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BRENDA support

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
XMIIGOLPHOKFCH-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
-
3-phenylpropanoate + CoA + ATP = 3-phenylpropionyl-CoA + AMP + diphosphate
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (9 results)

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

Product in Enzyme-catalyzed Reactions (27 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
hydrocinnamaldehyde + NAD+ + H2O = hydrocinnamate + NADH
show the reaction diagram
-
3-phenylpropionaldehyde + NAD+ + H2O = 3-phenylpropionate + NADH + H+
show the reaction diagram
-
phenylpropionaldehyde + H2O + O2 = phenylpropionic acid + H2O2
show the reaction diagram
-
phenylpropionaldehyde + H2O + oxidized benzyl viologen = phenylpropanoate + H+ + reduced benzyl viologen
show the reaction diagram
-
3-phenylpropanal + H2O + 2,6-dichlorophenol-indophenol = 3-phenylpropanoate + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
cinnamic acid + NADH + H+ = 3-phenylpropanoic acid + NAD+
show the reaction diagram
-
3-phenylpropionylcholine + H2O = 3-phenylpropionate + choline
show the reaction diagram
-
3-phenylpropionamide + H2O = 3-phenylpropionate + NH3
show the reaction diagram
-
phenyl-3-propionitrile + H2O = phenyl-3-propionic acid + NH3
show the reaction diagram
-

Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
1.8fold activation at 50 mM
-

Inhibitor in Enzyme-catalyzed Reactions (29 results)

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

3D Structure of Enzyme-Ligand-Complex (PDB) (64 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (5 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE

KM Value (6 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.4112
-
-

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
-
-

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
-
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
ChEBI
PubChem