print visible entries

print all entries

Ligand methyl caffeate

Basic Ligand Information

Molecular Structure

close all tables

open all tables

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

top print hide

Show Natural Substrate (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.73

methyl caffeate + H2O = caffeic acid + methanol

715959

-

Substrate in Enzyme-catalyzed Reactions (11 results)

top print hide

Show Substrate (11 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.42

methyl caffeate + H2O = methanol + caffeate

751883, 750582

-

3.1.1.73

methyl 3,4-dihydroxy cinnamate + H2O = ?

716678

-

3.1.1.73

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

669552

-

3.1.1.73

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

669560, 667277

-

3.1.1.73

methyl caffeate + 1-butanol = methanol + butyl caffeate

668435

-

3.1.1.73

methyl caffeate + H2O = ?

677293

-

3.1.1.73

methyl caffeate + H2O = caffeate + methanol

696900, 677627, 745564, 744982, 745097

-

3.1.1.73

methyl caffeate + H2O = caffeic acid + methanol

677734, 208306, 208307, 208316, 667273, 670723, 677293, 730880, 668435, 707256, 208317, 667243, 668444, 730768, 714585, 715959, 668448, 669551, 670751, 682498, 667276, 670762, 679050, 667790, 696900, 729012, 729036, 729875, 707264, 729086, 667461, 668555, 677627

-

3.1.1.73

methyl caffeate + H2O = methanol + caffeate

750398, 741805, 745896, 737854, 745566, 751703, 751979

-

3.1.1.73

methyl caffeate + H2O = methanol + caffeic acid

695792, 737514, 737582

-

3.1.1.73

9 entries

3.1.1.B10

methyl caffeate + H2O = ?

745896

-

Product in Enzyme-catalyzed Reactions (1 result)

top print hide

Show Product (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.42

5-caffeoylquinic acid + H2O = methyl caffeate + quinate

0

-

Inhibitor in Enzyme-catalyzed Reactions (4 results)

top print hide

Show Inhibitors (4 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.17.3.2

competitive inhibition of urate and superoxide anion formation

745109

-

2.3.1.262

-

756481

-

3.1.1.73

-

667277

-

3.4.21.26

90.5% inhibition at 0.5 mM

732660

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (27 results)

top print hide

Show Turnover Number (27 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

3.1.1.42

1.9

-

pH 7.5, 37°C

750582

3.1.1.73

-999

-

45°C, pH 6.0, isoenzyme FAE-I

677627

3.1.1.73

0.01

-

pH 6.0, 37°C, Y80S mutant enzyme

668555

3.1.1.73

0.02

-

pH 6.0, 37°C, Y80V mutant enzyme

668555

3.1.1.73

0.1

-

-

668444

3.1.1.73

0.133

-

-

669560

3.1.1.73

0.16

-

-

695792

3.1.1.73

0.18

-

mutant W144Y, pH 7.0, 37°C

745566

3.1.1.73

0.26

-

pH 6.0, 37°C, W260V mutant enzyme

668555

3.1.1.73

0.31

-

mutant W142F, pH 7.0, 37°C

745566

3.1.1.73

0.32

-

pH 6.0, 37°C, W260S mutant enzyme

668555

3.1.1.73

3.1

-

pH 6.0, 55°C

737582, 741805

3.1.1.73

4.8

-

37°C, pH 6.0

677627

3.1.1.73

4.8

-

pH 6.0, 37°C

667277

3.1.1.73

5.9

-

pH 6.0, 45°C

668435

3.1.1.73

5.92

-

45°C, pH 6.0, isoenzyme FAE-I

677627

3.1.1.73

7.9

-

45°C, pH 6.0, isoenzyme FAE-II

677627

3.1.1.73

20

-

pH 6.0, 37°C

745896

3.1.1.73

24.1

-

37°C, pH 6.0

677627

3.1.1.73

30

-

30°C

667243

3.1.1.73

34.1

-

pH 7.5, 37°C

737854

3.1.1.73

38.4

-

pH 7.5, 37°C

737854

3.1.1.73

234

-

isoenzyme FAEB

679050

3.1.1.73

278

-

pH 9.0, 30°C

737514

3.1.1.73

438

-

wild-type, pH 6.0, 37°C

751979

3.1.1.73

2306

-

pH 7.2, 30°C

750398

3.1.1.73

25 entries

3.1.1.B10

20

-

pH 6.0, 37°C

745896

K_M Value (32 results)

