Information on EC 1.4.3.4 - monoamine oxidase

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The expected taxonomic range for this enzyme is: Eukaryota

EC NUMBER
COMMENTARY hide
1.4.3.4
-
RECOMMENDED NAME
GeneOntology No.
monoamine oxidase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
RCH2NHR' + H2O + O2 = RCHO + R'NH2 + H2O2
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Deamination
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oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Arginine and proline metabolism
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aromatic biogenic amine degradation (bacteria)
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Biosynthesis of secondary metabolites
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dopamine degradation
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Drug metabolism - cytochrome P450
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Glycine, serine and threonine metabolism
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Histidine metabolism
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Isoquinoline alkaloid biosynthesis
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L-phenylalanine degradation IV (mammalian, via side chain)
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L-tryptophan degradation VI (via tryptamine)
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L-tryptophan degradation X (mammalian, via tryptamine)
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melatonin degradation II
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Metabolic pathways
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noradrenaline and adrenaline degradation
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Phenylalanine metabolism
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putrescine degradation III
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salidroside biosynthesis
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serotonin degradation
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tryptophan metabolism
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Tryptophan metabolism
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Tyrosine metabolism
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SYSTEMATIC NAME
IUBMB Comments
amine:oxygen oxidoreductase (deaminating)
A mitochondrial outer-membrane flavoprotein (FAD) that catalyses the oxidative deamination of neurotransmitters and biogenic amines [3]. Acts on primary amines, and also on some secondary and tertiary amines. It differs from EC 1.4.3.21, primary-amine oxidase as it can oxidize secondary and tertiary amines but not methylamine. This enzyme is inhibited by acetylenic compounds such as chlorgyline, 1-deprenyl and pargyline but, unlike EC 1.4.3.21 and EC 1.4.3.22 (diamine oxidase), it is not inhibited by semicarbazide.
CAS REGISTRY NUMBER
COMMENTARY hide
9001-66-5
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
cultivar Miechikara
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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
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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
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
of Turku strain
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Manually annotated by BRENDA team
white leghorn
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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
European lamprey
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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
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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
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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
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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
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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
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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
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Manually annotated by BRENDA team
female scrapie-infected hamsters
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
American mink, several isozymes
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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
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UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
MAO-A
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Manually annotated by BRENDA team
Wistar
SwissProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
-
monoamine oxidase are key role enzymes in the catabolism of amines like dopamine, norepinephrine, epinephrine, serotonin, and 2-phenylethylamine
physiological function
additional information
-
zMAO exhibits no immuno-chemical cross-reactivity with polyclonal anti-sera raised against human MAO-A
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(1R,6S)-3-methyl-6-phenyl-3-aza-bicyclo[4.1.0]heptane + H2O + O2
?
show the reaction diagram
-
MAO-B catalyzed ring alpha-carbon oxidation of 3-methyl-6-phenyl-3-aza-bicyclo[4.1.0]heptane is enantioselective with an almost 5fold preference for the (1R,6S) enantiomer based on Vmax/Km values
-
-
?
(1S,6R)-3-methyl-6-phenyl-3-azabicyclo[4.1.0]heptane + H2O + O2
?
show the reaction diagram
-
MAO-B catalyzed ring alpha-carbon oxidation of 3-methyl-6-phenyl-3-aza-bicyclo[4.1.0]heptane is enantioselective with an almost 5fold preference for the (1R,6S) enantiomer based on Vmax/Km values
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-
?
1,4-dibenzyl-1-cyclopropyl-1,2,3,6-tetrahydropyridine
?
show the reaction diagram
-
-
-
-
?
