Information on EC 1.4.3.4 - monoamine oxidase and Organism(s) Homo sapiens

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Homo sapiens


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The enzyme appears in selected viruses and cellular organisms

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
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
metabolism
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monoamine oxidase are key role enzymes in the catabolism of amines like dopamine, norepinephrine, epinephrine, serotonin, and 2-phenylethylamine
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
(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
-
-
?
1-methyl-4-(1-methylpyrrol-2-yl)-1,2,3,6-tetrahydropyridine + H2O + O2
?
show the reaction diagram
-
i.e. MMTP, is oxidized to the corresponding dihydropyridinium metabolite, MMDP+
-
-
?
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
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-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + H2O + O2
?
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-phenylethanal + NH3 + H2O2
show the reaction diagram
2-phenylethylamine + H2O + O2
?
show the reaction diagram
-
-
-
-
?
3-(4-(3-aminopropoxy)butoxy)-N-(thiophen-2-ylmethyl)propan-1-amine + H2O + O2
3-(4-[3-[(thiophen-2-ylmethyl)amino]propoxy]butoxy)propanal + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
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/FADredS 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/FADredimine, is a product of substrate binding to a second enzyme species
-
-
?
4-tyramine + H2O + O2
(4-hydroxyphenyl)acetaldehyde + NH3 + H2O2
show the reaction diagram
4-tyramine + H2O + O2
2-(4-hydroxyphenyl)acetaldehyde + NH3 + H2O2
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-methoxy-N,N-dimethyltryptamine + 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
dopamine + H2O + O2
?
show the reaction diagram
-
-
-
-
?
epinephrine + H2O + O2
?
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
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-
-
-
?
N1-(thiophen-2-ylmethyl)dodecane-1,12-diamine + H2O + O2
12-[(thiophen-2-ylmethyl)amino]dodecanal + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
N1-benzyl-N1-methyldodecane-1,12-diamine + H2O + O2
12-[benzyl(methyl)amino]dodecanal + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
N1-benzyldodecane-1,12-diamine + H2O + O2
12-(benzylamino)dodecanal + NH3 + H2O2
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
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-
?
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
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-
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?
phenylbutylamine + H2O + O2
2-phenylbutanal + NH3 + H2O2 + NH3 + H2O2
show the reaction diagram
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-
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?
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
-
-
-
-
?
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
-
-
-
?
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
-
-
-
-
?
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
-
1-methyl-4-phenylpyridinium is the ultimate product
-
-
?
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
?
show the reaction diagram
-
-
-
-
?
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
-
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
-
-
?
benzylamine + H2O + O2
benzaldehyde + 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
-
-
-
-
?
kynuramine + H2O + O2
3-(2-aminophenyl)-3-oxopropanal + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
norepinephrine + H2O + O2
