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Ligand Dodecanol

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

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

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Show Natural Substrate (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.3.20

1-dodecanol + O2 = dodecanal + H2O2

724083

-

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

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Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.2

lauryl aldehyde + NADPH = lauryl alcohol + NADP+

-

-

Substrate in Enzyme-catalyzed Reactions (34 results)

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Show Substrate (34 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.1

1-dodecanol + NAD+ = dodecanal + NADH

669540

-

1.1.1.1

dodecanol + NAD+ = dodecanal + NADH + H+

697660

-

1.1.1.1

2 entries

1.1.1.192

1-dodecanol + 2 NAD+ + H2O = dodecanoic acid + 2 NADH + 2 H+

712962

-

1.1.1.245

1-dodecanol + NAD+ = dodecanal + NADH

286381

-

1.1.1.71

dodecan-1-ol + NADP+ = dodecanal + NADPH

287277

-

1.1.3.13

dodecanol + O2 = dodecanal + H2O2

484921

-

1.1.3.13

n-dodecanol + O2 = n-dodecanal + H2O2

685404, 698659

-

1.1.3.20

1-dodecanol + O2 = dodecanal + H2O2

655590, 724083, 740470, 739922, 685778

-

1.1.3.20

dodecan-1-ol + O2 = dodecanal + H2O2

740469

-

1.1.3.20

dodecanol + O2 = dodecanal + H2O2

389735, 389739, 389734, 389737, 389738, 94404, 389732

-

1.1.3.13

2 entries

1.1.3.20

3 entries

1.1.99.20

1-dodecanol + acceptor = n-dodecanal + reduced acceptor

389904, 389908

-

2.3.1.188

feruloyl-CoA + 1-dodecanol = CoA + (E)-dodecyl 3-(4-hydroxy-3-methoxyphenyl)acrylate

700658, 700854

-

2.3.1.75

dodecan-1-ol + palmitoyl-CoA = CoA + dodecanyl palmitate

735489

-

2.3.1.75

myristoyl-CoA + dodecan-1-ol = dodecan-1-yl myristate + CoA

735353, 720358

-

2.3.1.75

acyl-CoA + dodecanol = CoA + dodecanyl acylester

756245

-

2.3.1.75

arachidoyl-CoA + dodecanol = dodecyl arachidonate + CoA

755872

-

2.3.1.75

decanoyl-CoA + dodecanol = dodecyl decanoate + CoA

755872

-

2.3.1.75

dodecanol + palmitoyl-CoA = dodecanyl palmitate + CoA

718651

-

2.3.1.75

eicosanoyl-CoA + dodecanol = dodecanyl eicosanoate + CoA

487485

-

2.3.1.75

eicosenoyl-CoA + dodecanol = dodecyl eicosenoate + CoA

755872, 743538

-

2.3.1.75

erucyl-CoA + dodecanol = dodecyl erucoate + CoA

755872

-

2.3.1.75

lauroyl-CoA + dodecanol = dodecyl laurate + CoA

755872

-

2.3.1.75

linolenoyl-CoA + dodecanol = dodecyl linolenate + CoA

755872

-

2.3.1.75

linoleoyl-CoA + dodecanol = dodecyl linoleate + CoA

743538

-

2.3.1.75

linoleoyl-CoA + dodecanol = dodecyl linolenate + CoA

755872

-

2.3.1.75

myristoyl-CoA + dodecanol = dodecyl myristate + CoA

755872

-

2.3.1.75

octadecenoyl-CoA + dodecanol = dodecanyl octadecanoate + CoA

487486

-

2.3.1.75

oleoyl-CoA + dodecanol = dodecyl oleate + CoA

755872

-

2.3.1.75

palmitoyl-CoA + dodecanol = CoA + dodecyl palmitate

755845

-

2.3.1.75

palmitoyl-CoA + dodecanol = dodecyl palmitate + CoA

755872, 755845

-

2.3.1.75

ricinoleyl-CoA + dodecanol = dodecyl ricinoleate + CoA

755872

-

2.3.1.75

stearoyl-CoA + dodecanol = dodecyl stearate + CoA

755872

-

2.3.1.75

20 entries

2.3.1.84

acetyl-CoA + dodecan-1-ol = CoA + dodecyl acetate

736721

-

2.8.2.2

3'-phosphoadenylylsulfate + 1-dodecanol = adenosine 3',5'-bisphosphate + 1-dodecyl sulfate

