Ligand arachidonic acid

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Basic Ligand Information

Molecular Structure
Picture of arachidonic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C20H32O2
arachidonic acid
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Synonyms:
(5Z,8Z,11Z,14Z)-eicosatetra-5,8,11,14-enoic acid, (5Z,8Z,11Z,14Z)-eicosatetraenoate, (5Z,8Z,11Z,14Z)-eicosatetraenoic acid, (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid, (5Z,8Z,11Z,14Z)-Icosatetraenoic acid, all-cis-5,8,11,14-Eicosatetraenoate, arachidonate, arachidonoate, cis-5,8,11,14-eicosatetraenoic acid

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (63 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
arachidonic acid + O2 + NADPH = 20-hydroxyeicosatetraenoic acid + H2O + NADP+
show the reaction diagram
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arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2 = 20-hydroxyarachidonic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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arachidonate + [reduced NADPH-hemoprotein reductase] + O2 = 20-hydroxy-5,8,11,14-eicosatetraenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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arachidonic acid + NADPH + H+ + O2 = 20-hydroxyeicosatetraenoic acid + NADP+ + H2O
show the reaction diagram
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ATP + arachidonate + CoA = AMP + diphosphate + arachidonoyl-CoA
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (12 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
dihomo-gamma-linolenic acid + ferrocytochrome b5 + O2 + H+ = arachidonic acid + ferricytochrome b5 + H2O
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arachidonoyl-CoA + H2O = CoA + arachidonate
show the reaction diagram
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anandamide + H2O = arachidonic acid + ethanolamine
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Substrate in Enzyme-catalyzed Reactions (209 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
arachidonate + O2 = ?
show the reaction diagram
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arachidonate + O2 = ?
show the reaction diagram
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arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2 = 20-hydroxyarachidonic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2 = 18-hydroxyarachidonic acid + [oxidized NADPH-hemoprotein reductase] + H2O
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arachidonic acid + ferrocytochrome b5 + O2 + H+ = eicosapentaenoic acid + ferricytochrome b5 + H2O
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arachidonate + ethanol = ethyl arachidonate + H2O
show the reaction diagram
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D-erythro-sphingosine + arachidonic acid = N-arachidonyl-D-erythro-sphingosine + H2O
show the reaction diagram
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arachidonic acid + O2 = 5-HPETE + 7-HPETE + 9-HPETE
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ATP + arachidonic acid + CoA = AMP + diphosphate + arachidonoyl-CoA
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (72 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
arachidonic acid hydroperoxide + tryparedoxin = arachidonic acid + oxidized tryparedoxin
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linolenic acid + AH2 + O2 = arachidonic acid + A + H2O
show the reaction diagram
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dihomo-gamma-linolenic acid + ferrocytochrome b5 + O2 + H+ = arachidonic acid + ferricytochrome b5 + H2O
show the reaction diagram
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cholesteryl arachidonate + H2O = cholesterol + arachidonic acid
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triarachidin + H2O = arachidonic acid + ?
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phosphatidylcholine + H2O = 1-acyl-2-oleoyl-sn-glycerophosphocholine + arachidonic acid
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1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine + H2O = 1-palmitoyl-sn-glycero-3-phosphocholine + arachidonate
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arachidonoyl-CoA + H2O = CoA + arachidonate
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2-arachidonoylglycerol + H2O = arachidonic acid + glycerol
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N-arachidonoyl-L-glutamate + H2O = arachidonate + L-glutamate
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Activator in Enzyme-catalyzed Reactions (33 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
maximal enzyme activity in the presence of 0.25-0.35 mM, inhibition above
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alone or a combination of gamma-linolenic acid and phosphatidylserine slightly enhances PKC zeta activity; slightly enhances PKC zeta activity
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enhances hyrolysis of phosphatidylinositol 4,5-diphosphate, membrane bound enzyme and cytosolic enzyme
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only in presence of Mg2+
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strong activation at 0.1 mM
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0.0503 mM half-maximal effective concentration, 0.0263 mM half-maximal effective concentration in the presence of actin
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Inhibitor in Enzyme-catalyzed Reactions (46 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.018 mM, complete inhibition, oxidation of estradiol
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autoinactivates 15-hLO-1 to a much greater extent than linoleic acid at high substrate concentrations. No autoinactivation at low substrate concentrations
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inhibits at 0.01 mM
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concentration above 10 microM
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the enzymatic activity significantly declines by treatment with 0.1 mM for 1 h
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0.045 mM, 50% inhibition
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0.5 mg/ml, 91.3% inhibition of mPIK-III
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IC50 value is 0.078 mM
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inhibits SMPP-1M, dissociates the catalytic subunit from the native holoenzyme, inhibits the regulatory action of the 110 kDa/21 kDa subunit complex on the catalytic subunit PP1C activity, the C-terminal half of the 110 kDa subunit is required for inhibition
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slight stimulation below 0.8 mM, approx. 50% inhibition at 3.2 mM
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50% inhibition at 0.0534 mM
-
IC50: 0.058 mM, complete inhibition at 0.1 mM
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irreversible inhibition, IC50 is 0.01 mM for inhibition of decatenation of kinetoplast DNA, effects on thermal transition of dsDNA, overview
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3D Structure of Enzyme-Ligand-Complex (PDB) (11 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (65 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
1.3
-
pH 6.5, 25°C
0.009
-
at pH 7.4 and 37°C
27
-
pH 8.0, 25°C, COX-2 mutant N580A

KM Value (146 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0203
-
pH 6.5, 25°C
0.228
-
-

Ki Value (9 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0018
-
pH 7.4, 37°C, recombinant CES1
0.0913
-
37°C, pH 7.0

IC50 Value (6 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.00023
-
induces time-dependent enzyme inactivation at concentrations 100fold lower than the Km-value, IC50: 0.00023 mM
0.002
-
pH 7.4, 37°C, recombinant CES1
0.078
-
IC50 value is 0.078 mM
0.058
-
IC50: 0.058 mM, complete inhibition at 0.1 mM
0.0003
-
-
0.01
-
irreversible inhibition, IC50 is 0.01 mM for inhibition of decatenation of kinetoplast DNA, effects on thermal transition of dsDNA, overview

References & Links