Ligand benzoate

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Basic Ligand Information

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


Show all pahtways known for Show all BRENDA pathways known for benzoate

Roles as Enzyme Ligand

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

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
benzoic acid + H2O2 = benzaldehyde + H2O + O2
-

In Vivo Product in Enzyme-catalyzed Reactions (21 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
benzaldehyde + NAD+ + H2O = benzoate + NADH + H+
-
show the reaction diagram
benzaldehyde + NADP+ + H2O = benzoate + NADPH
-
-
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
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Substrate in Enzyme-catalyzed Reactions (64 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
benzoic acid + H2O2 = ?
-
show the reaction diagram
benzoate + O2 = 3-hydroxy-6-oxoheptadienoic acid
-
show the reaction diagram
benzoate + NAD(P)H + O2 + H2O = benzoate dihydrodiol + ?
-
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
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show the reaction diagram
UDP-alpha-D-glucose + benzoic acid = UDP + 1-O-benzoyl-beta-D-glucose
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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] = 3-benzoyl-[acyl-carrier protein] + AMP + diphosphate
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Product in Enzyme-catalyzed Reactions (259 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
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 + 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
benzaldehyde + a quinone + H2O = benzoate + a quinol
-
-
show the reaction diagram
benzoylcholine + H2O = benzoate + choline
-
-
show the reaction diagram
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
-
780,
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
benzoyl-L-glutamic acid + H2O = benzoate + glutamate
-
-
show the reaction diagram
4-nitrophenyl benzoate + H2O = 4-nitrophenol + benzoate
-
-
show the reaction diagram
benzyloxycarbonyl-L-Lys benzoyl ester + H2O = benzyloxycarbonyl-L-Lys + benzoate
-
-
show the reaction diagram
Nalpha-benzoyl-L-Arg + H2O = benzoic acid + L-Arg
-
show the reaction diagram
benzylpenicillin + H2O = benzoate + 6-aminopenicillanate
-
-
show the reaction diagram
Nalpha-benzoyl-L-ornithine + H2O = benzoate + ornithine
-
-
show the reaction diagram
benzamide + H2O = benzoate + NH3
-
show the reaction diagram
benzoyl agmatine + H2O = benzoic acid + agmatine
-
show the reaction diagram
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
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Activator in Enzyme-catalyzed Reactions (5 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE

Inhibitor in Enzyme-catalyzed Reactions (117 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
0.03 mM: 40% inhibition; 40% inhibition of the reductive reaction at 0.03 mM
-
56% inhibition at 20 mM, no inhibition at 0.02-2.0 mM
-
64.86% inhibition at 10 mM
-
noncompetitive
-
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
-
2 mM, 48% inhibition
-
above 1 mM
-
competitive with 4-hydroxybenzoate
-
slight
-
0.2 mM, 50% inhibition
-
31% inhibition at 0.1 mM, 52% inhibition at 10 mM
-
48.8% inhibition at 10 mM
-
9% residual activity at 10 mM
-
competitive inhibition, 45% inhibition of diphenolase activity at 0.7 mM, 42% inhibition of monophenolase activity at 0.7 mM
-
effects of inhibitors on mushroom PPO are determined by using pyrogallol as substrate
-
is known to inhibit tyrosinase by chelating with copper. Acts in a similar manner to 1-hydroxy-2-oxo-1-phenylhydrazine
-
noncompetitive
-
competitive inhibition
-
non-competitive with respect to either NAD+ or benzaldehyde
-
inhibits reduction of (E)-2-methyl-2-butenoate
-
31% inhibition at 10 mM
-
43% inhibition at 10 mM
-
and derivatives
-
complete inhibition at 10 mM
-
37% residual activity at 10 mM
75 mM, 76% inhibition
a classical substrate-competitive inhibitor, effect of benzoate on the FAD-binding process to hDAAO apoprotein
about 80% inhibition at 0.2 mM
competitive
competitive inhibitor
D-phenylglycine oxidation
moderate inhibition (49.7% residual activity at 1 mM)
potent competitive inhibitor
0.1 mM, 98% inhibition
2% residual activity at 0.1 mM
-
complete inhibition at 1 mM
-
competitive
-
benzoic acid derivatives
-
substituted benzoic acids, benzoic acid compounds, noncompetitive inhibition
-
88% inhibition at 1 mM
-
5 mM, 31% loss of activity
-
competitive with respect to 1-napththalenemethanol
-
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
-
mixed-type inhibition
-
weak
-
competitive inhibitor of butyrate
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Metals and Ions (1 result)

