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Ligand caffeic acid

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

BRENDA

suberin monomers biosynthesis

KEGG

Biosynthesis of phenylpropanoids, Biosynthesis of secondary metabolites, Degradation of aromatic compounds, Phenylpropanoid biosynthesis

MetaCyc

caffeoylglucarate biosynthesis, chlorogenic acid degradation, coumarins biosynthesis (engineered), free phenylpropanoid acid biosynthesis, fungal bioluminescence, phenylpropanoids methylation (ice plant), suberin monomers biosynthesis, superpathway of scopolin and esculin biosynthesis, trans-caffeate degradation (aerobic) more

Show all BRENDA pathways known for caffeic acid

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (11 results)

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Show Natural Substrate (11 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.13.11.22

3,4-dihydroxy-trans-cinnamate + O2 = 3-(2-carboxyethenyl)-cis,cis-muconate

439540

-

1.14.18.1

caffeic acid + O2 = ?

745558

-

1.14.18.1

caffeic acid + O2 = ? + 2 H2O

746276

-

1.14.18.1

2 entries

2.1.1.104

S-adenosyl-L-methionine + caffeic acid = S-adenosyl-L-homocysteine + ferulic acid

706277

-

2.1.1.68

S-adenosyl-L-methionine + 3,4-dihydroxy-trans-cinnamate = S-adenosyl-L-homocysteine + 3-methoxy-4-hydroxy-trans-cinnamate

702917, 485539, 485546, 485543, 485530, 485542, 485531, 485534

-

2.1.1.68

S-adenosyl-L-methionine + caffeic acid = S-adenosyl-L-homocysteine + ferulic acid

757482, 758496

-

2.1.1.68

2 entries

2.4.1.177

UDP-glucose + caffeate = UDP + caffeoyl beta-D-glucoside

759563

-

2.4.1.7

sucrose + caffeic acid = D-fructose + caffeoyl-beta-D-glucoside

703795

-

2.8.2.1

3'-phosphoadenylyl sulfate + caffeic acid = adenosine 3',5'-bisphosphate + ?

677196

-

2.8.3.23

3,4-dihydroxyphenylpropanoyl-CoA + (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate = 3,4-dihydroxyphenylpropanoate + (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl-CoA

731177

-

6.2.1.12

ATP + caffeate + CoA = AMP + diphosphate + caffeoyl-CoA

728464, 727118, 732001

-

In Vivo Product in Enzyme-catalyzed Reactions (3 results)

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Show Natural Product (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.42

chlorogenate + H2O = caffeate + quinate

0

-

3.1.1.42

chlorogenic acid + H2O = caffeate + quinate

649390, 651606

-

3.1.1.42

2 entries

3.1.1.73

methyl caffeate + H2O = caffeic acid + methanol

0

-

Substrate in Enzyme-catalyzed Reactions (63 results)

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Show Substrate (63 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.10.3.1

caffeic acid + 1/2 O2 = caffeoyl quinone + H2O

440427, 440432, 440426, 440433

-

1.10.3.1

caffeic acid + O2 = ?

710798, 701876, 675167, 676649, 671593, 676381

-

1.10.3.1

caffeic acid + O2 = caffeoyl quinone + H2O

684646, 712219

-

1.10.3.2

(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid + O2 = ?

724662

-

1.10.3.2

caffeate + O2 = ? + H2O

687338

-

1.10.3.2

caffeic acid + 4-aminoantipyrine + O2 = ? + H2O

655631

-

1.10.3.2

caffeic acid + O2 = ?

684645, 396394, 396379, 396352, 396357, 687239, 396390, 743016

-

1.11.1.19

caffeic acid + H2O2 + H+ = ?

765206

-

1.11.1.19

caffeic acid + H2O2 + H+ = oxidized caffeic acid + H2O

764606

-

1.11.1.7

caffeic acid + H2O2 = ?

698044, 439765

-

1.11.1.7

caffeic acid + H2O2 = ? + H2O

743175

-

1.10.3.1

3 entries

1.10.3.2

4 entries

1.11.1.19

2 entries

1.11.1.7

2 entries

1.13.11.22

3,4-dihydroxy-trans-cinnamate + O2 = 3-(2-carboxyethenyl)-cis,cis-muconate

439540

-

1.13.11.3

caffeic acid + O2 = ?

725655, 742046, 743122

-

1.13.11.3

trans-3,4-dihydroxycinnamate + O2 = ?

439505, 439513

-

1.13.11.3

2 entries

1.14.14.9

caffeic acid + FADH2 + O2 = 3,4,5-trihydroxycinnamic acid + FAD + H2O

744140

-

1.14.18.1

caffeic acid + 1/2 O2 = caffeoyl quinone + H2O

636424, 636347, 690213, 686845, 686841, 636382, 687875, 636434, 636380, 636450, 686847, 687250, 689407, 636443

-

1.14.18.1

caffeic acid + O2 = ?