1-(4-bromophenyl)methanamine + H2O + O2
4-bromobenzaldehyde + NH3 + H2O2
show the reaction diagram
1-(4-chlorophenyl)methanamine + H2O + O2
4-chlorobenzaldehyde + NH3 + H2O2
show the reaction diagram
1-(4-fluorophenyl)methanamine + H2O + O2
4-fluorobenzaldehyde + NH3 + H2O2
show the reaction diagram
1-(4-methoxyphenyl)methanamine + H2O + O2
4-methoxybenzaldehyde + NH3 + H2O2
show the reaction diagram
1-(4-methylphenyl)methanamine + H2O + O2
4-methylbenzaldehyde + NH3 + H2O2
show the reaction diagram
1-methyl-3-(4-chlorophenyl)-3-pyrroline + H2O + O2
?
show the reaction diagram
1-methyl-3-phenyl-3-pyrroline + H2O + O2
1-methyl-3-phenylpyrrole + NH3 + H2O2
show the reaction diagram
1-methyl-4-(1-methylpyrrol-2-yl)-1,2,3,6-tetrahydropyridine + H2O + O2
?
show the reaction diagram
1-methyl-4-(1-methylpyrrol-2-yl)1,2,3,6-tetrahydropyridine + H2O + O2
?
show the reaction diagram
-
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + H2O + O2
1-methyl-4-phenyl-2,3-dihydropyridinium + 1-methyl-4-phenylpyridinium
show the reaction diagram
-
activation of the neurotoxin to neurotoxic pyridinium cations
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + H2O + O2
1-methyl-4-phenyl-2,3-dihydropyridinium + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + H2O + O2
1-methyl-4-phenylpyridinium + NH3 + H2O2
show the reaction diagram
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + H2O + O2
?
show the reaction diagram
1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine + H2O + O2
?
show the reaction diagram
-
-
-
?
1-methylhistamine + H2O + O2
1-methyl-1H-imidazol-4-ylacetaldehyde + NH3 + H2O2
show the reaction diagram
reaction with MAO-B at 1 mM substrate, no activity at 0.1 mM substrate
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-
?
1-methylhistamine + H2O + O2
?
show the reaction diagram
reaction with MAO-A at 1 mM substrate, no activity at 0.1 mM substrate
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?
1-methylhistamine + O2 + H2O
1-methyl-1H-imidazol-4-ylacetaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
?
1-[4-(trifluoromethyl)phenyl]methanamine + H2O + O2
4-(trifluoromethyl)benzaldehyde + NH3 + H2O2
show the reaction diagram
2 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + 2 H2O + 3 O2
1-methyl-4-phenyl-2,3-dihydropyridinium + 1-methyl-4-phenylpyridinium + 4 H2O2
show the reaction diagram
-
activation of the neurotoxin to neurotoxic pyridinium cations. MPTP easily crosses the blood-brain barrier and is preferentially metabolized by MAO-B present in glial cells to 1-methyl-4-phenyl-2,3-dihydropyridinium. This enzymatic metabolite is subsequently oxidized to 1-methyl-4-phenylpyridinium, which is selectively uptaken by dopaminergic cells, producing inhibition of complex I of mitochondria, energy depletion, oxidative stress and cell death
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine is metabolically oxidized by alpha-carbon oxidation by MAO enzymes to give 1-methyl-4-phenyl-2,3-dihydropyridinium and hydrogen peroxide, which, in a further step, is readily oxidized to 1-methyl-4-phenylpyridinium, that is a directly-acting neurotoxic substance
-
?
2-phenylethylamine + H2O + O2
2-phenylacetaldehyde + NH3 + H2O2
show the reaction diagram
-
the enzyme shows high substrate specificity for phenethylamine (100% activity)
-
-
?
2-phenylethylamine + H2O + O2
2-phenylethanal + NH3 + H2O2
show the reaction diagram
2-phenylethylamine + H2O + O2
?
show the reaction diagram
-
-
-
-
?
2-phenylethylamine + H2O + O2
phenylpyruvate + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
3-methyl-6-phenyl-3-aza-bicyclo[4.1.0]heptane + H2O + O2
?
show the reaction diagram
-
MAO-B selective substrate, no activity with MAO-A
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?
