Any feedback?
Please rate this page
(ligand.php)
(0/150)

BRENDA support

Ligand tetradecanoic acid

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.

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
-
myristic acid + 2 ferrocytochrome b5 + O2 + 2 H+ = (Z)-11-tetradecenoate + (E)-11-tetradecenoate + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
-

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
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
-
myristic acid + NADH + O2 + ATP + CoA = myristoleic acid + NAD+ + H2O + ?
show the reaction diagram
-
beta-D-glucosyl 4,4'-diaponeurosporenoic acid + myristate = [(6-O-myristoyl)-beta-D-glucosyl] 4,4'-diaponeurosporenoate + H2O
show the reaction diagram
-
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
-
ATP + tetradecanoate + CoA = AMP + diphosphate + tetradecanoyl-CoA
show the reaction diagram
-
ATP + myristic acid + protein = AMP + diphosphate + myristoyl-protein thiolester
show the reaction diagram
-
ATP + myristic acid + CoA = AMP + diphosphate + myristoyl-CoA
show the reaction diagram
-

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
-
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
-
myristoyl-L-carnitine + H2O = myristic acid + L-carnitine
show the reaction diagram
-
1-myristol-2[9(1-pyrenyl)-nonanoyl]-phosphatidylcholine + H2O = myristic acid + 2[9(1-pyrenyl)-nonanoyl]-phosphatidylcholine
show the reaction diagram
-
1-naphthyl myristate + H2O = 1-naphthol + myristate
show the reaction diagram
-
p-nitrophenyl myristate + H2O = 4-nitrophenol + myristate
show the reaction diagram
-
tetradecanoyl-[acyl-carrier protein] + H2O = [acyl-carrier protein] + tetradecanoate
show the reaction diagram
-
myristoyl-CoA + H2O = myristate + CoA
show the reaction diagram
-
myristoyl-CoA + H2O = myristate + CoA
show the reaction diagram
-
N-myristoyl-L-glutamate + H2O = myristoate + L-glutamate
show the reaction diagram
-
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
-
stimulates
-

Inhibitor in Enzyme-catalyzed Reactions (31 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
-

3D Structure of Enzyme-Ligand-Complex (PDB) (874 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