645784

-

Product in Enzyme-catalyzed Reactions (17 results)

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Show Product (17 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.2

dodecanal + NADPH = dodecanol + NADP+

-

-

1.1.1.2

lauryl aldehyde + NADPH = lauryl alcohol + NADP+

-

-

1.1.1.2

n-dodecanal + NADPH + H+ = n-dodecanol + NADP+

-

-

1.1.1.2

3 entries

1.1.1.21

1-dodecanal + NADPH + H+ = dodecanol + NADP+

-

-

1.1.1.71

dodecanal + NAD(P)H = dodecan-1-ol + NAD(P)+

287282

-

1.1.1.72

dodecanal + NADPH + H+ = dodecanol + NADP+

-

-

1.1.1.90

dodecanal + NADH + H+ = dodecanol + NAD+

-

-

1.14.15.3

dodecane + reduced rubredoxin + O2 = 1-dodecanol + oxidized rubredoxin + H2O

-

-

1.14.15.3

n-dodecane + 2 reduced rubredoxin + O2 + 2 H+ = 1-dodecanol + 2 oxidized rubredoxin + H2O

-

-

1.14.15.3

2 entries

1.2.1.84

lauroyl-CoA + 2 NADPH + 2 H+ = dodecanol + 2 NADP+ + coenzyme A

-

-

3.1.1.50

dodecanyl palmitate + H2O = dodecanol + palmitate

-

-

3.1.6.21

SDS + H2O = 1-dodecanol + sulfate + Na+

-

-

3.2.1.21

dodecyl-beta-D-glucopyranoside + H2O = dodecanol + beta-D-glucose

-

-

3.2.1.21

n-dodecyl-beta-D-glucopyranoside + H2O = n-dodecanol + D-Glucose

-

-

3.2.1.21

2 entries

3.2.1.B40

n-dodecyl beta-D-glucopyranoside + H2O = 1-dodecanol + beta-D-glucose

-

-

3.8.1.5

1-bromododecane + H2O = 1-dodecanol + bromide

-

-

3.8.1.5

1-chlorododecane + H2O = dodecanol + chloride

-

-

3.8.1.5

2 entries

Inhibitor in Enzyme-catalyzed Reactions (4 results)

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Show Inhibitors (4 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.2

in 100 mM MES buffer (pH 6.5) with 200 mM NADPH, 0.25 mM decanal, and 125 microg of FALDR fusion protein. 1 mM inhibits by 46%, 0.25 mM inhibits by 45%

695771

-

1.13.12.7

mixed-type inhibitor

658219

-

1.14.14.3

-

726677, 728822

-

1.14.14.3

-

726678

-

1.14.14.3

2 entries

3D Structure of Enzyme-Ligand-Complex (PDB) (12 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (12 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.97.1.12

5zgb, 3D-view

1.97.1.12

5zgh, 3D-view

1.97.1.12

5zgb, 3D-view

1.97.1.12

5zgh, 3D-view

1.97.1.12

5zgb, 3D-view

1.97.1.12

5zgh, 3D-view

1.97.1.12

5zgb, 3D-view

1.97.1.12

5zgh, 3D-view

1.97.1.12

5zgb, 3D-view

1.97.1.12

5zgh, 3D-view

1.97.1.12

10 entries

2.5.1.26

4bc7, 3D-view

3.5.1.99

3ppm, 3D-view

Enzyme Kinetic Parameters

K_M Value (12 results)

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Show KM Value (12 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.3.13

0.038

-

-

484921

1.1.3.13

1.86

-

-

685404

1.1.3.20

0.004

-

-

389739

1.1.3.20

0.0061

-

-

389738

1.1.3.20

0.008

-

aqueous phase

389737

1.1.3.20

0.059

-

5 mM, purified active LjFAO1 protein, compared to substrate preferences with the AtFAO3 gene of Arabidopsis thaliana

