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Ligand coniferyl alcohol

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

BRENDA

phenylpropanoid biosynthesis

KEGG

Biosynthesis of phenylpropanoids, Biosynthesis of secondary metabolites, Biosynthesis of various secondary metabolites - part 2, Phenylpropanoid biosynthesis

MetaCyc

capsiconiate biosynthesis, coniferin metabolism, coniferyl alcohol 9-methyl ester biosynthesis, eugenol and isoeugenol biosynthesis, justicidin B biosynthesis, matairesinol biosynthesis, phenylpropanoid biosynthesis, sesamin biosynthesis more

Show all BRENDA pathways known for coniferyl alcohol

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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

1.1.1.194

coniferyl alcohol + NADP+ = coniferyl aldehyde + NADPH + H+

389603, 347801, 389479, 389481, 760935, 389482

-

1.1.1.195

coniferol + NADP+ = coniferyl aldehyde + NADPH

657055

-

1.1.1.195

coniferyl alcohol + NADP+ = coniferyl aldehyde + NADPH + H+

741116, 741161, 740239, 670637, 740539, 738304, 670531

-

1.1.1.90

coniferyl alcohol + NAD(P)+ = coniferyl aldehyde + NAD(P)H + H+

692723

-

1.1.1.90

coniferyl alcohol + NAD+ = coniferyl aldehyde + NADH + H+

739587

-

1.1.1.195

2 entries

1.1.1.90

2 entries

2.4.1.111

UDPglucose + coniferyl alcohol = ?

488455, 488456, 488454

-

In Vivo Product in Enzyme-catalyzed Reactions (5 results)

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Show Natural Product (5 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.194

coniferyl aldehyde + NADPH + H+ = coniferyl alcohol + NADP+

-

-

1.1.1.195

coniferaldehyde + NADPH + H+ = coniferyl alcohol + NADP+

-

-

1.1.1.195

coniferyl aldehyde + NADPH + H+ = coniferyl alcohol + NADP+

-

-

1.1.1.195

coniferyl aldehyde + NADPH = coniferyl alcohol + NADP+

-

-

1.1.1.195

3 entries

3.2.1.126

coniferin + H2O = D-glucose + coniferol

650284, 653495

-

Substrate in Enzyme-catalyzed Reactions (23 results)

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Show Substrate (23 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.194

coniferyl alcohol + NADP+ = coniferyl aldehyde + NADPH + H+

389603, 347801, 389479, 389484, 389481, 760935, 389482, 739587

-

1.1.1.195

coniferol + NADP+ = coniferyl aldehyde + NADPH

657055

-

1.1.1.195

coniferyl alcohol + NADP+ = coniferyl aldehyde + NADPH + H+

347821, 347820, 347818, 347801, 347811, 347813, 347816, 288233, 288228, 347808, 700841, 668545, 739876, 741116, 347815, 347823, 347814, 347819, 741161, 670620, 740239, 670531, 700832, 670637, 726428, 724491, 740539, 738304

-

1.1.1.2

coniferyl alcohol + NADP+ = coniferaldehyde + NADPH + H+

654493

-

1.1.1.2

coniferyl alcohol + NADP+ = coniferylaldehyde + NADPH + H+

654493

-

1.1.1.90

coniferyl alcohol + NAD(P)+ = coniferyl aldehyde + NAD(P)H + H+

692723

-

1.1.1.90

coniferyl alcohol + NAD+ = coniferyl aldehyde + NADH + H+

389587, 724592, 654264, 692723, 724027, 739587

-

1.1.1.195

2 entries

1.1.1.2

2 entries

1.1.1.90

2 entries

1.1.1.91

coniferyl alcohol + NADP+ = coniferylaldehyde + NADPH + H+

389603, 389601, 389599

-

1.1.3.7

coniferyl alcohol + O2 = coniferyl aldehyde + H2O2

389844

-

1.10.3.2

coniferyl alcohol + O2 = ?

698523, 676943

-

1.10.3.2

coniferyl alcohol + O2 = ? + H2O

396398

-

1.10.3.2

2 entries

1.11.1.7

coniferyl alcohol + H2O2 = ?