?
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
tyramine + H2O + O2
?
show the reaction diagram
-
-
-
-
?
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
8alpha-S-cysteinyl-FAD
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1 mol per mol of enzyme
flavin
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-amphetamine
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reversible competitive inhibitor
(+/-)-6-hydroxytrypargine
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an indolylalkaloid toxin enzyme inhibitor from the venom of the colonial spider Parawixia bistriata, synthesized by reaction of 5-hydroxytryptamine hydrochloride with N-(3-[1,3]dioxolan-2-yl-propyl)-guanidine sulfate, overview
(1E,2E)-3-(furan-2-yl)-N-(prop-2-yn-1-yl)prop-2-en-1-imine
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(1R,2R)-(-)-psi-ephedrine
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IC50 for soluble enzyme: 5.03 mM, IC50 for immobilized enzyme: 88 mM, monoamine oxidase B; IC50 for soluble enzyme: 5.35 mM, IC50 for immobilized enzyme: 14.86 mM, monoamine oxidase A
(1S,2S)-(+)-psi-ephedrine
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IC50 for soluble enzyme: 0.88 mM, IC50 for immobilized enzyme: 1.77 mM, monoamine oxidase A; IC50 for soluble enzyme: 10 mM, IC50 for immobilized enzyme: 234 mM, monoamine oxidase B
(1Z)-2-methylcyclohexanone (4-phenyl-1,3-thiazol-2-yl)hydrazone
-
pKi: 7.39
(2-methylprop-2-en-1-yl)hydrazine
-
;
(2-phenylprop-2-en-1-yl)hydrazine
-
;
(2E)-1,3-diphenylprop-2-en-1-one
-
-
(2E)-1-(2-hydroxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
-
-
(2E)-1-(2-hydroxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl)-3-(4-methylphenyl)prop-2-en-1-one
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(2E)-1-(2-hydroxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl)-3-phenylprop-2-en-1-one
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(2E)-1-(4-methoxyphenyl)-3-[2-(trifluoromethyl)phenyl]prop-2-en-1-one
-
competitive inhibition
-
(2E)-1-(4-methoxyphenyl)-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one
-
; competitive inhibition
-
(2E)-1-[4-(benzyloxy)phenyl]-3-(4-chlorophenyl)prop-2-en-1-one
-
-
(2E)-2-(2,4-dioxo-1,3-thiazolidin-5-ylidene)-N-(3-hydroxyphenyl)ethanamide
-
-
(2E)-2-(2,4-dioxo-1,3-thiazolidin-5-ylidene)-N-phenylethanamide
-
-
(2E)-3-(2-fluorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
-
competitive inhibition
-
(2E)-3-(3-chlorophenyl)-N-(2-methyl-1H-indol-5-yl)prop-2-enamide
-
-
(2E)-3-(3-fluorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
-
competitive inhibition
-
(2E)-3-(4-chlorophenyl)-1-(2,4-dihydroxyphenyl)prop-2-en-1-one
-
inhibits MAO-A and MAO-B
(2E)-3-(4-chlorophenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
-
-
(2E)-3-(4-chlorophenyl)-1-(2-hydroxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl)prop-2-en-1-one
-
-
(2E)-3-(4-chlorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
-
-
(2E)-3-(4-chlorophenyl)-1-(4-fluoro-2-hydroxyphenyl)prop-2-en-1-one
-
-
(2E)-3-(4-chlorophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one
-
-
(2E)-3-(4-chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
-
-
(2E)-3-(4-fluorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
-
competitive inhibition
-
(2E)-3-[4-(benzyloxy)phenyl]-1-(2-hydroxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl)prop-2-en-1-one
-
-
(2E)-3-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)prop-2-en-1-one
-
-
(2E)-3-[4-(benzyloxy)phenyl]-1-(4-methoxyphenyl)prop-2-en-1-one
-
-
(2E)-N-(2-methyl-1H-indol-5-yl)-3-phenylprop-2-enamide
-
-
(2E,6E)-farnesol
-
-
(2S)-2-[4-(3-fluorobenzyloxy)benzylamino]propionamide
-
