Ligand 4-hydroxybutyrate

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Basic Ligand Information

Molecular Structure
Picture of 4-hydroxybutyrate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C4H8O3
4-hydroxybutyrate
SJZRECIVHVDYJC-UHFFFAOYSA-N
Synonyms:
4-hydroxy-butyric acid, 4-hydroxybutanoate, 4-hydroxybutanoic acid, 4-hydroxybutyric acid, 4-hydroxybuyrate, gamma-hydroxybutyrate, gamma-hydroxybutyric acid, gamma-hyroxybutyrate, hydroxy-n-butyrate


Show all pahtways known for Show all BRENDA pathways known for 4-hydroxybutyrate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
gamma-hydroxybutyrate + NADP+ = succinic semialdehyde + NADPH
-
show the reaction diagram
ATP + 4-hydroxybutanoate + CoA = AMP + diphosphate + 4-hydroxybutanoyl-CoA
-

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

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
succinic semialdehyde + NADPH + H+ = 4-hydroxybutyrate + NADP+
-
-
show the reaction diagram
succinic semialdehyde + NADPH + H+ = 4-hydroxybutyrate + NADP+
-
-
show the reaction diagram
succinic semialdehyde + NADPH + H+ = 4-hydroxybutyrate + NADP+
-

Substrate in Enzyme-catalyzed Reactions (17 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
4-hydroxybutyrate + NADP+ = 4-ketobutyrate + NADPH
-
show the reaction diagram
4-hydroxybutanoate + NAD+ = acetoacetate + NADH
-
show the reaction diagram
acetyl-CoA + gamma-hydroxybutyric acid = ?
-
show the reaction diagram
4-hydroxybutyrate + acetoacetyl-CoA = 4-hydroxybutanoyl-CoA + acetoacetate
-
show the reaction diagram
ATP + 4-hydroxybutanoate + CoA = AMP + diphosphate + 4-hydroxybutanoyl-CoA
-
show the reaction diagram
ATP + 4-hydroxybutanoate + CoA = ADP + phosphate + 4-hydroxybutanoyl-CoA
-

Product in Enzyme-catalyzed Reactions (22 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
succinic semialdehyde + NADPH + H+ = 4-hydroxybutyrate + NADP+
-
-
show the reaction diagram
succinic semialdehyde + NADH + H+ = 4-hydroxybutyrate + NAD+
-
-
show the reaction diagram
succinic semialdehyde + NADPH + H+ = 4-hydroxybutyrate + NADP+
-
-
show the reaction diagram
beta-alanine + pyruvate = 4-hydroxybutyrate + L-alanine
-
-
show the reaction diagram
gamma-butyrolactone + H2O = 4-hydroxybutanoic acid
-

Activator in Enzyme-catalyzed Reactions (1 result)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
slight activation
-

Inhibitor in Enzyme-catalyzed Reactions (3 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
mixed type inhibition with NADPH; mixed type inhibition with succinic semialdehyde
-
92 mM, pH 8, very slight inhibition
-

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (5 results)

COMMENTARY
EC NUMBER
LITERATURE
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
-
50
-
pH 7.5, 70°C
1.8
-
pH 7.9, 75°C
pH 7.9, 75°C, mutant enzyme W424G
2.5
-

KM Value (25 results)

COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
kidney
0.0022
-
enzyme from kidney, uncoupled assay
0.0022
-
enzyme from brain, uncoupled assay
0.0025
-
brain
0.0025
-
coupled reaction of gamma-hydroxybutyrate oxidation and D-glucuronate reduction, brain and kidney
0.00045
-
enzyme from brain, D-glucuronate reduction-coupled assay
0.00045
-
-
0.055
-
pH 9.0, 23°C
0.52
-
pH 8.5, 23°C
2.19
-
in 100 mM Tris-HCl buffer (pH 8.8), at 37°C
102
-
-
102
-
+/-0.012 mM, in overepressed HEK cells, in presence of 0.5 mM 2-oxoglutarate
0.067
-
+/- 0.006 mM, 30°C, pH 7.1
0.06
-
pH 7.1, 30°C
0.06
-
pH 7.1, 30°C, recombinant enzyme
0.067
-
pH 7.5, 25°C
33
-
-
140
-
pH 7.5, 70°C
2
-
pH 7.8, 85°C
0.7
-
pH 7.9, 75°C
pH 7.9, 75°C, mutant enzyme W424G
1.13
-
pH not specified in the publication, temperature not specified in the publication
0.37
-

Ki Value (3 results)

COMMENTARY
EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
LITERATURE
mixed type inhibition with NADPH
79.9
-
mixed type inhibition with succinic semialdehyde
93.5
-
standard conditions, inhibition by substrate analog
35
-

References & Links

Links to other databases for 4-hydroxybutyrate

ChEBI
PubChem
-
PubChem