712227, 745558, 713302, 710798

-

1.14.18.1

caffeic acid + O2 = ? + 2 H2O

744824, 746276, 745474

-

1.14.18.1

caffeic acid + O2 = caffeoyl quinone + H2O

697659, 684646, 699628, 712619, 712618

-

1.14.18.1

4 entries

1.2.1.30

caffeic acid + NADPH + ATP = 3-(3,4-dihydroxyphenyl)-2-propen-1-al + NADP+ + AMP + H2O

288183

-

1.5.99.12

N6-(2-isopentenyl)adenine + caffeic acid = adenine + 3-methylbut-2-enal + ?

654539

-

2.1.1.104

S-adenosyl-L-methionine + caffeic acid = ?

720716

-

2.1.1.104

S-adenosyl-L-methionine + caffeic acid = S-adenosyl-L-homocysteine + ?

757943

-

2.1.1.104

S-adenosyl-L-methionine + caffeic acid = S-adenosyl-L-homocysteine + ferulic acid

706277, 702477, 757935, 668599, 733869

-

2.1.1.104

3 entries

2.1.1.336

2 S-adenosyl-L-methionine + caffeic acid = 2 S-adenosyl-L-homocysteine + ferulic acid + isoferulic acid

756993, 756959

-

2.1.1.338

S-adenosyl-L-methionine + caffeic acid = S-adenosyl-L-homocysteine + ?

741150

-

2.1.1.6

caffeic acid + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + ?

441526, 441551

-

2.1.1.68

S-adenosyl-L-methionine + 3,4-dihydroxy-trans-cinnamate = S-adenosyl-L-homocysteine + 3-methoxy-4-hydroxy-trans-cinnamate

485546, 485072, 485071, 485067, 485065, 485073, 702477, 704880, 702917, 701663, 485531, 734970, 734491, 485545, 485530, 485541, 485542, 485547, 485543, 485538, 485539, 485534

-

2.1.1.68

S-adenosyl-L-methionine + caffeic acid = ?

720616, 720423, 720680, 675589

-

2.1.1.68

S-adenosyl-L-methionine + caffeic acid = S-adenosyl-L-homocysteine + 4-hydroxy-3-methoxy-trans-cinnamic acid

660104

-

2.1.1.68

S-adenosyl-L-methionine + caffeic acid = S-adenosyl-L-homocysteine + ?

718207

-

2.1.1.68

S-adenosyl-L-methionine + caffeic acid = S-adenosyl-L-homocysteine + ferulic acid

757482, 758496, 658800, 733559

-

2.1.1.68

5 entries

2.1.1.69

S-adenosyl-L-methionine + caffeic acid = S-adenosyl-L-homocysteine + ?

485549

-

2.1.1.78

S-adenosyl-L-methionine + caffeic acid = ?

485623

-

2.3.1.152

UDP-glucose + caffeic acid = ?

16328

-

2.4.1.104

UDP-glucose + caffeic acid = UDP + ?

488400, 488399, 488398

-

2.4.1.111

UDP-glucose + caffeic acid = UDP + ?

488454

-

2.4.1.120

UDP-glucose + caffeate = UDP + 1-caffeoyl-D-glucose

660293, 660175

-

2.4.1.120

UDP-alpha-D-glucose + caffeic acid = UDP + 1-O-caffeoyl-beta-D-glucose

488516, 488519

-

2.4.1.120

2 entries

2.4.1.126

UDPglucose + caffeic acid = UDP + 4-O-glucosyl-caffeic acid

639510

-

2.4.1.136

UDP-glucose + caffeate = UDP + 1-caffeoyl-beta-D-glucose

759916

-

2.4.1.177

UDP-alpha-D-glucose + caffeate = UDP + 1-O-caffeoyl-beta-D-glucose

637802

-

2.4.1.177

UDP-glucose + caffeate = UDP + caffeoyl beta-D-glucoside

759563

-

2.4.1.177

caffeic acid + UDP-glucose = UDP + caffeoyl-beta-D-glucoside

676590

-

2.4.1.237

UDP-glucose + caffeic acid = UDP + caffeic acid 4-O-beta-D-glucoside

489572

-

2.4.1.237

UDP-glucose + caffeic acid = UDP + caffeoyl 3-O-beta-D-glucoside

676370

-

2.4.1.35

UDP-glucose + caffeic acid = UDP + caffeoyl 3-O-beta-D-glucoside

757325, 657831

-

2.4.1.35

UDPglucose + caffeic acid = ?

