Ligand phenylacetate

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Basic Ligand Information

Molecular Structure
Picture of phenylacetate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C8H8O2
phenylacetate
WLJVXDMOQOGPHL-UHFFFAOYSA-N
Synonyms:
2-phenylacetate, 2-phenylacetic acid, 2-phenylethanoate, benzylformate, benzyl formate, phenyl-acetic acid, phenylacetic acid, phenyl acetic acid


Show all pahtways known for Show all BRENDA pathways known for phenylacetate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phenylacetate + [reduced NADPH-hemoprotein reductase] + O2 = (2-hydroxyphenyl)acetate + [oxidized NADPH-hemoprotein reductase] + H2O
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phenylacetate + H2O = phenol + acetate
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phenylacetate = toluene + CO2
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ATP + phenylacetate + CoA = AMP + diphosphate + phenylacetyl-CoA
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (26 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phenylacetaldehyde + H2O + oxidized ferredoxin = phenylacetate + H+ + reduced ferredoxin
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2-phenylethylamine + 2 H2O + 2 acceptor = 2-phenylacetic acid + NH3 + 2 reduced acceptor
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phenylacetamide = phenylacetic acid + NH3
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phenylacetonitrile + 2 H2O = phenylacetate + NH3
show the reaction diagram
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phenylacetonitrile + 2 H2O = phenylacetate + NH3
show the reaction diagram
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phenylacetonitrile + 2 H2O = phenylacetic acid + NH3
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (29 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phenylacetate + NADH + O2 + H2O = ?
show the reaction diagram
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phenylacetate + [reduced NADPH-hemoprotein reductase] + O2 = (2-hydroxyphenyl)acetate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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phenylacetic acid + ? = ?
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phenylacetic acid + H2O + O2 = ?
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UDPglucose + phenylacetic acid = UDP + phenylacetyl-beta-1-D-glucose
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phenylacetate + H2O = phenol + acetate
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phenylacetate = toluene + CO2
show the reaction diagram
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benzylformate = benzaldehyde + CO2
show the reaction diagram
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ATP + phenylacetate + CoA = ADP + phosphate + phenylacetyl-CoA
show the reaction diagram
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ATP + phenylacetate + CoA = AMP + diphosphate + phenylacetyl-CoA
show the reaction diagram
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ATP + phenylacetate + CoA = AMP + diphosphate + phenylacetyl-CoA
show the reaction diagram
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ATP + phenylacetate + CoA = AMP + phenylacetyl-CoA + diphosphate
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (259 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phenylpyruvate + NADPH + H+ + O2 = phenylacetate + NADP+ + H2O + CO2
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phenylacetaldehyde + NAD+ + H2O = phenylacetate + NADH + H+
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phenylacetaldehyde + NAD+ + H2O = phenylacetate + NADH + H+
show the reaction diagram
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phenylacetaldehyde + NAD+ + H2O = phenylacetate + NADH + H+
show the reaction diagram
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phenylacetaldehyde + NAD+ + H2O = phenylacetate + NADH + H+
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phenylpyruvate + O2 = phenylacetate + CO2
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phenylacetaldehyde + O2 = phenylacetate + H2O
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L-phenylglycine + H2O + O2 = phenylacetate + NH3 + H2O2
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2-phenylethylamine + 2 H2O + 2 acceptor = 2-phenylacetic acid + NH3 + 2 reduced acceptor
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penicillin G + H2O = 6-aminopenicillanic acid + phenylacetic acid
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phenylacetylthiocholine + H2O = thiocholine + phenylacetate
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methyl phenylacetate + H2O = methanol + phenylacetate
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phenylacetyl-CoA + H2O = CoA + phenylacetate
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phenylacetyl-CoA + H2O = phenylacetate + CoA
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phenylacetyl-CoA + H2O = phenylacetate + CoA
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benzyloxycarbonyl 4-nitrophenyl ester + H2O = benzyl formate + 4-nitrophenol
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N-(2-nitrophenyl)phenylacetamide + H2O = N-(2-nitrophenyl)aniline + phenylacetate
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N6-phenylacetyl-L-lysine + H2O = L-lysine + phenylacetate
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penicillin G + H2O = 6-aminopenicillanic acid + phenylacetic acid
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N-Phenylacetyl-D-Phe + H2O = Phenylacetate + D-Phe
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2,4-diketo-4-phenylbutyrate + H2O = pyruvate + phenylacetate
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L-phenylalanine = phenylacetic acid + CO2
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phenylacetonitrile + 2 H2O = phenylacetic acid + NH3
show the reaction diagram
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ADP + phosphate + phenylacetyl-CoA = ATP + phenylacetate + CoA
show the reaction diagram
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ADP + phosphate + phenylacetyl-CoA = ATP + phenylacetate + CoA
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activates, chelates and stabilizes Mn3+
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Inhibitor in Enzyme-catalyzed Reactions (43 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
inhibits both oxidation and oxygenation of L-Phe
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0.5 mM, 10% inhibition
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inhibits reduction of (E)-2-methyl-2-butenoate
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competitive
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30% inhibition with tyrosine at 3 mM and phenylacetic acid at 12 mM
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competitive with respect to 1-naphthalenemethanol
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competitive inhibition
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competitive
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3D Structure of Enzyme-Ligand-Complex (PDB) (52 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (18 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
147
-
-
1.3
1.9
pH 8.5, 30°C, recombinant enzyme

KM Value (21 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.16
-
-
13.1
-
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0.029
-
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0.329
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at pH 6.5 and 55°C
5.2
6.1
pH 8.5, 30°C, recombinant enzyme

Ki Value (20 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.098
-
-
20
-
value above
0.065
-
-
1.1
-
pH 7, 37°C
0.39
-
-
0.94
-
pH 6.5, 40°C, recombinant wild-type enzyme
0.2
-
-

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
1.27
-
at pH 7.5 and 25°C

References & Links

Links to other databases for phenylacetate

ChEBI
PubChem
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PubChem