3-phenyl-3-pyrroline + H2O + O2
4-phenyl-2H-pyrrole + ?
show the reaction diagram
-
4-phenyl-2H-pyrrole rapidly tautomerizes to 5-phenyl-2H-pyrrole
-
?
3-phenylethylamine + H2O + O2
?
show the reaction diagram
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-
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?
3-phenylpropylamine + H2O + O2
3-phenylpropanal + NH3 + H2O2
show the reaction diagram
-
-
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?
3-pyrroline + 2,4,5-trihydroxyphenylalanine quinone + H2O + O2
? + H2O2 + NH3
show the reaction diagram
3-pyrrolines are mechanism-based inactivators of the quinone-dependent amine oxidases but only substrates of the flavin-dependent amine oxidases
-
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?
4-aminomethylpyridine dihydrochloride + H2O + O2
?
show the reaction diagram
4-carboxybenzylamine + H2O + O2
?
show the reaction diagram
-
-
-
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?
4-dimethylaminophenethylamine + H2O + O2
?
show the reaction diagram
-
substrate of MAO-B
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-
?
4-dimethylaminophenylethylamine + H2O + O2
?
show the reaction diagram
-
substrate of MAO-B
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?
4-phenylbutylamine + H2O + O2
4-phenylbutanal + NH3 + H2O2
show the reaction diagram
-
proposed pathways for amine oxidation: the amine substrate may bind to oxidised enzyme (E/FADox), leading to the release of product imine via a binary (1) or ternary (2) pathway. The relative contributions of these pathways cannot be determined directly by steady-state approaches. In following pathway 1, the unoccupied reduced enzyme (E/FADred) is generated, to which substrate may also bind. Reoxidation of the E/FADred–S species (pathway 3) bypasses direct regeneration of E/FADox, with the consequence that imine released subsequent to this step, whether through the binary or ternary pathways leading from E/FADred–imine, is a product of substrate binding to a second enzyme species
-
-
?
4-phenylbutylamine + H2O + O2
?
show the reaction diagram
-
-
-
-
?
4-tyramine + H2O + O2
4-hydroxyphenylacetaldehyde + NH3 + H2O2
show the reaction diagram
4-tyramine + H2O + O2
?
show the reaction diagram
5-hydroxytryptamine + H2O + O2
(5-hydroxy-1H-indol-3-yl)acetaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
5-hydroxytryptamine + H2O + O2
?
show the reaction diagram
-
-
-
-
?
5-methoxy-N,N-dimethyltryptamine + H2O O2
?
show the reaction diagram
benzylamine + H2O + O2
benzaldehyde + NH3 + H2O2
show the reaction diagram
benzylamine + H2O + O2
benzylaldehyde + NH3 + H2O2
show the reaction diagram
benzylamine + O2 + H2O
benzaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
?
beta-phenylethylamine + H2O + O2
2-phenylethanal + NH3 + H2O2
show the reaction diagram
beta-phenylethylamine + H2O + O2
beta-phenylethanal + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
beta-phenylethylamine + O2 + H2O
beta-phenylethanal + NH3 + H2O2
show the reaction diagram
-
-
-
?
dopamine + H2O + O2
(3,4-dihydroxyphenyl)acetaldehyde + NH3 + H2O2
show the reaction diagram
dopamine + H2O + O2
?
show the reaction diagram
-
-
-
-
?
epinephrine + H2O + O2
?
show the reaction diagram
-
-
-
-
?
ethanolamine + H2O + O2
glycolaldehyde + NH3 + H2O2
show the reaction diagram
-
50% activity compared to n-propylamine
-
-
?
ethylamine + H2O + O2
ethanal + NH3 + H2O2
show the reaction diagram
hexylamine + H2O + O2
hexanal + NH3 + H2O2
show the reaction diagram
-
7% activity compared to n-propylamine
-
-
?
