Information on EC 1.17.3.2 - xanthine oxidase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
1.17.3.2
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RECOMMENDED NAME
GeneOntology No.
xanthine oxidase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
xanthine + H2O + O2 = urate + H2O2
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
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caffeine degradation III (bacteria, via demethylation)
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Caffeine metabolism
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Drug metabolism - other enzymes
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Metabolic pathways
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Purine metabolism
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theophylline degradation
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SYSTEMATIC NAME
IUBMB Comments
xanthine:oxygen oxidoreductase
An iron-molybdenum flavoprotein (FAD) containing [2Fe-2S] centres. Also oxidizes hypoxanthine, some other purines and pterins, and aldehydes, but is distinct from EC 1.2.3.1, aldehyde oxidase. Under some conditions the product is mainly superoxide rather than peroxide: RH + H2O + 2 O2 = ROH + 2 O2.- + 2 H+. The mammalian enzyme predominantly exists as an NAD-dependent dehydrogenase (EC 1.17.1.4, xanthine dehydrogenase). During purification the enzyme is largely converted to the O2-dependent xanthine oxidase form (EC 1.17.3.2). The conversion can be triggered by several mechanisms, including the oxidation of cysteine thiols to form disulfide bonds [4,5,7,10] [which can be catalysed by EC 1.8.4.7, enzyme-thiol transhydrogenase (glutathione-disulfide) in the presence of glutathione disulfide] or limited proteolysis, which results in irreversible conversion. The conversion can also occur in vivo [4,6,10].
CAS REGISTRY NUMBER
COMMENTARY hide
9002-17-9
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
S-2
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
KY 3074
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Manually annotated by BRENDA team
KY 3074
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Patas monkey
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Manually annotated by BRENDA team
Erythrocebus patas Patas monkey
Patas monkey
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
f. catus
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
lentil
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
male TO-2 cardiomyopathic Syrian hamsters
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Manually annotated by BRENDA team
Mus musculus BALB/c
male mice
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Rattus norvegicus Sprague-Dawley
male
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Manually annotated by BRENDA team
a cultivar resistant to Russian wheat aphid, biotype SA1, Diuraphis noxia; cv. Tugela, a cultivar sensitive to Russian wheat aphid, biotype SA1, Diuraphis noxia
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Manually annotated by BRENDA team
Triticum aestivum Tugela DN
a cultivar resistant to Russian wheat aphid, biotype SA1, Diuraphis noxia; cv. Tugela, a cultivar sensitive to Russian wheat aphid, biotype SA1, Diuraphis noxia
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1,3-dimethylxanthine + H2O + O2
1,3-dimethylurate + H2O2
show the reaction diagram
-
-
-
-
?
1,7-dimethylxanthine + H2O + O2
1,7-dimethylurate + H2o2
show the reaction diagram
-
-
-
-
?
1-methyl-2-hydroxypurine + H2O + O2
1-methyl-2-hydroxy-7,9-dihydropurin-8-one + H2O2
show the reaction diagram
-
-
-
?
1-methylxanthine + H2O + O2
1-methylurate + H2O2
show the reaction diagram
2,3-dihydroxybenzaldehyde + H2O + O2
2,3-dihydroxybenzoate + H2O2
show the reaction diagram
-
-
-
?
2,5-dihydroxybenzaldehyde + H2O + O2
?
show the reaction diagram
-
-
-
-
?
2,6-diaminopurine + H2O + O2
2,6-diamino-7,9-dihydro-8H-purin-8-one
show the reaction diagram
-
-
-
-
?
2-amino-4-hydroxypterin + H2O + O2
? + H2O2
show the reaction diagram
-
substrate inhibition kinetic pattern
-
-
?
2-amino-6-chloro-purine + H2O + O2
2-amino-6-chloro-7,9-dihydro-purin-8-one + H2O2
show the reaction diagram
-
-
-
-
?
2-hydroxybenzaldehyde + H2O + O2
2-hydroxybenzoate + H2O2
show the reaction diagram
-
-
-
-
?