top print hide

Show KM Value (32 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.1.1.42

0.1251

-

pH 7.5, 37°C

750582

3.1.1.73

0.02

-

37°C, pH 6.0

677627

3.1.1.73

0.02

-

pH 6.0, 37°C

667277

3.1.1.73

0.0285

-

pH 6.0, 37°C

745896

3.1.1.73

0.031

-

pH 6.0, 55°C

737582, 741805

3.1.1.73

0.057

-

mutant W144Y, pH 7.0, 37°C

745566

3.1.1.73

0.1

-

30°C

667243

3.1.1.73

0.12

-

mutant W142F, pH 7.0, 37°C

745566

3.1.1.73

0.123

-

pH 7.5, 37°C

737854

3.1.1.73

0.124

-

pH 7.5, 37°C

737854

3.1.1.73

0.13

-

-

670762

3.1.1.73

0.139

-

-

208316

3.1.1.73

0.139

-

37°C, pH 6.0

677627

3.1.1.73

0.14

-

-

669560

3.1.1.73

0.14

-

-

668444

3.1.1.73

0.158

-

isoenzyme FAEB

679050

3.1.1.73

0.196

-

pH 7, 40°C

668448

3.1.1.73

0.26

-

45°C, pH 6.0, isoenzyme FAE-I

677627

3.1.1.73

0.26

-

pH 6.0, 45°C

668435

3.1.1.73

0.387

-

40°C, pH 7.0

677734

3.1.1.73

0.53

-

pH 7.2, 30°C

750398

3.1.1.73

0.649

-

wild-type, pH 6.0, 37°C

751979

3.1.1.73

0.81

-

45°C, pH 6.0, isoenzyme FAE-II

677627

3.1.1.73

2.61

-

isozyme R43, pH 7.0, 50°C

730768

3.1.1.73

2.79

-

pH 9.0, 30°C

737514

3.1.1.73

3.02

-

pH 6.0, 37°C, Y80V mutant enzyme

668555

3.1.1.73

3.31

-

isozyme R18, pH 7.0, 50°C

730768

3.1.1.73

3.84

-

pH 6.0, 37°C, Y80S mutant enzyme

668555

3.1.1.73

4.1

-

pH 6.0, 37°C, W260S mutant enzyme

668555

3.1.1.73

4.72

-

pH 6.0, 37°C, W260V mutant enzyme

668555

3.1.1.73

140.7

-

-

695792

3.1.1.73

30 entries

3.1.1.B10

0.0285

-

pH 6.0, 37°C

745896

K_i Value (1 result)

top print hide

Show KI Value (1 entry)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.1.1.73

2.5

-

pH 6.0

667277

IC₅₀ Value (4 results)

top print hide

Show IC50 Value (4 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.17.3.2

0.012

-

pH 10.0, 25°C, inhibition of urate formation

745109

1.17.3.2

0.143

-

pH 10.0, 25°C, inhibition of urate formation

745109

1.17.3.2

2 entries

2.3.1.262

0.051

-

pH and temperature not specified in the publication

756481

3.4.21.26

0.005

-

pH and temperature not specified in the publication

732660

References & Links

Literature References (55)

top print hide

Show Reference (55 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

208306

8679110

Purification and characterization of a novel esterase induced by growth of Aspergillus niger on sugar-beet pulp

1996

Kroon, P.A.; Faulds, C.B.; Williamson, G.

Biotechnol. Appl. Biochem.

