Ligand xanthine

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Basic Ligand Information

Molecular Structure
Picture of xanthine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C5H4N4O2
xanthine
LRFVTYWOQMYALW-UHFFFAOYSA-N

Show all pahtways known for Show all pathways known for xanthine

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (20 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
xanthine + 2-oxoglutarate + O2 = urate + succinate + CO2
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xanthine + O2 + H2O = urate + H2O2
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5-phospho-alpha-D-ribose 1-diphosphate + xanthine = 9-(5-phospho-beta-D-ribosyl)xanthine + diphosphate
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In Vivo Product in Enzyme-catalyzed Reactions (26 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3-methylxanthine + O2 + NAD(P)H + H+ = xanthine + NAD(P)+ + H2O + formaldehyde
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hypoxanthine + NAD+ + H2O = xanthine + NADH
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hypoxanthine + O2 + H2O = xanthine + H2O2
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XMP + diphosphate = xanthine + 5-phospho-alpha-D-ribose 1-diphosphate
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alkylated DNA + H2O = 7-methyladenine + 7-methylguanine + 3-methyladenine + 3-methylguanine + purine + 6-chloropurine + xanthine + DNA
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guanine + H2O = xanthine + NH3
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Substrate in Enzyme-catalyzed Reactions (91 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
xanthine + 5-phospho-alpha-D-ribose 1-diphosphate = 3-ribosylxanthine 5'-phosphate + diphosphate
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5-phospho-alpha-D-ribose 1-diphosphate + xanthine = 9-(5-phospho-beta-D-ribosyl)xanthine + diphosphate
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tRNAqueuine + xanthine = tRNAxanthine + queuine
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inosine + xanthine = hypoxanthine + xanthosine
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xanthine + 5-phospho-alpha-D-ribose 1-diphosphate = xanthosine 5'-phosphate + diphosphate
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xanthine + H2O = ?
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Product in Enzyme-catalyzed Reactions (70 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
1-methylxanthine + O2 + NADH + H+ = xanthine + NAD+ + H2O + formaldehyde
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hypoxanthine + NAD+ + H2O = xanthine + NADH
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-
hypoxanthine + O2 + H2O = xanthine + H2O2
show the reaction diagram
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9-(5-phospho-beta-D-ribosyl)xanthine + diphosphate = 5-phospho-alpha-D-ribose 1-diphosphate + xanthine
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XMP + diphosphate = xanthine + 5-phospho-alpha-D-ribose 1-diphosphate
show the reaction diagram
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xanthosine + H2O = xanthine + D-ribose
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alkylated DNA + H2O = 7-methyladenine + 7-methylguanine + 3-methyladenine + 3-methylguanine + purine + 6-chloropurine + xanthine + DNA
show the reaction diagram
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xanthosine + H2O = xanthine + D-ribose
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6-amino-2-hydroxypurine + H2O = xanthine + NH3
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guanine + H2O = xanthine + NH3
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guanine + H2O = xanthine + NH3
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.4 mM, residual enzyme activity 110%

Inhibitor in Enzyme-catalyzed Reactions (33 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activity of NADH-GOGAT I significantly decreases in the presence of 10 mM xanthine
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significantly increases the apparent Km for glutamate and decreases velocity of N-acetylglutamate synthetase, with little effect on carbamoylphosphate synthase-1. Inhibition is reversed by supplementation with N-carbamylglutamate
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poor inhibitor of phosphorolysis of guanosine
1 mM, 35% inhibition
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for the mutant enzyms D143S and D143T, xanthine is competitive, with respect to guanine
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weak
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10 mM, 35.4% inhibition
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; pH-dependent inhibition, overview
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3D Structure of Enzyme-Ligand-Complex (PDB) (6 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (74 results)

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

KM Value (131 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.7
-
-

Ki Value (12 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.016
-
-
0.08
-
-
0.024
-
-
0.8
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above
0.14
-
-
0.00196
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in 25 mM Tris-HCl, 137 mM NaCl, 2.7 mM KCl, at pH 7.4 and 25°C

IC50 Value (3 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.17
-
pH 7.4, 37°C

References & Links

Links to other databases for xanthine

ChEBI
PubChem
ChEBI
PubChem