Ligand tetradecanoic acid

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Basic Ligand Information

Molecular Structure
Picture of tetradecanoic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C14H28O2
tetradecanoic acid
TUNFSRHWOTWDNC-UHFFFAOYSA-N
Synonyms:
(14,14,14-2H3)tetradecanoic acid, 1-tridecanecarboxylic acid, myristate, myristic acid, myristoate, n-tetradecanoate, tetradecanoate

Roles as Enzyme Ligand

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

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
myristic acid + H2O2 = ?
show the reaction diagram
myristic acid + [reduced NADPH-hemoprotein reductase] + O2 = 14-hydroxymyristic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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myristic acid + 2 ferrocytochrome b5 + O2 + 2 H+ = (Z)-11-tetradecenoate + (E)-11-tetradecenoate + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
tetradecanal + FMNH2 + O2 = tetradecanoate + FMN + H2O + hn
show the reaction diagram
-
-
trimyristin + H2O = dimyristin + myristate
show the reaction diagram
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tetradecanoyl-CoA + H2O = CoA + tetradecanoate
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (42 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
myristic acid + H2O2 = 13-hydroxymyristic acid + 12-hydroxymyristic acid + H2O
show the reaction diagram
-
myristic acid + ATP + CoA = myristoyl-CoA + AMP + diphosphate
show the reaction diagram
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myristic acid + NADH + O2 + ATP + CoA = myristoleic acid + NAD+ + H2O + ?
show the reaction diagram
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beta-D-glucosyl 4,4'-diaponeurosporenoic acid + myristate = [(6-O-myristoyl)-beta-D-glucosyl] 4,4'-diaponeurosporenoate + H2O
show the reaction diagram
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ATP + myristic acid = ADP + myristyl phosphate
show the reaction diagram
-
glycerol + myristic acid = monomyristin + H2O
show the reaction diagram
-
myristic acid + lyso-GM1a = ? + H2O
show the reaction diagram
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ATP + tetradecanoate + CoA = AMP + diphosphate + tetradecanoyl-CoA
show the reaction diagram
-
ATP + myristic acid + protein = AMP + diphosphate + myristoyl-protein thiolester
show the reaction diagram
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ATP + myristic acid + CoA = AMP + diphosphate + myristoyl-CoA
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (98 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
1-tetradecanol + 2 NAD+ + H2O = tetradecanoic acid + 2 NADH + 2 H+
show the reaction diagram
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-
tetradecanal + NADP+ = tetradecanoate + NADPH
show the reaction diagram
-
-
n-tetradecanal + NADP+ + H2O = n-tetradecanoate + NADPH + H+
show the reaction diagram
-
-
myristoyl-CoA + H2O = 2-myristoylmyristic acid + myristic acid + 14-heptacosanone + CoA
show the reaction diagram
-
-
4-nitrophenyl myristate + H2O = 4-nitrophenol + myristate
show the reaction diagram
-
-
1,2-dimyristoyl-sn-glycero-3-phosphate + H2O = 2-myristoyl-sn-glycero-3-phosphate + myristate
show the reaction diagram
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-
myristoyl-L-carnitine + H2O = myristic acid + L-carnitine
show the reaction diagram
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1-myristol-2[9(1-pyrenyl)-nonanoyl]-phosphatidylcholine + H2O = myristic acid + 2[9(1-pyrenyl)-nonanoyl]-phosphatidylcholine
show the reaction diagram
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1-naphthyl myristate + H2O = 1-naphthol + myristate
show the reaction diagram
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p-nitrophenyl myristate + H2O = 4-nitrophenol + myristate
show the reaction diagram
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tetradecanoyl-[acyl-carrier protein] + H2O = [acyl-carrier protein] + tetradecanoate
show the reaction diagram
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myristoyl-CoA + H2O = myristate + CoA
show the reaction diagram
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-
myristoyl-CoA + H2O = myristate + CoA
show the reaction diagram
-
-
N-myristoyl-L-glutamate + H2O = myristoate + L-glutamate
show the reaction diagram
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N-tetradecanoylethanolamine + H2O = tetradecanoic acid + ethanolamine
show the reaction diagram

Activator in Enzyme-catalyzed Reactions (10 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
stimulates translation of the enzyme about 1.8fold at 0.15 mM, upregulation
-
109% of the activitation with palmitic acid
-
a moderate dietary intake of myristic acid (1.8% total energy) and alpha-linolenic acid (0.9% total energy) increases LCAT activity
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stimulates
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Inhibitor in Enzyme-catalyzed Reactions (30 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.01 mM
-
0.05 mM, less than 10% inhibition
-
myristic acid hydroxylation is inhibited by 3,5,3',5'-tetramethylbenzidine oxidation in a 3,5,3',5'-tetramethylbenzidine concentration-dependent manner
isoform 2, 50% inhibition at 0.004 mM
-
IC50: 0.0784 mM, TbHK1
-
inhibition is non-competitive with respect to the substrate estrone
-
IC50: 0.27 mM
-
weak inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (818 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (17 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
4.03
-
pH 7.5, 25°C
59.8
-
CYP102A7, at pH 7.5, highest activity
0.96
-
pH not specified in the publication, temperature not specified in the publication

KM Value (27 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0263
-
pH 7.5, 25°C
0.001
-
below, pH 8.5, 30°C, recombinant enzyme
0.015
-
palmitic acid
0.001
-
below, pH 8.5, 30°C, recombinant enzyme
0.036
-
pH not specified in the publication, temperature not specified in the publication

Ki Value (2 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.00053
-
-
3.85
-
pH and temperature not specified in the publication

IC50 Value (9 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.011
-
pH 6.0
1
100
IC50 in the range 1-100 mM
0.0784
-
IC50: 0.0784 mM, TbHK1
0.009
-
pH 7.4, 37°C, recombinant CES1
0.27
-
IC50: 0.27 mM

References & Links

Links to other databases for tetradecanoic acid

ChEBI
PubChem
ChEBI
PubChem