histamine + H2O + O2
1H-imidazol-4-ylacetaldehyde + NH3 + H2O2
show the reaction diagram
histamine + H2O + O2
?
show the reaction diagram
histamine + O2 + H2O
1H-imidazol-4-ylacetaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
?
kynuramine + H2O + O2
3-(2-aminophenyl)-3-oxopropanal + NH3 + H2O2
show the reaction diagram
kynuramine + H2O + O2
4-hydroxyquinoline + NH3 + H2O2
show the reaction diagram
kynuramine + H2O + O2
?
show the reaction diagram
methoxytryptamine + H2O + O2
?
show the reaction diagram
methylamine + H2O + O2
formaldehyde + NH3 + H2O2
show the reaction diagram
-
34% activity compared to n-propylamine
-
-
?
n-butylamine + H2O + O2
butyraldehyde + NH3 + H2O2
show the reaction diagram
-
98% activity compared to n-propylamine
-
-
?
N-methylhistamine + H2O + O2
1H-imidazol-4-ylacetaldehyde + methylamine + H2O2
show the reaction diagram
n-pentylamine + H2O + O2
pentaldehyde + NH3 + H2O2
show the reaction diagram
-
56% activity compared to n-propylamine
-
-
?
n-propylamine + H2O + O2
propionaldehyde + NH3 + H2O2
show the reaction diagram
-
100% activity
-
-
?
noradrenaline + H2O + O2
?
show the reaction diagram
norepinephrine + H2O + O2
?
show the reaction diagram
-
-
-
-
?
p-nitrobenzylamine + H2O + O2
4-nitrobenzaldehyde + NH3 + H2O2
show the reaction diagram
p-nitrophenylethylamine + H2O + O2
4-nitrophenylacetaldehyde + NH3 + H2O2
show the reaction diagram
-
good substrate for wild-type and mutant enzymes Y435H, Y435F, Y435L and Y435W
-
-
?
p-trifluoromethyl-benzylamine + H2O + O2
4-trifluoromethylbenzaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
p-tyramine + H2O + O2
(4-hydroxyphenyl)acetaldehyde + NH3 + H2O2
show the reaction diagram
p-tyramine + H2O + O2
4-hydroxyphenylethanal + NH3 + H2O2
show the reaction diagram
phenylbutylamine + H2O + O2
2-phenylbutanal + NH3 + H2O2 + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
phenylethylamine + H2O + O2
2-phenylethanal + NH3 + H2O2
show the reaction diagram
phenylethylamine + H2O + O2
2-phenylethanal + NH3 + H2O2 + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
phenylethylamine + H2O + O2
phenylethanal + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
pyrrolidine + 2,4,5-trihydroxyphenylalanine quinone + H2O + O2
? + H2O2 + NH3
show the reaction diagram
-
-
-
?
RCH2NH2 + H2O + O2
RCHO + NH3 + H2O2
show the reaction diagram
serotonin + H2O + O2
(5-hydroxy-1H-indol-3-yl)acetaldehyde + NH3 + H2O
show the reaction diagram
-
-
-
-
?
serotonin + H2O + O2
(5-hydroxy-1H-indol-3-yl)acetaldehyde + NH3 + H2O2
show the reaction diagram
serotonin + O2 + H2O
(5-hydroxy-1H-indol-3-yl)acetaldehyde + NH3 + H2O2
show the reaction diagram
5-hydroxytryptamine, MAO-A
-
-
?
tryptamine + H2O + O2
(1H-indol-3-yl)acetaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
tryptamine + H2O + O2
1-H-indol-3-yl-acetaldehyde + NH3 + H2O2
show the reaction diagram
tryptamine + H2O + O2
1H-indol-3-yl-acetaldehyde + NH3 + H2O2
show the reaction diagram
tryptamine + H2O + O2
?
show the reaction diagram
-
-
-
-
?
tyramine + H2O + O2
(4-hydroxyphenyl)acetaldehyde + NH3 + H2O2
show the reaction diagram
tyramine + H2O + O2
4-hydroxyphenylethanal + NH3 + H2O2
show the reaction diagram
tyramine + H2O + O2
?
show the reaction diagram
tyramine + O2 + H2O
(4-hydroxyphenyl)acetaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
?
