Ligand 3-hydroxyanthranilic acid

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Basic Ligand Information

Molecular Structure
Picture of 3-hydroxyanthranilic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C7H7NO3
3-hydroxyanthranilic acid
WJXSWCUQABXPFS-UHFFFAOYSA-N
Synonyms:
2-amino-3-hydroxybenzoic acid, 3-hydroxanthranilate, 3-Hydroxy-anthranilate, 3-Hydroxyanthranilate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (12 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3-hydroxyanthranilic acid + O2 = 2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid + H2O
show the reaction diagram
-
S-adenosyl-L-methionine + 3-hydroxyanthranilate = S-adenosyl-L-homocysteine + 3-hydroxy-4-methylanthranilate
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE

Substrate in Enzyme-catalyzed Reactions (39 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3-hydroxyanthranilic acid + O2 = 2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid + H2O
show the reaction diagram
-
3-hydroxyanthranilic acid + H2O2 = ? + H2O
show the reaction diagram
-
3-hydroxyanthranilate + NADPH + O2 = ? + NADP+ + H2O
show the reaction diagram
-
3-hydroxyanthranilate + NADPH + O2 = ?
show the reaction diagram
-
3-hydroxyanthranilate + NADPH + O2 = ?
show the reaction diagram
-
3-hydroxyanthranilic acid + O2 = cinnabarinic acid + H2O
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
anthranilate + tetrahydrofolic acid + O2 = 3-hydroxyanthranilate + dihydrofolic acid + H2O2
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
induces
-
higher than 0.005 mM, 600% activation of N-acetyl-tyrosine hydroxylation, activation of 4-tert-butylphenol oxidation, shortens lag time of the enzyme
-
145% increase in pyridoxine 5-phosphate oxidase activity, 28% increase in pyridoxamine 5-phosphate oxidase activity
-

Inhibitor in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
20% inhibition at 0.05 mM
-
46% inhibition at 0.002 mM
-
0.8 mM, about 45% inhibition
-
competitive
-
IC50: 0.12 mM
-
0.001 mM in 0.06 mM Tris-HCl buffer
-

3D Structure of Enzyme-Ligand-Complex (PDB) (5 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (5 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.005
-
at pH 8.0 and 28°C

KM Value (19 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.78
-
-
0.64
-
-
0.018
-
at pH 8.0 and 28°C

Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.012
-
-

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.12
-
IC50: 0.12 mM

References & Links

Links to other databases for 3-hydroxyanthranilic acid

ChEBI
PubChem
ChEBI
PubChem