i.e. safinamide, a potent selective and reversible MAO-B inhibitor, occurs in two polymorphic forms. Both forms are orthorhombic and regarded as conformational polymorphs due to the differences in the orientation of the 3-fluorobenzyloxy and propanamide groups. Both structures pack with layers in the ac plane, structure overview
(3E)-7-hydroxy-3-[(4-methoxyphenyl)methylidene]-2,3-dihydro-4H-1-benzopyran-4-one
-
-
(5E)-3-(2-aminoethyl)-5-(2-methoxybenzylidene)-1,3-thiazolidine-2,4-dione
-
-
(5E)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)-1,3-thiazolidine-2,4-dione
-
-
(5E)-3-(2-aminoethyl)-5-[4-(dimethylamino)benzylidene]-1,3-thiazolidine-2,4-dione
-
-
(5E)-5-(3-bromobenzylidene)-1,3-thiazolidine-2,4-dione
-
-
(5E)-5-(4-chlorobenzylidene)-3-methyl-2-thioxo-1,3-thiazolidin-4-one
-
-
(5E)-5-(4-hydroxy-2,5-dimethoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
-
-
(5E)-5-(4-hydroxy-3-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
-
-
(5E)-5-(quinoxalin-6-ylmethylidene)-1,3-thiazolidine-2,4-dione
-
-
(5E)-5-benzylidene-2-imino-1,3-thiazolidin-4-one
-
-
(5E)-5-benzylidene-3-methyl-2-thioxo-1,3-thiazolidin-4-one
-
-
(5E)-5-[(3,5-dibromo-4-hydroxycyclohexa-1,4-dien-1-yl)methylidene]-1,3-thiazolidine-2,4-dione
-
-
(5R)-3-(3-fluoro-4-morpholin-4-ylphenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one
-
-
(5R)-3-[3-fluoro-4-(4-pyrazin-2-ylpiperazin-1-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one
-
-
(5R)-3-[4-(4-bromo-1H-imidazol-1-yl)-3-fluorophenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one
-
-
(5R,5'R)-3,3'-[1,4-diazepane-1,4-diylbis(3-fluorobenzene-4,1-diyl)]bis[5-(hydroxymethyl)-1,3-oxazolidin-2-one]
-
IC50: 0.001mM, at 0.15 mM kynuramine
(5S)-5-(aminomethyl)-3-(3-fluoro-4-morpholin-4-ylphenyl)-1,3-oxazolidin-2-one
-
-
(5S)-5-(aminomethyl)-3-[3-fluoro-4-(4-pyrazin-2-ylpiperazin-1-yl)phenyl]-1,3-oxazolidin-2-one
-
-
(5S)-5-(aminomethyl)-3-[4-(4-bromo-1H-imidazol-1-yl)-3-fluorophenyl]-1,3-oxazolidin-2-one
-
-
(5Z)-3-(2-aminoethyl)-5-(2-methoxybenzylidene)-1,3-thiazolidine-2,4-dione
-
L136468, binding mode, overview
(5Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)-1,3-thiazolidine-2,4-dione
-
A6355
(5Z)-3-(2-aminoethyl)-5-[4-(dimethylamino)benzylidene]-1,3-thiazolidine-2,4-dione
-
L136662
(5Z)-5-(quinoxalin-6-ylmethylidene)-1,3-thiazolidine-2,4-dione
-
AS605240, binding mode, overview
(aminomethyl)trimethylsilane
-
-
(E)-1-(2,3-dimethoxy-6-methylphenyl)-N-(prop-2-yn-1-yl)methanimine
-
-
(E)-1-(2,3-dimethylphenyl)-N-(prop-2-yn-1-yl)methanimine
-
-
(E)-1-(2-chloro-4-fluorophenyl)-N-(prop-2-yn-1-yl)methanimine
-
-
(E)-1-(2-chloroquinolin-3-yl)-N-(prop-2-yn-1-yl)methanimine
-
-
(E)-1-(4-methoxy-2,3-dimethylphenyl)-N-(prop-2-yn-1-yl)methanimine
-
-
(E)-1-(4-phenoxyphenyl)-N-(prop-2-yn-1-yl)methanimine
-
-
(E)-1-(5-bromo-2-methoxyphenyl)-N-(prop-2-yn-1-yl)methanimine
-
-
(E)-1-phenyl-N-(prop-2-yn-1-yl)methanimine
-
-
(E)-3-(2-methoxybenzylidene)-7-(6-(1,2,3,4-tetrahydroacridin-9-ylamino)hexyloxy)chroman-4-one
-
-
(E)-3-(3,4-dimethoxybenzylidene)-7-(6-(1,2,3,4-tetrahydroacridin-9-ylamino)hexyloxy)chroman-4-one
-
-
(E)-3-(3-methoxybenzylidene)-7-(6-(1,2,3,4-tetrahydroacridin-9-ylamino)hexyloxy)chroman-4-one
-
-
(E)-3-(4-(diethylamino)benzylidene)-7-(6-(1,2,3,4-tetrahydroacridin-9-ylamino)hexyloxy)chroman-4-one
-
-
(E)-3-(4-(dimethylamino)benzylidene)-7-(6-(1,2,3,4-tetrahydroacridin-9-ylamino)hexyloxy)chroman-4-one
-
-
(E)-3-(4-chlorobenzylidene)-7-(6-(1,2,3,4-tetrahydroacridin-9-ylamino)hexyloxy)chroman-4-one
-
-
(E)-3-(4-fluorobenzylidene)-7-(6-(1,2,3,4-tetrahydroacridin-9-ylamino)hexyloxy)chroman-4-one
-
-
(E)-3-(4-methoxybenzylidene)-7-(10-(1,2,3,4-tetrahydroacridin-9-ylamino)hexyloxy)chroman-4-one
-
-
