.2.1.12

0.0179

-

recombinant Q274H, pH 7.8, 30°C

728481

6.2.1.12

0.022

-

-

651117

6.2.1.12

0.022

-

M293P/K320L mutant enzyme

653597

6.2.1.12

0.023

-

room temperature

653477

6.2.1.12

0.025

-

4CL1, pH 7.8, room temperature

653481

6.2.1.12

0.02611

-

isoform 4CL4, pH and temperature not specified in the publication

746098

6.2.1.12

0.027

-

M293P/K320L mutant enzyme, pH 7.0, 30°C

653536

6.2.1.12

0.0272

-

isoform 4CL5, pH and temperature not specified in the publication

746098

6.2.1.12

0.029

-

recombinant isozyme 4CL3

694601

6.2.1.12

0.0302

-

isoform 4CL1, pH and temperature not specified in the publication

746036

6.2.1.12

0.031

-

-

620

6.2.1.12

0.032

-

ATP

620

6.2.1.12

0.032

-

isoenzyme 1

608

6.2.1.12

0.038

-

room temperature

653477

6.2.1.12

0.042

-

-

651117

6.2.1.12

0.042

-

4CL2

652422

6.2.1.12

0.042

-

isoenzyme I

615

6.2.1.12

0.05

-

4CL1

652422

6.2.1.12

0.05399

-

isoform 4CL3, pH and temperature not specified in the publication

746098

6.2.1.12

0.056

-

4CL1, pH 7.5, 30°C

653527

6.2.1.12

0.05679

-

isoform 4CL1, pH and temperature not specified in the publication

746098

6.2.1.12

0.08

-

room temperature

653496

6.2.1.12

0.103

-

pH not specified in the publication, 30°C, isozyme Os4Cl1

726875

6.2.1.12

0.136

-

pH not specified in the publication, 30°C, isozyme Os4Cl1

726875

6.2.1.12

0.143

-

pH not specified in the publication, 30°C, isozyme Os4Cl1

726875

6.2.1.12

0.1434

-

mutant enzyme H237A, at pH 7.5 and 25°C

746513

6.2.1.12

0.155

-

mutant enzyme M247Y, at pH 7.5 and 30°C

746000

6.2.1.12

0.1887

-

wild type enzyme, at pH 7.5 and 30°C

746000

6.2.1.12

0.212

-

pH not specified in the publication, 30°C, isozyme Os4Cl1

726875

6.2.1.12

0.22

-

4CL2, pH 7.8, room temperature

653481

6.2.1.12

0.2281

-

mutant enzyme Y239A, at pH 7.5 and 25°C

746513

6.2.1.12

0.233

-

wild-type enzyme

653597

6.2.1.12

0.233

-

wild-type enzyme, pH 7.0, 30°C

653536

6.2.1.12

0.246

-

-

676305

6.2.1.12

0.252

-

room temperature

653477

6.2.1.12

0.282

-

pH not specified in the publication, 30°C, isozyme Os4Cl3

726875

6.2.1.12

0.283

-

mutant enzyme M247Y/A251S, at pH 7.5 and 30°C

746000

6.2.1.12

0.389

-

mutant enzyme A251S, at pH 7.5 and 30°C

746000

6.2.1.12

0.5207

-

mutant enzyme M344A, at pH 7.5 and 25°C

746513

6.2.1.12

0.6149

-

mutant enzyme R435A, at pH 7.5 and 25°C

746513

2.4.1.81

6 entries

4.1.1.102

5 entries

4.3.1.24

2 entries

6.2.1.12

77 entries

K_i Value (8 results)

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Show KI Value (8 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.18.1

0.24

-

-

636380

2.4.1.194

5

-

-

636883

2.7.4.2

2.39

-

pH 7.4, 37°C

645179

4.2.1.1

0.00269

-

pH 8.3, 25°C, recombinant enzyme

748811

4.2.1.1

0.00433

-

pH 8.3, 25°C, recombinant enzyme

748811

4.2.1.1

0.00605

-

pH 8.3, 25°C, recombinant enzyme

748811

5.3.2.1

0.234

-

23°C, pH 6.5, mutant enzyme K32R

649881

5.3.2.1

0.375

-

23°C, pH 6.5, mutant enzyme K32A

649881

4.2.1.1

3 entries

5.3.2.1

2 entries

IC₅₀ Value (14 results)

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Show IC50 Value (14 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.1.1.239

0.199

-

pH 7.0, 37°C

740293

1.14.18.1

0.1156

-

in 0.1 M phosphate buffer (pH 7.0), at 37°C

713205

1.14.18.1

0.2

-

-

696563

1.14.18.1

0.5

-

-

699195

1.14.18.1

3.65

-

-

689440

1.14.18.1

4 entries

1.17.3.2

0.0969

-

pH 8.0, 37°C, versus xanthine

686866

3.1.1.117

0.83

-

pH 8.5, temperature not specified in the publication, recombinant wild-type enzyme

761510

3.1.1.117

4.84

-

pH 8.5, temperature not specified in the publication, recombinant mutant F174A

761510

3.1.1.117

26

-

pH 8.5, temperature not specified in the publication, recombinant mutant F174D

761510

3.4.15.1

2.8

-

37°C, pH not specified in the publication

731965

3.4.15.1

2.8

-

pH not specified in the publication, 37°C

731965

5.3.2.1

0.0015

-

-

703331

5.3.2.1

0.0181

0.1033

IC50 ketonase reaction 18.1 microM, pH 6.5, room temperatur, IC50 enolase reaction 103.3 microM, pH 6.2, room temperatur

661889

3.1.1.117

3 entries

3.4.15.1

2 entries

5.3.2.1

2 entries

7.2.2.19

0.04

-

pH 6.5, 37°C

689063

References & Links

Literature References (235)

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Show Reference (235 entries)

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