Ligand 3-Phenylpropionic acid

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Basic Ligand Information

Molecular Structure
Picture of 3-Phenylpropionic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C9H10O2
3-Phenylpropionic acid
AQHHHDLHHXJYJD-UHFFFAOYSA-N
Synonyms:
3-phenyl-propionate, 3-phenylpropanoate, 3-Phenylpropanoic acid, 3-Phenylpropionate, 3-phenylpropropionate, Beta-phenylpropionate, Beta-phenylpropionic acid, dihydrocinnamic acid, Hydrocinnamate, Hydrocinnamic acid, phenyl-3-propionic acid, phenylpropanoate, phenylpropionic acid

Show all pahtways known for Show all BRENDA pathways known for 3-Phenylpropionic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3-phenylpropanoate + electron-transfer flavoprotein EtfA-EtfB = trans-cinnamate + reduced electron-transfer flavoprotein EtfA-EtfB
show the reaction diagram
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3-phenylpropanoate + CoA + ATP = 3-phenylpropionyl-CoA + AMP + diphosphate
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3-phenylpropionate + NAD+ = 3-(2,3-dihydroxyphenyl) propionate + NADH + H+
show the reaction diagram
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3-phenylpropanoate + electron-transfer flavoprotein EtfA-EtfB = trans-cinnamate + reduced electron-transfer flavoprotein EtfA-EtfB
show the reaction diagram
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phenylpropionic acid + UDP-glucose = UDP + phenylpropionyl-beta-D-glucoside
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(E)-cinnamoyl-CoA + 3-phenylpropionate = (E)-cinnamate + 3-phenylpropionyl-CoA
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3-phenylpropanoate + CoA + ATP = 3-phenylpropionyl-CoA + AMP + diphosphate
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (24 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
hydrocinnamaldehyde + NAD+ + H2O = hydrocinnamate + NADH
show the reaction diagram
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3-phenylpropionaldehyde + NAD+ + H2O = 3-phenylpropionate + NADH + H+
show the reaction diagram
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phenylpropionaldehyde + H2O + oxidized benzyl viologen = phenylpropanoate + H+ + reduced benzyl viologen
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3-phenylpropanal + H2O + 2,6-dichlorophenol-indophenol = 3-phenylpropanoate + reduced 2,6-dichlorophenol-indophenol
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cinnamic acid + NADH = 3-phenylpropanoic acid + NAD+
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3-phenylpropionylcholine + H2O = 3-phenylpropionate + choline
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3-phenylpropionamide + H2O = 3-phenylpropionate + NH3
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phenyl-3-propionitrile + H2O = phenyl-3-propionic acid + NH3
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Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
1.8fold activation at 50 mM
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Inhibitor in Enzyme-catalyzed Reactions (28 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
competitive inhibition
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competitive towards L-Phe
40.5% inhibition at 1 mM
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inhibits reduction of (E)-2-methyl-2-butenoate
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competitive with L-Phe
inhibits amidase and esterase activity
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IC50: 0.0056 mM
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3D Structure of Enzyme-Ligand-Complex (PDB) (63 results)

Enzyme Kinetic Parameters

KM Value (1 result)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.4112
-
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Ki Value (8 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.017
-
-
2
-
37°C, pH 6.0
2.6
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IC50 Value (3 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
1
-
IC50 above 1.0 mM in 0.1 M phosphate buffer (pH 7.0), at 37°C
0.0431
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at pH 7.5 and 25°C
0.0056
-
IC50: 0.0056 mM

References & Links

Links to other databases for 3-Phenylpropionic acid

ChEBI
PubChem
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PubChem