(E)-3-(4-methoxybenzylidene)-7-(5-(1,2,3,4-tetrahydroacridin-9-ylamino)pentyloxy)chroman-4-one
-
-
(E)-3-(4-methoxybenzylidene)-7-(6-(1,2,3,4-tetrahydroacridin-9-ylamino)hexyloxy)chroman-4-one
-
-
(E)-3-(4-methoxybenzylidene)-7-(8-(1,2,3,4-tetrahydroacridin-9-ylamino)hexyloxy)chroman-4-one
-
-
(E)-3-(4-methoxybenzylidene)-7-(9-(1,2,3,4-tetrahydroacridin-9-ylamino)hexyloxy)chroman-4-one
-
-
(E)-3-(4-methylbenzylidene)-7-(6-(1,2,3,4-tetrahydroacridin-9-ylamino)hexyloxy)chroman-4-one
-
-
(E)-3-chlorocinnamic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester
-
-
(E)-5-(3-chlorostyryl)isatin
-
;
(E)-5-(3-fluorostyryl)isatin
-
;
(E)-5-styrylisatin
-
;
(E)-6-styrylisatin
-
;
(E)-7-(6-(1,2,3,4-tetrahydroacridin-9-ylamino)hexyloxy)-3-(3,4,5-trimethoxybenzylidene)chroman-4-one
-
-
-
(E)-7-(6-(6-chloro-1,2,3,4-tetrahydroacridin-9-ylamino)hexyloxy)-3-(4-methoxybenzylidene)chroman-4-one
-
-
(E)-7-(8-(6-chloro-1,2,3,4-tetrahydroacridin-9-ylamino)hexyloxy)3-(4-methoxybenzylidene)chroman-4-one
-
-
(E)-8-(3-chlorostyryl)caffeine
(E)-8-styrylcaffeine
-
reversible MAO-B inhibitor, a dual-target-directed drug inhibiting MAO-B and antagonizing A2A receptors
(E)-cinnamic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester
-
-
(E)-N-(prop-2-yn-1-yl)-1-(3,4,5-trimethoxyphenyl)methanimine
-
-
(E)-N-(prop-2-yn-1-yl)-1-[4-(pyridin-2-yl)phenyl]methanimine
-
-
(N-cyclopropyl-alpha-methylbenzylamine)
-
the inhibitor forms an adduct that allows reoxidation of the flavin on denaturation
(R)-2-[(2E)-2-(2-methylcyclohexylidene)hydrazinyl]-4-(4-nitrophenyl)-1,3-thiazole
-
-
(R)-4-(2,4-difluorophenyl)-2-[(2E)-2-(2-methylcyclohexylidene)hydrazinyl]-1,3-thiazole
-
-
(R)-4-(4-fluorophenyl)-2-[(2E)-2-(2-methylcyclohexylidene)hydrazinyl]-1,3-thiazole
-
-
(R)-4-[2-[(2E)-2-(2-methylcyclohexylidene)hydrazinyl]-1,3-thiazol-4-yl]benzonitrile
-
-
(R)-amphetamine
-
IC50 for soluble enzyme: 0.0311 mM, IC50 for immobilized enzyme: 0.0991 mM, monoamine oxidase A; IC50 for soluble enzyme: 0.246 mM, IC50 for immobilized enzyme: 4.03 mM, monoamine oxidase B
(R)-deprenyl
(R,S)-amphetamine
-
IC50 for soluble enzyme: 0.0031 mM, IC50 for immobilized enzyme: 0.0244 mM, monoamine oxidase A; IC50 for soluble enzyme: 0.0625 mM, IC50 for immobilized enzyme: 3 mM, monoamine oxidase B
(S)-2-[(2E)-2-(2-methylcyclohexylidene)hydrazinyl]-4-(4-nitrophenyl)-1,3-thiazole
-
-
(S)-4-(2,4-difluorophenyl)-2-[(2E)-2-(2-methylcyclohexylidene)hydrazinyl]-1,3-thiazole
-
-
(S)-4-(4-fluorophenyl)-2-[(2E)-2-(2-methylcyclohexylidene)hydrazinyl]-1,3-thiazole
-
-
(S)-4-[2-[(2E)-2-(2-methylcyclohexylidene)hydrazinyl]-1,3-thiazol-4-yl]benzonitrile
-
-
(Z)-3-fluoro-2-(4-methoxybenzyl)allylamine hydrochloride
i.e. LJP 1586. Potent, specific, and orally available inhibitor of SSAO activity is an effective anti-inflammatory compound in vivo; i.e. LJP 1586. Potent, specific, and orally available inhibitor of SSAO activity is an effective anti-inflammatory compound in vivo
1,2,3,4-tetrahydroacridin-9-amine
-
-
1,3,7-trimethyl-8-([3-(trifluoromethyl)benzyl]oxy)-3,7-dihydro-1H-purine-2,6-dione
-
-
1,3,7-trimethyl-8-[(3-methylbenzyl)oxy]-3,7-dihydro-1H-purine-2,6-dione
-
-
1,3-dimethyl-5-nitro-1H-indazole
-
-
1,4-diphenyl-1,3-butadiene
1,4-diphenyl-2-butene
