Ligand 2-phenylethylamine

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Basic Ligand Information

Molecular Structure
Picture of 2-phenylethylamine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C8H11N
2-phenylethylamine
BHHGXPLMPWCGHP-UHFFFAOYSA-N
Synonyms:
2-arylethylamine, 2-phenylethan-1-amine, 2-phenylethanamine, a 2-arylethylamine, beta-phenethylamine, beta-phenylethylamine, L-phenethylamine, phenethylamine, Phenylethylamine, phenylethyl amine

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (14 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phenethylamine + NADPH + O2 = phenethylamine N-oxide + NADP+ + H2O
show the reaction diagram
-
2-phenylethylamine + 2 H2O + 2 acceptor = 2-phenylacetic acid + NH3 + 2 reduced acceptor
show the reaction diagram
-
beta-phenylethylamine + H2O + 2,6-dichlorophenol indophenol = phenylacetaldehyde + NH3 + reduced 2,6-dichlorophenol indophenol
show the reaction diagram
acetyl-CoA + a 2-arylethylamine = CoA + an N-acetyl-2-arylethylamine
show the reaction diagram

In Vivo Product in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-phenylalanine = phenylethylamine + CO2
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (74 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phenylethylamine + ? = ?
show the reaction diagram
-
phenethylamine + NADPH + O2 = phenethylamine N-oxide + NADP+ + H2O
show the reaction diagram
-
2-phenylethylamine + H2O + O2 = 2-phenylethanal + NH3 + H2O2
show the reaction diagram
-
S-adenosyl-L-methionine + beta-phenylethylamine = ?
show the reaction diagram
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acetyl-CoA + beta-phenylethylamine = CoA + N-(2-phenylethyl)-acetaminde
show the reaction diagram
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acetyl-CoA + beta-phenylethylamine = CoA + N-acetylphenylethylamine
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (13 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
N-Acetyl-2-phenylethylamine + H2O = 2-Phenylethylamine + acetate
show the reaction diagram
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L-Phe = 2-phenylethylamine + CO2
show the reaction diagram
-
L-Phe = phenylethylamine + CO2
show the reaction diagram
-
-
L-phenylalanine = phenylethylamine + CO2
show the reaction diagram
-
-
L-phenylalanine = phenylethylamine + CO2
show the reaction diagram
-
-
5-L-glutamyl-beta-phenethylamine = 5-oxoproline + beta-phenethylamine
show the reaction diagram
-
-

Inhibitor in Enzyme-catalyzed Reactions (32 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
competitive inhibition
-
time-dependent, slowly reversible suicide inhibition. Addition of 2-phenylethylamine (10mM) to the enzyme results in immediate bleaching of the absorbance peak at 460 nm, a consequence of rapid reduction of the flavin cofactor by 2-phenylethylamine at steady state
-
80% inhibition with tyrosine at 3 mM and phenylethylamine at 12 mM
-
inhibits the reverse enzyme reaction
-
-
-

3D Structure of Enzyme-Ligand-Complex (PDB) (12 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (60 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
42
-
wild-type, pH 8.0, 22°C

KM Value (96 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
6.25
-
5-methyltetrahydrofolate as methyl donor

Ki Value (9 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.52
-
-
0.087
-
-
0.00398
-
-

IC50 Value (5 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0601
-
LOXL2 protein, at pH 8.0 and 37°C
27.8
-
pH 7.0, 25°C

References & Links

Links to other databases for 2-phenylethylamine

ChEBI
PubChem
ChEBI
PubChem