2-mercaptopurine + H2O + O2
8-hydroxy-2-mercaptopurine + H2O2
show the reaction diagram
-
no conversion to 2-thioxanthine
-
-
?
2-methoxybenzaldehyde + H2O + O2
2-methoxybenzoate + H2O2
show the reaction diagram
-
-
-
-
?
2-methylbenzaldehyde + H2O + O2
2-methylbenzoate + H2O2
show the reaction diagram
-
-
-
-
?
2-nitrobenzaldehyde + H2O + O2
2-nitrobenzoate + H2O2
show the reaction diagram
-
-
-
-
?
2-oxo-6-methylpurine + H2O + O2
? + H2O2
show the reaction diagram
-
low activity
-
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?
2-thioxanthine + H2O + O2
2-thiourate + H2O2
show the reaction diagram
-
-
-
-
?
2-thioxanthine + H2O + O2
2-thiouric acid + H2O2
show the reaction diagram
-
-
-
-
?
3,4-dihydroxybenzaldehyde + H2O + O2
3,4-dihydroxybenzoate + H2O2
show the reaction diagram
-
-
-
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?
3,4-dimethoxybenzaldehyde + H2O + O2
3,4-dimethoxybenzoate + H2O2
show the reaction diagram
-
-
-
-
?
3-hydroxy-4-methoxybenzaldehyde + H2O + O2
3-hydroxy-4-methoxybenzoate + H2O2
show the reaction diagram
-
-
-
-
?
3-hydroxybenzaldehyde + H2O + O2
3-hydroxybenzoate + H2O2
show the reaction diagram
-
-
-
-
?
3-methoxybenzaldehyde + H2O + O2
3-methoxybenzoate + H2O2
show the reaction diagram
-
-
-
-
?
3-methylbenzaldehyde + H2O + O2
3-methylbenzoate + H2O2
show the reaction diagram
-
-
-
-
?
3-methylhypoxanthine + H2O + O2
3-methylxanthine + H2O2
show the reaction diagram
-
-
-
?
3-methylxanthine + H2O + O2
3-methylurate + H2O2
show the reaction diagram
-
-
-
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?
3-nitrobenzaldehyde + H2O + O2
3-nitrobenzoate + H2O2
show the reaction diagram
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-
-
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?
4-hydroxy-3-methoxybenzaldehyde + H2O + O2
4-hydroxy-3-methoxybenzoate + H2O2
show the reaction diagram
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-
-
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?
4-hydroxybenzaldehyde + H2O + O2
4-hydroxybenzoate + H2O2
show the reaction diagram
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-
-
-
?
4-hydroxyphenylglycoaldehyde + H2O + O2
?
show the reaction diagram
-
-
-
-
?
4-methoxybenzaldehyde + H2O + O2
4-methoxybenzoate + H2O2
show the reaction diagram
-
-
-
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?
4-methylbenzaldehyde + H2O + O2
4-methylbenzoate + H2O2
show the reaction diagram
-
-
-
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?
4-nitrobenzaldehyde + H2O + O2
4-nitrobenzoate + H2O2
show the reaction diagram
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-
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?
5-chloro-6-[(2-iminopyrrolidin-1-yl)methyl]-3H-pyrimidin-4-one + H2O + O2
?
show the reaction diagram
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-
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?
6'-deoxyacyclovir + H2O + O2
acyclovir + H2O2
show the reaction diagram
-
prodrug of the antiviral agent acyclovir
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?
6,8-dihydroxypurine + H2O + O2
?
show the reaction diagram
-
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?
6,8-dihydroxypurine + H2O + O2
? + H2O2
show the reaction diagram
-
6,8-dihydroxypurine binding structure, overview
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-
?
6-amino-5-bromo-1H-pyrimidin-2-one + H2O + O2
?
show the reaction diagram
-
-
-
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?
6-amino-5-bromo-3H-pyrimidin-4-one + H2O + O2
?
show the reaction diagram
-
-
-
-
?
6-amino-5-bromopyrimidine + H2O + O2
?
show the reaction diagram
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-
-
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?
