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Ligand docosahexaenoic acid

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Basic Ligand Information

Molecular Structure
Picture of docosahexaenoic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C22H32O2
docosahexaenoic acid
MBMBGCFOFBJSGT-KUBAVDMBSA-N
Synonyms:
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate, (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid, (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexa-4,7,10,13,16,19-enoic acid, (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate, (4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoic acid, (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexenoate, 4,7,10,13,16,19-docosahexaenoic acid, 4,7,10,13,16,19-docosapentaenoic acid, 22:5 DELTA7,10,13,16,19-docosapentaenoic acid, 22:5(n-3), 22:6 DELTA4,7,10,13,16,19-docosahexaenoic acid, cis-4,7,10,13,16,19-docosahexaenoic acid, docosahexaenoate, docosahexaneoate, docosahexanoate, docosahexanoic acid, [4Z,7Z,10Z,13Z,16Z,19Z]-docosa-4,7,10,13,16,19-hexaenoic 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
docosahexaenoate + NADPH + H+ + O2 = 22-hydroxydocosahexaenoate + NADP+ + H2O
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (23 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
docosahexaenoic acid + O2 = ?
show the reaction diagram
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docosahexaenoic acid + O2 = ?
show the reaction diagram
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docosahexaenoic acid + O2 = ?
show the reaction diagram
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docosahexaenoic acid + [reduced NADPH-hemoprotein reductase] + O2 = 22-hydroxydocosahexaenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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docosahexaenoic acid + NAD(P)H + H+ + O2 = ? + NAD(P)+ + H2O
show the reaction diagram
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22:5 DELTA7,10,13,16,19-docosapentaenoic acid + 2 ferrocytochrome b5 + O2 + 2 H+ = 22:6 DELTA4,7,10,13,16,19-docosahexaenoic acid + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
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22:5(n-3) + reduced ferredoxin [iron-sulfur] cluster + O2 + H+ = docosa-4,7,10,13,16,19-hexaenoic acid + oxidized ferredoxin [iron-sulfur] cluster + H2O
show the reaction diagram
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D-erythro-sphingosine + (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexa-4,7,10,13,16,19-enoic acid = N-((4Z,7Z,10Z,13Z,16Z,19Z)-docosahexa-4,7,10,13,16,19-enoyl)-D-erythro-sphingosine + H2O
show the reaction diagram
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docosahexaenoic acid + lyso-GM1a = ? + H2O
show the reaction diagram
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(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexenoate = (4Z,7Z,9E,11E,16Z,19Z)-docosahexenoate
show the reaction diagram
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ATP + docosahexaenoate + CoA = ATP + diphosphate + docosahexaenoyl-CoA
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
22:5 DELTA7,10,13,16,19-docosapentaenoic acid + 2 ferrocytochrome b5 + O2 + 2 H+ = 22:6 DELTA4,7,10,13,16,19-docosahexaenoic acid + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
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1,2-didocosahexaenoyl-phosphatidylcholine + H2O = 2-docosahexaenoyl-lysophosphatidylcholine + docosahexaenoic acid
show the reaction diagram
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docosahexaenoyl-CoA + H2O = CoA + docosahexaenoate
show the reaction diagram
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docosahexaenoyl-CoA + H2O = CoA + docosahexaenoate
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE

Inhibitor in Enzyme-catalyzed Reactions (15 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.1 mM reduces the level of protein expression of GPx-4 by at least 50%
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35% inhibition at 0.02 mM
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isozyme 1, 50% inhibition at 0.011 mM, isozyme 2, 50% inhibition at 0.015 mM
50% inhibition at 0.0462 mM
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unlabeled, inhibition of docosahexaenoate activation
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3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (1 result)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
3.45
-
pH 8.0, 25°C, COX-2 mutant N580A

KM Value (7 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0019
-
pH 7, 22°C
0.222
-
pH 8.5, 30°C

Ki Value (3 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.089
-
37°C, pH 7.0

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0013
-
IC50: 0.0013 mM

References & Links

Links to other databases for docosahexaenoic acid

ChEBI
PubChem
ChEBI
PubChem