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Ligand 12-hydroxylauric acid

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

1.1.1.284

12-hydroxydodecanoic acid + glutathione + NAD+ = S-(11-carboxy)undecanyl-glutathione + NADH + H+

697214

-

In Vivo Product in Enzyme-catalyzed Reactions (2 results)

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Show Natural Product (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.80

lauric acid + [reduced NADPH-hemoprotein reductase] + O2 + H+ = 12-hydroxylauric acid + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

1.14.14.80

lauric acid + [reduced NADPH-hemoprotein reductase] + O2 = 12-hydroxylauric acid + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

1.14.14.80

2 entries

Substrate in Enzyme-catalyzed Reactions (10 results)

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Show Substrate (10 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.1

12-hydroxydodecanoate + NAD+ = 12-oxododecanoic acid + NADH

285566, 285569, 285571, 285608, 285651, 285604, 285650, 285615, 285602

1m6w, 3D-view

1.1.1.192

12-hydroxydodecanoic acid + NAD+ + H2O = ? + NADH

288324

-

1.1.1.284

12-hydroxydodecanoic acid + glutathione + NAD+ = S-(11-carboxy)undecanyl-glutathione + NADH + H+

654617, 697214

-

1.1.1.284

12-hydroxydodecanoic acid + glutathione + NAD+ = S-(11-carboxy)undecanylglutathione + NADH

657054

-

1.1.1.284

12-hydroxydodecanoic acid + NAD+ = ? + NADH

667724

-

1.1.1.284

12-hydroxydodedecanoic acid + glutathione + NAD+ = 12-oxododecanoic acid + ?

287893, 287892, 287891

-

1.1.1.284

4 entries

1.1.1.306

12-hydroxydodecanoic acid + NADH = ? + NAD+

288324

-

1.1.3.20

12-hydroxydodecanoic acid + O2 = ?

389738

-

1.14.14.49

12-hydroxy-dodecanoic acid + reduced NADPH-hemoprotein reductase + O2 = 12-oxo-dodecanoic acid + oxidized NADPH-hemoprotein reductase + H2O

742480

-

1.14.14.49

12-hydroxylauric acid + reduced NADPH-hemoprotein reductase + O2 = 12-hydroxy-dodecanoic acid + oxidized NADPH-hemoprotein reductase + H2O

742480

-

1.14.14.49

2 entries

Product in Enzyme-catalyzed Reactions (7 results)

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Show Product (7 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.11.2.1

lauric acid + H2O2 = omega-1-hydroxylauric acid + omega-2-hydroxylauric acid + omega-hydroxylauric acid + H2O

-

-

1.14.14.130

lauric acid + [reduced NADPH-hemoprotein reductase] + O2 = 12-hydroxydodecanoic acid + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

1.14.14.49

12-hydroxylauric acid + reduced NADPH-hemoprotein reductase + O2 = 12-hydroxy-dodecanoic acid + oxidized NADPH-hemoprotein reductase + H2O

-

-

1.14.14.80

lauric acid + [reduced NADPH-hemoprotein reductase] + O2 + H+ = 12-hydroxylauric acid + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

1.14.14.80

lauric acid + [reduced NADPH-hemoprotein reductase] + O2 = 12-hydroxylauric acid + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

1.14.15.3

lauric acid + NAD(P)H + H+ + O2 = 12-hydroxydodecanoic acid + NAD(P)+ + H2O

-

-

1.14.15.3

lauric acid + [reduced NADPH-hemoprotein reductase] + O2 = 12-hydroxydodecanoic acid + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

1.14.14.80

2 entries

1.14.15.3

2 entries

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.1

-

285602

1m6w, 3D-view

3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (1 entry)

EC NUMBER

ENZYME 3D STRUCTURE

1.1.1.1

1m6w, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (14 results)

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Show Turnover Number (14 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.1.1.1