685778

1.1.3.20

0.0596

-

pH and temperature not specified in the publication

724083

1.1.3.20

4

-

-

94404

1.1.3.20

40

-

octane/aqueous phase 99/1

389737

2.3.1.188

0.002

-

pH 7.0, 30°C

700854

2.3.1.188

0.005

-

pH 7.0, 30°C

700658

1.1.3.13

2 entries

1.1.3.20

7 entries

2.3.1.188

2 entries

2.8.2.2

0.33

-

pH 5.5, 37°C

645784

IC₅₀ Value (1 result)

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Show IC50 Value (1 entry)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.14.14.3

0.000482

-

in 50 mM phosphate buffer, pH 7.0 at 23°C

728822

References & Links

Literature References (43)

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Show Reference (43 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

94404

-

Enzymes of wax ester catabolism in jojoba

1981

Moreau, R.A.; Huang, A.H.C.

Methods Enzymol.

71

804-813

286381

-

Purification and properties of a nicotinamide adenine dinucleotide-linked cyclohexanol dehydrogenase from a Nocardia species

1980

Stirling, L.A.; Perry, J.J.

Curr. Microbiol.

4

37-40

287277

8162187

NADP-dependent alcohol dehydrogenases in bacteria and yeast: purification and partial characterization of the enzymes from Acinetobacter calcoaceticus and Saccharomyces cerevisiae

1994

Wales, M.R.; Fewson, C.A.

Microbiology

140

173-183

287282

4300551

The enzymatic reduction of retinal to retinol in rat intestine

1968

Fidge, N.H.; Goodman, D.S.

J. Biol. Chem.

243

4372-4379

389732

36040

Oxidation of fatty alcohol in the cotyledons of jojoba seedlings

1979

Moreau, R.A.; Huang, A.H.C.

Arch. Biochem. Biophys.

194

422-430

389734

-

Inducible long chain alcohol oxidase from alkane-grown Candida tropicalis

1988

Kemp, G.D.; Dickinson, F.M.; Ratledge, C.

Appl. Microbiol. Biotechnol.

29

370-374

389735

2227354

Evidence frr two fatty alcohol oxidases in the biosurfactant-producing yeast Candida (Torulopsis) bombicola

1990

Hommel, R.; Ratledge, C.

FEMS Microbiol. Lett.

70

183-186

389737

-

Activity and substrate specificity of the fatty alcohol oxidase of Candida tropicalis in organic solvents

1991

Kemp, G.D.; Dickinson, F.M.; Ratledge, C.

Appl. Microbiol. Biotechnol.

34

441-445

389738

1546949

Purification and some properties of alcohol oxidase from alkane-grown Candida tropicalis

1992

Dickinson, F.M.; Wadforth, C.

Biochem. J.

282

325-331

389739

10660617

A consensus sequence for long-chain fatty-acid alcohol oxidases from Candida identifies a family of genes involved in lipid.omega-oxidation in yeast with homologues in plants and bacteria

2000

Vanhanen, S.; West, M.; Kroon, J.T.M.; Lindner, N.; Casey, J.; Cheng, Q.; Elborough, K.M.; Slabas, A.R.

J. Biol. Chem.

275

4445-4452

389904

-

Identification of the prosthetic group and further characterization of a novel enzyme, polyethylne glycol dehydrogenase

1985

Kawai, F.; Yamanaka, H.; Ameyama, M.; Shinagawa, E.; Matsushita, K.; Adachi, O.

Agric. Biol. Chem.

49

1071-1076

389908

-

Purification and characterization of constitutive polyethylene glycol (PEG) dehydrogenase of a PEG 4000-utilizing Flavobacterium sp. No. 203

1989

Yamanaka, H.; Kawai, F.

J. Ferment. Bioeng.

67

324-330

484921

10904867

Gastropod mollusc aliphatic alcohol oxidase: subcellular localisation and properties

2000

Grewal, N.; Parveen, Z.; Large, A.; Perry, C.; Connock, M.

Comp. Biochem. Physiol. B

125

543-554

487485

-

Studies of biosynthesis of waxes by developing jojoba seed: III. Biosynthesis of wax esters from acetyl-CoA and long-chain alcohols

1981

Wu, X.Y.; Moreau, R.A.; Stumpf, P.K.

