Ligand 4-hydroxyphenylpropionic acid

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Basic Ligand Information

Molecular Structure
Picture of 4-hydroxyphenylpropionic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C9H10O3
4-hydroxyphenylpropionic acid
NMHMNPHRMNGLLB-UHFFFAOYSA-N
Synonyms:
3-(4-hydroxyphenyl)-propanoic acid, 3-(4-hydroxyphenyl)-propionate, 3-(4-hydroxyphenyl)propanoate, 3-(4-hydroxyphenyl)propanoic acid, 3-(4-hydroxyphenyl)propionate, 3-(4-hydroxyphenyl)propionic acid, 3-(p-hydroxyphenyl)propionic acid, 3-hydroxyphenylpropionic acid, 4-hydroxyphenyl propionic acid, 4-hydroxyphenyl propionic acid, dihydro-4-coumarate, dihydro-4-coumaric acid, p-hydroxyphenylpropionic acid, phloretate, phloretic acid


Show all pahtways known for Show all BRENDA pathways known for 4-hydroxyphenylpropionic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phloretate + electron-transfer flavoprotein EtfA-EtfB = 4-coumarate + reduced electron-transfer flavoprotein EtfA-EtfB
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE

Substrate in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3-(4-hydroxyphenyl)propanoic acid + H2O2 = ? + H2O
show the reaction diagram
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phloretate + electron-transfer flavoprotein EtfA-EtfB = 4-coumarate + reduced electron-transfer flavoprotein EtfA-EtfB
show the reaction diagram
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(E)-cinnamoyl-CoA + 3-(4-hydroxyphenyl)-propionate = (E)-cinnamate + 3-(4-hydroxyphenyl)-propionyl-CoA
show the reaction diagram
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ATP + dihydro-4-coumarate + CoA = AMP + diphosphate + dihydro-4-coumaroyl-CoA
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4-coumaric acid + NAD+ = 3-(4-hydroxyphenyl)propionic acid + NADH + H+
show the reaction diagram
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methyl 3-(4-hydroxyphenyl)propionate + H2O = methanol + 3-(4-hydroxyphenyl)propionate
show the reaction diagram
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methyl-3(4-hydroxyphenyl)-propionate + H2O = 3-(4-hydroxyphenyl)-propionate + methanol
show the reaction diagram
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p-hydroxyphenylpropionic acid ethyl ester + H2O = p-hydroxyphenylpropionic acid + ethanol
show the reaction diagram
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3-(4-hydroxyphenyl)propanenitrile + H2O = 3-(4-hydroxyphenyl)propanoic acid + NH3
show the reaction diagram
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3-hydroxyphenylpropionitrile + H2O = 3-hydroxyphenylpropionic acid + NH3
show the reaction diagram
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phloretin = 3-(4-hydroxyphenyl)propanoic acid
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
effects on enzyme kinetics with substrate N,N-dimethyl-4-phenylenediamine, overview
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19.6% inhibition at 1 mM
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2.5 mM, 46% inhibition
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i.e. phloretate, 30% product inhibition at 0.12 mM; product inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (3 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (11 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
300
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pH 7.0

KM Value (13 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
9.7
-
pH 7.0

IC50 Value (2 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
11.52
-
pH not specified in the publication, temperature not specified in the publication, MAO-A

References & Links

Links to other databases for 4-hydroxyphenylpropionic acid

ChEBI
PubChem
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PubChem