Ligand phenylacetaldehyde

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Basic Ligand Information

Molecular Structure
Picture of phenylacetaldehyde (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C8H8O
phenylacetaldehyde
DTUQWGWMVIHBKE-UHFFFAOYSA-N
Synonyms:
2-Phenyl-1-ethanal, 2-phenylacetaldehyde, 2-phenylethanal, 2-phenylethanone, beta-phenethyl aldehyde, beta-phenylethanal, phenyl-acetaldehyde, phenylacetaldehyd, phenyl acetaldehyde, phenylethanal, phenylethylaldehyde


Show all pahtways known for Show all BRENDA pathways known for phenylacetaldehyde

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
phenylacetaldehyde + NAD(P)H + H+ = 2-phenylethan-1-ol + NAD(P)+
show the reaction diagram
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phenylacetaldehyde + H2O + oxidized ferredoxin = phenylacetate + H+ + reduced ferredoxin
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (24 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-phenylethanol + NAD(P)+ = phenylacetaldehyde + NAD(P)H + H+
show the reaction diagram
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phenethyl alcohol + NAD(P)+ = phenylacetaldehyde + NAD(P)H + H+
show the reaction diagram
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phenylethanol + ferricytochrome c = phenylacetaldehyde + ferrocytochrome c
show the reaction diagram
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beta-phenylethylamine + H2O + 2,6-dichlorophenol indophenol = phenylacetaldehyde + NH3 + reduced 2,6-dichlorophenol indophenol
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L-phenylalanine + O2 + H2O = phenylacetaldehyde + CO2 + NH3 + H2O2
show the reaction diagram
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Phenylpyruvate = Phenylacetaldehyde + CO2
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (51 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phenylacetaldehyde + NADH = phenylethanol + NAD+
show the reaction diagram
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phenylacetaldehyde + NADH + H+ = phenylethanol + NAD+
show the reaction diagram
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phenylacetaldehyde + NADPH + H+ = phenylethanol + NADP+
show the reaction diagram
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phenylacetaldehyde + NAD(P)H + H+ = 2-phenylethan-1-ol + NAD(P)+
show the reaction diagram
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phenylacetaldehyde + NADH + H+ = 2-phenylethanol + NAD+
show the reaction diagram
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2-phenyl-1-ethanal + NADPH + O2 = ?
show the reaction diagram
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phenylacetaldehyde + ascorbate + O2 = ?
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+
show the reaction diagram
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2-phenylacetaldehyde + NAD+ + H2O = 2-phenylbenzoate + 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+
show the reaction diagram
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phenylacetaldehyde + O2 = phenylacetate + H2O
show the reaction diagram
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2-phenylethanal + hydroxypyruvate = (S)-1,3-dihydroxy-4-phenylbutan-2-one + CO2
show the reaction diagram
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L-threonine + phenylacetaldehyde = acetaldehyde + 4-phenyl-L-threonine
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pyruvate + phenylacetaldehyde = 3-hydroxy-4-phenyl-butan-2-one + CO2
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phenylacetaldehyde = ?
show the reaction diagram
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cyanide + phenylacetaldehyde = (2R)-2-hydroxy-3-phenylpropanenitrile
show the reaction diagram
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glycerone phosphate + phenylacetaldehyde = (3R,4S)-3,4-dihydroxy-2-oxo-5-phenylpentyl phosphate
show the reaction diagram
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glycine + phenylacetaldehyde = (2R,3S)-2-amino-3-hydroxy-4-phenylbutanoic acid + (2R,3R)-2-amino-3-hydroxy-4-phenylbutanoic acid
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phenylacetaldehyde + pyruvate = 5-benzyl-3-hydroxyfuran-2(5H)-one + H2O
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phenylacetaldehyde + dopamine = (1S)-1-(2-phenylethyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (113 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-phenylethanol + NAD(P)+ = phenylacetaldehyde + NAD(P)H + H+
show the reaction diagram
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phenylethanol + ferricytochrome c = phenylacetaldehyde + ferrocytochrome c
show the reaction diagram
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phenethyl alcohol + O2 = phenylacetaldehyde + H2O2
show the reaction diagram
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2-phenylethyl alcohol + O2 = 2-phenylacetaldehyde + H2O
show the reaction diagram
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beta-phenethyl alcohol + acceptor = beta-phenethyl aldehyde + reduced acceptor
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styrene + H2O2 = styrene oxide + benzaldehyde + phenylacetaldehyde + H2O
show the reaction diagram
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2-phenylethylamine + H2O + O2 = 2-phenylethanal + NH3 + H2O2
show the reaction diagram
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2-phenylethylamine + pyruvate = 2-phenylethanal + L-alanine
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L-phenylalanine + O2 + H2O = phenylacetaldehyde + CO2 + NH3 + H2O2
show the reaction diagram
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L-phenylalanine + O2 + H2O = phenylacetaldehyde + CO2 + NH3 + H2O2
show the reaction diagram
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Phenylpyruvate = Phenylacetaldehyde + CO2
show the reaction diagram
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phenylpyruvate = phenylethanal + CO2
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.1 mM causes 54% inhibition at 30°C
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1 mM, 54% inhibition
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50% inhibition at 7 mM
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7 mM, 50% inhibition
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substrate inhibition at high concentrations
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irreversible product inhibition, half-life of 15 min determined at a phenylacetaldehyde concentration of about 55 mM
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3D Structure of Enzyme-Ligand-Complex (PDB) (168 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (16 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
10.4
-
80°C, pH not specified in the publication
11.16
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pH 6.1, 30°C
1.7
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-
0.5
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100 mM H2NaPO4 pH 7.5, 100 mM NaCl, 20 mM 2-mercaptoethanol, 2 mM NAD+
0.23
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-
96.8
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pH 7.5
960
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pH 8.4, 85°C, benzyl viologen as electron acceptor
960
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with benzyl viologen as cosubstrate, at 85°C
4.4
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pH 7.6, 35°C
0.01
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at pH 7.5 and 28°C

KM Value (32 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.5
-
-
0.53
-
pH 6.1, 30°C
0.35
-
-
4.5
-
100 mM H2NaPO4 pH 7.5, 100 mM NaCl, 20 mM 2-mercaptoethanol, 2 mM NAD+
0.00535
-
-
0.25
-
2,6-dichlorophenol-indophenol as electron acceptor
0.076
-
pH 8.4, 85°C, benzyl viologen as electron acceptor
0.27
-
pH 7.6, 35°C
0.358
-
at pH 7.5 and 28°C
0.105
-
70°C, pH 8.0

Ki Value (2 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.53
-
-
4
-
Kis value, pH 7.6, 35°C

References & Links

Links to other databases for phenylacetaldehyde

ChEBI
PubChem
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PubChem