Lipids

16

897-902

487486

1481989

A high-performance liquid chromatography-based radiometric assay for acyl-CoA:alcohol transacylase from jojoba

1992

Garver, W.S.; Kemp, J.D.; Kuehn, G.D.

Anal. Biochem.

207

335-340

645784

8924618

Influence of substrate structure on the catalytic efficiency of hydroxysteroid sulfotransferase STa in the sulfation of alcohols

1996

Chen, G.; Banoglu, E.; Duffel, M.W.

Chem. Res. Toxicol.

9

67-74

655590

15358540

Functional identification of AtFao3, a membrane bound long chain alcohol oxidase in Arabidopsis thaliana

2004

Cheng, Q.; Liu, H.T.; Bombelli, P.; Smith, A.; Slabas, A.R.

FEBS Lett.

574

62-68

658219

15652187

Inhibition of firefly luciferase by alkane analogues

2005

Takehara, K.; Kamaya, H.; Ueda, I.

Biochim. Biophys. Acta

1721

124-129

669540

16243283

Purification and characterization of the alcohol dehydrogenase with a broad substrate specificity originated from 2-phenylethanol-assimilating Brevibacterium sp. KU 1309

2005

Hirano, J.; Miyamoto, K.; Ohta, H.

J. Biosci. Bioeng.

100

318-322

685404

18639656

Purification and properties of a novel broad substrate specific alcohol oxidase from Aspergillus terreus MTCC 6324

2008

Kumar, A.K.; Goswami, P.

Biochim. Biophys. Acta

1784

1552-1559

685778

18396913

Cloning and characterization of long-chain fatty alcohol oxidase LjFAO1 in lotus japonicus

2008

Zhao, S.; Lin, Z.; Ma, W.; Luo, D.; Cheng, Q.

Biotechnol. Prog.

24

773-779

695771

19270127

Purification, characterization, and potential bacterial wax production role of an NADPH-dependent fatty aldehyde reductase from Marinobacter aquaeolei VT8

2009

Wahlen, B.D.; Oswald, W.S.; Seefeldt, L.C.; Barney, B.M.

Appl. Environ. Microbiol.

75

2758-2764

697660

-

Effect of chain length on the activity of free and immobilized alcohol dehydrogenase towards aliphatic alcohols

2009

Cea, G.; Wilson, L.; Bolivar, J.; Markovits, A.; Illanes, A.

Enzyme Microb. Technol.

44

135-138

698659

19060312

Dissociation and reconstitution studies of a broad substrate specific multimeric alcohol oxidase protein produced by Aspergillus terreus

2009

Kumar, A.K.; Goswami, P.

J. Biochem.

145

259-265

700658

-

Formation of omega-feruloyloxypalmitic acid by an enzyme from wound-healing potato tuber disks

1994

Lotfy, S.; Negrel, J.; Javelle, F.

Phytochemistry

35

1419-1424

700854

-

Purification and characterization of hydroxycinnamoyl-coenzyme A:omega-hydroxypalmitic acid O-hydroxycinnamoyltransferase from tobacco (Nicotiana tabacum) cell-suspension cultures

1996

Lotfy, S.; Javelle, F.; Negrel, J.

Planta

199

475-480

712962

19383697

Two novel metal-independent long-chain alkyl alcohol dehydrogenases from Geobacillus thermodenitrificans NG80-2

2009

Liu, X.; Dong, Y.; Zhang, J.; Zhang, A.; Wang, L.; Feng, L.

Microbiology

155

2078-2085

718651

22685145

Differences in substrate specificities of five bacterial wax ester synthases

2012

Barney, B.M.; Wahlen, B.D.; Garner, E.; Wei, J.; Seefeldt, L.C.

Appl. Environ. Microbiol.

78

5734-5745

720358

20195781

Fatty acyl-CoA reductase and wax synthase from Euglena gracilis in the biosynthesis of medium-chain wax esters

2010

Teerawanichpan, P.; Qiu, X.