700707, 689651

-

1.14.14.B13

coniferyl alcohol + [reduced NADPH-hemoprotein reductase] + O2 = 5-hydroxyconiferyl alcohol + [oxidized NADPH-hemoprotein reductase] + H2O

743699

-

1.21.3.3

coniferyl alcohol + O2 = coniferyl aldehyde + H2O2

745326

-

2.1.1.104

S-adenosyl-L-methionine + coniferyl alcohol = S-adenosyl-L-homocysteine + sinapyl alcohol

757935

-

2.1.1.146

S-adenosyl-L-methionine + coniferyl alcohol = S-adenosyl-L-homocysteine + 4-methoxyconiferyl alcohol

757150

3tky, 3D-view

2.1.1.146

S-adenosyl-L-methionine + coniferyl alcohol = S-adenosyl-L-homocysteine + 4-methoxyconiferyl alcohol

757150

5cvj, 3D-view

2.1.1.146

S-adenosyl-L-methionine + coniferyl alcohol = S-adenosyl-L-homocysteine + 4-methoxyconiferyl alcohol

757150

5cvv, 3D-view

2.1.1.146

3 entries

2.3.1.196

benzoyl-CoA + coniferyl alcohol = coniferyl benzoate + CoA

736954

-

2.3.1.84

coniferyl alcohol + acetyl-CoA = coniferyl acetate + CoA

723419

-

2.4.1.111

UDP-glucose + coniferyl alcohol = UDP + coniferin

488455, 488460, 488461, 488454, 488458, 488457, 488459, 488456

-

2.4.1.111

UDPglucose + coniferyl alcohol = ?

488455, 488456, 488454

-

2.4.1.111

2 entries

2.4.1.218

UDP-glucose + coniferyl alcohol = UDP + coniferin

393095, 393094

-

Product in Enzyme-catalyzed Reactions (17 results)

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Show Product (17 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.194

coniferyl aldehyde + NADPH + H+ = coniferyl alcohol + NADP+

-

-

1.1.1.195

coniferyl aldehyde + NADPH = coniferol + NADP+

-

-

1.1.1.195

coniferaldehyde + NADPH + H+ = coniferyl alcohol + NADP+

-

-

1.1.1.195

coniferyl aldehyde + NADPH + H+ = coniferyl alcohol + NADP+

-

-

1.1.1.195

coniferyl aldehyde + NADPH = coniferyl alcohol + NADP+

-

-

1.1.1.195

4 entries

1.1.1.2

coniferaldehyde + NADPH = coniferyl alcohol + NADP+

-

-

1.1.1.90

coniferyl aldehyde + NADH + H+ = coniferyl alcohol + NAD+

-

-

1.1.1.91

coniferyl aldehyde + NADH + H+ = coniferyl alcohol + NAD+

-

-

1.1.3.38

eugenol + O2 = coniferyl alcohol + H2O

-

-

1.1.3.38

eugenol + O2 = coniferyl alcohol + H2O2

10665,

-

1.1.3.38

2 entries

1.2.1.30

ferulic acid + NADPH + ATP = ferulic acid + coniferyl aldehyde + coniferyl alcohol + NADP+ + AMP + phosphate

-

-

2.1.1.104

S-adenosyl-L-methionine + caffeoyl alcohol = S-adenosyl-L-homocysteine + coniferyl alcohol

-

-

2.1.1.68

S-adenosyl-L-methionine + caffeoyl alcohol = S-adenosyl-L-homocysteine + 4-[(1E)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenol

-

-

2.1.1.68

S-adenosyl-L-methionine + caffeoyl alcohol = S-adenosyl-L-homocysteine + coniferyl alcohol

-

-

2.1.1.68

2 entries

3.1.1.73

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

-

-

3.2.1.126

coniferin + H2O = coniferol + D-glucose

, 26041, 26044

-

3.2.1.126

coniferin + H2O = D-glucose + coniferol

, 650284, 653495

-

3.2.1.126

2 entries

Inhibitor in Enzyme-catalyzed Reactions (6 results)

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Show Inhibitors (6 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.194

the enzyme is inhibited by an excess of coniferyl alcohol from 0.017 mM

760935

-

1.1.1.195

competitive mechanism, substrate inhibition

668545

-

2.4.1.111

above 0.08 mM, Paul's scarlet rose

488454

-

3.3.1.1

coniferyl alcohol, molecular docking studies show that coniferyl alcohol is well docked into the active cavity of SAHH. Several H-bonds are formed between them, which stabilize coniferyl alcohol in the active site of rSAHH with a proper conformation

754286

-

3.3.1.1

-

754286

-

3.3.1.1

2 entries

4.3.1.24

competitive

716178

-

3D Structure of Enzyme-Ligand-Complex (PDB) (15 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (15 entries)

