Ligand 3-Indole-2-oxopropanoate

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Basic Ligand Information

Molecular Structure
Picture of 3-Indole-2-oxopropanoate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C11H9NO3
3-Indole-2-oxopropanoate
VWFJDQUYCIWHTN-YFVJMOTDSA-N
Synonyms:
(indol-3-yl)pyruvate, (indole-3-yl)pyruvate, 2-oxo-3-indolylpropanoate, 2-oxotryptophan, 3-(1H-indol-3-yl)-2-oxopropanoate, 3-(1H-indol-3-yl)-2-oxopropanoic acid, 3-(Indol-3-yl)pyruvate, 3-indole-2-oxopropionic acid, 3-indolepyruvate, 3-Indolpyruvate, beta-Indolylpyruvic acid, indo-3-pyruvate, indol-3 pyruvate, indol-3-pyruvate, indol-3-pyruvic acid, Indol-3-yl-pyruvate, indol-3-ylpyruvate, indol-3-ylpyruvic acid, Indole-3-pyruvate, indole-3-pyruvic acid, Indole pyruvate, Indolepyruvate, indolepyruvic acid, indolpyruvate, indolylpyruvate


Show all pahtways known for Show all BRENDA pathways known for 3-Indole-2-oxopropanoate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(indol-3-yl)pyruvate + NADPH + H+ + O2 = (indol-3-yl)acetate + NADP+ + H2O + CO2
show the reaction diagram
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(indol-3-yl)pyruvate + NH3 + NADH + H+ = L-tryptophan + NAD+ + H2O
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S-adenosyl-L-methionine + indolepyruvate = ?
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (19 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
indolelactate + NAD+ = indolepyruvate + NADH
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L-tryptophan + phenylpyruvate = 3-indole-2-oxopropanoate + L-phenylalanine
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L-tryptophan + pyruvate = indole-3-pyruvate + L-alanine
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (64 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
indolepyruvate + NAD(P)H = indolelactate + NAD(P)+
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indolepyruvate + NADH = indolelactate + NAD+
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indole-3-pyruvic acid + O2 = ?
show the reaction diagram
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3-indolepyruvate + O2 = ?
show the reaction diagram
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(indol-3-yl)pyruvate + NADPH + H+ + O2 = (indol-3-yl)acetate + NADP+ + H2O + CO2
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indol-3 pyruvate + CoA + 2 oxidized methyl viologen = ?
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indolpyruvate + CoA + oxidized ferredoxin = indolacetyl-CoA + CO2 + reduced ferredoxin
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indolepyruvate + 2,6-dichlorophenolindophenol + H2O = ? + reduced 2,6-dichlorophenolindophenol
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(indol-3-yl)pyruvate + NH3 + NADH + H+ = L-tryptophan + NAD+ + H2O
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dimethylallyl diphosphate + indole-3-pyruvic acid = diphosphate + 7-(3-methylbut-2-enyl)-indole-3-pyruvic acid
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L-glutamine + indol-3-pyruvate = 2-oxoglutaramate + ?
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2-oxo-3-indolylpropanoate + L-leucine = L-tryptophan + 4-methyl-2-oxovalerate
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indolepyruvate + L-aspartate = oxaloaspartate + L-tryptophan
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indolepyruvate + L-aspartate = L-tryptophan + oxaloacetate
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3-indole-2-oxopropanoate + L-glutamate = L-tryptophan + 2-oxoglutarate
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indole-3-pyruvate = indole-3-pyruvate
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (93 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
indolelactate + NAD+ = indolepyruvate + NADH
show the reaction diagram
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L-tryptophan + O2 = 2-oxotryptophan
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L-tryptophan + O2 = 3-(1H-indol-3-yl)-2-oxopropanoic acid + NH3
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L-tryptophan + H2O + NAD+ = 3-(1H-indol-3-yl)-2-oxopropanoate + NH3 + NADH
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L-tryptophan + H2O + 2 cytochrome b = 3-(1H-indol-3-yl)-2-oxopropanoic acid + NH3 + 2 reduced cytochrome b
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D-tryptophan + oxidized 2,6-dichloroindophenol + H2O = 3-indole-2-oxopropanoate + NH3 + reduced 2,6-dichloroindophenol
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2-oxosuccinamic acid + L-tryptophan = L-asparagine + 3-indole-2-oxopropanoate
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L-tryptophan + 2-oxoglutarate = 3-indole-2-oxopropanoate + L-glutamate
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L-tryptophan + 2-oxoglutarate = 3-indole-2-oxopropanoate + L-glutamate
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L-tryptophan + 2-oxoglutarate = 3-indole-2-oxopropanoate + L-glutamate
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tryptophan + glyoxylate = 3-indole-2-oxopropanoate + glycine
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tryptophan + glyoxylate = 3-indole-2-oxopropanoate + glycine
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L-tryptophan + pyruvate = indolepyruvate + L-alanine
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D-tryptophan + 2-oxoadipate = 3-indole-2-oxopropanoate + 2-aminoadipate
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2-oxo-4-methylthiobutanoate + L-tryptophan = L-methionine + 3-(1H-indol-3-yl)-2-oxopropanoate
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L-tryptophan + 2-oxoglutarate = 3-indole-2-oxopropanoate + L-glutamate
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L-tryptophan + pyruvate = indole-3-pyruvate + L-alanine
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indole-3-pyruvate = indole-3-pyruvate
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (15 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
substrate inhibition
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44% activity left at 1.1 mM
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substrate inhibition
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2.3 mM, 50% inhibition
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (17 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.433
-
pH 6.9, 85C, under argon
11
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cosubstrate methyl viologen, pH 7.0, 70C
16
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at pH 7.5 and 25C
480
-
pH 8.0, 25C
2.98
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KM Value (30 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.067
-
-
0.2
-
-
1.86
-
cosubstrate methyl viologen, pH 7.0, 70C
0.014
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at pH 7.5 and 25C
0.0048
-
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0.2
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with L-leucine, pH 8.0, 30C
0.16
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pH 8.0, 25C

Ki Value (13 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.014
-
at pH 11.0 and 25C
0.73
-
at pH 6.5, temperature not specified in the publication
2.3
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References & Links

Links to other databases for 3-Indole-2-oxopropanoate

ChEBI
PubChem
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PubChem