Ligand acetoacetate

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Basic Ligand Information

Molecular Structure
Picture of acetoacetate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C4H6O3
acetoacetate
WDJHALXBUFZDSR-UHFFFAOYSA-N
Synonyms:
3-Ketobutyrate, 3-oxo-n-butyric acid, 3-oxobutanoate, 3-oxobutanoic acid, 3-oxobutanone, 3-oxobutyrate, acetoacetic acid, acetylacetate


Show all pahtways known for Show all BRENDA pathways known for acetoacetate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acetoacetate + NADH + H+ = (R)-3-hydroxybutanoate + NAD+
show the reaction diagram
2-mercaptoethanesulfonate + acetoacetate + NADP+ = 2-(2-oxopropylthio)ethanesulfonate + CO2 + NADPH + H+
show the reaction diagram
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ATP + acetoacetate + CoA = AMP + diphosphate + acetoacetyl-CoA
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (13 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(S)-3-hydroxybutanoate + 2-oxoglutarate = acetoacetate + (R)-2-hydroxyglutarate
show the reaction diagram
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2-(2-oxopropylthio)ethanesulfonate + CO2 + NADPH = 2-mercaptoethanesulfonate + acetoacetate + NADP+
show the reaction diagram
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(5S)-5-amino-3-oxohexanoate + acetyl-CoA = L-3-aminobutanoyl-CoA + acetoacetate
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L-beta-amino-n-butyric acid + pyruvate = 3-oxo-n-butyric acid + alanine
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acetoacetyl-CoA + acetate = acetoacetate + acetyl-CoA
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butanoate + acetoacetyl-CoA = butanoyl-CoA + acetoacetate
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4-fumarylacetoacetate + H2O = acetoacetate + fumarate
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(S)-3-Hydroxy-3-methylglutaryl-CoA = Acetyl-CoA + acetoacetate
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acetone + CO2 + ATP + H2O = acetoacetate + AMP + phosphate
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Substrate in Enzyme-catalyzed Reactions (25 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acetoacetate + NADH + H+ = (R)-3-hydroxybutanoate + NAD+
show the reaction diagram
acetoacetate + NADH = ? + NAD+
show the reaction diagram
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3-oxobutanone + O2 = ?
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beta-alanyl-CoA + acetoacetate = ?
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beta-alanine + acetoacetate = malonic semialdehyde + 3-aminobutanoate
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acetyl-CoA + acetoacetate = acetate + acetoacetyl-CoA
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acetoacetate + H2O = acetate
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ATP + acetoacetate + CoA = AMP + diphosphate + acetoacetyl-CoA
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (64 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(5S)-5-amino-3-oxohexanoate + acetyl-CoA = L-3-aminobutanoyl-CoA + acetoacetate
show the reaction diagram
DL-3-amino-n-butanoate + pyruvate = 3-oxobutanoate + L-alanine
show the reaction diagram
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DL-3-aminobutyrate + 2-oxoglutarate = 3-oxobutyrate + L-glutamate
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acetoacetyl-CoA + acetate = acetoacetate + acetyl-CoA
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acetoacetylcholine + H2O = acetoacetate + choline
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acetoacetyl-CoA + H2O = acetoacetate + CoA
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acetoacetyl-CoA + H2O = acetoacetate + CoA
show the reaction diagram
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acetoacetyl-CoA + H2O = CoA + acetoacetate
show the reaction diagram
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acetoacetyl-CoA + H2O = CoA + acetoacetate
show the reaction diagram
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S-acetoacetylglutathione + H2O = acetoacetate + glutathione
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N-3-oxobutanoyl-L-homoserine lactone + H2O = L-homoserine lactone + 3-oxobutanoic acid
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Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE

Inhibitor in Enzyme-catalyzed Reactions (24 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
competitive inhibitor
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weak
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Ki 0.3 mM
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1 mM, 30% inhibition
treatment with 0.025-0.035 mM H2O2, 4-8 mM acetoacetate and high D-glucose of 25 mM causes a significant decrease in enzyme protein expression, enzyme activity, and H2S levels, and an increase in intracellular reactive oxygen species production compared with those in normal controls
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3D Structure of Enzyme-Ligand-Complex (PDB) (5 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (27 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
8.5
-
-
0.263
-
-
5.89
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pH 7.5, 30°C, recombinant enzyme

KM Value (62 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0091
-
-
6.3
-
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Ki Value (6 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
3
-
standard conditions, inhibition by substrate analog
0.5
-
pH 8.5, 30°C
0.3
-
-
0.021
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References & Links

Links to other databases for acetoacetate

ChEBI
PubChem
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PubChem