Ligand eicosapentaenoic acid

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Basic Ligand Information

Molecular Structure
Picture of eicosapentaenoic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C20H30O2
eicosapentaenoic acid
JAZBEHYOTPTENJ-JLNKQSITSA-N
Synonyms:
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate, (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoic acid, (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate, (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid, (5Z,8Z,11Z,14Z,17Z)-icosapentaenoate, (5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acid, 5,8,11,14,17-eicosapentaenoic acid, cis-5,8,11,14,17-eicosapentaenoic acid, eicosapentaenoate, icosapentaenoic acid

Show all pahtways known for Show all pathways known for eicosapentaenoic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate = (5Z,7E,9E,14Z,17Z)-eicosapentaenoate
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phosphatidylcholine + H2O = 2-acylglycerophosphocholine + eicosapentaenoic acid + docosapentaenoic acid + docosahexaenoic acid
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (20 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
eicosapentaenoic acid + O2 = 15-hydroxyeicosapentaenoic acid
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5,8,11,14,17-eicosapentaenoic acid + O2 = ?
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eicosapentaenoic acid + O2 = ?
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eicosapentaenoic acid + NAD(P)H + H+ + O2 = ? + NAD(P)+ + H2O
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D-erythro-sphingosine + eicosapentaenoic acid = N-eicosapentaenyl-D-erythro-sphingosine + H2O
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eicosapentaenoic acid + lyso-GM1a = ? + H2O
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(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate = (5Z,7E,9E,14Z,17Z)-eicosapentaenoate
show the reaction diagram
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ATP + 5,8,11,14,17-eicosapentaenoic acid + CoA = ATP + diphosphate + 5,8,11,14,17-eicosapentaenoyl-CoA
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ATP + eicosapentaenoate + CoA = AMP + diphosphate + eicosapentaenoyl-CoA
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Product in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
arachidonic acid + ferrocytochrome b5 + O2 + H+ = eicosapentaenoic acid + ferricytochrome b5 + H2O
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eicosatetraenoic acid + ferrocytochrome b5 + O2 + H+ = eicosapentaenoic acid + ferricytochrome b5 + H2O
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phosphatidylcholine + H2O = 2-acylglycerophosphocholine + eicosapentaenoic acid + docosapentaenoic acid + docosahexaenoic acid
show the reaction diagram
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eicosapentaenoyl-CoA + H2O = CoA + eicosapentaenoate
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eicosapentaenoyl-CoA + H2O = CoA + eicosapentaenoate
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Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
competitive inhibition of oxygenation of arachidonic acid
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Inhibitor in Enzyme-catalyzed Reactions (17 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
inhibits translation of the enzyme about 50% at 0.15 mM, downregulation, slightly increases downregulation of protein synthesis by cycloheximide
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the incubation of Jurkat cells with 0.1 mM eicosapentaenoic acid causes a significant decrease of catalase activity but not of protein or mRNA content
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19% inhibition at 0.02 mM
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50% inhibition at 0.0994 mM
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ACMSD mRNA levels in primary hepatocytes are decreased by the incubation with high concentrations of eicosapentaenoic acid
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slight
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3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (3 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
8.7
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pH 8.0, 25°C, COX-2 mutant N580A

KM Value (13 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0155
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Ki Value (2 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.025
-
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0.2475
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37°C, pH 7.0

IC50 Value (2 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.00065
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induces time-dependent enzyme inactivation at concentrations 100fold lower than the Km-value, IC50: 0.00065 mM
0.0003
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References & Links

Links to other databases for eicosapentaenoic acid

ChEBI
PubChem
ChEBI
PubChem