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

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     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:
Mus musculus
UNIPROT: Q64133
Word Map
The taxonomic range for the selected organisms is: Mus musculus
The enzyme appears in selected viruses and cellular organisms
Reaction Schemes
Synonyms
mao-b, mao-a, monoamine oxidase a, mao a, mao b, monoamine oxidase b, monoamine oxidase-b, monoamine oxidase-a, semicarbazide-sensitive amine oxidase, monoamine oxidase type b, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
adrenaline oxidase
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epinephrine oxidase
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MAO
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-
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MAO A
MAO B
MAO-A
MAO-B
monoamine oxidase
monoamine oxidase A
monoamine oxidase B
monoamine oxidase-A
244
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monoamine:O2 oxidoreductase (deaminating)
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serotonin deaminase
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tyraminase
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tyramine oxidase
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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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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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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
-
-
-
-
?
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
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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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-
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-
?
kynuramine + H2O + O2
3-(2-aminophenyl)-3-oxopropanal + NH3 + H2O2
show the reaction diagram
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-
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-
?
methoxytryptamine + H2O + O2
?
show the reaction diagram
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-
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?
tryptamine + H2O + O2
?
show the reaction diagram
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?
additional information
?
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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
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + H2O + O2
?
show the reaction diagram
-
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
-
-
-
-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
FAD
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covalently bound at the active site
INHIBITOR
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
-
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
-
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
-
a drug causing head-twitch response, IC50: 0.00018 mM
0.00018
5-fluorotryptamine
Mus musculus
-
a drug causing head-twitch response, IC50: 0.00018 mM
0.00018
6-fluoro-alpha-methyltryptamine
Mus musculus
-
a drug causing head-twitch response, IC50: 0.00018 mM
0.00018
6-fluorotryptamine
Mus musculus
-
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
-
assay at
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
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
-
both MAO A and MAO B are membrane-associated enzymes that are located specifically to the outer mitochondrial membrane
Manually annotated by BRENDA team
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
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
Sequence
AOFA_MOUSE
526
0
59602
Swiss-Prot
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
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
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Nakagawasai, O.; Arai, Y.; Satoh, S.e.; Satoh, N.; Neda, M.; Hozumi, M.; Oka, R.; Hiraga, H.; Tadano, T.
Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives
Neurotoxicology
25
223-232
2004
Mus musculus
Manually annotated by BRENDA team
Hubalek, F.; Binda, C.; Khalil, A.; Li, M.; Mattevi, A.; Castagnoli, N.; Edmondson, D.E.
Demonstration of isoleucine 199 as a structural determinant for the selective inhibition of human monoamine oxidase B by specific reversible inhibitors
J. Biol. Chem.
280
15761-15766
2005
Bos taurus, Bos taurus (P56560), Equus caballus, Homo sapiens, Homo sapiens (P21397), Homo sapiens (P27338), Mus musculus, Mus musculus (Q8BW75), Ovis aries, Rattus norvegicus (P19643)
Manually annotated by BRENDA team
Carpene, C.; Daviaud, D.; Boucher, J.; Bour, S.; Visentin, V.; Gres, S.; Duffaut, C.; Fontana, E.; Testar, X.; Saulnier-Blache, J.S.; Valet, P.
Short- and long-term insulin-like effects of monoamine oxidases and semicarbazide-sensitive amine oxidase substrates in cultured adipocytes
Metab. Clin. Exp.
55
1397-1405
2006
Mus musculus
Manually annotated by BRENDA team
Bortolato, M.; Chen, K.; Shih, J.C.
Monoamine oxidase inactivation: From pathophysiology to therapeutics
Adv. Drug Deliv. Rev.
60
1527-1533
2008
Homo sapiens (P21397), Homo sapiens (P27338), Mus musculus (Q64133)
Manually annotated by BRENDA team
Vishnivetskaya, G.B.; Skrinskaya, J.A.; Seif, I.; Popova, N.K.
Effect of MAO A deficiency on different kinds of aggression and social investigation in mice
Aggress. Behav.
33
1-6
2007
Mus musculus, Mus musculus (Q64133)
Manually annotated by BRENDA team
Hampp, G.; Ripperger, J.A.; Houben, T.; Schmutz, I.; Blex, C.; Perreau-Lenz, S.; Brunk, I.; Spanagel, R.; Ahnert-Hilger, G.; Meijer, J.H.; Albrecht, U.
Regulation of monoamine oxidase A by circadian-clock components implies clock influence on mood
Curr. Biol.
18
678-683
2008
Mus musculus, Mus musculus (Q64133)
Manually annotated by BRENDA team
Ogunrombi, M.O.; Malan, S.F.; TerreBlanche, G.; Castagnoli, K.; Castagnoli, N.; Bergh, J.J.; Petzer, J.P.
Neurotoxicity studies with the monoamine oxidase B substrate 1-methyl-3-phenyl-3-pyrroline
Life Sci.
81
458-467
2007
Bos taurus (P56560), Mus musculus, Mus musculus (Q8BW75), Papio sp.
Manually annotated by BRENDA team
He, X.J.; Uetsuka, K.; Nakayama, H.
Neural progenitor cells are protected against MPTP by MAO-B inhibitors
Neurotoxicology
29
1141-1146
2008
Mus musculus (Q8BW75)
Manually annotated by BRENDA team
Real, C.; Popa, D.; Seif, I.; Callebert, J.; Launay, J.M.; Adrien, J.; Escourrou, P.
Sleep apneas are increased in mice lacking monoamine oxidase A
Sleep
30
1295-1302
2007
Mus musculus (Q64133)
Manually annotated by BRENDA team
Lee, S.A.; Hwang, J.S.; Han, X.H.; Lee, C.; Lee, M.H.; Choe, S.G.; Hong, S.S.; Lee, D.; Lee, M.K.; Hwang, B.Y.
Methylpiperate derivatives from Piper longum and their inhibition of monoamine oxidase
Arch. Pharm. Res.
31
679-683
2008
Mus musculus, Mus musculus (Q64133), Mus musculus (Q8BW75)
Manually annotated by BRENDA team
Petzer, J.P.; Castagnoli, N.; Schwarzschild, M.A.; Chen, J.F.; Van der Schyf, C.J.
Dual-target-directed drugs that block monoamine oxidase B and adenosine A(2A) receptors for Parkinsons disease
Neurotherapeutics
6
141-151
2009
Homo sapiens (P27338), Mus musculus
Manually annotated by BRENDA team
Real, C.; Seif, I.; Adrien, J.; Escourrou, P.
Ondansetron and fluoxetine reduce sleep apnea in mice lacking monoamine oxidase A
Respir. Physiol. Neurobiol.
168
230-238
2009
Mus musculus
Manually annotated by BRENDA team
Shen, H.W.; Wu, C.; Jiang, X.L.; Yu, A.M.
Effects of monoamine oxidase inhibitor and cytochrome P450 2D6 status on 5-methoxy-N,N-dimethyltryptamine metabolism and pharmacokinetics
Biochem. Pharmacol.
80
122-128
2010
Homo sapiens, Mus musculus
Manually annotated by BRENDA team
Edmondson, D.E.; Binda, C.; Wang, J.; Upadhyay, A.K.; Mattevi, A.
Molecular and mechanistic properties of the membrane-bound mitochondrial monoamine oxidases
Biochemistry
48
4220-4230
2009
Bos taurus, Homo sapiens, Mus musculus, Rattus norvegicus
Manually annotated by BRENDA team
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