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Information on EC 1.4.3.4 - monoamine oxidase and Organism(s) Danio rerio and UniProt Accession Q6NSN2

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EC Tree
     1 Oxidoreductases
         1.4 Acting on the CH-NH2 group of donors
             1.4.3 With oxygen as acceptor
                1.4.3.4 monoamine oxidase
IUBMB Comments
A mitochondrial outer-membrane flavoprotein (FAD) that catalyses the oxidative deamination of neurotransmitters and biogenic amines . 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.
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This record set is specific for:
Danio rerio
UNIPROT: Q6NSN2
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The taxonomic range for the selected organisms is: Danio rerio
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Reaction Schemes
hide
RCH2NHR'
+
H2O
+
O2
=
RCHO
+
R'NH2
+
H2O2
+
+
=
+
+
Synonyms
monoamine oxidase, mao-b, mao-a, monoamine oxidase a, mao a, mao b, monoamine oxidase b, monoamine oxidase-b, monoamine oxidase-a, semicarbazide-sensitive amine oxidase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
adrenaline oxidase
-
-
-
-
epinephrine oxidase
-
-
-
-
monoamine oxidase
-
-
-
-
monoamine:O2 oxidoreductase (deaminating)
-
-
-
-
serotonin deaminase
-
-
-
-
tyraminase
-
-
-
-
tyramine oxidase
-
-
-
-
zMAO
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Deamination
-
-
-
-
redox reaction
-
-
-
-
oxidation
-
-
-
-
reduction
-
-
-
-
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
-
SUBSTRATE
PRODUCT                       
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-1,2,5,6-tetrahydropyridine + H2O + O2
?
show the reaction diagram
-
-
-
?
dopamine + H2O + O2
(3,4-dihydroxyphenyl)acetaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
?
phenylethylamine + H2O + O2
2-phenylethanal + NH3 + H2O2
show the reaction diagram
-
-
-
?
serotonin + H2O + O2
(5-hydroxy-1H-indol-3-yl)acetaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
?
tyramine + H2O + O2
(4-hydroxyphenyl)acetaldehyde + NH3 + H2O2
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-[4-(trifluoromethyl)phenyl]methanamine + H2O + O2
4-(trifluoromethyl)benzaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
2-phenylethylamine + H2O + O2
2-phenylethanal + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
4-carboxybenzylamine + H2O + O2
?
show the reaction diagram
-
-
-
-
?
4-phenylbutylamine + H2O + O2
?
show the reaction diagram
-
-
-
-
?
benzylamine + H2O + O2
benzaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
dopamine + H2O + O2
(3,4-dihydroxyphenyl)acetaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
kynuramine + H2O + O2
3-(2-aminophenyl)-3-oxopropanal + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
kynuramine + O2
4-hydroxyquinoline + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
serotonin + H2O + O2
(5-hydroxy-1H-indol-3-yl)acetaldehyde + NH3 + H2O2
show the reaction diagram
tyramine + H2O + O2
(4-hydroxyphenyl)acetaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
3-aminomethylpyridine is not a substrate
-
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
benzylamine + H2O + O2
benzaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
dopamine + H2O + O2
(3,4-dihydroxyphenyl)acetaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
kynuramine + H2O + O2
3-(2-aminophenyl)-3-oxopropanal + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
serotonin + H2O + O2
(5-hydroxy-1H-indol-3-yl)acetaldehyde + NH3 + H2O2
show the reaction diagram
tyramine + H2O + O2
(4-hydroxyphenyl)acetaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Clorgyline
complete inhibition at 0.01 mM
Deprenyl
complete inhibition at 0.01 mM
8-(3-chlorostyryl)-caffeine
-
-
D-amphetamine
-
-
Deprenyl
-
inhibits the enzyme in vivo by 34-70% depending on the age, reversible by 4-chlorophenylalanine. Deprenyl administration decreases locomotion, altered vertical positioning and increased heart rate in larvae in vivo, 4-chlorophenylalanine normalizes serotonin levels and rescues the behavioral alteration
Harmane
-
-
methylene blue
-
-
pirlindole mesylate
-
-
tetrindole mesylate
-
-
additional information
-
not inhibited by D-amphetamine, farnesol, safinamide, 1,4-diphenyl-1,3-butadiene, and 1,4-diphenyl-2-butene
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.103
1-(4-bromophenyl)methanamine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
0.094
1-(4-chlorophenyl)methanamine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
0.161
1-(4-fluorophenyl)methanamine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
0.0555
1-(4-methoxyphenyl)methanamine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
0.0678
1-(4-methylphenyl)methanamine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
0.115
1-[4-(trifluoromethyl)phenyl]methanamine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
86
2-Phenylethylamine
-
pH 7.4, 25°C
0.076
4-carboxybenzylamine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
0.185
4-phenylbutylamine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
0.0822 - 82
benzylamine
0.088
dopamine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
0.058