489108

-

2.4.1.177

3 entries

2.4.1.237

2 entries

2.4.1.35

2 entries

2.4.1.5

sucrose + caffeic acid = D-fructose + caffeic acid-3-O-alpha-D-glucopyranoside

757038

-

2.4.1.7

sucrose + caffeic acid = D-fructose + caffeoyl-beta-D-glucoside

703795

-

2.4.1.81

UDP-glucose + caffeic acid = UDP + 1-O-caffeoyl-beta-D-glucopyranose

759388

-

2.5.1.111

dimethylallyl diphosphate + caffeate = diphosphate + 3-O,4-O-bis-(dimethylallyl)caffeate

722465

-

2.5.1.111

dimethylallyl diphosphate + caffeate = diphosphate + 3-O-(dimethylallyl)caffeate

722465

-

2.5.1.111

dimethylallyl diphosphate + caffeate = diphosphate + 4-O-(dimethylallyl)caffeate

722465

-

2.8.2.1

3'-phosphoadenylyl sulfate + caffeic acid = adenosine 3',5'-bisphosphate + ?

677196

-

2.8.2.1

3'-phosphoadenylylsulfate + caffeic acid = adenosine 3',5'-bisphosphate + ?

661704

-

2.5.1.111

3 entries

2.8.2.1

2 entries

2.8.2.15

3'-phosphoadenylylsulfate + caffeic acid = adenosine 3',5'-bisphosphate + ?

660901

-

2.8.3.23

3,4-dihydroxyphenylpropanoyl-CoA + (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate = 3,4-dihydroxyphenylpropanoate + (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl-CoA

731177

-

3.2.1.168

rutin + caffeic acid = quercetin + caffeic acid 3'-O-rutinoside

753951

-

3.2.1.8

caffeic acid + H2O = ?

696821

-

4.1.1.102

caffeate = 3,4-dihydroxystyrene + CO2

762925, 733069

-

6.2.1.12

ATP + caffeate + CoA = AMP + diphosphate + caffeoyl-CoA

618, 612, 609, 605, 608, 651117, 652422, 603, 651262, 653477, 653536, 653597, 610, 611, 616, 620, 653527, 653496, 746109, 652146, 746513, 728512, 694601, 728464, 727118, 728204, 732001, 746098, 745004, 746000, 746036, 596, 595, 606, 614, 615, 726875, 693420, 662721, 694698

-

6.2.1.12

ATP + caffeic acid + CoA = AMP + diphosphate + caffeoyl-CoA

676302

-

6.2.1.12

2 entries

Product in Enzyme-catalyzed Reactions (35 results)

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Show Product (35 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.9

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

0

-

1.14.14.9

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

0

-

1.14.14.91

(2E)-3-(3-hydroxyphenyl)prop-2-enoic acid + [reduced NADPH-hemoprotein reductase] + O2 = (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid + [oxidized NADPH-hemoprotein reductase] + H2O

0

-

1.14.14.91

3-hydroxycinnamate + [reduced NADPH-hemoprotein reductase] + O2 = caffeate + [oxidized NADPH-hemoprotein reductase] + H2O

0

-

1.14.18.1

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

636382, 636434, 636380, 636450, 636424, 0

-

1.14.18.1

p-coumaric acid + O2 = caffeic acid + H2O

0

-

1.14.14.9

2 entries

1.14.14.91

2 entries

1.14.18.1

2 entries

1.14.99.15

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

0

-

2.4.1.299

1-O-caffeoyl-beta-D-glucose + cyanidin 3-O-beta-D-glucoside = caffeate + cyanidin 3,5-di-O-beta-D-glucoside

0

-

2.4.1.300

1-O-caffeoyl-beta-D-glucose + cyanidin 3-O-beta-D-glucoside = caffeate + cyanidin 3,7-di-O-beta-D-glucoside

0

-

2.4.1.300

caffeoyl-beta-D-glucose + cyanidin 3-O-rutinoside = caffeate + cyanidin 3-O-rutinoside-7-O-glucoside

0

-

3.1.1.20

rosmarinic acid + H2O = (2E)-3,4-dihydroxycinnamate + (2R)-3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate

0

-

3.1.1.20

chlorogenic acid + H2O = trans-caffeate + quinate

0

-

3.1.1.42

3-caffeoylquinic acid + H2O = caffeate + quinate

0

-

3.1.1.42

4-caffeoylquinic acid + H2O = caffeate + quinate

0

-

3.1.1.42

caffeoylshikimate + H2O = caffeate + shikimate

0

-

3.1.1.42

chlorogenate + H2O = caffeate + quinate

80931, 80932, 0

-

3.1.1.42

chlorogenic acid + H2O = caffeate + quinate

651606, 649390, 0

-

3.1.1.42

methyl caffeate + H2O = methanol + caffeate

0

-

2.4.1.300

2 entries

3.1.1.20

2 entries

3.1.1.42

6 entries

3.1.1.49

caffeoylcholine = caffeic acid + choline

80961, 0

-

3.1.1.73

methyl 3,4-dihydroxy cinnamate + H2O = methanol + 3,4-dihydroxycinnamic acid

0

-

3.1.1.73

methyl 3,4-dihydroxycinnamate + H2O = 3,4-dihydroxycinnamic acid + methanol

0

-

3.1.1.73

chlorogenate + H2O = caffeate + quinate

0

-

3.1.1.73

chlorogenic acid + H2O = caffeate + quinate

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

ethyl caffeate + H2O = ethanol + caffeate

0

-

3.1.1.73

methyl caffeate + H2O = caffeate + methanol

0

-

3.1.1.73

methyl caffeate + H2O = methanol + caffeate

0

-

3.1.1.73

phenethyl caffeate + H2O = phenylethanol + caffeate

0

-

3.1.1.73

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

0

-

3.1.1.73

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

0

-

3.1.1.73

methyl caffeate + H2O = caffeic acid + methanol

0

-

3.1.1.73

methyl caffeate + H2O = methanol + caffeic acid

0

-

3.1.1.73

14 entries

3.1.1.B10

chlorogenic acid + H2O = caffeic acid + (1S,3R,4R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid

0

-

4.3.1.25

L-DOPA = 3,4-dihydroxy-trans-cinnamate + NH3

0

-

Activator in Enzyme-catalyzed Reactions (6 results)

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Show Activating Compound (6 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.11.1.10

the total turnover number is almost 5fold higher than that obtained for the reference reaction

687888

-

1.14.18.1

effect of a range of diphenol treatments on the activation of latent red clover PPO tested. 91.9% activation

687251

-

2.3.1.95

presence of caffeic acid increases the total stilbene production by 1.8- to 1.9fold

756240

-

4.3.1.24

strong activation

34366, 34363

-

5.4.99.5

enzyme form CM3 is activated

3539

-

6.3.2.2

treatment of the cells with 100 and 500 microg/ml of caffeic acid increases gamma-GCS activities by 1.4- and 1.8fold compared to the control group, respectively. At the same doses of caffeic acid, the treated cells show increased levels of glutathione by 1.7- and 2.7fold compared to the control, respectively

703799

-

Inhibitor in Enzyme-catalyzed Reactions (83 results)

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Show Inhibitors (83 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.1

mixed type of inhibition

699982

-

1.1.1.195

-

739876

-

1.1.1.44

-

286866

-

1.1.1.62

18% inhibition at 0.05 mM

675981

-

1.1.1.64

18% inhibition at 0.05 mM

675981

-

1.13.11.12

-

702672, 711726

-

1.13.11.15

-

439614

-

1.13.11.3

-

439500

-

1.13.11.3

-

439501

-

1.13.11.3

2 entries

1.13.11.31

0.01 mM, 20-30% inhibition

395411

-

1.13.11.33

36.2% inhibition at 0.015 mM

685546

-

1.13.11.33

specific inhibition of 15-LO

686173

-

1.13.11.33

specific inhibitor of 15-LOX-1

706877

-

1.13.11.34

-

728431

-

1.13.11.34

-

702553, 705023, 711405

-

1.13.11.34

IC50: 0.046 mM

439461

-

1.13.11.34

micromolar 5-LOX inhibitory activity

711433

-

1.13.11.33

3 entries

1.13.11.34

4 entries

1.13.11.66

0.2 mM, 98% inhibition; 0.2 mM, 98% inhibition

718555

-

1.14.11.11

-

439275

-

1.14.11.2

competitive with respect to 2-oxoglutarate and ascorbate

439194

-

1.14.11.66

-

756531

-

1.14.11.66

a KDM4C inhibitor, that preferentially abolishes tumor-initiating cells in an ALDHbri+-derived xenograft model in vivo

745889

-

1.14.18.1

noncompetitive inhibition

689440

-

1.14.18.1

-

696667

-

1.14.18.1

10% inhibition at 0.1 mM

672587

-

1.14.18.1

6.6% inhibition at 1 mM

713205

-

1.14.18.1

i.e. 3,4-dihydroxycinnamic acid

696563

-

1.17.3.2

42.8% inhibition at 0.04 mM, 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

-

1.17.3.2

competitive inhibition of urate and superoxide anion formation

745109

-

1.14.11.66

2 entries

1.14.18.1

5 entries

1.17.3.2

2 entries

1.7.3.2

-

395021

-

2.1.1.4

in vitro N-acetylserotonin methyltransferase activity is significantly and competitively inhibited by caffeic acid, a substrate of the caffeic acid O-methyltransferase, 73% inhibition at 0.01 mM, 93% at 0.1 mM

734389

-

2.1.1.6

-

686194

-

2.1.1.6

COMT from liver, using 2-hydroxyestradiol as substrate, in Tris-HCl buffer (10 mM, pH 7.4), at 37°C; COMT from liver, using 4-hydroxyestradiol as substrate, in Tris-HCl buffer (10 mM, pH 7.4), at 37°C; COMT from placenta, using 2-hydroxyestradiol as substrate, in Tris-HCl buffer (10 mM, pH 7.4), at 37°C; COMT from placenta, using 4-hydroxyestradiol as substrate, in Tris-HCl buffer (10 mM, pH 7.4), at 37°C

