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Ligand 5-Hydroxyconiferaldehyde

Basic Ligand Information

Molecular Structure

Related pathways

Show all BRENDA pathways known for 5-Hydroxyconiferaldehyde

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Roles as Enzyme Ligand

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

1.14.14.B13

coniferaldehyde + [reduced NADPH-hemoprotein reductase] + O2 = 5-hydroxyconiferaldehyde + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

1.2.1.44

5-hydroxyferuloyl-CoA + NADPH + H+ = 5-hydroxyconiferaldehyde + CoA + NADP+

-

-

1.2.1.44

5-hydroxyferuloyl-CoA + NADPH + H+ = 5-hydroxyferulic aldehyde + CoA + NADP+

-

-

1.2.1.44

2 entries

Substrate in Enzyme-catalyzed Reactions (12 results)

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Show Substrate (12 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.195

5-hydroxyconiferyl aldehyde + NADP+ = 5-hydroxyconiferyl alcohol + NADPH + H+

739335

-

1.1.1.195

5-hydroxyconiferyl aldehyde + NADPH + H+ = 5-hydroxyconiferyl alcohol + NADP+

712611

-

1.1.1.195

5-hydroxyconiferyl aldehyde + NADPH = 5-hydroxyconiferyl alcohol + NADP+

670458

-

1.1.1.195

5-hydroxyconiferylaldehyde + NADP+ = 5-hydroxyconiferyl alcohol + NADPH + H+

739335

-

1.1.1.195

5-hydroxyconiferylaldehyde + NADPH + H+ = 5-hydroxyconiferyl alcohol + NADP+

739335

-

1.1.1.195

5 entries

1.3.1.102

5-hydroxyconiferyl aldehyde + NADP+ = dihydro-5-hydroxyconiferyl aldehyde + NADPH + H+

744897

-

2.1.1.104

S-adenosyl-L-methionine + 5-hydroxyconiferaldehyde = ?

720716, 758068

-

2.1.1.104

S-adenosyl-L-methionine + 5-hydroxyconiferaldehyde = S-adenosyl-L-homocysteine + sinapaldehyde

485067, 702477

-

2.1.1.68

S-adenosyl-L-methionine + 5-hydroxyconiferaldehyde = ?

720680

-

2.1.1.68

S-adenosyl-L-methionine + 5-hydroxyconiferaldehyde = S-adenosyl-L-homocysteine + 5-methoxyconiferaldehyde

658800, 660104, 702477, 718207, 734970

-

2.1.1.68

S-adenosyl-L-methionine + 5-hydroxyconiferaldehyde = S-adenosyl-L-homocysteine + sinapaldehyde

485067, 485531, 485539

-

2.1.1.68

S-adenosyl-L-methionine + 5-hydroxyconiferyl aldehyde = ?

720616

-

2.1.1.104

2 entries

2.1.1.68

4 entries

Product in Enzyme-catalyzed Reactions (4 results)

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Show Product (4 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.9

coniferaldehyde + FADH2 + O2 = 5-hydroxyconiferaldehyde + FAD + H2O

-

-

1.14.14.B13

coniferaldehyde + [reduced NADPH-hemoprotein reductase] + O2 = 5-hydroxyconiferaldehyde + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

1.2.1.44

5-hydroxyferuloyl-CoA + NADPH + H+ = 5-hydroxyconiferaldehyde + CoA + NADP+

-

-

1.2.1.44

5-hydroxyferuloyl-CoA + NADPH + H+ = 5-hydroxyferulic aldehyde + CoA + NADP+

288234, 288230, -

-

1.2.1.44

2 entries

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.68

-

734970

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (5 results)

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Show Turnover Number (5 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.1.1.195

0.005

-

isoform CAD1, at pH 6.0 and 25°C

739335

1.1.1.195

0.007

-

isoform CAD2, at pH 6.0 and 25°C

739335

1.3.1.102

0.161

-

pH and temperature not specified in the publication, recombinant isozyme PaDBR1 mutant C56Y

744897

1.3.1.102

0.169

-

pH and temperature not specified in the publication, recombinant wild-type isozyme PaDBR2

744897

1.1.1.195

2 entries

1.3.1.102

2 entries

2.1.1.68

2.85

-

pH 7.5, temperature not specified in the publication

720616

K_M Value (27 results)

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Show KM Value (27 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.195

0.0244

-

pH not specified in the publication, temperature not specified in the publication