EC NUMBER

ENZYME 3D STRUCTURE

2.1.1.146

3tky, 3D-view

2.1.1.146

5cvj, 3D-view

2.1.1.146

5cvv, 3D-view

2.1.1.146

3tky, 3D-view

2.1.1.146

5cvj, 3D-view

2.1.1.146

5cvv, 3D-view

2.1.1.146

3tky, 3D-view

2.1.1.146

5cvj, 3D-view

2.1.1.146

5cvv, 3D-view

2.1.1.146

3tky, 3D-view

2.1.1.146

5cvj, 3D-view

2.1.1.146

5cvv, 3D-view

2.1.1.146

3tky, 3D-view

2.1.1.146

5cvj, 3D-view

2.1.1.146

5cvv, 3D-view

2.1.1.146

15 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (17 results)

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Show Turnover Number (17 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.1.1.194

25.8

-

recombinant enzyme, at pH 8.5 and 40°C

739587

1.1.1.195

0.43

-

pH 6.25, 30°C, recombinant CAD1-1

670569

1.1.1.195

0.99

-

pH 6.25, 30°C, recombinant CAD1-7

670569

1.1.1.195

3.5

-

pH 7.5, 37°C, recombinant enzyme

668545

1.1.1.195

8.75

-

pH 8.8, 40°C

739876

1.1.1.195

13.2

-

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

724491

1.1.1.195

16.3

-

pH 8.8, 40°C

740539

1.1.1.90

25.8

-

recombinant enzyme, pH 8.5, 30°C

739587

1.1.1.90

69.7

-

native enzyme, pH 8.5, 30°C

739587

1.1.1.90

69.7

-

pH 8.0, 30°C

724592

2.1.1.146

0.049

-

pH 7.5, 30°C, recombinant enzyme mutant MOMT8

757150

2.1.1.146

0.063

-

pH 7.5, 30°C, recombinant enzyme mutant MOMT9

757150

2.1.1.146

0.069

-

pH 7.5, 30°C, recombinant enzyme mutant MOMT5

757150

2.1.1.146

0.247

-

pH 7.5, 30°C, recombinant enzyme mutant MOMT3

757150

2.1.1.146

0.528

-

pH 7.5, 30°C, recombinant enzyme mutant MOMT4

757150

2.3.1.84

0.81

-

recombinant protein with acetyl-CoA, pH 7.5, 20°C

723419

2.3.1.84

2.05

-

recombinant protein with acetyl-CoA, pH 6.0, 20°C

723419

1.1.1.195

6 entries

1.1.1.90

3 entries

2.1.1.146

5 entries

2.3.1.84

2 entries

K_M Value (42 results)

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Show KM Value (42 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.194