6-cyanopurine + H2O + O2
6-cyano-7,9-dihydropurine-8-one
show the reaction diagram
-
-
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?
6-formylpterin + H2O + O2
?
show the reaction diagram
-
-
-
-
?
6-formylpterin + H2O + O2
? + H2O2
show the reaction diagram
-
-
-
-
?
6-mercaptopurine + 2 H2O + 2 O2
6-thiouric acid + 2 H2O2
show the reaction diagram
6-mercaptopurine + H2O + O2
6-mercapto-7,9-dihydropurin-8-one + H2O2
show the reaction diagram
-
4.4% of activity with xanthin
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?
6-mercaptopurine + H2O + O2
?
show the reaction diagram
-
an anticancer drug
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?
6-thioxanthine + H2O + O2
6-thiourate + H2O2
show the reaction diagram
6-thioxanthine + H2O + O2
6-thiouric acid + H2O2
show the reaction diagram
-
-
-
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?
7-alkylpteridin-4-one + H2O + O2
7-alkyllumazine + H2O2
show the reaction diagram
-
-
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?
7-methylxanthine + H2O + O2
7-methylurate + H2O2
show the reaction diagram
-
-
-
-
?
7-phenylpteridin-4-one + H2O + O2
7-phenyllumazine + H2O2
show the reaction diagram
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-
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?
7H-pyrrolo[2,3-d]pyrimidin-2(1H)-one + H2O + O2
?
show the reaction diagram
-
-
-
-
?
7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one + H2O + O2
?
show the reaction diagram
-
-
-
-
?
7H-pyrrolo[2,3-d]pyrimidine + H2O + O2
?
show the reaction diagram
-
-
-
-
?
acetaldehyde + H2O + O2
acetic acid + H2O2
show the reaction diagram
adenine + H2O + O2
6-amino-7,9-dihydropurin-8-one + H2O2
show the reaction diagram
adenine + H2O + O2
? + H2O2
show the reaction diagram
-
substrate inhibition kinetic pattern
-
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?
allopurinol + H2O + O2
?
show the reaction diagram
allopurinol + H2O + O2
oxypurinol + H2O2
show the reaction diagram
benzaldehyde + H2O + O2
benzoate + H2O2
show the reaction diagram
butanal + H2O + O2
butanoate + H2O2
show the reaction diagram
-
-
-
?
carboxylic aldehyde + H2O + O2
carboxylic acid + H2O2
show the reaction diagram
formycin B + H2O + O2
?
show the reaction diagram
-
-
-
-
?
FYX-051 + O2 + H2O
?
show the reaction diagram
-
the structure of bovine XOR exposed to the slow-reacting substrate FYX-051 shows a covalent intermediate of the hydroxylation reaction, in which the hydroxyl oxygen bridged the molybdenumatom and the acceptor carbon atom of the aromatic ring of the substrate
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-
?
glyceraldehyde-3-phosphate + H2O + O2
?
show the reaction diagram
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-
-
-
?
glyceryl trinitrate + 2,3-dihydroxybenzaldehyde
?
show the reaction diagram
-
-
-
-
?
glyceryl trinitrate + NADH
? + NAD+ + H2O
show the reaction diagram
-
-
further reaction of organic nitrite with thiols or ascorbate leads to generation of NO or nitrosothiols
-
?
glyceryl trinitrate + xanthine
urate + ?
show the reaction diagram
-
-
-
-
?
guanine + H2O + O2
2-amino-1,7,8-trihydro-6H-purin-8-one + H2O2
show the reaction diagram
hypoxanthine + 2 H2O + 2 O2
urate + 2 H2O2
show the reaction diagram
hypoxanthine + H2O + O2
urate + H2O2
show the reaction diagram
-
-
-
-
?
hypoxanthine + NAD+ + H2O
xanthine + NADH
show the reaction diagram
-
-
-
?
indole-3-acetaldehyde + H2O + O2
?
show the reaction diagram
-
-
-
-
?
indole-3-aldehyde + H2O + O2
?
show the reaction diagram
-
-
-
-
?
isosorbide dinitrate + 2,3-dihydroxybenzaldehyde
?
show the reaction diagram
-
-
-
-
?
isosorbide dinitrate + NADH
? + NAD+ + H2O
show the reaction diagram
-
-
further reaction of organic nitrite with thiols or ascorbate leads to generation of NO or nitrosothiols
-
?
isosorbide dinitrate + xanthine
urate + ?
show the reaction diagram
-
-
-
-
?
lumazine + H2O + O2
? + H2O2
show the reaction diagram
-
classical Michaelis-Menten hyperbolic saturation kinetic pattern
-
-
?