Lipids

45

263-273

724083

23525937

An overview on alcohol oxidases and their potential applications

2013

Goswami, P.; Chinnadayyala, S.S.; Chakraborty, M.; Kumar, A.K.; Kakoti, A.

Appl. Microbiol. Biotechnol.

97

4259-4275

726677

21478609

Inhibition of electrochemically controlled bioluminescence of bacterial luciferase by n-alkyl alcohols

2011

Yamasaki, S.; Yamada, S.; Takehara, K.

Anal. Sci.

27

357

726678

23059999

Immobilization of bacterial luciferase into poly(N-isopropylacrylamide) film for electrochemical control of a bioluminescence reaction

2012

Kawanami, Y.; Yamasaki, S.; Yamada, S.; Takehara, K.

Anal. Sci.

28

1013-1015

728822

-

Serendipitous discovery of two highly selective inhibitors of bacterial luciferase

2013

Kim, T.; Spiegel, D.

Tetrahedron

69

7692-7698

735353

23730681

Detailed characterization of the substrate specificity of mouse wax synthase

2013

Miklaszewska, M.; Kawinski, A.; Banas, A.

Acta Biochim. Pol.

60

209-215

735489

23087036

Identification of a residue affecting fatty alcohol selectivity in wax ester synthase

2013

Barney, B.; Mann, R.; Ohlert, J.

Appl. Environ. Microbiol.

79

396-399

736721

26801935

The yeast ATF1 acetyltransferase efficiently acetylates insect pheromone alcohols: implications for the biological production of moth pheromones

2016

Ding, B.J.; Lager, I.; Bansal, S.; Durrett, T.P.; Stymne, S.; Loefstedt, C.

Lipids

51

469-475

739922

27383605

Identification of the fatty alcohol oxidase FAO1 from Starmerella bombicola and improved novel glycolipids production in an FAO1 knockout mutant

2016

Takahashi, F.; Igarashi, K.; Hagihara, H.

Appl. Microbiol. Biotechnol.

100

9519-9528

740469

24931727

A newly identified fatty alcohol oxidase gene is mainly responsible for the oxidation of long-chain omega-hydroxy fatty acids in Yarrowia lipolytica

2014

Gatter, M.; Foerster, A.; Baer, K.; Winter, M.; Otto, C.; Petzsch, P.; Jezkova, M.; Bahr, K.; Pfeiffer, M.; Matthaeus, F.; Barth, G.

FEMS Yeast Res.

14

858-872

740470

25805841

Alcohol dehydrogenases and an alcohol oxidase involved in the assimilation of exogenous fatty alcohols in Yarrowia lipolytica

2015

Iwama, R.; Kobayashi, S.; Ohta, A.; Horiuchi, H.; Fukuda, R.

FEMS Yeast Res.

15

fov014

743538

27297992

Biochemical characterization and substrate specificity of jojoba fatty acyl-CoA reductase and jojoba wax synthase

2016

Miklaszewska, M.; Banas, A.

Plant Sci.

249

84-92

755845

27474711

Role of wax ester synthase/acyl coenzyme A diacylglycerol acyltransferase in oleaginous Streptomyces sp. strain G25

2016

Roettig, A.; Strittmatter, C.S.; Schauer, J.; Hiessl, S.; Poehlein, A.; Daniel, R.; Steinbuechel, A.

Appl. Environ. Microbiol.

82

5969-5981

755872

29502182

Wax synthase MhWS2 from Marinobacter hydrocarbonoclasticus substrate specificity and biotechnological potential for wax ester production

2018

Miklaszewska, M.; Dittrich-Domergue, F.; Banas, A.; Domergue, F.

Appl. Microbiol. Biotechnol.

102

4063-4074

756245

28725265

Two bifunctional enzymes from the marine protist Thraustochytrium roseum biochemical characterization of wax ester synthase/acyl-CoA diacylglycerol acyltransferase activity catalyzing wax ester and triacylglycerol synthesis

2017

Zhang, N.; Mao, Z.; Luo, L.; Wan, X.; Huang, F.; Gong, Y.

Biotechnol. Biofuels

10

185

Links to other databases for Dodecanol

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Show Links (1 entry)

ChEBI

PubChem

-