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BRENDA support

Ligand Hydroxypyruvate

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Basic Ligand Information

Molecular Structure
Picture of Hydroxypyruvate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C3H4O4
Hydroxypyruvate
HHDDCCUIIUWNGJ-UHFFFAOYSA-N
Synonyms:
2-oxo-3-hydroxypropionate, 2-oxo-3-hydroxypropionic acid, 3-hydroxy-2-oxopropanoate, 3-hydroxy-2-oxopropanoic acid, 3-Hydroxy-2-oxopropionate, 3-hydroxy-2-oxopropionic acid, 3-hydroxypyruvate, beta-Hydroxypyruvate, hydroxy-pyruvate
Pathway Source
Pathways
BRENDA
glycine metabolism, serine metabolism
KEGG
Biosynthesis of secondary metabolites, Carbon metabolism, Glycine, serine and threonine metabolism, Glyoxylate and dicarboxylate metabolism, Methane metabolism more
MetaCyc
formaldehyde assimilation I (serine pathway), L-serine biosynthesis II, photorespiration I, photorespiration II, photorespiration III


Show all pahtways known for Show all BRENDA pathways known for Hydroxypyruvate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (15 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
hydroxypyruvate + NADH = D-glycerate + NAD+
show the reaction diagram
-
L-asparagine + 3-hydroxypyruvate = 2-oxosuccinamate + L-serine
show the reaction diagram
-
L-alanine + 3-hydroxypyruvate = pyruvate + L-serine
show the reaction diagram
L-serine + 3-hydroxypyruvate = 3-hydroxypyruvate + L-serine
show the reaction diagram
L-alanine + 3-hydroxypyruvate = pyruvate + L-serine
show the reaction diagram