705398

-

2.1.1.6

2 entries

2.1.1.68

23% residual activity at 0.1 mM

757324

-

2.3.1.172

10 mM, complete inhibition

656032

-

2.3.1.224

38% residual activity at 1 mM

720699

-

2.3.1.5

4 mM, 37.6% suppression. Dose-dependent enzyme inhibition in cytosolic and intact cell examinations

660714

-

2.3.1.5

4 mM, 37.9% suppression. Dose-dependent enzyme inhibition in cytosolic and intact cell examinations

660714

-

2.3.1.5

4 mM, 39.7% suppression. Dose-dependent enzyme inhibition in cytosolic and intact cell examinations

660714

-

2.3.1.5

4 mM, 65.3% suppression. Dose-dependent enzyme inhibition in cytosolic and intact cell examinations

660714

-

2.3.1.5

4 mM, 83.7% suppression. Dose-dependent enzyme inhibition in cytosolic and intact cell examinations

660714

-

2.3.1.5

inhibits NAT1 but not NAT2

686256

-

2.3.1.5

non-competitive

677267

-

2.3.1.5

7 entries

2.3.1.99

-

487784

-

2.5.1.54

isoenzyme DS-Co

639782

-

2.5.1.93

30% inhibition

738205

-

2.7.1.71

1 mM, 44% inhibition

641902

-

2.7.11.26

0.02 mg/ml caffeic acid decreases the activating phosphorylation of GSK-3beta

705453

-

2.8.2.1

inhibition of P-PST and M-PST

645686

-

3.1.1.42

-

80932

-

3.2.1.1

IC50 is 4.8 mM

666544

-

3.2.1.1

mixed-type inhibition, almost all activities of isozymes PPA-I and PPA-II are lost in the presence of 4 mM

704143

-

3.2.1.1

2 entries

3.2.1.20

-

709294

-

3.2.1.3

noncompetitive inhibition

750886

-

3.2.1.48

noncompetitive

750886

-

3.4.15.1

-

707653, 731965

-

3.4.15.1

IC50: about 1.7 mM

669026

-

3.4.15.1

2 entries

3.4.21.26

93.8% inhibition at 0.5 mM

732660

-

3.4.23.46

-

753331

-

3.5.1.98

80% residual activity at 0.5 mM

711439

-

3.5.3.1

0.1 mM, 56.98% inhibition

754290

-

3.5.3.1

inhibiting arginase activity by caffeic acid and chlorogenic acid might be a possible mechanism by which they exert their cardio-protective effect

752912

-

3.5.3.1

2 entries

3.5.4.1

-

718465

-

3.5.4.B9

-

718465

-

4.1.1.22

slight inhibition

680301

-

4.2.1.1

-

748811

6yri, 3D-view

4.2.2.10

enzyme activitiy of pectin lyase decreases significantly when 0.1 mg/l of caffic acid is added

699281

-

4.2.2.2

42% inhibition at 0.01 mM, 67% inhibition at 0.05 mM

666570

-

4.3.1.24

-

34364

-

4.3.1.24

-

34345, 34353, 34357, 34364

-

4.3.1.24

0.1 mM, slight

34358

-

4.3.1.24

3 entries

4.3.1.25

-

34365

-

4.99.1.10

-

743514

-

5.3.2.1

-

703331

3hof, 3D-view

5.3.2.1

-

703331

3hof, 3D-view

5.3.2.1

IC50 ketonase reaction 0.5 microM, pH 6.5, room temperatur, IC50 enolase reaction 2.0 microM, pH 6.2, room temperatur

661889

3hof, 3D-view

5.4.99.5

enzyme form CM1 is inhibited

3539

-

5.4.99.5

enzyme form CM1 is inhibited; enzyme form CM2 is inhibited

3539

-

5.4.99.5

enzyme forms CM1 and CM2 are inhibited, enzyme form CM3 is unaffected

3538

-

6.2.1.12

inhibition above 0.2 mM

620

-

6.2.1.12

strong competitive inhibitor for the other substrates

653527

-

5.3.2.1

3 entries

5.4.99.5

3 entries

6.2.1.12

2 entries

6.4.1.2

-

702619

-

7.2.2.19

-

689063

-

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

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

EC NUMBER

ENZYME 3D STRUCTURE

2.7.11.24

4n0s, 3D-view

4.2.1.1

6yri, 3D-view

5.3.2.1

3hof, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (29 results)

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Show Turnover Number (29 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.10.3.1