0.333

-

-

285566

1.1.1.1

1.03

-

isoenzyme TT-ADH

285650

1.1.1.1

1.27

-

isoenzyme ADH-3, pH 10.0

285604

1.1.1.1

1.45

-

enzyme form ADH-3

285615

1.1.1.1

2.2

-

isoenzyme BB-ADH

285650

1.1.1.1

2.43

-

-

285602

1.1.1.1

2.77

-

isoenzyme AA-ADH

285650

1.1.1.1

2.95

-

-

285608

1.1.1.1

3.03

-

-

285571

1.1.1.1

3.83

-

isoenzyme ADH-12, pH 10.0

285604

1.1.1.1

4

-

-

285569

1.1.1.1

20

-

isoenzyme ADH-1, pH 10.0

285604

1.1.1.284

0.217

-

-

287893

1.1.1.284

5.6

-

pH 10, 25°C

657054

1.1.1.1

12 entries

1.1.1.284

2 entries

K_M Value (19 results)

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Show KM Value (19 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.1

0.013

-

isoenzyme ADH-3, pH 10.0

285604

1.1.1.1

0.02

-

isoenzyme BB-ADH

285650

1.1.1.1

0.04

-

enzyme form ADH-3

285615

1.1.1.1

0.047

-

-

285651

1.1.1.1

0.048

-

-

285608

1.1.1.1

0.05

-

isoenzyme BB-ADH and isoenzyme ADH-TT

285650

1.1.1.1

0.056

-

-

285566

1.1.1.1

0.06

-

isoenzyme AA-ADH

285650

1.1.1.1

0.1

-

-

285571

1.1.1.1

0.1

-

isoenzyme ADH-1, pH 10.0

285604

1.1.1.1

0.23

-

0.1 M glycine-NaOH buffer, pH 10.0, 25°C

285569

1.1.1.1

1.4

-

isoenzyme ADH-1, pH 10.0

285604

1.1.1.1

2.3

-

isoenzyme TT-ADH

285650

1.1.1.1

13 entries

1.1.1.192

1.7

-

-

288324

1.1.1.284

0.041

-

wild type enzyme, pH 10

667724

1.1.1.284

0.16

-

mutant R368L, pH 10

667724

1.1.1.284

0.68

-

mutant E67L, pH 10

667724

1.1.1.284

4.7

-

pH 10, 25°C

657054

1.1.1.284

4 entries

1.1.1.306

1.7

-

-

288324

References & Links

Literature References (19)

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Show Reference (19 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

285566

2936344

Organ-specific human alcohol dehydrogenase: isolation and characterization of isozymes from testis

1986

Dafeldecker, W.P.; Vallee, B.L.

Biochem. Biophys. Res. Commun.

134

1056-1063

285569

6397223

Physical and enzymatic properties of a class II alcohol dehydrogenase isozyme of human liver: pi-ADH

1984

Ditlow, C.C.; Holmquist, B.; Morelock, M.M.; Vallee, B.L.

Biochemistry

23

6363-6368

285571

6375718

Physical and enzymatic properties of a class III isozyme of human liver alcohol dehydrogenase: chi-ADH

1984

Wagner, F.W.; Pares, X.; Holmquist, B.; Vallee, B.L.

Biochemistry

23

2193-2199

285602

3178842

A genuine organ specific alcohol dehydrogenase from hamster testes: isolation, characterization and developmental changes

1988

Keung, W.M.

Biochem. Biophys. Res. Commun.

156

38-45

285604

3816781

Characterization of three isoenzymes of rat alcohol dehydrogenase. Tissue distribution and physical and enzymatic properties

1987

Julia, P.; Farres, J.; Pares, X.

Eur. J. Biochem.

162

179-189

285608

7876099

Expression and kinetic characterization of recombinant human stomach alcohol dehydrogenase. Active-site amino acid sequence explains substrate specificity copared with liver isozymes

1995

Kedishvili, N.Y.; Bosron, W.F.; Stone, C.L.; Hurley, T.D.; Peggs, C.F.; Thomasson, H.R.; Popov, K.M.; Carr, L.G.; Edenberg, H.J.; Li, T.K.