712611

1.1.1.195

0.09318

-

isoform CAD1, at pH 6.0 and 25°C

739335

1.1.1.195

0.152

-

isoform CAD2, at pH 6.0 and 25°C

739335

1.3.1.102

0.2026

-

pH and temperature not specified in the publication, recombinant isozyme PaDBR1 mutant C56Y

744897

1.3.1.102

0.3081

-

pH and temperature not specified in the publication, recombinant wild-type isozyme PaDBR2

744897

1.1.1.195

3 entries

1.3.1.102

2 entries

2.1.1.104

0.0173

-

-

702477

2.1.1.68

0.00086

-

pH 6.5, 22°C

734970

2.1.1.68

0.001

-

mutant enzyme N131E

660104

2.1.1.68

0.0011

-

pH 7.5, 22°C

734970

2.1.1.68

0.0018

-

recombinant enzyme

485067

2.1.1.68

0.005

-

-

485530

2.1.1.68

0.005

-

wild type

485531

2.1.1.68

0.005

-

wild-type enzyme

660104

2.1.1.68

0.008

-

mutant enzyme H183K

660104

2.1.1.68

0.01

-

mutant enzyme F172Y

660104

2.1.1.68

0.011

-

mutant enzyme A162T

660104

2.1.1.68

0.012

-

mutant enzyme N131K

660104

2.1.1.68

0.013

-

mutant enzyme L136Y

660104

2.1.1.68

0.013

-

mutant enzyme N131L

660104

2.1.1.68

0.017

-

mutant enzyme N324Y

660104

2.1.1.68

0.01731

-

-

702477

2.1.1.68

0.0179

-

pH 7.5, temperature not specified in the publication

720616

2.1.1.68

0.0185

-

pH 7.5, 30°C

658800

2.1.1.68

0.028

-

mutant enzyme M130L

660104

2.1.1.68

0.041

-

mutant enzyme N324H/M130L

660104

2.1.1.68

0.041

-

pH and temperature not specified in the publication

718207

2.1.1.68

0.12

-

mutant enzyme N131D

660104

2.1.1.68

21 entries

K_i Value (2 results)

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Show KI Value (2 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.1.1.68

0.0027

-

pH 7.5, 22°C

734970

2.1.1.68

0.01

-

pH 6.5, 22°C

734970

2.1.1.68

2 entries

References & Links

Literature References (21)

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Show Reference (21 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

288230

7454

Enzymic synthesis of lignin precursors. Purification and properties of a cinnamoyl-CoA: NADPH reductase from cell suspension cultures of soybean (Glycine max)

1976

Wengenmayer, H.; Ebel, J.; Grisebach, H.

Eur. J. Biochem.

65

529-536

288234

236926

Reduction of coenzyme A thioesters of cinnamic acids with an enzyme preparation from lignifying tissue of Forsythia

1975

Gross, G.G.; Kreiten, W.

FEBS Lett.

54

259-262

485067

11169195

Substrate preferences of O-methyltransferases in alfalfa suggest new pathways for 3-O-methylation of monolignols

2001

Parvathi, K.; Chen, F.; Guo, D.; Blount, J.W.; Dixon, R.A.

Plant J.

25

193-202

485530

12084820

Probing the mysteries of lignin biosynthesis: The crystal structure of caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase provides new insights

2002

Eckardt, N.A.

Plant Cell

14

1185-1189

485531

12084826

Structural basis for the modulation of lignin monomer methylation by caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase

2002

Zubieta, C.; Kota, P.; Ferrer, J.L.; Dixon, R.A.; Noel, J.P.

Plant Cell

14

1265-1277

485539

11430990

Caffeoyl coenzyme A O-methyltransferase and lignin biosynthesis

2001

Ye, Z.H.; Zhong, R.; Morrison, W.H.; Himmelsbach, D.S.

Phytochemistry

57

1177-1185

658800

-

Transgenic down-regulation of caffeic acid O-methyltransferase (COMT) led to improved digestibility in tall fescue (Festuca arundinacea)

2004

Chen, L.; Auh, C.K.; Dowling, P.; Bell, J.; Lehmann, D.; Wang, Z.Y.

Funct. Plant Biol.

31

235-245

660104

15081283

O-Methylation of benzaldehyde derivatives by "lignin specific" caffeic acid 3-O-methyltransferase

2004

Kota, P.; Guo, D.; Zubieta, C.; Noel, J.; Dixon, R.A.

