Information on EC 1.4.3.4 - monoamine oxidase and Organism(s) Mus musculus and UniProt Accession Q64133

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Mus musculus
UNIPROT: Q64133


The taxonomic range for the selected organisms is: Mus musculus

The enzyme appears in selected viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.4.3.4
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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 mechanism of C-H bond cleavage, overview
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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
aromatic biogenic amine degradation (bacteria)
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dopamine degradation
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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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noradrenaline and adrenaline degradation
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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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Glycine, serine and threonine metabolism
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Arginine and proline metabolism
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Histidine metabolism
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Tyrosine metabolism
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Phenylalanine metabolism
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Tryptophan metabolism
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Isoquinoline alkaloid biosynthesis
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Drug metabolism - cytochrome P450
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Metabolic pathways
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Biosynthesis of secondary metabolites
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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
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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the first step of the bioactivation of the Parkinsonian-inducing pro-neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, MPTP, is catalyzed by MAO-B, resulting in the ultimate product, 1-methyl-4-phenylpyridinium, a mitochondrial toxin that causes selective degeneration of nigrostriatal dopaminergic neurons in humans and experimental animals
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
kynuramine + H2O + O2
3-(2-aminophenyl)-3-oxopropanal + NH3 + H2O2
show the reaction diagram
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?
1-methyl-3-(4-chlorophenyl)-3-pyrroline + H2O + O2
?
show the reaction diagram
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?
1-methyl-3-phenyl-3-pyrroline + H2O + O2
1-methyl-3-phenylpyrrole + NH3 + H2O2
show the reaction diagram
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oxidation is a 2-electron process. Rapid clearance of 1-methyl-3-phenylpyrrole from the brain may contribute to their lack of neurotoxicity
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?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + H2O + O2
1-methyl-4-phenylpyridinium + NH3 + H2O2
show the reaction diagram
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the parkinsonian inducing agent 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine is oxidized to 1-methyl-4-phenylpyridinium MPP+, a 4-electron oxidation product and a potent mitochondrial toxin
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?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + 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
monoamine oxidase B
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?
dopamine + H2O + O2
(3,4-dihydroxyphenyl)acetaldehyde + NH3 + H2O2
show the reaction diagram
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?
kynuramine + H2O + O2
3-(2-aminophenyl)-3-oxopropanal + NH3 + H2O2
show the reaction diagram
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?
methoxytryptamine + H2O + O2
?
show the reaction diagram
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?
tryptamine + H2O + O2
?
show the reaction diagram
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?
additional information
?
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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
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1-methyl-4-phenylpyridinium is the ultimate product
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?
5-methoxy-N,N-dimethyltryptamine + H2O + O2
?
show the reaction diagram
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i.e. 5-MeO-DMT, a psychoactive indolealkylamine drug found in a variety of plant preparations, e.g. Virola snuffs and Ayahuasca, and venom of psychoactive toads, e.g. Colorado River Bufo alvarius. 5-MeO-DMT is known as a nonselective 5-HT receptor agonist. MAO-A eliminates the drug 5-MeO-DMT through oxidative deamination
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?
dopamine + H2O + O2
(3,4-dihydroxyphenyl)acetaldehyde + NH3 + H2O2
show the reaction diagram
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?
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
FAD
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covalently bound at the active site
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2E,4E)-5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienamide
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i.e. guineensine, isolated from dried fruits of Piper longum, competitive inhibition
(2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide
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i.e. methylpiperate, isolated from dried fruits of Piper longum, competitive inhibition
(2E,4E)-5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienamide
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i.e. guineensine, isolated from dried fruits of Piper longum, competitive inhibition
(2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide
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i.e. methylpiperate, isolated from dried fruits of Piper longum, competitive inhibition
(E)-8-(3-chlorostyryl)caffeine
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reversible MAO-B inhibitor, a dual-target-directed drug inhibiting MAO-B and antagonizing A2A receptors
(E)-8-styrylcaffeine
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reversible MAO-B inhibitor, a dual-target-directed drug inhibiting MAO-B and antagonizing A2A receptors
5-fluoro-alpha-methyltryptamine
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a drug causing head-twitch response, IC50: 0.00018 mM
5-fluorotryptamine
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a drug causing head-twitch response, IC50: 0.00018 mM
6-fluoro-alpha-methyltryptamine
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a drug causing head-twitch response, IC50: 0.00018 mM
6-fluorotryptamine
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a drug causing head-twitch response, IC50: 0.00018 mM
8-(3-chlorostyryl)caffeine
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monoamine oxidase B
Caffeine
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a dual-target-directed drug inhibiting MAO-B and antagonizing A2A receptors
Harmaline
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KF-17837
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a dual-target-directed drug inhibiting MAO-B and antagonizing A2A receptors
KW-6002
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a dual-target-directed drug inhibiting MAO-B and antagonizing A2A receptors
[(E)-1,3-dipropyl-7-methyl-8-(2-(3-thienyl)ethenyl)]xanthine
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a dual-target-directed drug inhibiting MAO-B and antagonizing A2A receptors
additional information
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.021 - 0.0635
1-methyl-3-(4-chlorophenyl)-3-pyrroline
0.125 - 0.461
1-methyl-3-phenyl-3-pyrroline
0.0521 - 0.797
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
additional information
additional information
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0235
(2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide
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inhibition of MAO-A
0.0013
(2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide
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inhibition of MAO-B
0.000032
5-fluoro-alpha-methyltryptamine
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0.0016
6-fluoro-alpha-methyltryptamine
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0.0002
8-(3-chlorostyryl)caffeine
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monoamine oxidase B
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.139
(2E,4E)-5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienamide
Mus musculus;
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inhibition of MAO-A
0.0271
(2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide
Mus musculus;
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inhibition of MAO-A
0.0016 - 0.139
(2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide
0.00018
5-fluoro-alpha-methyltryptamine
Mus musculus;
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a drug causing head-twitch response, IC50: 0.00018 mM
0.00018
5-fluorotryptamine
Mus musculus;
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a drug causing head-twitch response, IC50: 0.00018 mM
0.00018
6-fluoro-alpha-methyltryptamine
Mus musculus;
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a drug causing head-twitch response, IC50: 0.00018 mM
0.00018
6-fluorotryptamine
Mus musculus;
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a drug causing head-twitch response, IC50: 0.00018 mM
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.4
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assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
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assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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monoamine oxidase A promoter is regulated by the circadian-clock components BMAL1, NPAS2, and PER2. A mutation in the clock gene Per2 in mice leads to reduced expression and activity of MAOA in the mesolimbic dopaminergic system
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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both MAO A and MAO B are membrane-associated enzymes that are located specifically to the outer mitochondrial membrane
Manually annotated by BRENDA team
PDB
SCOP
CATH
UNIPROT
ORGANISM
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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construction of transgenic mice lacking monoamine oxidase A. The mice exhibit about 3fold higher rates of central sleep apnea than wild-types, linked to enhanced 5-hydroxytryptamine levels. Acute ondansetron and fluoxetine, and 13-day chronic fluoxetine decreas by 80% the total apnea index in the mutant mice during non-rapid eye movement sleep, with no statistically significant effect on apnea in C3H mice. Our study shows that both drugs reduce the frequency of apneic episodes attributable to increased monoamine levels in this model of MAOA deficiency, phenotypes, detailed overview
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
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MAOA deficiency is associated with increased sleep apnea in mice and suggest that an acute or chronic excess of serotonin contributes to this phenotype
medicine