N1-methylnicotinamide + H2O + O2
?
show the reaction diagram
NADH + H2O + O2
NAD+ + H2O2
show the reaction diagram
nitrate + 2,3-dihydroxybenzaldehyde
nitrite + ?
show the reaction diagram
-
-
-
-
?
nitrate + NADH
nitrite + NAD+ + H2O
show the reaction diagram
nitrate + xanthine
nitrite + urate + ?
show the reaction diagram
-
-
-
-
?
nitrite + 2,3-dihydroxybenzaldehyde
NO + ?
show the reaction diagram
-
NO generation occurs under aerobic conditions and is regulated by O2 tension, pH, nitrite, and reducing substrate concentrations
-
-
?
nitrite + NADH
NO + NAD+ + H2O
show the reaction diagram
nitrite + O2 + hypoxanthine
peroxynitrite + ?
show the reaction diagram
-
-
-
-
?
nitrite + O2 + pterin
peroxynitrite + ?
show the reaction diagram
-
-
-
-
?
nitrite + xanthine
NO + ?
show the reaction diagram
o-hydroxybenzaldehyde + H2O + O2
o-hydroxybenzoate + H2O2
show the reaction diagram
-
-
-
?
organic nitrate + NADH
organic nitrite + NAD+ + H2O
show the reaction diagram
-
organic nitrite is the initial product in the process of xanthine oxidase mediated organic nitrate biotransformation and is the precursor of NO and nitrosothiols, serving as the link between organic nitrate and soluble guanylyl cyclase
-
-
?
propanal + H2O + O2
propanoate + H2O2
show the reaction diagram
-
-
-
?
pteridine + H2O + O2
?
show the reaction diagram
pterin + H2O + O2
?
show the reaction diagram
-
fluorometric assay method
-
-
?
pterin + H2O + O2
isoxanthopterin + H2O2
show the reaction diagram
-
-
-
?
pterine + NAD+
? + H2O + NADH
show the reaction diagram
-
-
-
?
purine + H2O + O2
7,9-dihydropurin-8-one + H2O2
show the reaction diagram
purine + H2O + O2
?
show the reaction diagram
purine + NAD+
? + H2O + NADH
show the reaction diagram
-
-
-
?
pyridine-2-aldehyde + H2O + O2
?
show the reaction diagram
-
-
-
-
?
pyridine-4-aldehyde + H2O + O2
?
show the reaction diagram
-
-
-
-
?
pyrimidine derivatives + H2O + O2
?
show the reaction diagram
pyrimidine-3-aldehyde + H2O + O2
?
show the reaction diagram
-
-
-
-
?
salicylaldehyde + H2O + O2
salicylic acid + H2O2
show the reaction diagram
-
-
-
?
succinate semialdehyde + H2O + O2
succinate + H2O2
show the reaction diagram
-
-
-
-
?
xanthine + 2,6-dichlorophenolindophenol + H2O
urate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
-
?
xanthine + cytochrome c + H2O
urate + reduced cytochrome c
show the reaction diagram
-
-
-
-
?
xanthine + H2O + O2
?
show the reaction diagram
-
-
-
-
?
xanthine + H2O + O2
superoxide + urate + ?
show the reaction diagram
-
-
-
-
?
xanthine + H2O + O2
urate + H2O2
show the reaction diagram
xanthine + H2O + O2
uric acid + H2O2
show the reaction diagram
xanthine + methylene blue + O2
urate + reduced methylene blue
show the reaction diagram
-
-
-
-
?
