Ligand dodecanoic acid

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Basic Ligand Information

Molecular Structure
Picture of dodecanoic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C12H24O2
dodecanoic acid
POULHZVOKOAJMA-UHFFFAOYSA-N
Synonyms:
dodecanoate, laurate, laureate, lauric acid, lauroate, n-dodecanoate, n-laurate

Show all pahtways known for Show all pathways known for dodecanoic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
dodecanoate + [reduced NADPH-hemoprotein reductase] + O2 = 7-hydroxydodecanoate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
1-lauroyl-rac-glycerol + H2O = glycerol + lauric acid
show the reaction diagram
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dodecanoyl-CoA + H2O = dodecanoate + CoA
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dodecanoyl-[acyl-carrier protein] + H2O = [acyl-carrier protein] + dodecanoate
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (39 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
lauric acid + H2O2 = undecanal + CO2 + H2O
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lauric acid + H2O2 = ?
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lauric acid + ATP + CoA = lauroyl-CoA + AMP + diphosphate
show the reaction diagram
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lauric acid + O2 + reduced adrenodoxin [iron-sulfur] cluster + H+ = ? + H2O + oxidized adrenodoxin [iron-sulfur] cluster
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lauric acid + ATP + NADPH + H+ = lauraldehyde + AMP + diphosphate + NADP+
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dodecanoic acid + S-adenosyl-L-methionine = methyl dodecanoate + S-adenosyl-L-homocysteine
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D-erythro-sphingosine + lauric acid = N-lauroyl-D-erythro-sphingosine + H2O
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lauric acid + lyso-GM1a = ? + H2O
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ATP + n-laurate + CoA = AMP + diphosphate + n-lauroyl-CoA
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ATP + laurate = diphosphate + lauroyl adenylate
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dodecanoic acid + CoA + ATP = dodecanoyl-CoA + AMP + diphosphate
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Product in Enzyme-catalyzed Reactions (171 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
dodecanal + NADP+ + H2O = dodecanoate + NADPH + H+
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dodecyl aldehyde + H2O + O2 = dodecanoic acid + H2O2
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dodecanal + a quinone + H2O = dodecanoate + a quinol
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dodecanoyl-CoA + H2O = dodecanoate + CoA
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4-nitrophenyl laurate + H2O = 4-nitrophenol + laurate
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lauroyl-L-carnitine + H2O = lauric acid + L-carnitine
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p-nitrophenyl laurate + H2O = p-nitrophenol + laurate
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p-nitrophenyl laurate + H2O = p-nitrophenol + lauric acid
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p-nitrophenyl laurate + H2O = p-nitrophenol + laurate
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4-nitrophenyl dodecanoate + H2O = 4-nitrophenol + dodecanoate
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4-nitrophenyl laurate + H2O = 4-nitrophenyl + laurate
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lauroyl-CoA = lauroate + CoA
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dodecanoyl-[acyl-carrier protein] + H2O = [acyl-carrier protein] + dodecanoate
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N-lauroylethanolamine + H2O = lauric acid + ethanolamine
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N-dodecanoylethanolamine + H2O = dodecanoic acid + ethanolamine
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dodecanenitrile + H2O = dodecanoic acid + NH3
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dodecanenitrile + H2O = dodecanoate + NH3
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Activator in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
plus carbon monoxide, greater stimulation compared to laurate alone or carbon monoxide alone, decrease of stimulation in the presence of NADPH; stimulation
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enhancement factor: 0.1 in absence of Triton X-100, 2.3 in presence of 0.1% Triton X-100
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presence of 5 mM ATP, inhibitory above 0.25 mM. Presence of 0.05 mM ATP, stimulating up to 0.3 mM, inhibitory above
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Inhibitor in Enzyme-catalyzed Reactions (26 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
inhibits ADH3 irrespective of substrate
0.05 mM, less than 10% inhibition
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competitive inhibition
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isoform 1, 50% inhibition at 0.0167 mM, isoform 2, 50% inhibition at 0.0186 mM
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IC50 below 1 mM
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IC50: 0.0758 mM, TbHK1
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40 microM, about 60% inhibition
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at pH 5
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presence of 5 mM ATP, inhibitory above 0.25 mM. Presence of 0.05 mM ATP, stimulating up to 0.3 mM, inhibitory above
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weak inhibition
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weak inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (20 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (28 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
27.7
-
CYP102A7, at pH 7.5
1165
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pH 7.8, 37C
0.0017
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at pH 7.5 and 25C

KM Value (33 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.055
-
-
0.102
-
CYP102A7, at pH 7.5
0.103
-
pH 7.8, 37C
0.02
-
-
0.025
-
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Ki Value (12 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE

IC50 Value (7 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0012
-
IC50: 0.0012 mM
0.419
-
pH 6.9, 37C
1
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IC50 below 1 mM
0.0758
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IC50: 0.0758 mM, TbHK1

References & Links

Links to other databases for dodecanoic acid

ChEBI
PubChem
ChEBI
PubChem