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-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + H2O + O2
?
show the reaction diagram
2 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + 2 H2O + 3 O2
1-methyl-4-phenyl-2,3-dihydropyridinium + 1-methyl-4-phenylpyridinium + 4 H2O2
show the reaction diagram
-
activation of the neurotoxin to neurotoxic pyridinium cations. MPTP easily crosses the blood-brain barrier and is preferentially metabolized by MAO-B present in glial cells to 1-methyl-4-phenyl-2,3-dihydropyridinium. This enzymatic metabolite is subsequently oxidized to 1-methyl-4-phenylpyridinium, which is selectively uptaken by dopaminergic cells, producing inhibition of complex I of mitochondria, energy depletion, oxidative stress and cell death
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine is metabolically oxidized by alpha-carbon oxidation by MAO enzymes to give 1-methyl-4-phenyl-2,3-dihydropyridinium and hydrogen peroxide, which, in a further step, is readily oxidized to 1-methyl-4-phenylpyridinium, that is a directly-acting neurotoxic substance
-
?
2-phenylethylamine + H2O + O2
2-phenylethanal + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
2-phenylethylamine + H2O + O2
?
show the reaction diagram
-
-
-
-
?
3-phenylethylamine + H2O + O2
?
show the reaction diagram
-
-
-
-
?
4-dimethylaminophenylethylamine + H2O + O2
?
show the reaction diagram
-
substrate of MAO-B
-
-
?
4-tyramine + H2O + O2
4-hydroxyphenylacetaldehyde + NH3 + H2O2
show the reaction diagram
-
in vivo activity, overview
-
-
?
5-hydroxytryptamine + H2O + O2
(5-hydroxy-1H-indol-3-yl)acetaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
5-methoxy-N,N-dimethyltryptamine + H2O O2
?
show the reaction diagram
benzylamine + H2O + O2
benzaldehyde + NH3 + H2O2
show the reaction diagram
benzylamine + H2O + O2
benzylaldehyde + NH3 + H2O2
show the reaction diagram
dopamine + H2O + O2
(3,4-dihydroxyphenyl)acetaldehyde + NH3 + H2O2
show the reaction diagram
dopamine + H2O + O2
?
show the reaction diagram
-
-
-
-
?
epinephrine + H2O + O2
?
show the reaction diagram
-
-
-
-
?
histamine + H2O + O2
1H-imidazol-4-ylacetaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
histamine + H2O + O2
?
show the reaction diagram
-
-
-
-
?
kynuramine + H2O + O2
3-(2-aminophenyl)-3-oxopropanal + NH3 + H2O2
show the reaction diagram
noradrenaline + H2O + O2
?
show the reaction diagram
-
-
-
-
?
norepinephrine + H2O + O2
?
show the reaction diagram
-
-
-
-
?
phenylethylamine + H2O + O2
2-phenylethanal + NH3 + H2O2
show the reaction diagram
RCH2NH2 + H2O + O2
RCHO + NH3 + H2O2
show the reaction diagram
serotonin + H2O + O2
(5-hydroxy-1H-indol-3-yl)acetaldehyde + NH3 + H2O2
show the reaction diagram
tryptamine + H2O + O2
(1H-indol-3-yl)acetaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
tryptamine + H2O + O2
1-H-indol-3-yl-acetaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
tyramine + H2O + O2
(4-hydroxyphenyl)acetaldehyde + NH3 + H2O2
show the reaction diagram
tyramine + H2O + O2
?
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
8alpha-S-cysteinyl-FAD
-
1 mol per mol of enzyme
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Cu2+