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Information on EC 1.2.3.1 - aldehyde oxidase
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1.2.3.1 aldehyde oxidaseIUBMB Comments
Contains molybdenum, [2Fe-2S] centres and FAD. The enzyme from liver exhibits a broad substrate specificity, and is involved in the metabolism of xenobiotics, including the oxidation of N-heterocycles and aldehydes and the reduction of N-oxides, nitrosamines, hydroxamic acids, azo dyes, nitropolycyclic aromatic hydrocarbons, and sulfoxides [4,6].
The enzyme is also responsible for the oxidation of retinal, an activity that was initially attributed to a distinct enzyme (EC 1.2.3.11, retinal oxidase) [5,7].
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Word Map
- 1.2.3.1
- xanthine
- molybdenum
- allopurinol
- oxidases
- menadione
- benzaldehyde
-
abscisic
- n-oxide
-
n-heterocyclic
- moco
- phthalazine
- raloxifene
-
molybdenum-containing
-
xanthinuria
- hydralazine
-
oxidase-mediated
-
drug-drug
-
molybdoenzymes
- sulphite
- o6-benzylguanine
- molybdopterin
-
flavin-containing
- disulfiram
- n1-methylnicotinamide
- oxypurinol
- nutrition
- medicine
-
hypouricemia
-
amidoxime
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oxidase-catalyzed
- pharmacology
- synthesis
- degradation
- cyp2a6
-
nitroreduction
- imidacloprid
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neonicotinoids
- phenanthridine
The enzyme appears in viruses and cellular organisms
Synonyms
aldehyde oxidase, aldehyde oxidase 1, retinal oxidase, formate oxidase, maox3, atraaox2, aldehyde oxidase 3, aldehyde oxidase 2, aldehyde:oxygen oxidoreductase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
Aao4
AHO2
aldehyde oxidase 1
aldehyde oxidase 2
aldehyde oxidase 3
aldehyde oxidase 4
ALOD
AO
AO1
AO2
AO3
AOH1
AOH2
AOH3
AOX
AOX1
AOX2
AOX3
AOX4
EC 1.2.3.11
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-
formerly
-
FOD
formate oxidase
mAOX3
quinoline oxidase
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-
-
-
Retinal oxidase
retinene oxidase
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-
-
-
Retinal oxidase
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-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
an aldehyde + H2O + O2 = a carboxylate + H2O2
-
-
-
-
an aldehyde + H2O + O2 = a carboxylate + H2O2
base catalyzed mechanism. Residue E1265 acts as an active site base that abstracts a proton from the Mo-OH group, which in turn undertakes a nucleophilic attack on the substrate benzaldehyde. After hydride transfer to the Mo= S group, the initial intermediate breaks down, with the transient formation of a paramagnetic MoV species, followed by displacement of product by a water molecule to return to the starting LMoVIOS(OH) state. The roles of residues Met884 and Val806 are stabilization of substrate binding
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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-
-
-
redox reaction
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-
-
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reduction
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-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
aldehyde:oxygen oxidoreductase
Contains molybdenum, [2Fe-2S] centres and FAD. The enzyme from liver exhibits a broad substrate specificity, and is involved in the metabolism of xenobiotics, including the oxidation of N-heterocycles and aldehydes and the reduction of N-oxides, nitrosamines, hydroxamic acids, azo dyes, nitropolycyclic aromatic hydrocarbons, and sulfoxides [4,6].
The enzyme is also responsible for the oxidation of retinal, an activity that was initially attributed to a distinct enzyme (EC 1.2.3.11, retinal oxidase) [5,7].
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CAS REGISTRY NUMBER
COMMENTARY
9029-07-6
-
9033-52-7
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(+)-4-(4-cyanoanilino)-5,6-dihydro-7-hydroxy-7H-cyclopenta-[d]-pyrimidine + H2O + O2
?
-
i.e. (S)-RS-8359
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-
?
(+)-4-(4-cyanoanilino)-5,6-dihydro-7-hydroxy-7H-cyclopenta[d]-pyrimidine + H2O + O2
?
-
i.e. (S)-RS-8359
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-
?
(+)-biotin (+)-sulfoxide methyl ester + acetaldehyde + H2O
?
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under anaerobic conditions
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-
?
(+/-)-4-(4-cyanoanilino)-5,6-dihydro-7-hydroxy-7H-cyclopenta-[d]-pyrimidine + H2O + O2
?