0.00303

-

at pH 7.9 and 30°C

760935

1.1.1.194

0.28

-

recombinant enzyme, at pH 8.5 and 40°C

739587

1.1.1.194

0.83

-

-

347801

1.1.1.195

0.00098

-

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

724491

1.1.1.195

0.0014

-

with NADP+

347815

1.1.1.195

0.005

-

pH 8.8, 40°C

739876

1.1.1.195

0.0069

-

-

347819

1.1.1.195

0.0075

-

-

700832

1.1.1.195

0.0075

-

pH 8.8, temperature not specified in the publication

700832

1.1.1.195

0.0096

-

pH 8.8, 40°C

740539

1.1.1.195

0.011

-

-

347801

1.1.1.195

0.0181

-

pH 8.8, 37°C

726428

1.1.1.195

0.032

-

-

347811

1.1.1.195

0.051

-

purified isoform CAD-C

347820

1.1.1.195

0.11

-

pH 7.5, 37°C, recombinant enzyme

668545

1.1.1.195

0.117

-

-

700832

1.1.1.195

0.117

-

pH 8.8, temperature not specified in the publication

700832

1.1.1.195

0.14

-

CAD2 isoform

347821

1.1.1.195

0.241

-

with NAD+

347815

1.1.1.195

0.247

-

pH 6.25, 30°C, recombinant CAD1-1

670569

1.1.1.195

0.325

-

pH 6.25, 30°C, recombinant CAD1-7

670569

1.1.1.195

0.414

-

isoform CAD-B

347820

1.1.1.195

0.52

-

CAD1 isoform

347821

1.1.1.195

0.677

-

isoform CAD-A

347820

1.1.1.90

0.044

-

-

389587

1.1.1.90

0.13

-

native enzyme, pH 8.5, 30°C

739587

1.1.1.90

0.13

-

pH 8.0, 30°C

724592

1.1.1.90

0.28

-

recombinant enzyme, pH 8.5, 30°C

739587

1.1.1.194

3 entries

1.1.1.195

21 entries

1.1.1.90

4 entries

1.1.1.91

0.55

-

-

389601

1.10.3.2

0.002

-

isoenzyme lac90

396398

1.14.14.B13

0.003

-

pH 7.8, 30°C

743699

2.1.1.146

0.0114

-

pH 7.5, 30°C, recombinant enzyme mutant MOMT5

757150

2.1.1.146

0.0161

-

pH 7.5, 30°C, recombinant enzyme mutant MOMT8

757150

2.1.1.146

0.0161

-

pH 7.5, 30°C, recombinant enzyme mutant MOMT9

757150

2.1.1.146

0.1926

-

pH 7.5, 30°C, recombinant enzyme mutant MOMT4

757150

2.1.1.146

0.1985

-

pH 7.5, 30°C, recombinant enzyme mutant MOMT3

757150

2.3.1.84

0.0275

-

apparent KM value of recombinant protein with acetyl-CoA, pH 7.5, 20°C

723419

2.3.1.84

0.0565

-

apparent KM value of recombinant protein with acetyl-CoA, pH 6.0, 20°C

723419

2.4.1.111

0.0033

-

-

488454

2.4.1.111

0.0037

-

-

488457

2.4.1.111

0.1196

-

-

488458

2.4.1.111

0.25

-

-

488455, 488456

2.1.1.146

5 entries

2.3.1.84

2 entries

2.4.1.111

4 entries

K_i Value (1 result)

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Show KI Value (1 entry)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

4.3.1.24

0.032

-

pH 8.5, 55°C

716178

IC₅₀ Value (1 result)

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Show IC50 Value (1 entry)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

3.3.1.1

0.000034

-

pH 6.5, 41°C, recombinant enzyme

754286

References & Links

Literature References (74)

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Show Reference (74 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

10665

8529652

Substrate specificity of flavin-dependent vanillyl-alcohol oxidase from Penicillium simplicissimum. Evidence for the production of 4-hydroxycinnamyl alcohols from 4-allylphenols

1995

Fraaije, M.W.; Veeger, C.; van Berkel, W.J.H.

Eur. J. Biochem.

234

271-277

26041

25181

Characterization of beta-glucosidase isoenzymes possibly involved in lignification from chick pea (Cicer arietinum L.) cell suspension cultures

1978

Hösel, W.; Surholt, E.; Borgmann, E.

Eur. J. Biochem.

84

487-492

26044

7765617

Purification of an acidic coniferin-hydrolysing beta-glucosidase from developing xylem of Pinus banksiana

1994

Leinhos, V.; Udagama-Randeniya, P.V.; Savidge, R.A.

Phytochemistry

37

311-315

288228

6365550

Purification and properties of cinnamoyl-CoA reductase and cinnamyl alcohol dehydrogenase from poplar stems (Populus X euramericana)

1984

Sarni, F.; Grand, C.; Boudet, A.M.

Eur. J. Biochem.

139

259-265

288233

7042334

Enzymic synthesis of lignin precursors. Comparison of cinnamoyl-CoA reductase and cinnamyl alcohol:NADP+ dehydrogenase from spruce (Picea abies L.) and soybean (Glycine max L.)

1981

Luderitz, T.; Grisebach, H.

Eur. J. Biochem.

119

115-124

347801

1250

Purification and properties of isoenzymes of cinnamyl-alcohol dehydrogenase from soybean-cell-suspension cultures

1975

Wyrambik, D.; Grisebach, H.

Eur. J. Biochem.

59

9-15

347808

-

Regulatory role of cinnamyl alcohol dehydrogenase in the formation of guaiacyl and syringyl lignins

1982

Kutsuki, H.; Shimada, M.; Higuchi, T.

Phytochemistry

21

19-23

347811

-

Purification and properties of cinnamyl alcohol dehydrogenase from higher plants involved in lignin biosynthesis

1974

Mansell, R.L.; Gross, G.G.; Stöckigt, J.; Franke, H.; Zenk, M.H.

Phytochemistry

13

2427-2435

347813

-

Stereospecificity of cinnamoyl alcohol dehydrogenase and synthesis of stereospecifically labelled coniferyl alcohol

1978

Klischies, M.; Stöckigt, J.; Zenk, M.H.

Phytochemistry

17

1523-1525

347814

8373826

A molecular model for cinnamyl alcohol dehydrogenase, a plant aromatic alcohol dehydrogenase involved in lignification

1993

McKie, J.H.; Jaouhari, R.; Douglas, K.T.; Goffner, D.; Feuillet, C.; Grima-Pettenati, J.; Boudet, A.M.; Baltas, M.; Gorrichon, L.