In Vivo Product in Enzyme-catalyzed Reactions (17 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
D-glycerate + NAD+ = hydroxypyruvate + NADH + H+
show the reaction diagram
-
L-serine + H2O + NAD+ = 3-hydroxypyruvate + NH3 + NADH + NH3 + NADH + H+
show the reaction diagram
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L-Ser + H2O + O2 = 2-oxo-3-hydroxypropionic acid + NH3 + H2O2
show the reaction diagram
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D-serine + 2-oxoglutarate = 3-hydroxy-2-oxopropanoate + D-glutamate
show the reaction diagram
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L-serine + pyruvate = 3-hydroxypyruvate + L-alanine
show the reaction diagram
tartronic semialdehyde = hydroxypyruvate
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (106 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
hydroxypyruvate + ? = ?
show the reaction diagram
-
hydroxypyruvate + NADPH = 2,3-dihydroxypropanoate + NADP+
show the reaction diagram
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hydroxypyruvate + NADPH + H+ = 2,3-dihydroxypropanoate + NADP+
show the reaction diagram
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3-hydroxypyruvate + NADH + H+ = ?
show the reaction diagram
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hydroxypyruvate + NAD(P)H + H+ = glycerate + NAD(P)+
show the reaction diagram
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hydroxypyruvate + NAD(P)H = D-glycerate + NAD(P)+ + H+
show the reaction diagram
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beta-hydroxypyruvate + O2 = 2,3-dioxopropionate + H2O2
show the reaction diagram
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hydroxypyruvate + NAD+ + H2O = ?
show the reaction diagram
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3-hydroxypyruvate + CoA + NADP+ = hydoxyacetyl-CoA + CO2 + NADPH
show the reaction diagram
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hydroxypyruvate + CoA + 2 methyl viologen = ?
show the reaction diagram
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hydroxypyruvate + CoA + 2 methyl viologen = ?
show the reaction diagram
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hydroxypyruvate + NAD+ = pyruvate + NADH
show the reaction diagram
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L-Ala + hydroxypyruvate + NADH = ?
show the reaction diagram
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Gly + hydroxypyruvate + NADH = ?
show the reaction diagram
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Taurine + 3-hydroxypyruvate + NADH = ?
show the reaction diagram
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L-Met + hydroxypyruvate + NADH = ?
show the reaction diagram
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hydroxypyruvate + formaldehyde = CO2 + dihydroxyacetone
show the reaction diagram
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hydroxypyruvate = ? + CO2
show the reaction diagram
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hydroxypyruvate + D-glyceraldehyde 3-phosphate = D-xylulose 5-phosphate + CO2
show the reaction diagram
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L-asparagine + 3-hydroxypyruvate = 2-oxosuccinamate + L-serine
show the reaction diagram
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L-glutamine + 3-hydroxypyruvate = 2-oxoglutaramate + L-serine
show the reaction diagram
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L-phenylalanine + hydroxypyruvate = phenylpyruvate + L-serine
show the reaction diagram
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L-kynurenine + hydroxypyruvate = 4-(2-aminophenyl)-2,4-dioxobutanoate + L-serine
show the reaction diagram
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L-glutamine + 3-hydroxypyruvate = 2-oxoglutaramate + L-serine
show the reaction diagram
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beta-hydroxypyruvate + phosphorylated histidine-containing protein = ? + histidine-containing protein
show the reaction diagram
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Hydroxypyruvate = Glycolaldehyde + CO2
show the reaction diagram
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Hydroxypyruvate = 2-Hydroxy-3-oxopropanoate
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (72 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
D-glycerate + NAD+ = hydroxypyruvate + NADH + H+
show the reaction diagram
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mesoxalic semialdehyde + NADH = hydroxypyruvate + NAD+
show the reaction diagram
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D-glycerate + NAD+ = hydroxypyruvate + NADH + H+
show the reaction diagram
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glycerate + O2 = hydroxypyruvate + H2O2
show the reaction diagram
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D-glycerate + acceptor = hydroxypyruvate + reduced acceptor
show the reaction diagram
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L-serine + H2O + NAD+ = 3-hydroxy-2-oxopropanoate + NH3 + NADH
show the reaction diagram
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D-serine + NAD+ + H2O = 3-hydroxy-2-oxopropanoate + NH3 + NADH + H+
show the reaction diagram
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D-serine + oxidized 2,6-dichloroindophenol + H2O = 3-hydroxy-2-oxopropanoate + NH3 + reduced 2,6-dichloroindophenol
show the reaction diagram
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L-serine + 2-oxoglutarate = 3-hydroxy-2-oxopropionic acid + L-glutamate
show the reaction diagram
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2-oxosuccinamic acid + L-serine = L-asparagine + 3-hydroxy-2-oxopropanoate
show the reaction diagram
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serine + 2-oxoglutarate = 3-hydroxy-2-oxopropanoate + glutamate
show the reaction diagram
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glyoxylate + L-serine = hydroxypyruvate + glycine
show the reaction diagram
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L-serine + glyoxylate = 3-hydroxy-2-oxopropanoate + glycine
show the reaction diagram
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L-serine + 2-oxoglutarate = 3-hydroxy-2-oxopropanoate + L-glutamate
show the reaction diagram
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L-serine + 4,5-dioxopentanoate = 5-aminolevulinate + 3-hydroxy-2-oxopropanoate
show the reaction diagram
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L-serine + 2-oxoglutarate = 3-hydroxy-2-oxopropanoic acid + L-glutamate
show the reaction diagram
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L-serine + phenylpyruvate = 3-hydroxy-2-oxopropanoate + L-phenylalanine
show the reaction diagram
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L-serine + glyoxylate = 3-hydroxy-2-oxopropanoate + glycine
show the reaction diagram
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L-serine + pyruvate = 3-hydroxy-2-oxopropanoate + L-alanine
show the reaction diagram
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L-serine + 2-oxobutanoate = 3-hydroxy-2-oxopropanoate + 2-aminobutanoate
show the reaction diagram
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D-serine + 2-oxoadipate = 3-hydroxy-2-oxopropanoate + 2-aminoadipate
show the reaction diagram
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pyruvate + L-serine = L-alanine + 3-hydroxy-2-oxopropanoate
show the reaction diagram
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L-Leu = 3-Hydroxy-2-oxopropionate + NH3
show the reaction diagram
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tartronic semialdehyde = hydroxypyruvate
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
slight activation
-
slight activation, pyruvate analog
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Inhibitor in Enzyme-catalyzed Reactions (26 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
product inhibition at a concentration above 4 mM, 99% inhibition of the reverse reaction at 0.5 mM
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hydroxypyruvate at 1 mM inhibits the enzyme activity by 45%
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inhibitor of octopine formation
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progressive inactivation of enzyme with kinetics of suicide inhibition, mechanism
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Ki: 0.0125 mM
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an irreversible, time-dependent inhibitor, causes inactivation of mandelate racemase. Protection from inactivation by the competitive inhibitor benzohydroxamate. 3-Hydroxypyruvate undergoes Schiff-base formation with Lys166 at the active site, followed by formation of an aldehyde/enol(ate) adduct

3D Structure of Enzyme-Ligand-Complex (PDB) (37 results)

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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (57 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.25
-
pH 7.0, 37°C
5.47
-
-

KM Value (118 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.065
-
-
2.9
-
in 100 mM Tris-HC1 buffer, pH 8.0, at 30°C
0.0005
-
-
8.5
-
-
8.31
-
-
8
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pH 8.4, 37ºC
4
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pH 8.4-9.2, 15°C

Ki Value (10 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
19
-
pH 7.0, 30°C, recombinant enzyme
0.3
-
pH 6.0, 70°C
0.0125
-
-
0.21
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time-dependent inhibition, value similar to that of (S)-lysine

References & Links

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Links to other databases for Hydroxypyruvate

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ChEBI
PubChem
ChEBI
PubChem