23

255-262

208307

9449810

Purification and characterization of a feruloyl esterase from the fungus Penicillium expansum

1997

Donaghy, J.; McKay, A.M.

J. Appl. Microbiol.

83

718-726

208316

11082184

A modular esterase from Penicillium funiculosum which releases ferulic acid from plant cell walls and binds crystalline cellulose contains a carbohydrate binding module

2000

Kroon, P.A.; Williamson, G.; Fish, N.M.; Archer, D.B.; Belshaw, N.J.

Eur. J. Biochem.

267

6740-6752

208317

10747226

Purification and characterization of an extracellular feruloyl esterase from the thermophilic anaerobe Clostridium stercorarium

2000

Donaghy, J.A.; Bronnenmeier, K.; Soto-Kelly, P.F.; McKay, A.M.

J. Appl. Microbiol.

88

458-466

667243

12957952

Purification and properties of a feruloyl esterase involved in lignocellulose degradation by Aureobasidium pullulans

2003

Rumbold, K.; Biely, P.; Mastihubova, M.; Gudelj, M.; Gubitz, G.; Robra, K.H.; Prior, B.A.

Appl. Environ. Microbiol.

69

5622-5626

667273

12466893

Mono- and dimeric ferulic acid release from brewer's spent grain by fungal feruloyl esterases

2002

Faulds, C.B.; Sancho, A.I.; Bartolome, B.

Appl. Microbiol. Biotechnol.

60

489-494

667276

14595525

Identification of a type-D feruloyl esterase from Neurospora crassa

2004

Crepin, V.F.; Faulds, C.B.; Connerton, I.F.

Appl. Microbiol. Biotechnol.

63

567-570

667277

14661116

Functional classification of the microbial feruloyl esterases

2004

Crepin, V.F.; Faulds, C.B.; Connerton, I.F.

Appl. Microbiol. Biotechnol.

63

647-652

667461

11931668

The Aspergillus niger faeB gene encodes a second feruloyl esterase involved in pectin and xylan degradation and is specifically induced in the presence of aromatic compounds

2002

de Vries, R.P.; vanKuyk, P.A.; Kester, H.C.; Visser, J.

Biochem. J.

363

377-386

667790

15716038

Mutational analysis of a feruloyl esterase from Aspergillus awamori involved in substrate discrimination and pH dependence

2005

Koseki, T.; Takahashi, K.; Fushinobu, S.; Iefuji, H.; Iwano, K.; Hashizume, K.; Matsuzawa, H.

Biochim. Biophys. Acta

1722

200-208

668435

-

Purification and characterization of a Fusarium oxysporum feruloyl esterase (FoFAE-I) catalysing transesterification of phenolic acid esters

2003

Topakas, E.; Stamatis, H.; Mastihubova, M.; Biely, P.; Kekos, D.; Macris, B.J.; Christakopoulos, P.

Enzyme Microb. Technol.

33

729-737

668444

-

Sporotrichum thermophile type C feruloyl esterase (StFaeC): purification, characterization, and its use for phenolic acid (sugar) ester synthesis

2005

Topakas, E.; Vafiadi, C.; Stamatis, H.; Christakopoulos, P.

Enzyme Microb. Technol.

36

729-736

668448

-

Production and characterization of a type B feruloyl esterase from Fusarium proliferatum NRRL 26517

2006

Shin, H.D.; Chen, R.R.

Enzyme Microb. Technol.

38

478-485

668555

16128806

Probing the determinants of substrate specificity of a feruloyl esterase, AnFaeA, from Aspergillus niger

2005

Faulds, C.B.; Molina, R.; Gonzalez, R.; Husband, F.; Juge, N.; Sanz-Aparicio, J.; Hermoso, J.A.

FEBS J.

272

4362-4371

669551

15006424

The feruloyl esterase system of Talaromyces stipitatus: production of three discrete feruloyl esterases, including a novel enzyme, TsFaeC, with a broad substrate specificity

2004

Garcia-Conesa, M.T.; Crepin, V.F.; Goldson, A.J.; Williamson, G.; Cummings, N.J.; Connerton, I.F.; Faulds, C.B.; Kroon, P.A.

