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-oxopropionate, 3-hydroxy-2-oxopropionic acid, 3-hydroxypyruvate, beta-Hydroxypyruvate, hydroxy-pyruvate


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

Roles as Enzyme Ligand

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

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
hydroxypyruvate + NADH = D-glycerate + NAD+
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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L-alanine + 3-hydroxypyruvate = pyruvate + L-serine
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
D-glycerate + NAD+ = hydroxypyruvate + NADH + H+
show the reaction diagram
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-
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
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L-serine + glyoxylate = 3-hydroxypyruvate + glycine
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L-serine + pyruvate = 3-hydroxypyruvate + L-alanine
show the reaction diagram
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tartronic semialdehyde = hydroxypyruvate
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (85 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
hydroxypyruvate + ? = ?
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hydroxypyruvate + NADPH = 2,3-dihydroxypropanoate + NADP+
show the reaction diagram
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hydroxypyruvate + NADH + H+ = D-glycerate + NAD+
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
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hydroxypyruvate + NAD+ + H2O = ?
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3-hydroxypyruvate + CoA + NADP+ = hydoxyacetyl-CoA + CO2 + NADPH
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hydroxypyruvate + CoA + 2 methyl viologen = ?
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hydroxypyruvate + CoA + 2 methyl viologen = ?
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hydroxypyruvate + NAD+ = pyruvate + NADH
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L-Ala + hydroxypyruvate + NADH = ?
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Gly + hydroxypyruvate + NADH = ?
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Taurine + 3-hydroxypyruvate + NADH = ?
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L-Met + hydroxypyruvate + NADH = ?
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hydroxypyruvate + formaldehyde = CO2 + dihydroxyacetone
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hydroxypyruvate = ? + CO2
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hydroxypyruvate + D-glyceraldehyde 3-phosphate = D-xylulose 5-phosphate + CO2
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L-glutamine + 3-hydroxypyruvate = 2-oxoglutaramate + L-serine
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L-alanine + hydroxypyruvate = pyruvate + L-serine
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L-phenylalanine + hydroxypyruvate = phenylpyruvate + L-serine
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L-kynurenine + hydroxypyruvate = 4-(2-aminophenyl)-2,4-dioxobutanoate + L-serine
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L-glutamine + 3-hydroxypyruvate = 2-oxoglutaramate + L-serine
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beta-hydroxypyruvate + phosphorylated histidine-containing protein = ? + histidine-containing protein
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Hydroxypyruvate = Glycolaldehyde + CO2
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Hydroxypyruvate = 2-Hydroxy-3-oxopropanoate
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Product in Enzyme-catalyzed Reactions (63 results)

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

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
slight activation
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slight activation, pyruvate analog
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Inhibitor in Enzyme-catalyzed Reactions (25 results)

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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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) (9 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (37 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
9.1
-
pH 6.5, 25°C
0.25
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pH 7.0, 37°C
5.47
-
-

KM Value (98 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.065
-
-
3.5
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pH 6.5, 25°C
2.9
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in 100 mM Tris-HC1 buffer, pH 8.0, at 30°C
0.0005
-
-
8.5
-
-
8.31
-
-
8
-
pH 8.4, 37ºC
4
-
pH 8.4-9.2, 15°C

Ki Value (10 results)

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
-
time-dependent inhibition, value similar to that of (S)-lysine

References & Links

Links to other databases for Hydroxypyruvate

ChEBI
PubChem
ChEBI
PubChem