Ligand stearoyl-CoA

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Basic Ligand Information

Molecular Structure
Picture of stearoyl-CoA (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C39H70N7O17P3S
stearoyl-CoA
SIARJEKBADXQJG-LFZQUHGESA-N
Synonyms:
fatty-acyl-CoA, fatty-acyl-CoA thioester, fatty acid-CoA, fatty acyl-CoA, fatty acyl-CoA/cis, fatty acyl-CoA/trans, fatty acyl-CoA ester, fatty acyl CoA/cis, fatty acyl CoA/trans, long-chain fatty-acyl-CoA, long-chain fatty acyl-CoA, octadecanoyl-CoA, stearyl-CoA, stearyl CoA

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (31 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
stearoyl-CoA + reduced acceptor + O2 = oleoyl-CoA + acceptor + 2 H2O
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octadecanoyl-CoA + NADPH + H+ = octadecanal + CoA + NADP+
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stearoyl-CoA + NADPH = octadecanal + CoA + NADP+
show the reaction diagram
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stearoyl-CoA + dolichol = CoA + dolichyl stearate
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monoacylglycerol + fatty acyl-CoA = diacylglycerol + CoA
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stearoyl-CoA + 1-oleoyl-lysophosphatidylcholine = CoA + 1-oleoyl-2-stearoyl-lysophosphatidylcholine
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long-chain fatty acyl-CoA + cholesterol = CoA + cholesteryl long-chain fatty acyl ester
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stearoyl-CoA + H2O = CoA + stearate
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In Vivo Product in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
ATP + octadecanoate + CoA = AMP + diphosphate + octadecanoyl-CoA
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (173 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
octadecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyoctadecanoyl-CoA + succinate + CO2
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stearoyl-CoA + [reduced NADPH-hemoprotein reductase] + O2 = 18-hydroxystearoyl-CoA + [oxidized NADPH-hemoprotein reductase] + H2O
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stearoyl-CoA + electron donor + O2 = 9-octadecenoyl-CoA + acceptor + H2O
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stearoyl-CoA + reduced acceptor + O2 = oleoyl-CoA + acceptor + 2 H2O
show the reaction diagram
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fatty acyl-CoA + NAD(P)H + H+ = fatty aldehyde + CoA + NAD(P)+
show the reaction diagram
stearoyl-CoA + NADPH = octadecanal + CoA + NADP+
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stearoyl-CoA + myelin proteolipid protein = CoA + myelin proteolipid O-stearoylprotein
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stearoyl-CoA + 1-alkenylglycerophosphoethanolamine = CoA + 1-alkenyl-2-stearoylglycerophosphoethanolamine
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stearoyl-CoA + dolichol = CoA + dolichyl stearate
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stearoyl-CoA + glycine = CoA + N-stearoyl-glycine
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stearoyl-CoA + malonyl-[acyl-carrier protein] = 3-oxo-arachidoyl-[acyl-carrier protein] + CoA + CO2
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stearoyl-CoA + L-carnitine = CoA + L-stearoylcarnitine
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stearoyl-CoA + [rhodopsin]-L-cysteine = [rhodopsin]-S-stearoyl-L-cysteine + CoA
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octan-1-ol + stearoyl-CoA = 1-octyl stearate + CoA
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stearoyl-CoA + a sphingoid base = an N-(stearoyl)-sphingoid base + CoA
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stearoyl-CoA + 2-acyl-sn-glycerol 3-phosphate = CoA + 1-stearoyl-2-acyl-sn-glycerol 3-phosphate
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2 malonyl-CoA + 2 stearoyl-CoA = 6-heptadecyl-4-hydroxy-2H-pyran-2-one + 4-hydroxy-6-(2-oxononadecyl)-2H-pyran-2-one + 2 CoA + 2 CO2
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stearoyl-CoA + retinol = CoA + retinylstearate
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stearoyl-CoA + octopamine = CoA + N-stearoyloctopamine
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stearoyl-CoA + glycylpeptide = N-stearoylglycylpeptide + CoA
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stearoyl-CoA + glycerophosphocholine = CoA + 1-stearoyl-sn-glycero-3-phosphocholine
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stearoyl-CoA + H2O = ?
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stearoyl-CoA + H2O = CoA + stearate
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
fatty acid + ATP + CoA = fatty acyl-CoA + AMP
show the reaction diagram
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trans-2,3-dehydrostearoyl-CoA + NADPH = stearoyl-CoA + NADP+
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2-trans-octadecenoyl-CoA + NAD(P)H = octadecanoyl-CoA + NAD(P)+
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ATP + octadecanoate + CoA = AMP + diphosphate + octadecanoyl-CoA
show the reaction diagram
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ATP + stearate + CoA = AMP + diphosphate + stearyl-CoA
show the reaction diagram
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octadecanoic acid + CoA + ATP = octadecanoyl-CoA + AMP + diphosphate
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (22 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
92% residual activity at 0.1 mM
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about 40% inhibition at 0.2 mM
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competitive inhibitor of P5CR NAD(P)H-dependent thioproline dehydrogenase activity
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strongly inhibitory at 0.002 mM
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above 0.064 mM
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3D Structure of Enzyme-Ligand-Complex (PDB) (62 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (20 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.006
-
pH 7.5, 37C, recombinant enzyme
0.667
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K304E mutant enzyme, ferricenium assay
0.083
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pH not specified in the publication, temperature not specified in the publication
0.059
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pH 8.0, temperature not specified in the publication

KM Value (55 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0083
-
-
0.0319
-
pH 7.5, 37C, recombinant enzyme
0.05
-
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0.02566
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0.0064
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pH and temperature not specified in the publication
0.003
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pH 7.4, 25C
0.0129
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pH not specified in the publication, temperature not specified in the publication
0.006
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pH 8.0, temperature not specified in the publication

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.2
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at 37C

References & Links

Links to other databases for stearoyl-CoA

ChEBI
PubChem
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PubChem