Biochim. Biophys. Acta

1202

61-69

347815

7547988

Site-directed mutagenesis of a serine residue in cinnamyl alcohol dehydrogenase, a plant NADPH-dependent dehydrogenase, affects the specificity for the coenzyme

1995

Lauvergeat, V.; Kennedy, K.; Feuillet, C.; McKie, J.H.; Gorrichon, L.; Baltas, M.; Boudet, A.M.; Grima-Pettenati, J.; Douglas, K.T.

Biochemistry

34

12426-12434

347816

9377488

A novel type of pathogen defense-related cinnamyl alcohol dehydrogenase

1997

Logemann, E.; Reinold, S.; Somssich, I.E.; Hahlbrock, K.

Biol. Chem.

378

909-913

347818

16668801

Purification, characterization, and cloning of cinnamyl alcohol dehydrogenase in loblolly pine (Pinus taeda L.)

1992

O'Malley, D.M.; Porter, S.; Sederoff, R.R.

Plant Physiol.

98

1364-1371

347819

7763430

Purification and partial sequences of Aralia cordata cinnamyl alcohol dehydrogenase

1993

Hibino, T.; Shibata, D.; Umezawa, T.; Higuchi, T.

Phytochemistry

32

565-567

347820

-

Differential induction of cinnamyl alcohol dehydrogenase during defensive lignification in wheat (Triticum aestivum). Characterization of the major inducible form

1999

Mitchell, H.J.; Hall, S.A.; Stratford, R.; Hall, J.L.; Barber, M.S.

Planta

208

31-37

347821

7765663

Purification and characterization of cinnamyl alcohol dehydrogenase isoforms from Phaseolus vulgaris

1994

Grima-Pettenati, J.; Campargue, C.; Boudet, A.; Boudet, A.M.

Phytochemistry

37

941-947

347823

9526508

A novel aromatic alcohol dehydrogenase in higher plants: molecular cloning and expression

1998

Goffner, D.; Van Doorsselaere, J.; Yahiaoui, N.; Samaj, J.; Grima-Pettenati, J.; Boudet, A.M.

Plant Mol. Biol.

36

755-765

389479

16667295

Stress responses in alfalfa (Medicago sativa L.). I. Induction of phenylpropanoid biosynthesis and hydrolytic enzymes in elicitor-treated cell suspension cultures

1990

Dalkin, K.; Edwards, R.; Edington, B.; Dixon, R.A.

Plant Physiol.

92

440-446

389481

1148277

Phenolic metabolism in petunia tissues. I. Characteristic responses of enzymes involved in different steps of polyphenol synthesis to different hormonal influences

1975

Ranjeva, R.; Boudet, A.M.; Harada, H.; Marigo, G.

Biochim. Biophys. Acta

399

23-30

389482

-

Three novel enzymes involved in the reduction of ferulic acid to coniferyl alcohol in higher plants: ferulate:CoA Ligase, feruloyl-CoA reductase and coniferyl alcohol oxidoreductase

1973

Gross, G.G.; Stöckigt, J.; Mansell, R.L.; Zenk, M.H.

FEBS Lett.

31

283-286

389484

-

Levels of beta-glucan and lignin in elongating internodes of deepwater rice

1992

Sauter, M.; Kende, H.

Plant Cell Physiol.

33

1089-1097

389587

3060114

Benzyl alcohol dehydrogenase and benzaldehyde dehydrogenase II from Acinetobacter calcoaceticus. Substrate specificities and inhibition studies

1988

MacKintosh, R.W.; Fewson, C.A.

Biochem. J.

255

653-661

389599

4389864

Reduction of aromatic acids to aldehydes and alcohols in the cell-free system. 2. Purification and properties of aryl-alcohol: NADP-oxidoreductase from Neurospora crassa

1969

Gross, G.G.; Zenk, M.H.

Eur. J. Biochem.

8

420-425

389601

-

Enzymes involved in the reduction of ferulic acid to coniferyl alcohol during the aging of disks of swede root tissue

1975

Rhodes, Michael J.C.; Wooltorton, Leonard S.C.

Phytochemistry

14

1235-1240

389603

-

Multiple forms and specificity of coniferyl alcohol dehydrogenase from cambial regions of higher plants

1976

Mansell, Richard L.; Barbel, Gareth R.; Zenk, Meinhart H.

Phytochemistry

15

1849-1853

389844

-

Aromatic alcohol oxidase: a new membrane-bound H2O2-generating enzyme in alimentary tiddues of the slug Arion ater

1989

Mann, V.; Large, A.; Khan, S.; Malik, Z.; Connock, M.J.

J. Exp. Zool.

251

265-274

393094

11937332

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Links to other databases for coniferyl alcohol

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