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-((1H-indol-3-yl)-methylene)-hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(1-(coumarin-3-yl)-ethylidene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(1-(furan-2-yl)ethylidene)-hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(1-(naphthalen-2-yl)ethylidene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(1-(pyridin-2-yl)-ethylidene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(1-(pyridin-3-yl)-ethylidene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(1-(pyridin-4-yl)-ethylidene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(1-(thiophen-2-yl)-ethylidene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(2-methylcyclohexylidene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(2-methylcyclopentylidene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(3-methylcyclohexylidene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(3-methylcyclopentylidene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(4-methylcyclohexylidene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(benzodioxol-5-ylmethylene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(furan-2-ylmethylene)-hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(furan-2-ylmethylene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(heptan-2-ylidene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(naphthalen-1-ylmethylene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(octan-2-ylidene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(pentan-2-ylidene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(pentan-3-ylidene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(propan-2-ylidene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(pyridin-3-ylmethylene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(pyridin-4-ylmethylene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(thiophen-2-ylmethylene)hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-cycloheptylidene-hydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-cyclohexylidenehydrazine
-
-
1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-cyclopentylidenehydrazine
-
-
1-(4-chlorobutyl)-5-nitro-1H-indazol-3-ol
-
-
1-(4-guanidinobutoxy)-6-hydroxy-1,2,3,4-tetrahydro-beta-carboline
-
an indolylalkaloid toxin enzyme inhibitor from the venom of the colonial spider Parawixia bistriata
1-(N-methylthiocarbamoyl)-3-(3-methoxyphenyl)-4,5-dihydropyrazole
-
-
1-(N-methylthiocarbamoyl)-3-(3-methylphenyl)-4,5-dihydropyrazole
-
-
1-(N-methylthiocarbamoyl)-3-(4-chlorophenyl)-4-methyl-4,5-dihydropyrazole
-
-
1-(N-methylthiocarbamoyl)-3-(4-fluorophenyl)-4,5-dihydropyrazole
-
-
1-(N-methylthiocarbamoyl)-3-(4-methoxyphenyl)-4,5-dihydropyrazole
-
-
1-(N-methylthiocarbamoyl)-3-(4-methoxyphenyl)-4-methyl-4,5-dihydropyrazole
-
-
1-(N-methylthiocarbamoyl)-3-(4-methylphenyl)-4,5-dihydropyrazole
-
-
1-benzyl-5-nitro-1H-indazol-3-ol
-
-
1-guanidino-6-hydroxy-3,5-dihydro-beta-carboline
-
an indolylalkaloid toxin enzyme inhibitor from the venom of the colonial spider Parawixia bistriata
1-methyl-4-phenylpyridinium
-
-
1-methyl-5-nitro-1H-indazol-3-ol
-
inhibits MAO-B by 34% at 0.015 mM
1-methyl-N-(2-methyl-1H-indol-5-yl)-1lambda4-pyridine-3-carboxamide
-
-
1-O-n-octyl-beta-D-glucopyranoside
-
at concentrations well below the critical micelle concentration
1-phenylcyclopropylamine
-
the inhibitor forms an irreversible flavin adduct
1-thiocarbamoyl-3-(4-methoxyphenyl)-4,5-dihydropyrazole
-
-
1-thiocarbamoyl-3-(4-methoxyphenyl)-4-methyl-4,5-dihydropyrazole
-
-
1-thiocarbamoyl-3-(4-methylphenyl)-4,5-dihydropyrazole
-
-
2,2'-dipyridyl disulfide
-
-
2,4-dichloro-N'-(nonan-5-yl)benzohydrazide
-
-
2,4-dichlorobenzaldehyde (4-methyl-1,3-thiazol-2-yl)hydrazone
-
pKi: 7.92
2,4-dichlorobenzaldehyde (4-phenyl-1,3-thiazol-2-yl)hydrazone
-
pKi: 7.03
2,4-dimethoxy-5-hydroxybenzaldehyde
-
IC50: 0.042 mM, monoamine oxidase A; IC50: 0.39 mM
2,6-dimethoxyphenol
-
IC50: 0.0624 mM, monoamine oxidase A; IC50: above 0.5 mM, monoamine oxidase B
2-(2,4-dichlorophenyl)-4-(nonan-5-yl)-4H-1,3,4-oxadiazin-5(6H)-one
-
-
2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(3-hydroxyphenyl)acetamide
-
6164872
2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-phenylacetamide
