Ligand 3-(1H-imidazol-4-yl)-2-oxopropanoate

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Basic Ligand Information

Molecular Structure
Picture of 3-(1H-imidazol-4-yl)-2-oxopropanoate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C6H6N2O3
3-(1H-imidazol-4-yl)-2-oxopropanoate
JEJNWEREQWMOHB-UHFFFAOYSA-N
Synonyms:
(imidazol-5-yl)pyruvate, 2-oxo-3-(1H-imidazol-4yl)-propionic acid, 2-oxo-4-imidazolepropionic acid, 2-oxohistidine, 3-((1H-imidazo)-4-yl)-2-oxopropanoate, 3-(1H-imidazol-4-yl)-2-oxopropanoic acid, 3-(1H-imidazol-4-yl)-2-oxopropionic acid, 3-(4-imidazole)pyruvate, 3-(imidazol-4-yl)-2-oxopropanoate, 3-(Imidazol-5-yl)pyruvate, alpha-Keto-4-imidazolepropionic acid, Imidazol-5-yl-pyruvate, Imidazolepyruvate, Imidazole pyruvate

Show all pahtways known for Show all BRENDA pathways known for 3-(1H-imidazol-4-yl)-2-oxopropanoate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
imidazol-5-yl-pyruvate + L-glutamate = histidine + 2-oxoglutarate
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(S)-3-(imidazol-5-yl)lactate + NAD(P)+ = 3-(imidazol-5-yl)pyruvate + NAD(P)H
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
imidazolepyruvate + O2 + NAD(P)H + H+ = 5-hydroxyimidazolepyruvate + NAD(P)+ + H2O
show the reaction diagram
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3-(4-imidazole)pyruvate + glyoxylate = ?
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Product in Enzyme-catalyzed Reactions (60 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(S)-3-(imidazol-5-yl)lactate + NAD(P)+ = 3-(imidazol-5-yl)pyruvate + NAD(P)H
show the reaction diagram
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L-histidine + H2O + NAD+ = 3-(1H-imidazol-4-yl)-2-oxopropanoate + NH3 + NADH
show the reaction diagram
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D-His + H2O + O2 = 3-(1H-imidazol-4-yl)-2-oxopropanoic acid + NH3 + H2O2
show the reaction diagram
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L-His + O2 + H2O = 2-oxo-3-(1H-imidazol-4yl)-propionic acid + NH3 + H2O2
show the reaction diagram
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L-histidine + O2 + H2O = 3-(1H-imidazol-4-yl)-2-oxopropanoate + NH3 + H2O2
show the reaction diagram
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L-histidine + H2O + O2 = 2-oxohistidine + NH3 + H2O2
show the reaction diagram
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L-histidine + H2O + 2 cytochrome b = 2-oxo-4-imidazolepropionic acid + NH3 + 2 reduced cytochrome b
show the reaction diagram
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D-histidine + oxidized 2,6-dichloroindophenol + H2O = 3-(1H-imidazol-4-yl)-2-oxopropanoate + NH3 + reduced 2,6-dichloroindophenol
show the reaction diagram
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L-histidine + 4-(methylsulfanyl)-2-oxobutanoate = 3-((1H-imidazo)-4-yl)-2-oxopropanoate + L-methionine
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2-oxosuccinamic acid + L-histidine = L-asparagine + 3-(1H-imidazol-4-yl)-2-oxopropanoate
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L-histidine + 2-oxoglutarate = 3-(1H-imidazol-4-yl)-2-oxopropanoate + L-glutamate
show the reaction diagram
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phenylpyruvate + DL-histidine = phenylalanine + 3-(1H-imidazol-4-yl)-2-oxopropanoate
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L-histidine + 4,5-dioxopentanoate = 5-aminolevulinate + 3-(1H-imidazol-4-yl)-2-oxopropanoate
show the reaction diagram
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L-histidine + 2-oxoglutarate = 3-(1H-imidazol-4-yl)-2-oxopropanoic acid + L-glutamate
show the reaction diagram
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L-histidine + pyruvate = 3-(1H-imidazol-4-yl)-2-oxopropanoate + L-alanine
show the reaction diagram
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L-histidine + glyoxylate = 3-(1H-imidazol-4-yl)-2-oxopropanoate + glycine
show the reaction diagram
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histidine + glyoxylate = 3-(1H-imidazol-4-yl)-2-oxopropanoate + glycine
show the reaction diagram
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L-histidine + glyoxylate = 3-(1H-imidazol-4-yl)-2-oxopropanoate + glycine
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
56% inhibition at 4.5 mM
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non-competitive
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Enzyme Kinetic Parameters

KM Value (2 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
2.5
-
pH 8.0, 30°C
7.4
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IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0625
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IC50: 0.0625 mM

References & Links

Links to other databases for 3-(1H-imidazol-4-yl)-2-oxopropanoate

ChEBI
PubChem
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PubChem