J. Biotechnol.

108

227-241

669552

15639097

Comparison of mesophilic and thermophilic feruloyl esterases: characterization of their substrate specificity for methyl phenylalkanoates

2005

Topakas, E.; Christakopoulos, P.; Faulds, C.B.

J. Biotechnol.

115

355-366

669560

16584797

The feruloyl esterase system of Talaromyces stipitatus: Determining the hydrolytic and synthetic specificity of TsFaeC

2006

Vafiadi, C.; Topakas, E.; Christakopoulos, P.; Faulds, C.B.

J. Biotechnol.

125

210-221

670723

-

Feruloyl esterase from Aspergillus niger: a comparison of the production in solid state and submerged fermentation

2002

Asther, M.; Haon, M.; Roussos, S.; Record, E.; Delattre, M.; Lesage-Meessen, L.; Labat, M.; Asther, M.

Process Biochem.

38

685-691

670751

12767807

Production and characterization of the Talaromyces stipitatus feruloyl esterase FAEC in Pichia pastoris: identification of the nucleophilic serine

2003

Crepin, V.F.; Faulds, C.B.; Connerton, I.F.

Protein Expr. Purif.

29

176-184

670762

15294290

Homologous expression of the feruloyl esterase B gene from Aspergillus niger and characterization of the recombinant enzyme

2004

Levasseur, A.; Benoit, I.; Asther, M.; Asther, M.; Record, E.

Protein Expr. Purif.

37

126-133

677293

17989872

Feruloyl esterases as biotechnological tools: current and future perspectives

2007

Fazary, A.E.; Ju, Y.H.

Acta Biochim. Biophys. Sin.

39

811-828

677627

16702605

Feruloyl esterase: a key enzyme in biomass degradation

2006

Wong, D.W.

Appl. Biochem. Biotechnol.

133

87-112

677734

17043824

A type B feruloyl esterase from Aspergillus nidulans with broad pH applicability

2007

Shin, H.D.; Chen, R.R.

Appl. Microbiol. Biotechnol.

73

1323-1330

679050

16697997

Feruloyl esterases as a tool for the release of phenolic compounds from agro-industrial by-products

2006

Benoit, I.; Navarro, D.; Marnet, N.; Rakotomanomana, N.; Lesage-Meessen, L.; Sigoillot, J.C.; Asther, M.; Asther, M.

Carbohydr. Res.

341

1820-1827

682498

-

Microbial production, characterization and applications of feruloyl esterases

2007

Topakas, E.; Vafiadi, C.; Christakopoulos, P.

Proc. Biochem.

42

497-509

695792

18414848

Cloning, characterization and functional expression of an alkalitolerant type C feruloyl esterase from Fusarium oxysporum

2008

Moukouli, M.; Topakas, E.; Christakopoulos, P.

Appl. Microbiol. Biotechnol.

79

245-254

696900

17973091

Biotechnological applications and potential of fungal feruloyl esterases based on prevalence, classification and biochemical diversity

2008

Benoit, I.; Danchin, E.G.; Bleichrodt, R.; Vries, R.P.

Biotechnol. Lett.

30

387-396

707256

19756576

Characterization of a chimeric enzyme comprising feruloyl esterase and family 42 carbohydrate-binding module

2010

Koseki, T.; Mochizuki, K.; Kisara, H.; Miyanaga, A.; Fushinobu, S.; Murayama, T.; Shiono, Y.

Appl. Microbiol. Biotechnol.

86

155-161

707264

20127235

Thermostable feruloyl esterase for the bioproduction of ferulic acid from triticale bran

2010

Abokitse, K.; Wu, M.; Bergeron, H.; Grosse, S.; Lau, P.C.

Appl. Microbiol. Biotechnol.