-
6163851
2-(2-benzofuranyl)-2-imidazoline
-
at micromolar concentrations, to a site distinct from the active site on at least two forms of the pure enzyme, probably corresponding to oxidised and reduced enzyme states
2-(2-chlorophenyl)-4-(nonan-5-yl)-4H-1,3,4-oxadiazin-5(6H)-one
-
-
2-(2-cycloheptylidenehydrazinyl)-4-(2,4-dichlorophenyl)-1,3-thiazole
-
-
2-(2-cycloheptylidenehydrazinyl)-4-(2,4-difluorophenyl)-1,3-thiazole
-
-
2-(2-cycloheptylidenehydrazinyl)-4-(4-fluorophenyl)-1,3-thiazole
-
-
2-(2-cycloheptylidenehydrazinyl)-4-(4-methoxyphenyl)-1,3-thiazole
-
-
2-(2-cycloheptylidenehydrazinyl)-4-(4-methylphenyl)-1,3-thiazole
-
-
2-(2-cycloheptylidenehydrazinyl)-4-(4-nitrophenyl)-1,3-thiazole
-
-
2-(2-cycloheptylidenehydrazinyl)-4-phenyl-1,3-thiazole
-
-
2-(2-cyclohexylidenehydrazinyl)-4-(2,4-difluorophenyl)-1,3-thiazole
-
-
2-(2-cyclohexylidenehydrazinyl)-4-(4-fluorophenyl)-1,3-thiazole
-
-
2-(2-cyclohexylidenehydrazinyl)-4-(4-methoxyphenyl)-1,3-thiazole
-
-
2-(2-cyclohexylidenehydrazinyl)-4-(4-methylphenyl)-1,3-thiazole
-
-
2-(2-cyclohexylidenehydrazinyl)-4-(4-nitrophenyl)-1,3-thiazole
-
-
2-(2-cyclohexylidenehydrazinyl)-4-phenyl-1,3-thiazole
-
-
2-(2-cyclopentylidenehydrazinyl)-4-(2,4-dichlorophenyl)-1,3-thiazole
-
-
2-(2-cyclopentylidenehydrazinyl)-4-(2,4-difluorophenyl)-1,3-thiazole
-
-
2-(2-cyclopentylidenehydrazinyl)-4-(4-fluorophenyl)-1,3-thiazole
-
-
2-(2-cyclopentylidenehydrazinyl)-4-(4-methoxyphenyl)-1,3-thiazole
-
-
2-(2-cyclopentylidenehydrazinyl)-4-(4-methylphenyl)-1,3-thiazole
-
-
2-(2-cyclopentylidenehydrazinyl)-4-(4-nitrophenyl)-1,3-thiazole
-
-
2-(2-cyclopentylidenehydrazinyl)-4-phenyl-1,3-thiazole
-
-
2-(2-ethoxylpyridin-3-yl)-4-(nonan-5-yl)-4H-1,3,4-oxadiazin-5(6H)-one
-
-
2-(3,4,5-trimethoxyphenyl)-4-(nonan-5-yl)-4H-1,3,4-oxadiazin-5(6H)-one
-
-
2-(3,5-dimethylphenyl)-4-(nonan-5-yl)-4H-1,3,4-oxadiazin-5(6H)-one
-
-
2-(3-methylphenyl)-4-(butoxycarbonylethyl)-4H-1,3,4-oxadiazin-5(6H)-one
-
-
2-(4'-benzyloxyphenyl)thiomorpholin-5-one
-
-
2-(4'-benzyloxyphenyl)thiomorpholine oxalate
-
-
2-(4'-butoxyphenyl)thiomorpholin-5-one
-
-
2-(4'-butoxyphenyl)thiomorpholine oxalate
-
-
2-(4'-ethoxyphenyl)thiomorpholin-5-one
-
-
2-(4'-ethoxyphenyl)thiomorpholine oxalate
-
-
2-(4'-methoxyphenyl)thiomorpholin-5-one
-
-
2-(4'-methoxyphenyl)thiomorpholine oxalate
-
-
2-(4'-propoxyphenyl)thiomorpholin-5-one
-
-
2-(4'-propoxyphenyl)thiomorpholine oxalate
-
-
2-(4,5-dihydroimidazol-2-yl)-isoquinoline
-
reversible non-competitive/mixed inhibitor
2-(4,5-dihydroimidazol-2-yl)-quinoline
-
reversible non-competitive/mixed inhibitor
2-(4-bromophenyl)cyclopropanamine
-
-
2-(4-chlorophenyl)-4-(nonan-5-yl)-4H-1,3,4-oxadiazin-5(6H)-one
-
-
2-(4-ethylphenyl)-4-(cyanoethyl)-4H-1,3,4-oxadiazin-5(6H)-one
-
-
2-(4-ethylphenyl)-4-(nonan-5-yl)-4H-1,3,4-oxadiazin-5(6H)-one
-
-
2-(4-fluorophenyl)-4-(cyanoethyl)-4H-1,3,4-oxadiazin-5(6H)-one
-
-
2-(4-methoxyphenyl)cyclopropanamine
-
-
2-(5,7-dibromobenzofuran-2-yl)-imidazoline
-
reversible non-competitive/mixed inhibitor
2-(aminooxy)-1-(3,4-dimethoxyphenyl)ethanol
-
;
2-(aminooxy)-1-phenylethanol
-
;
2-(benzo[d][1,3]dioxol-5-yl)-4-(nonan-5-yl)-4H-1,3,4-oxadiazin-5(6H)-one
-
-
2-(methyl[4-[(E)-(prop-2-yn-1-ylimino)methyl]phenyl]amino)ethanol
-
-
2-(naphthalen-1-yl)cyclopropanamine
-
-
2-(naphthalen-2-yl)-4-(nonan-5-yl)-4H-1,3,4-oxadiazin-5(6H)-one
-
-
2-(thiophen-3-yl)cyclopropanamine
-
-
2-chloro-5-[(E)-(prop-2-yn-1-ylimino)methyl]phenol
-
-
2-chloro-N'-(nonan-5-yl)benzohydrazide
-
-
2-ethoxy-6-[(E)-(prop-2-yn-1-ylimino)methyl]phenol
-
-
2-ethoxy-N'-(nonan-5-yl)nicotinohydrazide
-
-
2-methoxyphenol
-
IC50: 0.175 mM, monoamine oxidase A; IC50: above 0.5 mM, monoamine oxidase B
2-methyl-5-methylaniline
-