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i.e. RS-8359
-
-
?
(1S)-camphor oxime + H2O + 2-hydroxypyrimidine
(1S)-camphor + (1S)-camphor imine + NH3
-
other electron acceptors are N-methylnicotinamide, butyraldehyde and benzaldehyde
the corresponding ketimine is an intermediate
?
(S)-4-(4-cyanoanilino)-5,6-dihydro-7-hydroxy-7H-cyclopenta[d]-pyrimidine + H2O + O2
? + H2O2
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i.e. S-8359
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-
?
(Z)-11-hexadecenal + H2O + O2
(Z)-11-hexadecenoic acid + H2O2
-
-
-
-
?
(Z)-9-tetradecenal + H2O + O2
(Z)-9-tetradecenoic acid + H2O2
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-
-
-
?
1-methoxy-2-naphthaldehyde + H2O + O2
1-methoxy-2-naphthoic acid + H2O2
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-
-
-
?
1-naphthaldehyde + H2O + O2
1-naphthalene carboxylic acid + H2O2
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-
-
?
2,4-dihydroxybenzaldehyde + H2O + O2
2,4-dihydroxybenzoate + H2O2
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-
-
?
2-fluoro-N-methyl-4-[7-(6-quinolinylmethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzamide + H2O + O2
?
-
i.e. c-met inhibitor capmatinib
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-
?
2-methyl-E-2-butenal + H2O + O2
2-methyl-E-2-butenoic acid + H2O2
-
-
-
?
2-[(6-[[6-(1-methyl-1H-pyrazol-4-yl)[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl)amino]ethan-1-ol + H2O + O2
? + H2O2
3 brimonidine + 4 H2O + 4 O2
2-oxobrimonidine + 3-oxobrimonidine + 2,3-dioxobrimonidine + 4 H2O2
3,4-dihydroxybenzaldehyde + H2O + O2
3,4-dihydroxybenzoate + H2O2
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38.2% of the rate with benzaldehyde
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-
?
3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine N-oxide + electron donor
3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine + an electron acceptor
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electron donors are 2-hydroxypyrimidine, N1-methylnicotinamide, benzaldehyde or butyraldehyde under anaerobic conditions
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-
?
3-methoxy-2-naphthaldehyde + H2O + O2
3-methoxy-2-naphthoic acid + H2O2
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-
-
-
?
3-methoxy-4-hydroxybenzaldehyde + H2O + O2
3-methoxy-4-hydroxybenzoate + H2O2
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-
-
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?
4-(dimethylamino)cinnamaldehyde + H2O + O2
4-(dimethylamino)cinnamic acid + H2O2
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-
-
?
4-(dimethylamino)cinnamaldehyde + nitrite + H2O + O2
? + nitric oxide
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in the presence of typical aldehyde substrates like 4-(dimethylamino)cinnamaldehyde or NADH, aldehyde oxidase reduces nitrite to nitric oxide
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?
4-hydroxyl-2-nonenal + H2O + O2
4-hydroxy-2-nonenoate + H2O2
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-
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?
4-hydroxypyrazolo(3,4-d)pyrimidine + O2 + H2O
4,6-dihydroxypyrazolo(3,4-d)pyrimidine + H2O2
4-hydroxypyrimidine + H2O + O2
?
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ferricyanide as electron acceptor under aerobic conditions
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-
?
4-nitrobenzaldehyde + H2O + O2
4-nitrobenzoate + H2O2
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-
-
?
5-bromo-N-(4,5-dihydro-1H-imidazol-2-yl)-6-quinoxalinamine + H2O + O2
?
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i.e. brimonidine
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-
?
5-nitroquinoline + H2O + O2
2-oxo-5-nitroquinoline + 5-aminoquinoline + 2-oxo-5-aminoquinoline
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-
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?
6-chloroquinazolin-4(3H)-one + H2O + O2
6-chloroquinazoline-2,4(1H,3H)-dione + H2O2
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-
-
-
?
6-dimethyloamino-2-naphthaldehyde + H2O + O2
6-dimethylamino-2-naphthoic acid + H2O2
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-
-
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?
6-ethyl-5H-dibenz(c,e)azepine + H2O + O2
?
-
2,6-dichlorophenol-indophenol as electron acceptor
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-
?
6-methoxy-2-naphthaldehyde + H2O + O2
6-methoxy-2-naphthoic acid + H2O2
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-
-
-
?