Phytochemistry

65

837-846

670458

16633561

Crystal structures and catalytic mechanism of the Arabidopsis cinnamyl alcohol dehydrogenases AtCAD5 and AtCAD4

2006

Youn, B.; Camacho, R.; Moinuddin, S.G.; Lee, C.; Davin, L.B.; Lewis, N.G.; Kang, C.

Org. Biomol. Chem.

4

1687-1697

702477

17976886

Characterization of a caffeic acid 3-O-methyltransferase from wheat and its function in lignin biosynthesis

2008

Ma, Q.; Xu, Y.

Biochimie

90

515-524

712611

20400532

Functional analysis of a cinnamyl alcohol dehydrogenase involved in lignin biosynthesis in wheat

2010

Ma, Q.H.

J. Exp. Bot.

61

2735-2744

718207

15118832

Characterization of a multifunctional methyltransferase from the orchid Vanilla planifolia

2004

Pak, F.E.; Gropper, S.; Dai, W.D.; Havkin-Frenkel, D.; Belanger, F.C.

Plant Cell Rep.

22

959-966

720616

20652169

Insights into lignin primary structure and deconstruction from Arabidopsis thaliana COMT (caffeic acid O-methyl transferase) mutant Atomt1

2010

Moinuddin, S.G.; Jourdes, M.; Laskar, D.D.; Ki, C.; Cardenas, C.L.; Kim, K.W.; Zhang, D.; Davin, L.B.; Lewis, N.G.

Org. Biomol. Chem.

8

3928-3946

720680

21177481

Structure-function analyses of a caffeic acid O-methyltransferase from perennial ryegrass reveal the molecular basis for substrate preference

2010

Louie, G.V.; Bowman, M.E.; Tu, Y.; Mouradov, A.; Spangenberg, G.; Noel, J.P.

Plant Cell

22

4114-4127

720716

21629984

Functional characterization of two new members of the caffeoyl CoA O-methyltransferase-like gene family from Vanilla planifolia reveals a new class of plastid-localized O-methyltransferases

2011

Widiez, T.; Hartman, T.G.; Dudai, N.; Yan, Q.; Lawton, M.; Havkin-Frenkel, D.; Belanger, F.C.

Plant Mol. Biol.

76

475-488

734970

24948836

Determination of the structure and catalytic mechanism of Sorghum bicolor caffeic acid O-methyltransferase and the structural impact of three brown midrib12 mutations

2014

Green, A.R.; Lewis, K.M.; Barr, J.T.; Jones, J.P.; Lu, F.; Ralph, J.; Vermerris, W.; Sattler, S.E.; Kang, C.

Plant Physiol.

165

1440-1456

739335

23774375

Molecular cloning and biochemical characterization of two cinnamyl alcohol dehydrogenases from a liverwort Plagiochasma appendiculatum

2013

Sun, Y.; Wu, Y.; Zhao, Y.; Han, X.; Lou, H.; Cheng, A.

Plant Physiol. Biochem.

70

133-141

744897

23954295

A single amino acid determines the catalytic efficiency of two alkenal double bond reductases produced by the liverwort Plagiochasma appendiculatum

2013

Wu, Y.; Cai, Y.; Sun, Y.; Xu, R.; Yu, H.; Han, X.; Lou, H.; Cheng, A.

FEBS Lett.

587

3122-3128

744897

23954295

A single amino acid determines the catalytic efficiency of two alkenal double bond reductases produced by the liverwort Plagiochasma appendiculatum

2013

Wu, Y.; Cai, Y.; Sun, Y.; Xu, R.; Yu, H.; Han, X.; Lou, H.; Cheng, A.

FEBS Lett.

587

3122-3128

758068

30685696

Isolation and functional characterization of two caffeoyl coenzyme A 3-O-methyltransferases from the fern species Polypodiodes amoena

2019

Zhang, X.S.; Ni, R.; Wang, P.Y.; Zhu, T.T.; Sun, C.J.; Lou, H.X.; Cheng, A.X.

Plant Physiol. Biochem.

136

169-177

758068

30685696

Isolation and functional characterization of two caffeoyl coenzyme A 3-O-methyltransferases from the fern species Polypodiodes amoena

2019

Zhang, X.S.; Ni, R.; Wang, P.Y.; Zhu, T.T.; Sun, C.J.; Lou, H.X.; Cheng, A.X.

Plant Physiol. Biochem.

136

169-177

744897

2 entries

758068

2 entries

Links to other databases for 5-Hydroxyconiferaldehyde

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Show Links (1 entry)