IC50: 0.15 mM, monoamine oxidase A; IC50: above 0.5 mM
2-methylbenzaldehyde (4-methyl-1,3-thiazol-2-yl)hydrazone
-
pKi: 7.45
2-methylbenzaldehyde (4-phenyl-1,3-thiazol-2-yl)hydrazone
-
pKi: 7.18
2-oxo-2H-chromen-7-yl benzenesulfonate
-
-
2-oxo-N-(2,3,5,6-tetrafluoropyridin-4-yl)-2H-chromene-3-carboxamide
-
-
2-oxo-N-(pentafluorophenyl)-2H-chromene-3-carboxamide
-
-
2-oxo-N-(propan-2-yl)-2H-chromene-3-carboxamide
-
-
2-oxo-N-[3-(trifluoromethyl)phenyl]-2H-chromene-3-carboxamide
-
-
2-oxo-N-[4-(propan-2-yl)phenyl]-2H-chromene-3-carboxamide
-
-
2-phenyl-4-(cyanoethyl)-4H-1,3,4-oxadiazin-5(6H)-one
-
-
2-phenylcyclopropylamine
-
the inhibitor forms an adduct that allows reoxidation of the flavin on denaturation
2-Phenylethylamine
-
time-dependent, slowly reversible suicide inhibition. Addition of 2-phenylethylamine (10mM) to the enzyme results in immediate bleaching of the absorbance peak at 460 nm, a consequence of rapid reduction of the flavin cofactor by 2-phenylethylamine at steady state
2-phenylthiomorpholin-5-one
-
-
2-phenylthiomorpholine oxalate
-
-
2-[(1E,3E)-4-(3-chlorophenyl)buta-1,3-dien-1-yl]-3,5,7-trimethyl-3H-imidazo[4,5-c]pyridine-4,6(5H,7H)-dione
-
-
2-[(2E)-2-(2-methylcyclohexylidene)hydrazinyl]-4-(4-methylphenyl)-1,3-thiazole
-
-
2-[(2E)-2-(2-methylcyclohexylidene)hydrazinyl]-4-(4-nitrophenyl)-1,3-thiazole
-
-
2-[(2E)-2-(2-methylcyclohexylidene)hydrazinyl]-4-phenyl-1,3-thiazole
-
-
2-[(E)-(prop-2-yn-1-ylimino)methyl]benzene-1,4-diol
-
-
2-[2-(4-methylcyclohexylidene)hydrazinyl]-4-(4-methylphenyl)-1,3-thiazole
-
-
2-[2-(4-methylcyclohexylidene)hydrazinyl]-4-(4-nitrophenyl)-1,3-thiazole
-
-
2-[2-(4-methylcyclohexylidene)hydrazinyl]-4-phenyl-1,3-thiazole
-
-
2-[4-(trifluoromethyl)phenyl]cyclopropanamine
-
-
2-{[(3,4-dimethyl-2-oxo-2H-chromen-7-yl)oxy]methyl}benzonitrile
-
-
3,4,5-trimethoxy-N'-(nonan-5-yl)benzohydrazide
-
-
3,4-dichloro-N-(2-methyl-1H-indol-5-yl)benzamide
-
-
3,4-dimethoxy-(benzylidene)-prop-2-ynylamine
-
-
3,4-dimethoxyaniline
-
IC50: 0.131 mM, monoamine oxidase A
3,4-dimethoxybenzaldehyde (4-methyl-1,3-thiazol-2-yl)hydrazone
-
pKi: 7.88
3,4-dimethoxybenzaldehyde (4-phenyl-1,3-thiazol-2-yl)hydrazone
-
pKi: 7.52
3,4-dimethyl-2-oxo-2H-chromen-7-yl 4-methoxybenzenesulfonate
-
-
3,4-dimethyl-2-oxo-2H-chromen-7-yl benzenesulfonate
-
-
3,4-dimethyl-7-(2-oxo-2-phenylethoxy)-2H-chromen-2-one
-
-
3,4-dimethyl-7-[(3-nitrobenzyl)oxy]-2H-chromen-2-one
-
-
3,4-dimethyl-7-[(pentafluorobenzyl)oxy]-2H-chromen-2-one
-
-
3,4-dimethyl-7-{[3-(trifluoromethoxy)benzyl]oxy}-2H-chromen-2-one
-
-
3,5,7-trimethyl-2-[(1E,3E)-4-phenylbuta-1,3-dien-1-yl]-3H-imidazo[4,5-c]pyridine-4,6(5H,7H)-dione
-
-
3,5-dimethyl-(1H-pyrrol-2-ylmethylene)-prop-2-ynyl-amine
-
-
3,5-dimethyl-N'-(nonan-5-yl)benzohydrazide
-
-
3-(2-chlorophenyl)-5H-indeno[1,2-c]pyridazin-5-one
-
-
3-(2-naphthyl)-5H-indeno[1,2-c]pyridazin-5-one
-
-
3-(2-nitrophenyl)-5H-indeno[1,2-c]pyridazin-5-one
-
-
3-(3-bromophenyl)-5H-indeno[1,2-c]pyridazin-5-one
-
-
3-(3-fluorophenyl)-5H-indeno[1,2-c]pyridazin-5-one
-
-
3-(3-methoxyphenyl)-5H-indeno[1,2-c]pyridazin-5-one
-
-
3-(4-bromophenyl)-5H-indeno[1,2-c]pyridazin-5-one
-
-
3-(4-hydroxyphenyl)-2-(4-oxo-2-thioxo-1,3-thiazolidin-3-yl)propanoic acid
-
-
3-(4-hydroxyphenyl)propionic acid
-
-
3-(4-methoxybenzyl)-7-(6-(1,2,3,4-tetrahydroacridin-9-ylamino)hexyloxy)chroman-4-one
-
-
3-(4-methoxyphenyl)-5H-indeno[1,2-c]pyridazin-5-one
-
-
3-(4-nitrophenyl)-5H-indeno[1,2-c]pyridazin-5-one
-
-
3-(5-oxo-5H-indeno[1,2-c]pyridazin-3-yl)benzonitrile
-
-
3-(benzyloxy)-5-nitro-1H-indazole
-
-
3-(benzyloxy)-6a,10a-dihydro-6H-benzo[c]chromen-6-one
-
-
3-benzyl-5-nitro-1H-indazole
-
-
3-benzyl-5H-indeno[1,2-c]pyridazin-5-one
-
-
3-chloro-N-(2-methyl-1H-indol-5-yl)benzamide