xanthine + NAD+ + H2O
urate + NADH
show the reaction diagram
-
-
-
?
xanthine + NO2-
uric acid + NO
show the reaction diagram
xanthine + O2 + H2O
urate + H2O2
show the reaction diagram
xanthine + thionine + O2
urate + reduced thionine
show the reaction diagram
-
-
-
-
?
xanthopterin + H2O + O2
?
show the reaction diagram
-
-
-
-
?
xanthopterin + H2O + O2
? + H2O2
show the reaction diagram
-
substrate activation kinetic pattern
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
1-methylxanthine + H2O + O2
1-methylurate + H2O2
show the reaction diagram
-
-
-
-
?
6-mercaptopurine + 2 H2O + 2 O2
6-thiouric acid + 2 H2O2
show the reaction diagram
6-mercaptopurine + H2O + O2
?
show the reaction diagram
-
an anticancer drug
-
-
?
carboxylic aldehyde + H2O + O2
carboxylic acid + H2O2
show the reaction diagram
hypoxanthine + 2 H2O + 2 O2
urate + 2 H2O2
show the reaction diagram
nitrate + NADH
nitrite + NAD+ + H2O
show the reaction diagram
-
reaction can be an important source of NO production in ischemic tissues
-
-
?
nitrite + NADH
NO + NAD+ + H2O
show the reaction diagram
-
reaction can be an important source of NO production in ischemic tissues
-
-
?
organic nitrate + NADH
organic nitrite + NAD+ + H2O
show the reaction diagram
-
organic nitrite is the initial product in the process of xanthine oxidase mediated organic nitrate biotransformation and is the precursor of NO and nitrosothiols, serving as the link between organic nitrate and soluble guanylyl cyclase
-
-
?
pteridine + H2O + O2
?
show the reaction diagram
purine + H2O + O2
?
show the reaction diagram
xanthine + H2O + O2
urate + H2O2
show the reaction diagram
xanthine + O2 + H2O
urate + H2O2
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
molybdenum cofactor
molybdopterin
-
one cofactor per subunit, oxidation of xanthine takes place at this center, electrons are rapidly distributed to the other centers by intramolecular electron transfer
NAD+
-
-
[2Fe-2S] cluster
-
two N-terminal non-identical iron-sulfur clusters of the [2Fe-2S]-type
additional information
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Cd2+
inhibitory effect
CoCl2
-
increased activity of xanthine oxidase in cells exposed to CoCl2 and subsequent increase in reactive oxygen species derived from enzyme activity, which results in accumulation of hypoxia-inducible factor 1alpha. Blockade of enzyme activity by allopurinol, N-acetyl-L-cysteine or siRNA significantly attenuates expression of hypoxia-inducible factor 1alpha and thus the induction of genes such as erythropoietin and vascular endothelial growth factor
Fe
-
a molybdenum-iron-flavoenzyme
Mo4+
-
the Mo(VI) ion at the active site is reduced to Mo(IV), which then transfers two electrons, via the 2Fe-2S clusters, to the FAD cofactor
Molybdenum
Zn2+
inhibitory effect
additional information
-
the molybdenum center is located in a separate subunit from the Fe/S- and flavin-containing parts of the enzyme
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-one
-
a flavone compound from Selaginellaceae with antiviral activity
(4'-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine
-
-
(E)-9-nitro-octadec-9-en-1-ol
-
slight inhibition
(E)-9-nitro-octadec-9-enoic acid
-
strong inhibition
1,2,4-triazolo[1,5-a]pyrimidine
-
poor inhibitor
1,2-Dihydroxybenzene 3,5-disulfonic acid
-
inhibits reaction with cytochrome c
1,3,6,7-tetrahydroxy-9H-xanthen-9-one
-
-
