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Ligand coniferol

Basic Ligand Information

Molecular Structure

Related pathways

Pathway Source

Pathways

BRENDA

phenylpropanoid biosynthesis

KEGG

Biosynthesis of phenylpropanoids, Biosynthesis of secondary metabolites, Biosynthesis of various plant secondary metabolites, 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 coniferol

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (7 results)

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Show Natural Substrate (7 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.194

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

389482, 389603, 347801, 389479, 389481, 760935

-

1.1.1.195

coniferol + NADP+ = coniferyl aldehyde + NADPH

657055

-

1.1.1.195

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

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

-

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

1.1.1.91

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

760935

-

2.4.1.111

UDPglucose + coniferyl alcohol = ?

488455, 488456, 488454

-

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

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Show Natural Product (6 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+

-

-

3.2.1.126

coniferin + H2O = D-glucose + coniferol

650284, 653495

-

3.2.1.126

coniferin + H2O = D-glucose + coniferyl alcohol

-

-

1.1.1.195

3 entries

3.2.1.126

2 entries

Substrate in Enzyme-catalyzed Reactions (27 results)

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Show Substrate (27 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.194

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

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

-

1.1.1.195

coniferol + NADP+ = coniferyl aldehyde + NADPH

657055

-

1.1.1.195

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

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

-

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, 654264, 692723, 724592, 724027, 739587

-

1.1.1.91

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

760935

-

1.1.1.91

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

389601, 389603, 389599

-

1.1.1.195

2 entries

1.1.1.2

2 entries

1.1.1.90

2 entries

1.1.1.91

2 entries

1.1.3.7

coniferyl alcohol + O2 = coniferyl aldehyde + H2O2

389844

-

1.10.3.2

coniferyl alcohol + O2 = ?

676943, 698523

-

1.10.3.2

coniferyl alcohol + O2 = ? + H2O

396398

-

1.11.1.19

coniferyl alcohol + H2O2 + H+ = ?

742674

-

1.11.1.19

coniferyl alcohol + H2O2 + H+ = coniferaldehyde + H2O

742674

-

1.11.1.7

coniferyl alcohol + H2O2 = ?

689651, 700707

-

1.11.1.7

coniferyl alcohol + H2O2 = ? + H2O

765164

-

1.10.3.2

2 entries

1.11.1.19

2 entries

1.11.1.7

2 entries

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

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

393094, 393095

-

Product in Enzyme-catalyzed Reactions (18 results)

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Show Product (18 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 + H2O = coniferyl alcohol + H2O2

10665, -

-

1.1.3.B5

eugenol + O2 + H2O = coniferyl alcohol + H2O2

-

-

1.2.1.30

ferulic acid + NADPH + H+ + ATP = ferulic acid + coniferyl aldehyde + coniferyl alcohol + NADP+ + AMP + diphosphate

-

-

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

coniferin + H2O = D-glucose + coniferyl alcohol

-

-

3.2.1.126

3 entries

Inhibitor in Enzyme-catalyzed Reactions (7 results)

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Show Inhibitors (7 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

-

1.1.1.91

inhibited by an excess of the substrate from 0.017 mM

760935

-

2.4.1.111

above 0.08 mM, Paul's scarlet rose

488454

-

3.13.2.1

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

-

3.13.2.1

-

754286

-

3.13.2.1

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 (43 results)

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Show KM Value (43 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

1.1.1.91

0.00303

-

25°C, pH 7.9

760935

1.1.1.91

0.55

-

-

389601

1.1.1.194

3 entries

1.1.1.195

21 entries

1.1.1.90

4 entries

1.1.1.91

2 entries

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

3.13.2.1

0.000034

-

pH 6.5, 41°C, recombinant enzyme

754286

References & Links

Literature References (83)

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Show Reference (83 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

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Inhibition by substrates of a coniferyl alcohol dehydrogenase purified from sugarcane stalks

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