Ligand acetoacetyl-CoA

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Basic Ligand Information

Molecular Structure
Picture of acetoacetyl-CoA (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C25H40N7O18P3S
acetoacetyl-CoA
OJFDKHTZOUZBOS-CITAKDKDSA-N
Synonyms:
3-acetoacetyl-CoA, 3-oxobutyryl-CoA, acetoacetyl CoA, S-acetoacetyl-CoA
Pathway Source
Pathways


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

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (35 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3-acetoacetyl-CoA + NADPH + H+ = (S)-3-hydroxybutanoyl-CoA + NADP+
show the reaction diagram
CoA + acetoacetyl-CoA = 2 acetyl-CoA
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acetoacetyl-CoA + acetate = acetoacetate + acetyl-CoA
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-
butanoate + acetoacetyl-CoA = butanoyl-CoA + acetoacetate
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acetoacetyl-CoA + H2O = ?
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ATP + L-isoleucine + acetoacetyl-CoA = AMP + diphosphate + tenuazonic acid + CoA
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (39 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acetyl-CoA = acetoacetyl-CoA + CoA
show the reaction diagram
-
-
2 acetyl-CoA = CoA + acetoacetyl-CoA
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succinyl-CoA + acetoacetate = succinate + acetoacetyl-CoA
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-
ATP + acetoacetate + CoA = AMP + diphosphate + acetoacetyl-CoA
show the reaction diagram
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-

Substrate in Enzyme-catalyzed Reactions (151 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acetoacetyl-CoA + NADPH = NADP+ + ?
show the reaction diagram
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3-acetoacetyl-CoA + NADPH + H+ = (S)-3-hydroxybutanoyl-CoA + NADP+
show the reaction diagram
acetoacetyl-CoA + NADH = 3-hydroxybutyryl-CoA + NAD+
show the reaction diagram
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acetoacetyl-CoA + NADH = 3-hydroxybutanoyl-CoA + NAD+
show the reaction diagram
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acetoacetyl-CoA + oxaloacetate = 3-oxoglutaryl-CoA + pyruvate
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acetoacetyl-CoA + L-carnitine = acetoacetyl-L-carnitine + CoA
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acetoacetyl-CoA + CoA = acetyl-CoA + acetyl-CoA
show the reaction diagram
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acetoacetyl-CoA + phosphate = acetoacetylphosphate + CoA
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acetoacetyl-CoA + acyl-carrier protein = CoA + acetoacetyl-[acyl-carrier protein]
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acetoacetyl-CoA + gentamicin = CoA + N3'-acetoacetyl-gentamicin
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acetoacetyl-CoA + L-(-)carnitine = O-acetoacetyl(-)carnitine + CoASH
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acetoacetyl-CoA + apo-[acyl-carrier protein] = ? + holo-[acyl-carrier protein]
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acetoacetyl-CoA + acetate = acetoacetate + acetyl-CoA
show the reaction diagram
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acetoacetyl-CoA + H2O = acetoacetate + CoA
show the reaction diagram
-
acetoacetyl-CoA + H2O = CoA + acetoacetate
show the reaction diagram
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acetoacetyl-CoA + H2O = CoA + acetoacetate
show the reaction diagram
-
acetoacetyl-CoA + H2O = 3-oxobutanoic acid + CoA
show the reaction diagram
-
acetoacetyl-CoA + H2O = ?
show the reaction diagram
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ATP + L-isoleucine + acetoacetyl-CoA = AMP + diphosphate + tenuazonic acid + CoA
show the reaction diagram
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ATP + acetoacetyl-CoA + HCO3- = ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (84 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3-hydroxybutyryl-CoA + NAD+ = acetoacetyl-CoA + NADH
show the reaction diagram
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-
acetyl-CoA = acetoacetyl-CoA + CoA
show the reaction diagram
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-
acetoacetyl-L-carnitine + CoA = acetoacetyl-CoA + L-carnitine
show the reaction diagram
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2 acetyl-CoA = CoA + acetoacetyl-CoA
show the reaction diagram
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acetoacetyl-ACP + acetyl-CoA = acetyl-ACP + acetoacetyl-CoA
show the reaction diagram
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acetyl-CoA + malonyl-CoA = 3-oxobutyryl-CoA + CoA
show the reaction diagram
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O-acetoacetyl(-)carnitine + CoASH = acetoacetyl-CoA + L-(-)carnitine
show the reaction diagram
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acetyl-CoA + acetoacetate = acetate + acetoacetyl-CoA
show the reaction diagram
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succinyl-CoA + acetoacetate = succinate + acetoacetyl-CoA
show the reaction diagram
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ATP + acetoacetate + CoA = AMP + diphosphate + acetoacetyl-CoA
show the reaction diagram
-

Activator in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
slight activation
-
activates
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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 (83 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
1 mM, 29% inhibition
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inhibition of both isozymes at 0.02 mM and at 0.1 mM
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0.1 mM, 44% inhibtion
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non-competitive inhibition
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0.1 mM, 25% inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (30 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (48 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
14.8
-
pH 7.0, 25°C, recombinant wild-type enzyme, degradative reaction
35
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pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay
0.36
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pH 8.2, 30°C

KM Value (160 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.02
0.022
-
0.05
-
pH 6.5, 25°C
0.155
-
-
0.014
-
-
0.065
-
-
1.1
-
-
0.33
-
pH 8, 37°C, Vmax: 30 micromol/min/mg, wild-type
0.048
-
-
2.5
-
pH 8.2, 30°C

Ki Value (32 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.00006
-
(S)-2-methylbutyryl-CoA as substrate
0.0022
-
pH 7.4, competitive versus acetyl-CoA hydrolysis
0.13
-
pH 8.1
0.12
-
recombinant enzyme, pH 8.0, 30°C

References & Links

Links to other databases for acetoacetyl-CoA

ChEBI
PubChem
ChEBI
PubChem