COMMENTARY
EC NUMBER
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
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3D Structure of Enzyme-Ligand-Complex (PDB) (322 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (16 results)

COMMENTARY
EC NUMBER
LITERATURE
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
at pH 6.8 temperature not specified in the publication
4.4
-
in the presence of saturating amounts of NADH-cytochrome c reductase
367
-
pH 7, 25°C
8.6
-
-
4.5
-
reconstituted enzyme system consisting of benzoate 4-hydroxylase i.e. P450rm, cytochrome P450 reductase, NADPH and dilauroylphosphatidylcholine
0.667
-
reconstituted enzyme system consisting of benzoate 4-hydroxylase, cytochrome P450 reductase, NADPH and dilauroylphosphatidylcholine
0.04
-
turnover rate in microsomes
mutant enzyme N361S, at pH 6.5 and 30°C
0.028
-
wild type enzyme, at pH 6.5 and 30°C
0.003
-
pH 7.5, 20°C
0.0058
-
pH 7.7, 30°C
-
433
-
pH 8.0, 31°C, recombinant wild-type enzyme
2
8
pH 7.2, 30°C
0.0018
-

KM Value (40 results)

COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
-
0.0039
-
pH 7, 25°C
0.026
-
at pH 8.5 and 25°C
0.00558
-
reaction in H2O
0.0367
-
reaction in D2O
0.055
-
pH and temperature not specified in the publication
0.362
-
with reduced carbamoyl methyl viologen as cosubstrate, pH 5.5
53
-
with reduced carbamoyl methyl viologen as cosubstrate, pH 4.5
31
-
wild type enzyme, at pH 6.5 and 30°C
0.341
-
mutant enzyme N361S, at pH 6.5 and 30°C
0.0631
-
apparent Km-value of plant-purified protein, pH 7.5, 20°C
1.1
-
apparent Km-value of recombinant protein, pH 7.5, 20°C
1.6
-
apparent Km-value, pH 7.7, 30°C
pH 7.5, 20°C
1.72
-
-
0.5026
-
chitosan-chitin nanowhiskers supported lipase, pH not specified in the publication, 50°C
34.04
-
-
0.007
-
37°C
0.016
-
-
0.0006
0.002
pH 8.0, 31°C, recombinant wild-type enzyme
0.0044
-
pH 7.5, 22°C
0.045
-
-
0.01
-
in Tris-HCl at pH 8.0
0.12
-
benzoate, , aerobically induced enzyme
0.011
-
-
0.011
-
apparent value, at pH 9.0
0.03
-
anaerobically induced enzyme
0.009
-
-
0.03
-
isoenzyme E3
0.075
-
isoenzyme E2
0.035
-
pH 7.2, 30°C
1.1
-

Ki Value (19 results)

COMMENTARY
EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
LITERATURE
competitive inhibition with respect to 2-oxoglutarate and noncompetitive with respect to Fe2+ and the peptide substrate
3.1
-
vs. p-coumaric acid
0.7
-
vs. O2
0.45
-
vs. caffeic acid
0.75
-
versus different substrates, pH and temperature not specified in the publication
0.53
0.6
pH 6.5, 35°C
0.0131
-
in 75 mM sodium diphosphate buffer (pH 8.3) at 25°C
0.4
-
pH 8.0, 37°C
12.5
-
pH and temperature not specified in the publication
0.002
-
at pH 7.0 and 25°C
0.007
-
-
7
-
pH 7, 37°C
0.28
-
pH 7.6, 25°C, recombinant wild-type enzyme
0.033
-

IC50 Value (9 results)

COMMENTARY
EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
LITERATURE
recombinant enzyme, pH 6.5, 50°C
8.79
-
diphenolase activity, at pH 5.0 and 30°C
4.33
-
monophenolase activity, at pH 7.0 and 40°C
0.9
-
pH 8.0, 20°C
10.2
-
pH and temperature not specified in the publication
0.016
-
37°C, pH not specified in the publication
6.2
-
pH not specified in the publication, 37°C
6.2
-

References & Links

Links to other databases for benzoate

ChEBI
PubChem
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PubChem