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BRENDA support

Ligand 2-oxobutanoic acid

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Basic Ligand Information

Molecular Structure
Picture of 2-oxobutanoic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C4H6O3
2-oxobutanoic acid
TYEYBOSBBBHJIV-UHFFFAOYSA-N
Synonyms:
2-ketobutanoate, 2-ketobutanoic acid, 2-Ketobutyrate, 2-ketobutyric acid, 2-oxo-3-methylpropanoate, 2-oxo-butanoate, 2-oxo-butanoic acid, 2-oxo-butyrate, 2-oxo-butyric acid, 2-oxo-n-butanoate, 2-Oxo-n-butanoate analogues, 2-oxobutanoate, 2-oxobutyrate, 2-oxobutyric acid, 3-Methyl-2-oxopropanoate, 3-methylpyruvate, alpha-keto-butyric acid, alpha-ketobutanoate, alpha-Ketobutyrate, alpha-Ketobutyric acid, Ketobutyrate
Pathway Source
Pathways
BRENDA
cysteine metabolism, isoleucine metabolism, methionine metabolism, threonine metabolism
KEGG
2-Oxocarboxylic acid metabolism, Biosynthesis of amino acids, Biosynthesis of secondary metabolites, C5-Branched dibasic acid metabolism, Cysteine and methionine metabolism more
MetaCyc
2-oxobutanoate degradation I, 2-oxobutanoate degradation II, dimethyl sulfide biosynthesis from methionine, homocysteine and cysteine interconversion, hydrogen sulfide biosynthesis II (mammalian) more


Show all pahtways known for Show all BRENDA pathways known for 2-oxobutanoic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (10 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE

In Vivo Product in Enzyme-catalyzed Reactions (21 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
DL-2-hydroxybutyrate + O2 = 2-oxobutyrate + H2O2
show the reaction diagram
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D-2-aminobutyrate + H2O + O2 = 2-oxobutyrate + NH3 + H2O2
show the reaction diagram
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D-threonine + 2-oxoglutarate = 2-oxobutanoate + D-glutamate
show the reaction diagram
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L-threonine = alpha-ketobutyrate + NH3
show the reaction diagram
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L-threonine = 2-oxobutanoate + NH3
show the reaction diagram
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L-methionine + H2O = methanethiol + NH3 + 2-oxobutanoate
show the reaction diagram
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L-homocysteine + H2O = hydrogen sulfide + NH3 + 2-oxobutanoate
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (196 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-oxo-butyric acid + NADH + H+ = 2-hydroxybutyric acid + NAD+
show the reaction diagram
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2-oxobutyrate + NAD(P)H + H+ = 2-hydroxybutyrate + NAD(P)+
show the reaction diagram
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2-oxobutyric acid + NADPH = 2-hydroxybutyric acid + NADP+
show the reaction diagram
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2-oxobutyrate + NADH = isovalerate + NAD+
show the reaction diagram
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2-oxobutyrate + NADH + H+ = 2-hydroxybutyrate + NAD+
show the reaction diagram
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2-ketobutyrate + NADPH + H+ = ?
show the reaction diagram
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(2R)-hydroxy-4-methylpentanoate + 2-oxo-butyrate = 2-oxo-4-methylpentanoate + (2R)-hydroxybutyrate
show the reaction diagram
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2-oxobutyrate + CoA + NADP+ = propionyl-CoA + CO2 + NADPH
show the reaction diagram
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alpha-ketobutyrate + phosphate + O2 + H2O = ? + H2O2
show the reaction diagram
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2-oxobutanoate + [dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] lipoyllysine = [dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(propanoyl)dihydrolipoyllysine + CO2
show the reaction diagram
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2-oxobutyrate + methyl viologen = ?
show the reaction diagram
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2-ketobutyrate + CoA + oxidized ferredoxin = propanoyl-CoA + CO2 + reduced ferredoxin
show the reaction diagram
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methylamine + alpha-ketobutyrate + NADPH = glutamic acid + H2O + NADP+
show the reaction diagram
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2-oxobutanoate + NH3 + NADH = 2-aminobutanoate + NAD+ + H2O
show the reaction diagram
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2-oxobutanoate + NH3 + NADH + H+ = L-2-aminobutanoate + H2O + NAD+
show the reaction diagram
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L-Ala + 2-oxobutanoate + NADH = ?
show the reaction diagram
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alpha-ketobutanoate + methylamine + NADPH = N-methyl-2-aminobutanoate + NADP+ + H2O
show the reaction diagram
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Taurine + 2-oxobutanoate + NADH = ?
show the reaction diagram
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L-ornithine + 2-oxo-butanoic acid + NADPH + H+ = ? + NADP+ + H2O
show the reaction diagram
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L-Met + 2-oxobutanoate + NADH = ?
show the reaction diagram
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L-lysine + alpha-ketobutyrate + NADH = ?
show the reaction diagram
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propionaldehyde + 2-oxobutanoic acid = 4-hydroxyhexan-3-one + CO2
show the reaction diagram
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2-oxobutanoate + (3E)-4-(4-chlorophenyl)but-3-en-2-one = ?
show the reaction diagram
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2-oxobutyrate + CoA = propionyl-CoA + formate
show the reaction diagram
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acetyl-CoA + 2-oxobutyrate + H2O = ?
show the reaction diagram
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acetyl-CoA + H2O + 2-oxobutanoate = (R)-2-ethylmalate + CoA
show the reaction diagram
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L-aspartate + 2-oxobutyrate = oxaloacetate + 2-aminobutyrate
show the reaction diagram
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L-alanine + 2-oxobutanoate = pyruvate + 2-aminobutanoate
show the reaction diagram
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L-asparagine + 2-oxobutanoate = 2-oxosuccinamate + 2-aminobutanoate
show the reaction diagram
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L-lysine + 2-oxobutanoate = 2-aminoadipate 6-semialdehyde + 2-aminobutanoate
show the reaction diagram
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L-histidine + 2-oxobutyrate = imidazol-5-yl-pyruvate + 2-aminobutanoate
show the reaction diagram
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(R)-3-amino-2-methylpropanoate + 2-oxo-n-butanoate = 2-methyl-3-oxopropanoate + 2-amino-n-butanoate
show the reaction diagram
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L-alanine + 2-oxobutyrate = pyruvate + 2-aminobutanoate
show the reaction diagram
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L-glutamine + 2-oxobutyrate = 2-oxoglutaramate + 2-aminobutyrate
show the reaction diagram
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alpha-ketobutyric acid + putrescine = L-aspartate + 4-aminobutanal
show the reaction diagram
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L-glutarate + 2-oxobutanoate = 2-oxoglutarate + 2-aminobutanoate
show the reaction diagram
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2-aminobutanoate + 2-oxobutyrate = succinate semialdehyde + ?
show the reaction diagram
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alpha-ketobutyrate + phosphorylated histidine-containing protein = phosphoenolbutyrate + histidine-containing protein
show the reaction diagram
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ATP + 2-ketobutyrate + H2O = ?
show the reaction diagram
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alpha-ketobutyrate + H2O = ?
show the reaction diagram
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2-oxobutanoic acid = ?
show the reaction diagram
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2-oxobutanoate + acetaldehyde = ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (140 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
DL-2-hydroxybutyrate + NAD+ = 2-oxobutyrate + NADH
show the reaction diagram
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D-2-hydroxybutyrate + NAD+ = 2-oxobutyrate + NADH + H+
show the reaction diagram
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(S)-2-hydroxybutyrate + ferricytochrome c = 2-oxobutyrate + ferrocytochrome c
show the reaction diagram
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DL-2-hydroxybutyrate + ferricytochrome c-553 = 2-ketobutyrate + ferrocytochrome c-553
show the reaction diagram
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D-2-hydroxybutyrate + ubiquinone-10 = 2-oxobutyrate + ubiquinol-10
show the reaction diagram
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2-hydroxybutanoate + NAD+ = 2-oxobutanoate + NADH
show the reaction diagram
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1,2-dihydroxy-3-oxopent-1-ene + O2 = 2-oxo-butanoate + formate
show the reaction diagram
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L-2-aminobutanoate + H2O + NAD+ = 2-oxobutanoate + NH3 + NADH + H+
show the reaction diagram
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L-2-amino-n-butyric acid + H2O + NAD+ = 2-oxobutanoate + NADH + NH3
show the reaction diagram
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2-aminobutyrate + H2O + NADP+ = 2-oxobutyrate + NH3 + NADPH
show the reaction diagram
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L-2-aminobutyrate + H2O + NAD+ = 2-oxobutyrate + NADH + NH3
show the reaction diagram
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D-2-aminobutyrate + H2O + O2 = 2-oxobutyrate + H2O2
show the reaction diagram
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D-2-aminobutyrate + H2O + O2 = 2-oxobutyrate + NH3 + H2O2
show the reaction diagram
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D-2-amino-n-butyrate + oxidized 2,6-dichlorophenolindophenol + H2O = 2-oxobutyrate + NH3 + reduced 2,6-dichloroindophenol
show the reaction diagram
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D-isoleucine + H2O + 2,6-dichlorophenolindophenol = 3-methyl-2-oxopropanoate + NH3 + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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D-isoleucine + oxidized 2,6-dichloroindophenol + H2O = 3-methyl-2-oxopropanoate + NH3 + reduced 2,6-dichloroindophenol
show the reaction diagram
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S-adenosyl-L-methionine + pyruvate = S-adenosyl-L-homocysteine + 2-oxobutyrate
show the reaction diagram
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pyruvate + L-2-aminobutanoate = L-alanine + 2-oxobutanoate
show the reaction diagram
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2-oxosuccinamic acid + L-2-aminobutanoic acid = L-asparagine + 2-oxobutanoate
show the reaction diagram
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pyruvate + 2-aminoisobutanoate = L-alanine + 2-oxo-3-methylpropanoate
show the reaction diagram
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L-2-aminobutanoate + phenylpyruvate = L-phenylalanine + 2-oxobutanoate
show the reaction diagram
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(S)-2-aminobutyrate + pyruvate = 2-oxobutanoate + L-alanine
show the reaction diagram
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2-aminobutyrate + glyoxylate = 2-oxobutanoate + glycine
show the reaction diagram
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L-vinylglycine = 2-oxobutyrate + NH3
show the reaction diagram
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3-methyloxaloacetate = 2-oxobutanoate + CO2
show the reaction diagram
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2-oxo-3-methyl-4-hydroxypentanoate = 2-oxobutyrate + acetaldehyde
show the reaction diagram
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citramalate = 2-oxobutanoate + ?
show the reaction diagram
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Thr + ? = 2-oxobutanoate + ?
show the reaction diagram
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2-amino-3-butenoic acid = 2-oxobutyric acid + NH3
show the reaction diagram
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L-threonine O-sulfate = 2-oxobutanoate + NH3 + SO42-
show the reaction diagram
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D-threonine = 2-oxobutanoate + NH3
show the reaction diagram
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L-threonine = 2-oxobutyrate + NH3
show the reaction diagram
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L-threonine = 2-oxobutanoate + NH3
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (3 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
2.2 mM, catecholase activity: 140%
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slight activation, pyruvate analog
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can partially replace pyruvate, which is required for reaction
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Inhibitor in Enzyme-catalyzed Reactions (38 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
substrate inhibition
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10 mM, 29% inhibition
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inactivation under anaerobic conditions
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non-competitive inhibition at 5 mM
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competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
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0.1 mM, complete inhibition
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slight substrate inhibition
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1 mM, 50% inhibition
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weak
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competitive inhibition
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competitive, Ki for 2-keto-4-hydroxybutyrate cleavage: 53 mM, Ki for 2-keto-4-hydroxyglutarate cleavage: 52 mM
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competitive with respect to DL-4-carboxy-4-hydroxy-2-oxoadipate
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competitive inhibition
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20 mM: 49.3% inhibition, not reversed by 5 mM AMP
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3D Structure of Enzyme-Ligand-Complex (PDB) (5 results)

