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BRENDA support

Ligand benzoic acid

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Basic Ligand Information

Molecular Structure
Picture of benzoic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C7H6O2
benzoic acid
WPYMKLBDIGXBTP-UHFFFAOYSA-N
Synonyms:
aromatic acid, benzoate


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

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (19 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
benzoate + NADPH + H+ + ATP = benzaldehyde + NADP+ + AMP + diphosphate
show the reaction diagram
benzoic acid + H2O2 = benzaldehyde + H2O + O2
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (21 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
benzaldehyde + NAD+ + H2O = benzoate + NADH + H+
show the reaction diagram
-
aromatic aldehyde + O2 + H2O = aromatic acid + H2O2
show the reaction diagram
-
Benzoyl-CoA + H2O = Benzoate + CoA
show the reaction diagram
-
hippurate + H2O = benzoate + glycine
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (67 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
benzoate + O2 = 3-hydroxy-6-oxoheptadienoic acid
show the reaction diagram
-
benzoate + NAD(P)H + O2 + H2O = benzoate dihydrodiol + ?
show the reaction diagram
-
benzoate + Ti(III) citrate + 2 H+ = benzaldehyde + Ti(I) citrate + H2O
show the reaction diagram
-
benzoate + H2O + O2 = ?
show the reaction diagram
-
S-adenosyl-L-methionine + benzoate = S-adenosyl-L-homocysteine + methyl benzoate
show the reaction diagram
-
S-adenosyl-L-methionine + benzoate = S-adenosyl-L-homocysteine + methyl benzoate
show the reaction diagram
-
S-adenosyl-L-methionine + benzoic acid = S-adenosyl-L-homocysteine + benzoic acid methyl ester
show the reaction diagram
-
UDP-alpha-D-glucose + benzoic acid = UDP + 1-O-benzoyl-beta-D-glucose
show the reaction diagram
-
UDPglucose + benzoate = UDP + benzoyl-beta-D-glucose
show the reaction diagram
-
UDP-glucose + benzoic acid = UDP + benzoyl-beta-D-glucoside
show the reaction diagram
-
UDP-glucose + benzoic acid = UDP + benzoyl 3-O-beta-D-glucoside
show the reaction diagram
-
UDP-alpha-D-glucose + benzoic acid = ?
show the reaction diagram
-
UDPalpha-D-glucose + benzoic acid = UDP + 1-O-benzoyl-beta-D-glucose
show the reaction diagram
-
ATP + benzoate = ?
show the reaction diagram
-
eugenol + benzoic acid = eugenyl benzoate
show the reaction diagram
-
ATP + benzoate + CoA = AMP + benzoyl-CoA + diphosphate
show the reaction diagram
-
Benzoate + CoA + ATP = Benzoyl-CoA + AMP + diphosphate
show the reaction diagram
-
ATP + benzoate + a holo-[acyl-carrier protein] = benzoyl-[acyl-carrier protein] + AMP + diphosphate
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (264 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
benzaldehyde + NADP+ = benzoic acid + NADPH
show the reaction diagram
-
benzaldehyde + O2 = benzoic acid + H2O2
show the reaction diagram
-
benzaldehyde + acceptor + H2O = benzoic acid + reduced acceptor
show the reaction diagram
-
5-phenylheme + electron donor + O2 = biliverdin IXalpha + Fe2+ + CO + oxidized eletron donor + H2O + benzoic acid
show the reaction diagram
-
benzaldehyde + H2O + O2 = benzoate + H2O2
show the reaction diagram
-
benzaldehyde + NAD+ + H2O = benzoate + NADH + H+
show the reaction diagram
-
benzaldehyde + NAD+ + H2O = benzoate + NADH + H+
show the reaction diagram
-
benzaldehyde + NAD+ + H2O = benzoate + NADH + H+
show the reaction diagram
-
benzaldehyde + NAD+ + H2O = benzoic acid + NADH + H+
show the reaction diagram
-
benzaldehyde + NADP+ + benzoyladenosine 5'-monophosphate + phosphate = benzoate + NADPH + ATP
show the reaction diagram
benzaldehyde + NAD+ + H2O = benzoate + NADH + H+
show the reaction diagram
-
benzaldehyde + NAD+ + H2O = benzoate + NADH + H+
show the reaction diagram
-
benzaldehyde + NAD+ + H2O = benzoate + NADH + 2 H+
show the reaction diagram
-
benzaldehyde + NAD+ + H2O = benzoate + NADH + H+
show the reaction diagram
-
benzaldehyde + NADP+ + H2O = benzoate + NADPH + H+
show the reaction diagram
-
benzaldehyde + NADP+ + H2O = benzoate + NADPH + 2 H+
show the reaction diagram
-
benzaldehyde + NAD+ + H2O = benzoate + NADH + H+
show the reaction diagram
-
benzaldehyde + NAD+ + H2O = benzoate + NADH + H+
show the reaction diagram
-
benzaldehyde + NAD+ + H2O = benzoate + NADH + H+
show the reaction diagram
-
benzaldehyde + 2,6-dichloroindophenol = benzoic acid + H2O2
show the reaction diagram
-
benzaldehyde + oxidized 2,6-dichloroindophenol + H2O = benzoic acid + reduced 2,6-dichloroindophenol
show the reaction diagram
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benzaldehyde + a quinone + H2O = benzoate + a quinol
show the reaction diagram
-
benzoylcholine + H2O = benzoate + choline
show the reaction diagram
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4-nitrophenyl benzoate + H2O = 4-nitrophenol + benzoate
show the reaction diagram
-
benzoyl-CoA + H2O = CoA + benzoate
show the reaction diagram
-
benzoyl-CoA + H2O = CoA + benzoate
show the reaction diagram
-
Benzoyl-CoA + H2O = Benzoate + CoA
show the reaction diagram
-
N-benzoyl-D-Ala + H2O = benzoate + D-Ala
show the reaction diagram
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benzoyl-L-glutamic acid + H2O = benzoate + glutamate
show the reaction diagram
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4-nitrophenyl benzoate + H2O = 4-nitrophenol + benzoate
show the reaction diagram
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benzyloxycarbonyl-L-Lys benzoyl ester + H2O = benzyloxycarbonyl-L-Lys + benzoate
show the reaction diagram
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Nalpha-benzoyl-L-Arg + H2O = benzoic acid + L-Arg
show the reaction diagram
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Nalpha-benzoyl-L-ornithine + H2O = benzoate + ornithine
show the reaction diagram
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benzamide + H2O = benzoate + NH3
show the reaction diagram
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benzoyl agmatine + H2O = benzoic acid + agmatine
show the reaction diagram
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N-benzoyl-L-glutamate + H2O = benzoate + L-glutamate
show the reaction diagram
-
N-benzoylglycine + H2O = benzoate + glycine
show the reaction diagram
-
benzylcarbamate + H2O = CO2 + NH3 + benzoate
show the reaction diagram
-
benzoyl adenylate + H2O = benzoic acid + AMP
show the reaction diagram
-
2-hydroxy-6-oxo-6-(2'-aminophenyl)hexa-2,4-dienoic acid + H2O = benzoic acid + 2-hydroxypenta-2,4-dienoic acid
show the reaction diagram
-
2-hydroxy-6-oxo-6-(2'-aminophenyl)hexa-2,4-dienoate + H2O = 2-hydroxypenta-2,4-dienoate + benzoate
show the reaction diagram
-