87

195-203

714585

20821249

Novel bacterial ferulic acid esterase from Cellvibrio japonicus and its application in ferulic acid release and xylan hydrolysis

2011

McClendon, S.D.; Shin, H.D.; Chen, R.R.

Biotechnol. Lett.

33

47-54

715959

-

Immobilization of feruloyl esterases in mesoporous materials leads to improved transesterification yield

2011

Thoern, C.; Gustafsson, H.; Olsson, L.

J. Mol. Catal. B

72

57-64

716678

20877647

Combining substrate specificity analysis with support vector classifiers reveals feruloyl esterase as a phylogenetically informative protein group

2010

Olivares-Hernandez, R.; Sunner, H.; Frisvad, J.C.; Olsson, L.; Nielsen, J.; Panagiotou, G.

PLoS ONE

5

e12781

729012

24142352

A feruloyl esterase (FAE) characterized by relatively high thermostability from the edible mushroom Russula virescens

2014

Wang, L.; Zhang, R.; Ma, Z.; Wang, H.; Ng, T.

Appl. Biochem. Biotechnol.

172

993-1003

729036

23793626

Characterization of a feruloyl esterase from Lactobacillus plantarum

2013

Esteban-Torres, M.; Reveron, I.; Mancheno, J.M.; de Las Rivas, B.; Munoz, R.

Appl. Environ. Microbiol.

79

5130-5136

729086

23649351

Metagenomic mining of feruloyl esterases from termite enteric flora

2014

Rashamuse, K.; Ronneburg, T.; Sanyika, W.; Mathiba, K.; Mmutlane, E.; Brady, D.

Appl. Microbiol. Biotechnol.

98

727-737

729875

25065258

Feruloyl esterase from the edible mushroom Panus giganteus: a potential dietary supplement

2014

Wang, L.; Ma, Z.; Du, F.; Wang, H.; Ng, T.B.

J. Agric. Food Chem.

62

7822-7827

730768

25093500

Application of two newly identified and characterized feruloyl esterases from Streptomyces sp. in the enzymatic production of ferulic acid from agricultural biomass

2014

Uraji, M.; Arima, J.; Inoue, Y.; Harazono, K.; Hatanaka, T.

PLoS ONE

9

e104584

730880

23981381

Expression, purification and characterization of a feruloyl esterase A from Aspergillus flavus

2013

Zhang, S.B.; Zhai, H.C.; Wang, L.; Yu, G.H.

Protein Expr. Purif.

92

36-40

732660

24085498

In vitro evaluation of caffeoyl and cinnamoyl derivatives as potential prolyl oligopeptidase inhibitors

2013

Adolpho, L.O.; Marin, D.; Puigpinos, A.; Mendieta, L.; Tarrago, T.; Morel, A.F.; Giralt, E.; Dalcol, I.I.

Planta Med.

79

1531-1535

737514

26497017

Biochemical characterization of a halotolerant feruloyl esterase from Actinomyces spp.: refolding and activity following thermal deactivation

2016

Hunt, C.; Tanksale, A.; Haritos, V.

Appl. Microbiol. Biotechnol.

100

1777-1787

737582

-

Acidic-alkaline ferulic acid esterase from Chaetomium thermophilum var. dissitum: Molecular cloning and characterization of recombinant enzyme expressed in Pichia pastoris

2016

Dotsenko, G.; Tong, X.; Pilgaard, B.; Busk, P.; Lange, L.

Biocatal. Agricult. Biotechnol.

5

48-55

737854

27566510

Feruloyl esterases from Schizophyllum commune to treat food industry side-streams

2016

Nieter, A.; Kelle, S.; Linke, D.; Berger, R.

Biores. Technol.

220

38-46

741805

-

Acidic-alkaline ferulic acid esterase from Chaetomium thermophilum var. dissitum Molecular cloning and characterization of recombinant enzyme expressed in Pichia pastoris

2016

Dotsenko, G.; Tong, X.; Pilgaard, B.; Busk, P.; Lange, L.

Biocatal. Agricult. Biotechnol.