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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (81 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.5
-
pH 7.0, 37°C
80
-
pH 7.5
0.167
-
pH 8.0, 37°C
0.17
-
pH 6.7, 30°C
13
-
pH 8.6, 37°C
143
-
pH 8.5, 82°C
35.38
-
mutant W121L/H227I, pH 9, 30°C
99
-
pH 9.5, 21°C
99
-
-
526
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wild type enzyme, in 50 mM triethanolamine buffer, pH 7.0, at 25°C
5.98
-
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KM Value (139 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
40
-
pH 7.0, 37°C
0.45
-
pH 7.0, 30°C
4.56
-
pH 8.0, 37°C, wild-type enzyme
0.016
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pH 6.7, 30°C
0.205
-
pH 8.6, 37°C
35.12
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mutant W121L/H227I, pH 9, 30°C
153
-
at pH 7.0
2.9
-
-
100
-
cosubstrate L-asparagine
14
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cosubstrate D-alanine
1.4
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with L-tryptophan, pH 8.0, 30°C
2.7
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pH 8.0, 37°C, alanine as amino donor

Ki Value (12 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
7.6
-
-
9.9
-
competitive inhibition with respect to 2-oxoglutarate and noncompetitive with respect to Fe2+ and the peptide substrate
2.25
-
assay with whole enzyme complex
4.8
-
pH 8.5, 82°C
31
-
-
0.025
-
-
6.1
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pH 8, 30°C
0.5
-
pH 8.0, 25°C
0.34
-
pH 8.0, 25°C

IC50 Value (1 result)

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EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
3
-
pH 7.5, 37°C

References & Links

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Links to other databases for 2-oxobutanoic acid

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ChEBI
PubChem
ChEBI
PubChem