Activator in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
134% relative activity at 10 mM
-
enhances NADH-peroxidase activity in the presence of Mn2+
-
1 mM, 1.1fold activation
-
increases the rate of NADP oxidation by 4-hydroxybenzoate, no hydroxylation during subsequent reoxidation by O2
-
stimulates
-

Inhibitor in Enzyme-catalyzed Reactions (135 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.03 mM: 40% inhibition; 40% inhibition of the reductive reaction at 0.03 mM
-
48.4% inhibition at 0.015 mM, active site binding structure
-
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
-
competitive inhibitor
-
competitive inhibition
-
non-competitive with respect to either NAD+ or benzaldehyde
-
inhibits reduction of (E)-2-methyl-2-butenoate
-
0.1 mM, 98% inhibition
-
complete inhibition at 1 mM
-
competitive
-
88% inhibition at 1 mM
-
5 mM, 31% loss of activity
-
competitive with respect to 1-naphththalenemethanol
-
83.1% residual activity at 1 mM
-
greatly inhibits the enzyme activity
-
inhibition of cytosolic enzyme
-
inhibits amidase and esterase activity
-
weak
-
competitive inhibitor; competitive inhibitor
-
34 mM, 63% inhibition
-
uncompetitive inhibition of enzyme form PAL68, non-competitive inhibition of enzyme form PAL116
-
maximal inhibition of 2% (highest inhibition achieved relative to that in absence of inhibitor by varying the concentration of the inhibitor at a given concentration of other substrates pyruvate 0.5 mM and 0.4 mM L-aspartate-4-semialdehyde), in a coupled assay with recombinant dihydrodipicolinate reductase
-
competitive inhibitor of butyrate
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Metals and Ions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
in orthorhombic 1 form, the benzoate ion is present close to the Cp residue in both fully folded subunits the benzoate ion is not observed in the six oxidized subunits in which the disulfide bond is formed
-

3D Structure of Enzyme-Ligand-Complex (PDB) (328 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (21 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.0018
-
pH 7.2, 30°C

KM Value (45 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
5.1
-
-
0.5026
-
-
34.04
-
chitosan-chitin nanowhiskers supported lipase, pH not specified in the publication, 50°C
0.007
-
-
1.1
-
pH 7.2, 30°C

Ki Value (19 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
4.9
-
-
9.9
-
-
3.1
-
competitive inhibition with respect to 2-oxoglutarate and noncompetitive with respect to Fe2+ and the peptide substrate
3.1
-
-
0.53
-
-
1.7
-
-
0.28
-
pH 7, 37°C
0.033
-
pH 7.6, 25°C, recombinant wild-type enzyme

IC50 Value (9 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
8.79
-
recombinant enzyme, pH 6.5, 50°C
1.2
-
-
0.016
-
pH and temperature not specified in the publication

References & Links

Links to other databases for benzoic acid

ChEBI
PubChem
ChEBI
PubChem