1-(4'-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine
-
-
1-(4'-trifluoromethylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine
-
-
1-(9-ethyl-9H-carbazol-3-yl)-3,4-diphenylazetidin-2-one
-
-
1-(9-ethyl-9H-carbazol-3-yl)-3-phenyl-4-m-totylazetidin-2-one
-
-
1-(9-ethyl-9H-carbazol-3-yl)-3-phenyl-4-p-tolylazetidin-2-one
-
-
1-(9-ethyl-9H-carbazol-3-yl)-4-(2-nitrophenyl)-3-phenylazetidin-2-one
-
-
1-(9-ethyl-9H-carbazol-3-yl)-4-(3-methoxyphenyl)-3-phenylazetidin-2-one
-
-
1-(9-ethyl-9H-carbazol-3-yl)-4-(3-nitrophenyl)-3-phenylazetidin-2-one
-
-
1-(9-ethyl-9H-carbazol-3-yl)-4-(4-fluorophenyl)-3-phenylazetidin-2-one
-
-
1-(9-ethyl-9H-carbazol-3-yl)-4-(4-methoxyphenyl)-3-phenylazetidin-2-one
-
-
1-(9-ethyl-9H-carbazol-3-yl)-4-(4-nitrophenyl)-3-phenylazetidin-2-one
-
-
1-4-tolyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine
-
-
1-O-(4''-O-caffeoyl)-beta-glucopyranosyl-1,4-dihydroxy-2-(3',3'-dimethylallyl)benzene
-
-
1-[(2,4-dichlorobenzyl)oxy]-3,6,7-trihydroxy-9H-xanthen-9-one
-
-
1-[(2,6-dichlorobenzyl)oxy]-3,6,7-trihydroxy-9H-xanthen-9-one
-
-
1-[(2-bromobenzyl)oxy]-3,6,7-trihydroxy-9H-xanthen-9-one
-
-
1-[(2-chlorobenzyl)oxy]-3,6,7-trihydroxy-9H-xanthen-9-one
-
-
1-[(2-fluorobenzyl)oxy]-3,6,7-trihydroxy-9H-xanthen-9-one
-
-
1-[(3-bromobenzyl)oxy]-3,6,7-trihydroxy-9H-xanthen-9-one
-
-
1-[(3-chlorobenzyl)oxy]-3,6,7-trihydroxy-9H-xanthen-9-one
-
-
1-[(3-fluorobenzyl)oxy]-3,6,7-trihydroxy-9H-xanthen-9-one
-
-
1-[(4-bromobenzyl)oxy]-3,6,7-trihydroxy-9H-xanthen-9-one
-
-
1-[(4-chlorobenzyl)oxy]-3,6,7-trihydroxy-9H-xanthen-9-one
-
-
1-[(4-fluorobenzyl)oxy]-3,6,7-trihydroxy-9H-xanthen-9-one
-
-
1-[3-cyano-4-(2,2-dimethylpropoxy)phenyl]-1H-pyrazole-4-carboxylic acid
10-nitro-octadec-9,12-dienoic acid
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-
10-nitro-octadec-9-enoic acid
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-
12-nitro-octadec-9,12-dienoic acid
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-
13-nitro-octadec-9,12-dienoic acid
-
-
2,4-Diamino-6-hydroxy-s-triazine
-
-
2,4-dihydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]benzaldehyde
-
-
2,4-Dinitrofluorobenzene
-
-
2,6-Diaminopurine
-
poor inhibitor
2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
-
competitive, 50% inhibition at 0.00022 mM
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
-
competitive, 50% inhibition at 0.00124 mM
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one
-
competitive, 50% inhibition at 0.00019 mM; competitive, 50% inhibition at 0.00020 mM
2-Amino-4-hydroxy-6-formylpterine
2-Amino-4-hydroxypterine-6-aldehyde
-
-
2-amino-6-chloropurine
-
poor inhibitor
2-amino-6-hydroxy-8-mercaptopurine
-
mixed-type inhibition, the inhibitor specifically blocks the enzyme activity with the drug 6-mercaptopurine, but does affect activity with xanthine and hypoxanthine to a lesser extent, overview
2-amino-6-purine thiol
-
competitive inhibitor, the inhibitor specifically blocks the enzyme activity with the drug 6-mercaptopurine, but does affect activity with xanthine and hypoxanthine to a lesser extent, overview
2-Aminopurine
-
poor inhibitor
2-chloro-6(methylamino)purine
-
competitive
2-chloroadenine
-
substrate analogue
2-coumaric acid
-
competitively inhibits the enzyme by binding to the active site, have a protective effect against reactive oxygen species in cells, structure-function relationship, computational molecular docking, overview
