Ligand 4-hydroxyphenylacetic acid

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.

Basic Ligand Information

Molecular Structure
Picture of 4-hydroxyphenylacetic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C8H8O3
4-hydroxyphenylacetic acid
XQXPVVBIMDBYFF-UHFFFAOYSA-N
Synonyms:
(4-hydroxyphenyl)acetate, (4-hydroxyphenyl)acetic acid, (4-hydroxyphenyl)glyoxylate, 2-(4-hydroxyphenyl)acetate, 4-hydroxyphenylacetate, 4-hydroxy phenyl acetic acid, 4-hydroxyphenyl acetic acid, 4-hydroxyphenylactate, p-hydroxyphenylacetate, p-hydroxyphenylacetic acid, [4-hydroxyphenyl]acetic acid

Show all pahtways known for Show all pathways known for 4-hydroxyphenylacetic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (22 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4-hydroxyphenylacetate + H+ = 4-cresol + CO2
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
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2 + 4-hydroxyphenylacetate
show the reaction diagram
-
-
4-hydroxyphenylacetaldehyde + NAD+ + H2O = 4-hydroxyphenylacetate + NADH + H+
show the reaction diagram
-
-
4-hydroxyphenylacetaldehyde + NAD+ = 4-hydroxyphenylacetate + NADH + H+
show the reaction diagram
-
4-hydroxyphenylpyruvate + O2 = 4-hydroxyphenylacetate + CO2
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (39 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4-hydroxyphenylacetic acid + O2 = ?
show the reaction diagram
-
4-hydroxyphenylacetate + NADH + O2 + H2O = 3,4-dihydroxyphenylacetate + OH- + NAD+
show the reaction diagram
-
4-hydroxyphenylacetate + NAD(P)H + O2 = homogentisate + NAD(P)+ + H2O
show the reaction diagram
-
peroxynitrite + 4-hydroxyphenylacetic acid + NADPH + H+ = 4-hydroxyl-3-nitro-phenylacetic acid + NADP+ + H2O
show the reaction diagram
-
4-Hydroxyphenylacetate + NADH + O2 = 2,4-Dihydroxyphenylacetate + NAD+
show the reaction diagram
-
4-hydroxyphenyl acetic acid + O2 = ?
show the reaction diagram
-
ATP + 4-hydroxyphenylacetate + CoA = AMP + diphosphate + 4-hydroxyphenylacetyl-CoA
show the reaction diagram
-
ATP + 2-(4-hydroxyphenyl)acetate + CoA = ADP + phosphate + 2-(4-hydroxyphenyl)acetyl-CoA
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (16 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2 + 4-hydroxyphenylacetate
show the reaction diagram
-
-
(4-hydroxyphenyl)acetyl-CoA + O2 = (4-hydroxyphenyl)glyoxylate + CoA
show the reaction diagram
-
-
4-methoxyphenylacetate + AH2 + O2 = 4-hydroxyphenylacetate + formaldehyde + A + H2O
show the reaction diagram
-
-
p-hydroxyphenylacetaldehyde + NAD+ + H2O = p-hydroxyphenylacetate + NADH
show the reaction diagram
-
-
4-hydroxyphenylacetaldehyde + NAD+ + H2O = 4-hydroxyphenylacetate + NADH + H+
show the reaction diagram
-
-
4-hydroxyphenylacetaldehyde + NAD+ = 4-hydroxyphenylacetate + NADH + H+
show the reaction diagram
-
4-hydroxyphenylpyruvate + O2 = 4-hydroxyphenylacetate + CO2
show the reaction diagram
-
D-4-hydroxy-phenylglycine + H2O + O2 = (4-hydroxyphenyl)acetic acid + NH3 + H2O2
show the reaction diagram
-
-
4-hydroxyphenylacetyl-CoA + H2O = CoA + 4-hydroxyphenylacetate
show the reaction diagram
-
-
4-hydroxyphenylacetyl-CoA + H2O = 4-hydroxyphenylacetate + CoA
show the reaction diagram
-
-
p-hydroxybenzylpenicillin + H2O = 6-aminopenicillanate + p-hydroxyphenylacetic acid
show the reaction diagram
4-hydroxyphenylacetonitrile + H2O = 4-hydroxyphenylacetic acid + NH3
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.4 mM, approx. 30% activation
-
stimulates
-

Inhibitor in Enzyme-catalyzed Reactions (19 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
effects on enzyme kinetics with substrate N,N-dimethyl-4-phenylenediamine, overview
-
80 mM, complete inhibition, substrate analogue
-
2 mM, 16% inhibition
-
47% inhibition at 4.5 mM
-
74% inhibition with tyrosine at 3 mM and (4-hydroxyphenyl)acetic acid at 12 mM
-

3D Structure of Enzyme-Ligand-Complex (PDB) (6 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (10 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
1.17
-
pH and temperature not specified in the publication

KM Value (17 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.031
-
-
0.54
-
pH and temperature not specified in the publication

Ki Value (6 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.8
-
-
0.074
-
-

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
20.28
-
pH not specified in the publication, temperature not specified in the publication, MAO-A

References & Links

Links to other databases for 4-hydroxyphenylacetic acid

ChEBI
PubChem
ChEBI
PubChem