Ligand anthranilic acid

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Basic Ligand Information

Molecular Structure
Picture of anthranilic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C7H7NO2
anthranilic acid
RWZYAGGXGHYGMB-UHFFFAOYSA-N
Synonyms:
2-amino benzoate, 2-Aminobenzoate, 2-aminobenzoic acid, 2-Carboxy-1-phenylamine, anthranilate, o-aminobenzoate, o-aminobenzoic acid
Pathway Source
Pathways


Show all pahtways known for Show all BRENDA pathways known for anthranilic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (18 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
anthranilate + NADPH + O2 = 2,3-dihydroxybenzoate + NADP+ + NH3
show the reaction diagram
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S-adenosyl-L-methionine + anthranilate = S-adenosyl-L-homocysteine + N-methylanthranilate
show the reaction diagram
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S-adenosyl-L-methionine + anthranilate = ?
show the reaction diagram
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S-adenosyl-L-methionine + anthranilate = S-adenosyl-L-homocysteine + O-methyl anthranilate
show the reaction diagram
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acetyl-CoA + o-aminobenzoic acid = CoA + N-acetyl-o-aminobenzoic acid
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (16 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2,3-dihydroxyindole + O2 = anthranilate + CO2
show the reaction diagram
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2-(4-dimethylaminophenyl)diazenylbenzoate + 2 NADH + 2 H+ = anthranilate + N,N-dimethyl-1,4-phenylenediamine + 2 NAD+
show the reaction diagram
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2-aminobenzoyl-CoA + H2O = 2-aminobenzoate + CoA
show the reaction diagram
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N-formylanthranilic acid + H2O = formate + anthranilic acid
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2-aminobenzonitrile + 2 H2O = 2-aminobenzoic acid + NH3
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (61 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
anthranilate + NADH + 2 H+ + O2 = 2-aminophenol + NAD+ + H2O + CO2
show the reaction diagram
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anthranilate + NADH + H+ + O2 = 5-hydroxyanthranilate + NAD+ + H2O
show the reaction diagram
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anthranilate + NAD(P)H + O2 = 2-hydroxyaniline + NAD(P)+ + H2O2 + CO2
show the reaction diagram
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anthranilate + NADPH + O2 = 2,3-dihydroxybenzoate + NADP+ + NH3
show the reaction diagram
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anthranilate + tetrahydrofolic acid + O2 = 3-hydroxyanthranilate + dihydrofolic acid + H2O2
show the reaction diagram
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anthranilate + FADH2 + chloride + O2 + H+ = 5-chloro-anthranilate + FAD + 2 H2O
show the reaction diagram
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anthranilate + FADH2 + chloride + O2 + H+ = 5-chloro-anthranilate + FAD + 2 H2O
show the reaction diagram
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S-adenosyl-L-methionine + anthranilate = S-adenosyl-L-homocysteine + N-methylanthranilate
show the reaction diagram
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S-adenosyl-L-methionine + anthranilic acid = S-adenosyl-L-homocysteine + methyl anthranilate
show the reaction diagram
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S-adenosyl-L-methionine + anthranilate = S-adenosyl-L-homocysteine + O-methyl anthranilate
show the reaction diagram
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malonyl-CoA + anthranilate = CoA + N-malonylanthranilate
show the reaction diagram
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acetyl-CoA + o-aminobenzoic acid = CoA + N-acetyl-o-aminobenzoic acid
show the reaction diagram
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UDP-alpha-D-glucose + anthranilic acid = UDP + 1-O-anthraniloyl-beta-D-glucose
show the reaction diagram
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2-aminobenzoate + UDPglucuronate = UDP + ?
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anthranilic acid + UDP-glucose = ?
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thiamine + o-aminobenzoic acid = 4-methyl-5-(2-hydroxyethyl)-thiazole + 2-[[(4-amino-2-methylpyrimidin-5-yl)methyl]amino]benzoic acid
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ATP + anthranilate = ?
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2-Aminobenzoate = Aniline + CO2
show the reaction diagram
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ATP + 2-aminobenzoate + CoA = AMP + diphosphate + 2-aminobenzoyl-CoA
show the reaction diagram
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ATP + 2-aminobenzoate + CoA = AMP + diphosphate + 2-aminobenzoyl-CoA
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (41 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2,3-dihydroxyindole + O2 = anthranilate + CO2
show the reaction diagram
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methyl 2-aminobenzoate + H2O = methanol + 2-aminobenzoate
show the reaction diagram
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2-aminobenzoyl-CoA + H2O = 2-aminobenzoate + CoA
show the reaction diagram
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2-aminobenzonitrile + 2 H2O = 2-aminobenzoic acid + NH3
show the reaction diagram
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2-hydroxy-6-oxo-6-(2-aminophenyl)hexa-2,4-dienoate + H2O = anthranilate + 2-hydroxypenta-2,4-dienoate
show the reaction diagram
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2-hydroxy-6-oxo-6-(2-aminophenyl)hexa-2,4-dienoic acid + H2O = 2-aminobenzoic acid + 2-hydroxypenta-2,4-dienoic acid
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
induces, the enzyme activity increases with an increase in the concentration of anthranilate in the growth medium, optimal amounts of the enzyme are synthesized when the concentration of anthranilate is 1 mg/ml, further increase in the concentration results in a considerable decrease in the growth of the organism as well in the enzyme activity
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Inhibitor in Enzyme-catalyzed Reactions (53 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
competitive inhibition
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22% inhibition at 2 mM and 11% inhibition at 0.2 mM
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above 1 mM
-
competitive inhibitor with benzoic acid as a substrate
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75% activity left at 1.1 mM
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weak
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weak inhibition
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competitive
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competitive
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3D Structure of Enzyme-Ligand-Complex (PDB) (17 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (41 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
3.9
-
pH 8.0, 31°C, recombinant wild-type enzyme

KM Value (58 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.12
-
-
0.028
-
30°C, pH 7.0
0.012
-
-
0.48
-
-
13
-
-
2.74
-
pH 8.0, 21°C
37
-
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Ki Value (9 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.87
-
20 mM Tris-HCl, pH 8.0, 25°C
0.261
-
-
1.6
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in 75 mM sodium diphosphate buffer (pH 8.3) at 25°C
0.03
-
-

References & Links

Links to other databases for anthranilic acid

ChEBI
PubChem
ChEBI
PubChem