2-hydroxy-4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]benzaldehyde
-
a resveratrol derivative
2-hydroxy-6-methylpurine
-
interacts with Arg880 in both active sites of the nezyme dimer, binding structure, overview
2-hydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]-4-methoxybenzaldehyde
-
a resveratrol derivative
2-methoxycinnamic acid
-
competitively inhibits the enzyme by binding to the active site, have a protective effect against reactive oxygen species in cells, structure-function relationship, computational molecular docking, overview
2-[(2,3-dimethylphenoxy)methyl]-7-methyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one
2-[(2,4-dimethylphenoxy)methyl]-7-methyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one
2-[(2-bromophenoxy)methyl]-7-methyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one
2-[(2-chlorophenoxy)methyl]-7-methyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one
2-[(2-fluorophenoxy)methyl]-7-methyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one
2-[(3-bromophenoxy)methyl]-7-methyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one
2-[(3-chlorophenoxy)methyl]-7-methyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one
2-[(3-fluorophenoxy)methyl]-7-methyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one
2-[(4-bromophenoxy)methyl]-7-methyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one
2-[(4-chloro-3-methylphenoxy)methyl]-7-methyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one
2-[(4-chlorophenoxy)methyl]-7-methyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one
2-[(4-fluorophenoxy)methyl]-7-methyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one
2-[(4-methoxyphenoxy)methyl]-7-methyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one
2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylic acid
-
i.e. febuxostat, TEI-6720, or TMX-67, mixed-type inhibition of both the oxidized and reduced form of xanthine oxidase
2-[[(3,6,7-trihydroxy-9-oxo-9H-xanthen-1-yl)oxy]methyl]benzonitrile
-
-
3,3',4,4'-Tetrahydroxychalcone
-
-
3,4-di-O-caffeoylquinic acid methyl ester
-
reversible inhibition, IC50: 0.0036 mM
3,4-Dihydroxybenzaldehyde
-
mixed type inhibition, 50% inhibition at 0.0568 mM
3,5-di-O-caffeoylquinic acid
-
-
3,6,7-trihydroxy-1-[(2-methylbenzyl)oxy]-9H-xanthen-9-one
-
-
3,6,7-trihydroxy-1-[(2-nitrobenzyl)oxy]-9H-xanthen-9-one
-
-
3,6,7-trihydroxy-1-[(3-methylbenzyl)oxy]-9H-xanthen-9-one
-
-
3,6,7-trihydroxy-1-[(3-nitrobenzyl)oxy]-9H-xanthen-9-one
-
-
3,6,7-trihydroxy-1-[(4-methylbenzyl)oxy]-9H-xanthen-9-one
-
-
3,6,7-trihydroxy-1-[(4-nitrobenzyl)oxy]-9H-xanthen-9-one
-
-
3-coumaric acid
-
competitively inhibits the enzyme by binding to the active site, have a protective effect against reactive oxygen species in cells, structure-function relationship, computational molecular docking, overview
3-methoxycinnamic acid
-
competitively inhibits the enzyme by binding to the active site, have a protective effect against reactive oxygen species in cells, structure-function relationship, computational molecular docking, overview
3-[[(3,6,7-trihydroxy-9-oxo-9H-xanthen-1-yl)oxy]methyl]benzonitrile
-
-
4'-methylether robustaflavone
-
a flavone compound from Selaginellaceae with antiviral activity
4,5-di-O-caffeoylquinic acid
-
-
4,5-di-O-caffeoylquinic acid methyl ester
-
reversible inhibition
4-(2-bromophenyl)-1-(9-ethyl-9H-carbazol-3-yl)-3-phenylazetidin-2-one