Ligand oleoyl-CoA

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Basic Ligand Information

Molecular Structure
Picture of oleoyl-CoA (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C39H68N7O17P3S
oleoyl-CoA
XDUHQPOXLUAVEE-BPMMELMSSA-N
Synonyms:
(9Z)-octadecenoyl-CoA, cis-9-octadecenoyl-CoA, oleoyl-[CoA], S-[(9Z)-octadec-9-enoyl]-CoA


Show all pahtways known for Show all BRENDA pathways known for oleoyl-CoA

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (33 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
oleoyl-CoA + NADPH + H+ = oleic aldehyde + CoA + NADP+
show the reaction diagram
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oleoyl-CoA + dolichol = CoA + dolichyl oleate
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oleoyl-CoA + sn-glycerol 3-phosphate = CoA + 1-oleoyl-sn-glycerol 3-phosphate
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oleoyl-CoA + 1-alkenyl-glycero-3-phosphorylcholine = CoA + 1-alkenyl-2-oleoyl-glycero-3-phosphorylcholine
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oleoyl-CoA + sphingolipid = N-(oleoyl)-sphingolipid + CoA
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oleoyl-CoA + H2O = CoA + oleate
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oleoyl-CoA + H2O = oleate + CoA
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
stearoyl-CoA + reduced acceptor + O2 = oleoyl-CoA + acceptor + 2 H2O
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (268 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
oleoyl-CoA + [reduced NADPH-hemoprotein reductase] + O2 = 18-hydroxyoleoyl-CoA + [oxidized NADPH-hemoprotein reductase] + H2O
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oleoyl-CoA + NADPH + H+ = oleic aldehyde + CoA + NADP+
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oleoyl-CoA + NADPH + H+ = (9Z)-octadec-9-enal + CoA + NADP+
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oleoyl-CoA + NADPH = (9Z)-octadecenal + CoA + NADP+
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oleoyl-CoA + O2 = 2-trans-9-trans-octadecendienoyl-CoA + H2O2
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oleoyl-CoA + oxidized electron transfer flavoprotein = ? + reduced electron transfer flavoprotein
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oleoyl-CoA + myelin proteolipid protein = CoA + myelin proteolipid O-oleoylprotein
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oleoyl-CoA + dolichol = CoA + dolichyl oleate
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1-alkyl-2-lyso-glyceryl phosphorylcholine + oleoyl-CoA = ?
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oleoyl-CoA + L-carnitine = CoA + L-oleoylcarnitine
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oleoyl-CoA + 1-alkenyl-glycero-3-phosphorylcholine = CoA + 1-alkenyl-2-oleoyl-glycero-3-phosphorylcholine
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octan-1-ol + oleoyl-CoA = 1-octyl oleate + CoA
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oleoyl-CoA + L-serine = CoA + 2-amino-1-hydroxy-11-cis-eicosen-3-one + CO2
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oleoyl-CoA + 2-acyl-sn-glycerol 3-phosphate = CoA + 1-oleoyl-2-acyl-sn-glycerol 3-phosphate
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oleoyl-CoA + alkyl-lyso-glycero-3-phosphoethanolamine = CoA + 1-alkyl-2-oleoyl-glycero-3-phosphoethanolamine
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oleoyl-CoA + octopamine = CoA + N-oleoyloctopamine
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oleoyl-CoA + H2O = oleic acid + CoA
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oleoyl-CoA = oleate + CoA
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (21 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
oleic acid + ATP + CoA = oleoyl-CoA + AMP + diphosphate
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stearoyl-CoA + reduced acceptor + O2 = oleoyl-CoA + acceptor + 2 H2O
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GTP + oleate + CoA = GDP + phosphate + oleoyl-CoA
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ATP + oleate + CoA = AMP + diphosphate + oleoyl-CoA
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Activator in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.02-0.05 mM, enhances activity about 2fold
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activation in decreasing order: acetyl-CoA, n-propanyl-CoA, n-butanoyl-CoA, malonyl-CoA/ CoA, acetoacetyl-CoA, oleoyl-CoA
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Inhibitor in Enzyme-catalyzed Reactions (33 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
2.0 mM, 9% inhibition of NADP+-dependent reaction, 90% inhibition of NAD+-dependent reaction
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above 0.05 M
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substrate inhibition; substrate inhibition
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2 mM, 87% inhibition
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inhibition of oleoyl-CoA synthesis
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3D Structure of Enzyme-Ligand-Complex (PDB) (36 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (6 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.075
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pH 8.0, temperature not specified in the publication

KM Value (101 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0065
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0.046
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0.0044
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pH not specified in the publication, temperature not specified in the publication
0.0036
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pH 8.0, temperature not specified in the publication

Ki Value (13 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.15
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24°C, pH 7.8, inhibition of NAD+-dependent reaction

IC50 Value (2 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.021
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at pH 8.0, temperature not specified in the publication
0.021
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pH 8.0, temperature not specified in the publication

References & Links

Links to other databases for oleoyl-CoA

ChEBI
PubChem
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PubChem