106

-

-

440432

1.11.1.7

189

-

pH 5.0, 16°C

743175

1.14.18.1

1450

-

-

636347

1.5.99.12

0.3

-

pH 6.5, recombinant enzyme

654539

2.1.1.104

0.068

-

pH 7.5, 37°C, in presence of 0.1 mM Co2+

668599

2.1.1.336

0.00038

-

pH 7.8, 37°C

756993

2.1.1.336

0.0023

-

pH 9.0, 37°C, product: isoferulic acid

756959

2.1.1.336

0.0032

-

pH 9.0, 37°C, product: ferulic acid

756959

2.1.1.336

3 entries

2.1.1.68

0.62

-

pH 7.5, temperature not specified in the publication

720616

6.2.1.12

0.0087

-

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

728512

6.2.1.12

0.014

-

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

728512

6.2.1.12

0.036

-

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

728512

6.2.1.12

0.0445

-

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

728512

6.2.1.12

0.084

-

wild type enzyme, at pH 7.5 and 30°C

746000

6.2.1.12

0.13

-

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

746036

6.2.1.12

0.217

-

mutant enzyme M247Y, at pH 7.5 and 30°C

746000

6.2.1.12

0.255

-

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

728512

6.2.1.12

0.36

-

pH 7.5, 22°C

728204

6.2.1.12

0.44

-

pH 7.5, 30°C

728464

6.2.1.12

0.78

-

pH 7.5, 22°C

728204

6.2.1.12

0.8

-

pH 7.5, 22°C

728204

6.2.1.12

0.92

-

pH 7.8, 22°C

727118

6.2.1.12

1.43

-

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

746098

6.2.1.12

1.6

-

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

746036

6.2.1.12

1.66

-

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

746098

6.2.1.12

2.652

-

wild type enzyme, at pH 7.5 and 25°C

746513

6.2.1.12

5.81

-

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

746098

6.2.1.12

5.84

-

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

746098

6.2.1.12

31.4

-

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

746098

6.2.1.12

20 entries

K_M Value (118 results)

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Show KM Value (118 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.10.3.1