J. Biol. Chem.

270

3625-3630

285615

2789998

Characterization of Coturnix quail liver alcohol dehydrogenase enzymes

1989

Nussrallah, B.A.; Dam, R.; Wagner, F.W.

Biochemistry

28

6245-6251

285650

8730210

Isolation and characterization of three alcohol dehydrogenase isozymes from Syrian golden hamster

1996

Keung, W.M.

Alcohol. Clin. Exp. Res.

20

213-220

285651

2099148

Identification of a human stomach alcohol dehydrogenase with distinctive kinetic properties

1990

Yin, S.J.; Wang, M.F.; Liao, C.S.; Chen, C.M.; Wu, C.W.

Biochem. Int.

22

829-835

287891

10213000

Maize glutathione-dependent formaldehyde dehydrogenase. Protein sequence and catalytic properties

1999

Wippermann, U.; Fliegmann, J.; Bauw, G.; Langebartels, C.; Maier, K.; Sandermann, H.Jr.

Planta

208

12-18

287892

8631716

Characterization of a glutathione-dependent formaldehyde dehydrogenase from Rhodobacter sphaeroides

1996

Barber, R.D.; Rott, M.A.; Donohue, T.J.

J. Bacteriol.

178

1386-1393

287893

10978156

Kinetic mechanism of human glutathione-dependent formaldehyde dehydrogenase

2000

Sanghani, P.C.; Stone, C.L.; Ray, B.D.; Pindel, E.V.; Hurley, T.D.; Bosron, W.F.

Biochemistry

39

10720-10729

288324

1597190

NAD-linked, factor-dependent formaldehyde dehydrogenase or trimeric, zinc-containing, long-chain alcohol dehydrogenase from Amycolatopsis methanolica

1992

Van Ophem, P.W.; Van Beeumen, J.; Duine, J.A.

Eur. J. Biochem.

206

511-518

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

654617

12196016

Human glutathione-dependent formaldehyde dehydrogenase. Structures of apo, binary, and inhibitory ternary complexes

2002

Sanghani, P.C.; Robinson, H.; Bosron, W.F.; Hurley, T.D.

Biochemistry

41

10778-10786

657054

12913179

Enhanced formaldehyde detoxification by overexpression of glutathione-dependent formaldehyde dehydrogenase from Arabidopsis

2003

Achkor, H.; Diaz, M.; Fernandez, M.R.; Biosca, J.A.; Pares, X.; Martinez, M.C.

Plant Physiol.

132

2248-2255

667724

16605250

Structure-function relationships in human glutathione-dependent formaldehyde dehydrogenase. Role of Glu-67 and Arg-368 in the catalytic mechanism

2006

Sanghani, P.C.; Davis, W.I.; Zhai, L.; Robinson, H.

Biochemistry

45

4819-4830

697214

19011746

Medium- and short-chain dehydrogenase/reductase gene and protein families: Dual functions of alcohol dehydrogenase 3: implications with focus on formaldehyde dehydrogenase and S-nitrosoglutathione reductase activities

2008

Staab, C.A.; Hellgren, M.; Hoeoeg, J.O.

Cell. Mol. Life Sci.

65

3950-3960

742480

17868380

Characterization of a methyl jasmonate and wounding-responsive cytochrome P450 of Arabidopsis thaliana catalyzing dicarboxylic fatty acid formation in vitro

2007

Kandel, S.; Sauveplane, V.; Compagnon, V.; Franke, R.; Millet, Y.; Schreiber, L.; Werck-Reichhart, D.; Pinot, F.

FEBS J.

274

5116-5127

Links to other databases for 12-hydroxylauric acid

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Show Links (1 entry)

ChEBI

PubChem