kynuramine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
0.108 - 0.14
O2
0.069
serotonin
-
at 25°C in 50 mM potassium phosphate, pH 7.4
0.018
tyramine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.67
1-(4-bromophenyl)methanamine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
0.58
1-(4-chlorophenyl)methanamine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
0.25
1-(4-fluorophenyl)methanamine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
0.14
1-(4-methoxyphenyl)methanamine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
0.12
1-(4-methylphenyl)methanamine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
1.57
1-[4-(trifluoromethyl)phenyl]methanamine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
3.4
2-Phenylethylamine
-
pH 7.4, 25°C
0.088
4-carboxybenzylamine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
2.07
4-phenylbutylamine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
0.078 - 0.08
benzylamine
4.03
dopamine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
1.25
kynuramine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
0.093 - 5.4
O2
3.12
serotonin
-
at 25°C in 50 mM potassium phosphate, pH 7.4
7.78
tyramine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.4
2-Phenylethylamine
-
pH 7.4, 25°C
0.0095
benzylamine
-
pH 7.4, 25°C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0024
8-(3-chlorostyryl)-caffeine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
0.038
D-amphetamine
-
at 25°C in 50 mM potassium phosphate, pH 7.4
0.013
Harmane
-
at 25°C in 50 mM potassium phosphate, pH 7.4
0.000004
methylene blue
-
at 25°C in 50 mM potassium phosphate, pH 7.4
0.0024
pirlindole mesylate
-
at 25°C in 50 mM potassium phosphate, pH 7.4
0.0341
tetrindole mesylate
-
at 25°C in 50 mM potassium phosphate, pH 7.4
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.243
brain enzyme
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.4
-
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
-
assay at
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
SwissProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
MAO expression and activity are located in or adjacent to serotonergic nuclei and their targets especially in the ventral hypothalamus
Manually annotated by BRENDA team
-
MAO expression and activity are located in or adjacent to serotonergic nuclei and their targets especially in the ventral hypothalamus
Manually annotated by BRENDA team
-
development of MAO expression follows a similar time course as the serotonin system
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
zMAO exhibits no immuno-chemical cross-reactivity with polyclonal anti-sera raised against human MAO-A
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
AOF_DANRE
522
0
58765
Swiss-Prot
other Location (Reliability: 2)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
58525
-
x * 58525, mass spectrometry, x * 60000, recombinant enzyme, SDS-PAGE
60000
-
x * 58525, mass spectrometry, x * 60000, recombinant enzyme, SDS-PAGE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
-
x * 58525, mass spectrometry, x * 60000, recombinant enzyme, SDS-PAGE
additional information
-
zMAO peptide mapping using tryptic digestion, overview
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant zMAO from Pichia pastoris mitochondria to homogeneity from membranes by treatment with phospholipase A and Triton X-100, ultracentrifugation, and hydroxyapatite chromatography
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Pichia pastoris
-
functional expression of zMAO in Pichia pastoris mitochondria with the gene encoding zMAO under control of the methanol oxidase promotor
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
Ni2+ and Pb2+ reduce the expression of MAO in brain after exposure over 24 h and 72 h, overview
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Anichtchik, O.; Sallinen, V.; Peitsaro, N.; Panula, P.
Distinct structure and activity of monoamine oxidase in the brain of zebrafish (Danio rerio)
J. Comp. Neurol.
498
593-610
2006
Danio rerio (Q6NSN2), Danio rerio
Manually annotated by BRENDA team
Senatori, O.; Setini, A.; Scirocco, A.; Nicotra, A.
Effect of short-time exposures to nickel and lead on brain monoamine oxidase from Danio rerio and Poecilia reticulata
Environ. Toxicol.
24
309-313
2009
Poecilia reticulata (Q0PGS2), Poecilia reticulata, Danio rerio (Q6NSN2), Danio rerio
Manually annotated by BRENDA team
Sallinen, V.; Sundvik, M.; Reenilae, I.; Peitsaro, N.; Khrustalyov, D.; Anichtchik, O.; Toleikyte, G.; Kaslin, J.; Panula, P.
Hyperserotonergic phenotype after monoamine oxidase inhibition in larval zebrafish
J. Neurochem.
109
403-415
2009
Danio rerio, Danio rerio Turku
Manually annotated by BRENDA team
Arslan, B.K.; Edmondson, D.E.
Expression of zebrafish (Danio rerio) monoamine oxidase (MAO) in Pichia pastoris: purification and comparison with human MAO A and MAO B
Protein Expr. Purif.
70
290-297
2010
Danio rerio
Manually annotated by BRENDA team
Aldeco, M.; Arslan, B.K.; Edmondson, D.E.
Catalytic and inhibitor binding properties of zebrafish monoamine oxidase (zMAO): comparisons with human MAO A and MAO B
Comp. Biochem. Physiol. B
159
78-83
2011
Danio rerio
Manually annotated by BRENDA team