5

48-55

744982

28626449

Characterization of feruloyl esterases produced by the four lactobacillus species L. amylovorus, L. acidophilus, L. farciminis and L. fermentum, isolated from ensiled corn stover

2017

Xu, Z.; He, H.; Zhang, S.; Guo, T.; Kong, J.

Front. Microbiol.

8

941

745097

27519296

An acidic feruloyl esterase from the mushroom Lactarius hatsudake A potential animal feed supplement

2016

Wang, L.; Li, Z.; Zhu, M.; Meng, L.; Wang, H.; Ng, T.B.

Int. J. Biol. Macromol.

93

290-295

745109

26940252

Suppression of superoxide anion generation catalyzed by xanthine oxidase with alkyl caffeates and the scavenging activity

2016

Masuoka, N.; Kubo, I.

Int. J. Food Sci. Nutr.

67

283-287

745564

-

Biochemical characterization of a novel feruloyl esterase from Penicillium piceum and its application in biomass bioconversion

2016

Gao, L.; Wang, M.; Chen, S.; Zhang, D.

J. Mol. Catal. B

133

S388-S394

745566

-

An unusual feruloyl esterase from Aspergillus oryzae two tryptophan residues play a crucial role for the activity

2016

Koseki, T.; Handa, H.; Watanabe, Y.; Ohtsuka, M.; Shiono, Y.

J. Mol. Catal. B

133

S560-S568

745896

28159727

A p-coumaroyl esterase from Rhizoctonia solani with a pronounced chlorogenic acid esterase activity

2017

Nieter, A.; Kelle, S.; Linke, D.; Berger, R.G.

New Biotechnol.

37

153-161

750398

-

Type C feruloyl esterase from Aspergillus ochraceus A butanol specific biocatalyst for the synthesis of hydroxycinnamates in a ternary solvent system

2018

Romero-Borbon, E.; Grajales-Hernandez, D.; Armendariz-Ruiz, M.; Ramirez-Velasco, L.; Rodriguez-Gonzalez, J.; Cira-Chavez, L.; Estrada-Alvarado, M.; Mateos-Diaz, J.

Electron. J. Biotechnol.

35

1-9

750582

27173527

Heterologous production and characterization of a chlorogenate esterase from Ustilago maydis with a potential use in baking

2016

Nieter, A.; Kelle, S.; Takenberg, M.; Linke, D.; Bunzel, M.; Popper, L.; Berger, R.G.

Food Chem.

209

1-9

751703

29174720

Fungal feruloyl esterases Functional validation of genome mining based enzyme discovery including uncharacterized subfamilies

2018

Dilokpimol, A.; Maekelae, M.R.; Varriale, S.; Zhou, M.; Cerullo, G.; Gidijala, L.; Hinkka, H.; Bras, J.L.A.; Juetten, P.; Piechot, A.; Verhaert, R.; Hilden, K.S.; Faraco, V.; de Vries, R.P.

New Biotechnol.

41

9-14

751883

27783981

Characterization and purification of a bacterial chlorogenic acid esterase detected during the extraction of chlorogenic acid from arbuscular mycorrhizal tomato roots

2016

Negrel, J.; Javelle, F.; Morandi, D.; Lucchi, G.

Plant Physiol. Biochem.

109

308-318

751979

29795702

Tailoring the specificity of the type C feruloyl esterase FoFaeC from Fusarium oxysporum towards methyl sinapate by rational redesign based on small molecule docking simulations

2018

Antonopoulou, I.; Hunt, C.; Cerullo, G.; Varriale, S.; Gerogianni, A.; Faraco, V.; Rova, U.; Christakopoulos, P.

PLoS ONE

13

e0198127

756481

28195681

Recent advances in the discovery of PqsD inhibitors as antimicrobial agents

2017

Zhou, Z.; Ma, S.

ChemMedChem

12

420-425

Links to other databases for methyl caffeate

top print hide

Show Links (1 entry)

ChEBI

PubChem