5

-

-

440432

1.10.3.1

9.5

-

pH 6.5, 25°C

676649

1.10.3.1

2 entries

1.10.3.2

0.043

-

-

396394

1.11.1.7

0.08

-

covalently bound POD from artichoke leaves, apparent Km value

698044

1.11.1.7

0.1

-

covalently bound POD from artichoke heads, apparent Km value

698044

1.11.1.7

0.167

-

pH 5.0, 16°C

743175

1.11.1.7

0.19

-

ionically bound POD from artichoke heads, apparent Km value

698044

1.11.1.7

0.59

-

soluble POD from artichoke heads, apparent Km value

698044

1.11.1.7

1.59

-

soluble POD from artichoke leaves, apparent Km value

698044

1.11.1.7

1.9

-

ionically bound POD from artichoke leaves, apparent Km value

698044

1.11.1.7

7 entries

1.13.11.3

0.014

-

pH 7.5, 38°C

725655

1.14.18.1

0.037

-

pH 8.5, 15°C

745474

1.14.18.1

0.2

-

-

636382

1.14.18.1

0.42

-

-

636450

1.14.18.1

0.9

-

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

697659

1.14.18.1

1.69

-

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

697659

1.14.18.1

3.6

-

-

686847

1.14.18.1

6.43

-

-

636347

1.14.18.1

174.5

-

at pH 6.0, 20°C

712618

2.1.1.104

0.039

-

recombinant enzyme, 30°C

706277

2.1.1.104

0.0688

-

-

702477

2.1.1.104

0.088

-

pH 7.5, 37°C, in presence of 0.1 mM Co2+

668599

2.1.1.336

0.02032

-

pH 7.8, 37°C

756993

2.1.1.336

0.12

-

pH 9.0, 37°C, product: isoferulic acid

756959

2.1.1.336

0.225

-

pH 9.0, 37°C, product: ferulic acid

756959

2.1.1.68

0.009

-

mutant enzyme N131K

660104

2.1.1.68

0.01

-

mutant enzyme L136Y

660104

2.1.1.68

0.01013

-

isoform COMT2, in 50 mM Tris-HCl, pH 7.5, at 30°C

701663

2.1.1.68

0.012

-

pH 6.5, 22°C

734970

2.1.1.68

0.012

-

mutant enzyme A162T

660104

2.1.1.68

0.0242

-

pH 7.5, temperature not specified in the publication

720616

2.1.1.68

0.026

-

30°C, pH 7.5

720423

2.1.1.68

0.02874

-

isoform COMT1, in 50 mM Tris-HCl, pH 7.5, at 30°C

701663

2.1.1.68

0.032

-

mutant enzyme N324H/M130L

660104

2.1.1.68

0.043

-

-

485530

2.1.1.68

0.043

-

wild type

485531

2.1.1.68

0.043

-

wild-type enzyme

660104

2.1.1.68

0.0497

-

pH 7.5, 30°C

658800

2.1.1.68

0.05

-

-

485547

2.1.1.68

0.053

-

isozyme I

485541

2.1.1.68

0.058

-

-

485542

2.1.1.68

0.059

-

isozyme II

485541

2.1.1.68

0.06

-

recombinant enzyme

485067

2.1.1.68

0.068

-

-

485546

2.1.1.68

0.06875

-

-

702477

2.1.1.68

0.069

-

when S-adenosyl-L-methionine is supplied at a constant concentration of 1 mM

675589

2.1.1.68

0.1

-

isozyme I

485543

2.1.1.68

0.121

-

mutant enzyme N131D

660104

2.1.1.68

0.133

-

-

485545

2.1.1.68

0.133

-

mutant enzyme N324Y

660104

2.1.1.68

0.14

-

mutant enzyme H183K

660104

2.1.1.68

0.214

-

mutant enzyme N131E

660104

2.1.1.68

0.22

-

pH 8.0, 37°C

734491

2.1.1.68

0.25

-

pH and temperature not specified in the publication

718207

2.1.1.68

0.335

-

mutant enzyme N131L

660104

1.14.18.1

8 entries

2.1.1.104

3 entries

2.1.1.336

3 entries

2.1.1.68

30 entries

2.1.1.78

0.001

-

second substrate caffeic acid

485623

2.4.1.120

2.3

-

-

660175

2.4.1.126

0.0015

-

-

639510

2.4.1.177

0.7077

-

-

676590

2.4.1.35

0.32

-

pH 7.0, 30°C

657831

2.8.3.23

0.075

-

pH 7.5, 40°C

731177

6.2.1.12

0.0009

-

pH 7.5, 22°C

728204

6.2.1.12

0.001

-

wild type enzyme, at pH 7.5 and 25°C

746513

6.2.1.12

0.00494

-

pH 7.5, 30°C

728464

6.2.1.12

0.005

-

K457S mutant enzyme

651262

6.2.1.12

0.0058

-

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

728512

6.2.1.12

0.0068

-

pH 7.5, 22°C

728204

6.2.1.12

0.0109

-

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

728512

6.2.1.12

0.011

-

room temperature

653477

6.2.1.12

0.0125

-

pH 7.5, 22°C

728204

6.2.1.12

0.013

-

-

651117

6.2.1.12

0.013

-

4CL2

652422

6.2.1.12

0.014

-

2-coumarate

611

6.2.1.12

0.014

-

isoenzyme 2

608

6.2.1.12

0.014

-

K211S mutant enzyme

651262

6.2.1.12

0.0149

-

pH 7.8, 22°C

727118

6.2.1.12

0.0161

-

-

609

6.2.1.12

0.018

-

C403A mutant enzyme

651262

6.2.1.12

0.02

-

room temperature

653477

6.2.1.12

0.022

-

wild-type enzyme

653597

6.2.1.12

0.024

-

wild type

651262

6.2.1.12

0.024

-

wild type enzyme

652146

6.2.1.12

0.024

-

wild-type enzyme, pH 7.0, 30°C

653536

6.2.1.12

0.025

-

30°C, pH 7.0

732001

6.2.1.12

0.025

-

recombinant isozyme 4CL1

694601

6.2.1.12

0.0261

-

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

728512

6.2.1.12

0.02631

-

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

746098

6.2.1.12

0.02643

-

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

746098

6.2.1.12

0.0276

-

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

728512

6.2.1.12

0.028

-

E401Q mutant enzyme

651262

6.2.1.12

0.0293

-

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

728512

6.2.1.12

0.0296

-

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

746036

6.2.1.12

0.033

-

-

651117

6.2.1.12

0.034

-

-

651117

6.2.1.12

0.035

-

4CL1, pH 7.5, 30°C

653527

6.2.1.12

0.037

-

isozyme 4CL2, at pH 7.8 and 32°C

694698

6.2.1.12

0.04

-

isoenzyme 1

608

6.2.1.12

0.041

-

M293P/K320L mutant enzyme

653597

6.2.1.12

0.042

-

4CL2, pH 7.5, 30°C

653527

6.2.1.12

0.0423

-

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

746036

6.2.1.12

0.04414

-

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

746098

6.2.1.12

0.045

-

recombinant isozyme 4CL2

694601

6.2.1.12

0.048

-

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

653536

6.2.1.12

0.0484

-

isozyme 4CL1, pH 7.8, 32°C

694698

6.2.1.12

0.05

-

-

651117

6.2.1.12

0.05

-

4CL3

652422

6.2.1.12

0.06132

-

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

746098

6.2.1.12

0.081

-

4CL1

652422

6.2.1.12

0.08417

-

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

746098

6.2.1.12

0.154

-

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

726875

6.2.1.12

0.1929

-

mutant enzyme M247Y, at pH 7.5 and 30°C

746000

6.2.1.12

0.2089

-

wild type enzyme, at pH 7.5 and 30°C

746000

6.2.1.12

0.234

-

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

726875

6.2.1.12

0.262

-

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

726875

6.2.1.12

0.282

-

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

726875

6.2.1.12

0.374

-

room temperature

653477

6.2.1.12

0.4

-

R449Q mutant enzyme

651262

6.2.1.12

0.725

-

recombinant isozyme 4CL3

694601

6.2.1.12

57 entries

K_i Value (12 results)

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Show KI Value (12 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.1

0.00008

-

at 37°C in 0.1 M Na-K phosphate buffer (pH 7.4)

