Ligand homogentisic acid

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Basic Ligand Information

Molecular Structure
Picture of homogentisic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C8H8O4
homogentisic acid
IGMNYECMUMZDDF-UHFFFAOYSA-N
Synonyms:
2,5-dihydroxyphenylacetate, 2,5-dihydroxyphenylacetate (homogentisate), 2,5-dihydroxyphenylacetic acid, homogentisate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
geranylgeranyl diphosphate + homogentisate = diphosphate + 6-geranylgeranyl-2-methylbenzene-1,4-diol + CO2
show the reaction diagram
-
all-trans-nonaprenyl diphosphate + homogentisate = diphosphate + 2-methyl-6-all-trans-nonaprenylbenzene-1,4-diol + CO2
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (6 results)

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

Substrate in Enzyme-catalyzed Reactions (19 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2,5-dihydroxyphenylacetate + ? = ?
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4-hydroxyphenylacetate + NAD(P)H + O2 = homogentisate + NAD(P)+ + H2O
show the reaction diagram
-
homogentisic acid lactone + H2O = homogentisic acid
show the reaction diagram
-
-
5-hydroxy-3H-benzofuran-2-one + H2O = homogentisic acid
show the reaction diagram
-
-

Inhibitor in Enzyme-catalyzed Reactions (8 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
50% inhibition at 4.5 mM
-
93% inhibition
-
half-maximal inhibition with 15 micromolar
-
competitive inhibition, has minimal cytotoxicity against mammalian cells. Homogentisic acid binds to the active site of the racemase
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3D Structure of Enzyme-Ligand-Complex (PDB) (3 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (7 results)

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

KM Value (16 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.006
-
pH 7.5, 28°C
0.04
-
pH 8.5, 28°C

Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0517
-
pH 11.0, 35°C, recombinant His-tagged enzyme

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0125
-
pH 11.0, 35°C, recombinant His-tagged enzyme

References & Links

Links to other databases for homogentisic acid

ChEBI
PubChem
ChEBI
PubChem