6-methoxyquinazolin-4(3H)-one + H2O + O2
6-methoxyquinazoline-2,4(1H,3H)-dione + H2O2
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-
-
-
?
6-methylquinazolin-4(3H)-one + H2O + O2
6-methylquinazoline-2,4(1H,3H)-dione + H2O2
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-
-
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?
6-methylthiopurine + H2O + O2
6-methylthio-8-hydroxypurine + H2O2
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2,6-dichlorophenol indophenol can also act as electron acceptor
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-
?
6-[[6-(1-methyl-1H-pyrazol-4-yl)[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]-N-(oxetan-3-yl)quinolin-3-amine + H2O + O2
? + H2O2
6-[[6-(1-methyl-1H-pyrazol-4-yl)[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]-N-(oxolan-3-yl)quinolin-3-amine + H2O + O2
? + H2O2
6-[[6-(1-methyl-1H-pyrazol-4-yl)[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]-N-[(oxolan-3-yl)methyl]quinolin-3-amine + H2O + O2
? + H2O2
6-[[6-(1-methyl-1H-pyrazol-4-yl)[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinoline + H2O + O2
? + H2O2
7-methoxy-1-naphthaldehyde + H2O + O2
7-methoxy-2-naphthoic acid + H2O2
-
-
-
-
?
acetamiprid + H2O + O2
? + H2O2
-
i.e. (1E)-N-[(6-chloropyridin-3-yl)methyl]-N'-cyano-N-methylethanimidamide, enzyme system coupled with Drosophila nicotinic acetylcholine receptor, little inactivation of neonicotinoid insecticide substrate
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-
?
acrolein + H2O + O2
?
results indicate that AtraAOX2 also functions as a xenobiotic-degrading enzyme
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-
?
allopurinol + H2O + 2,6-dichlorophenolindophenol
? + reduced 2,6-dichlorophenolindophenol
-
-
-
?
anthracene-9-carboxaldehyde + H2O + O2
anthracene-9-carboxylate + H2O2
-
-
-
-
?
benzaldehyde + 2,6-dichlorophenol indophenol
?
natural electron acceptor of enzyme is molecular oxygen, DCPIP i.e., 2,6-dichlorophenol indophenol
-
-
?
benzaldehyde + H2O + 2,6-dichlorophenolindophenol
benzoate + reduced 2,6-dichlorophenolindophenol
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-
-
?
benzamidoxime + H2O + 2-hydroxypyrimidine
benzamidine + ?
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other electron acceptors are N-methylnicotinamide, butyraldehyde and benzaldehyde
-
-
?
BIBX1382 + H2O + O2
BIBU1476 + ?
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high hepatic clearance of 17 to 18 ml/(min * kg)
product identification by high-resolution mass spectrometry
-
?
carbazeran + H2O + O2
carbazeran phthalazinone + ?
-
high hepatic clearance of 17 to 18 ml/(min * kg)
product identification by high-resolution mass spectrometry
-
?
chloroacetaldehyde + H2O + O2
chloroacetic acid + H2O2
-
2,6-dichlorophenol-indophenol as electron acceptor
-
-
?
cis-5-fluoro-2-methyl-1-[p-(methylsulfinyl)benzylindenyl]indene-3-acetic acid + electron acceptor + H2O
5-fluoro-2-methyl-1-[p-(methylthio)benzylindenyl]indene-3-acetic acid + ?
clothianidin + H2O + O2
? + H2O2
-
i.e. (2E)-2-[([(2-chloro-1,3-thiazol-5-yl)methyl]amino)(methylamino)methylene]-1-hydroxy-1-oxodiazanium, enzyme system coupled with Drosophila nicotinic acetylcholine receptor, strong inactivation of neonicotinoid insecticide substrate
-
-
?
clothianidin + NMNH
nitroso-clothianidin + amino-clothianidin + ?
-
-
-
-
?
desmethyl-thiamethoxam + H2O + O2
? + H2O2
-
i.e. (4E)-3-[(2-chloro-1,3-thiazol-5-yl)methyl]-N-nitro-1,3,5-oxadiazinan-4-imine, enzyme system coupled with Drosophila nicotinic acetylcholine receptor, strong inactivation of neonicotinoid insecticide substrate
-
-
?
dibenzyl sulfoxide + acetaldehyde + H2O
?
-
under anaerobic conditions
-
-
?