699982

1.13.11.15

0.3

-

-

439614

1.14.11.2

0.018

-

-

439194

2.3.1.99

0.82

-

-

487784

3.2.1.1

1.12

-

isozyme PPA-I, at pH 6.9 and 30°C

704143

3.2.1.1

1.64

-

isozyme PPA-II, at pH 6.9 and 30°C

704143

3.2.1.1

2 entries

3.5.1.98

0.01084

-

pH and temperature not specified in the publication

711439

4.2.1.1

0.00536

-

pH 8.3, 25°C, recombinant enzyme

748811

4.2.1.1

0.00592

-

pH 8.3, 25°C, recombinant enzyme

748811

4.2.1.1

0.0067

-

pH 8.3, 25°C, recombinant enzyme

748811

6.2.1.12

0.004

-

4CL1 with 4-coumarate as substrate, pH 7.5, 30°C

653527

6.2.1.12

0.012

-

4CL2 with 4-coumarate as substrate, pH 7.5, 30°C

653527

4.2.1.1

3 entries

6.2.1.12

2 entries

IC₅₀ Value (37 results)

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Show IC50 Value (37 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.13.11.12

0.6

-

25°C, pH not specified in the publication

711726

1.13.11.12

0.6

-

at pH 9.0

702672

1.13.11.34

0.003

-

pH and temperature not specified in the publication

728431

1.13.11.34

0.004

-

-

705023

1.13.11.34

0.004

-

pH and temperature not specified in the publication

711405, 711433

1.13.11.34

0.025

-

-

702553

1.13.11.34

0.046

-

IC50: 0.046 mM

439461

1.13.11.12

2 entries

1.13.11.34

5 entries

1.14.11.66

0.0137

-

pH and temperature not specified in the publication

756531

1.14.18.1

0.4

-

-

696563

1.14.18.1

0.97

-

-

689440

1.14.18.1

1

-

IC50 above 1.0 mM in 0.1 M phosphate buffer (pH 7.0), at 37°C

713205

1.17.3.2

0.0115

-

above, pH 10.0, 25°C, inhibition of urate formation

745109

1.17.3.2

0.0654

-

pH 8.0, 37°C, competitive versus xanthine

686866

1.17.3.2

0.0654

-

pH 8.0, 37°C, versus xanthine

686866

1.17.3.2

0.2

-

above, pH 10.0, 25°C, inhibition of urate formation

745109

3.2.1.1

0.37

-

isozyme PPA-II, at pH 6.9 and 30°C

704143

3.2.1.1

0.4

-

isozyme PPA-I, at pH 6.9 and 30°C

704143

3.2.1.1

4.8

-

IC50 is 4.8 mM

666544

3.2.1.20

0.49

-

substrate sucrose

709294

3.2.1.20

0.74

-

substrate maltose

709294

3.2.1.3

0.0565

-

pH not specified in the publication, 37°C, recombinant glucoamylase subunit Ct-MGAM

750886

3.2.1.3

0.0582

-

pH not specified in the publication, 37°C, recombinant glucoamylase subunit Ct-SI

750886

3.4.15.1

1.7

-

IC50: about 1.7 mM

669026

3.4.15.1

2.1

-

37°C, pH not specified in the publication

731965

3.4.15.1

2.1

-

pH not specified in the publication, 37°C

731965

3.4.15.1

2.527

-

pH 8.3, 37°C

707653

1.14.18.1

3 entries

1.17.3.2

4 entries

3.2.1.1

3 entries

3.2.1.20

2 entries

3.2.1.3

2 entries

3.4.15.1

4 entries

3.4.21.26

0.0125

-

pH and temperature not specified in the publication

732660

3.4.23.46

0.2

-

at pH 4.5 and 23°C

753331

3.5.1.98

2.54

-

pH and temperature not specified in the publication

711439

3.5.3.1

0.0219

-

pH 9.5, 37°C, activity in intracellular amastigote

754290

3.5.3.1

0.0608

-

pH 9.5, 37°C, activity in promastigote

754290

3.5.3.1

2 entries

3.5.4.1

0.085

-

pH 7.4, 37°C

718465

3.5.4.B9

0.085

-

at pH 7.8 and 37°C

718465

5.3.2.1

0.0005

0.002

IC50 ketonase reaction 0.5 microM, pH 6.5, room temperatur, IC50 enolase reaction 2.0 microM, pH 6.2, room temperatur

661889

6.4.1.2

0.000663

-

ACC1

702619

6.4.1.2

0.001

-

above, ACC2

702619

6.4.1.2

2 entries

7.2.2.19

0.0027

-

pH 6.5, 37°C

689063

References & Links

Literature References (266)

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Show Reference (266 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

595

9177055

3-Hydroxybenzoate:coenzyme A ligase and 4-coumarate:coenzyme A ligase from cultured cells of Centaurium erythraea

1997

Barillas, W.; Beerhues, L.

Planta

202

112-116

596

-

Facile enzymic synthesis of caffeoyl CoA

1997

Meng, H.; Campbell, W.H.

Phytochemistry

44

605-608

603

7646065

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