-
-
3-chlorobenzoic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester
-
-
3-hydroxyphenylacetic acid
-
-
3-methoxy-1-methyl-5-nitro-1H-indazole
-
inhibits MAO-B by 52% at 0.015 mM
3-methoxy-5-nitro-1H-indazole
-
-
3-methoxyphenol
-
IC50: 0.024 mM, monoamine oxidase A
3-methyl-5-nitro-1H-indazole
-
-
3-methyl-8-(4,4,4-trifluoro-butoxy)indeno[1.2-c]pyridazin-5-one
-
the experimentally tested model compound is docked computationally to the active site of the MAO-B enzyme. The AutoDock 3.0.5 program is employed to perform automated molecular docking. The free energies of binding and inhibition constants (Ki) of the docked compounds are calculated by the Lamarckian Genetic Algorithm of AutoDock 3.0.5. Excellent to good correlations between the calculated and experimental Ki values are obtained
3-[(2-methyl-1H-indol-5-yl)carbamoyl]benzene-1-sulfonic acid
-
-
3-[(5E)-5-benzylidene-2,4-dioxo-1,3-thiazolidin-3-yl]propanenitrile
-
-
3-[(5E)-5-benzylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]propanoic acid
-
-
3-[(E)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)amino]benzoic acid
-
R598127
3-[(E)-(prop-2-yn-1-ylimino)methyl]naphthalen-2-ol
-
-
3-[(E)-2-phenylvinyl]-5H-indeno[1,2-c]pyridazin-5-one
-
-
3-[4-(trifluoromethyl)phenyl]-5H-indeno[1,2-c]pyridazin-5-one
-
-
3-{[(3,4-dimethyl-2-oxo-2H-chromen-7-yl)oxy]methyl}benzonitrile
-
-
4-(2,4-dichlorophenyl)-2-[(2E)-2-(2-methylcyclohexylidene)hydrazinyl]-1,3-thiazole
-
-
4-(2,4-dichlorophenyl)-2-[2-(4-methylcyclohexylidene)hydrazinyl]-1,3-thiazole
-
-
4-(2,4-difluorophenyl)-2-[(2E)-2-(2-methylcyclohexylidene)hydrazinyl]-1,3-thiazole
-
-
4-(2,4-difluorophenyl)-2-[2-(4-methylcyclohexylidene)hydrazinyl]-1,3-thiazole
-
-
4-(4-chlorophenyl)-2-(2-cycloheptylidenehydrazinyl)-1,3-thiazole
-
-
4-(4-chlorophenyl)-2-(2-cyclohexylidenehydrazinyl)-1,3-thiazole
-
-
4-(4-chlorophenyl)-2-(2-cyclopentylidenehydrazinyl)-1,3-thiazole
-
-
4-(4-chlorophenyl)-2-[(2E)-2-(2-methylcyclohexylidene)hydrazinyl]-1,3-thiazole
-
-
4-(4-chlorophenyl)-2-[2-(4-methylcyclohexylidene)hydrazinyl]-1,3-thiazole
-
-
4-(4-fluorophenyl)-2-[(2E)-2-(2-methylcyclohexylidene)hydrazinyl]-1,3-thiazole
-
-
4-(4-fluorophenyl)-2-[2-(4-methylcyclohexylidene)hydrazinyl]-1,3-thiazole
-
-
4-(4-methoxyphenyl)-2-[(2E)-2-(2-methylcyclohexylidene)hydrazinyl]-1,3-thiazole
-
-
4-(4-methoxyphenyl)-2-[2-(4-methylcyclohexylidene)hydrazinyl]-1,3-thiazole
-
-
4-chloro-N'-(nonan-5-yl)benzohydrazide
-
-
4-chlorobenzaldehyde (4-methyl-1,3-thiazol-2-yl)hydrazone
-
pKi: 7.42
4-chlorobenzaldehyde (4-phenyl-1,3-thiazol-2-yl)hydrazone
-
pKi: 7.0
4-ethyl-N'-(nonan-5-yl)benzohydrazide
-
-
4-hydroxy-3-methoxy-alpha(methylaminomethyl)benzyl alcohol
-
IC50: 0.0089 mM, monoamine oxidase B; IC50: 0.0134 mM, monoamine oxidase A
4-Hydroxy-3-methoxybenzylamine
-
IC50: 0.13 mM, monoamine oxidase A; IC50: 0.382 mM, monoamine oxidase B
4-hydroxy-3-methoxyphenethyl alcohol
-
IC50: 0.18 mM, monoamine oxidase A
4-hydroxy-3-methoxyphenyl acetone
-
IC50: 0.0302 mM, monoamine oxidase A
4-hydroxyphenylacetic acid
-
-
4-methoxybenzaldehyde (4-methyl-1,3-thiazol-2-yl)hydrazone
-
pKi: 7.72
4-methoxybenzaldehyde (4-phenyl-1,3-thiazol-2-yl)hydrazone
-
pKi: 7.3
4-methylbenzaldehyde (4-methyl-1,3-thiazol-2-yl)hydrazone
-
pKi: 6.69
4-methylbenzaldehyde (4-phenyl-1,3-thiazol-2-yl)hydrazone
-
pKi: 7.67
4-methylcyclohexanone (4-phenyl-1,3-thiazol-2-yl)hydrazone
-
pKi: 7.0
4-oxo-4H-chromene-3-carboxylic acid
-
specific for MAO-B
4-[(2E)-3-(4-chlorophenyl)prop-2-enoyl]phenyl methanesulfinate
-
-
4-[(E)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)amino]benzoic acid
-
-
4-[2-(2-cycloheptylidenehydrazinyl)-1,3-thiazol-4-yl]benzonitrile
-
-
4-[2-(2-cyclohexylidenehydrazinyl)-1,3-thiazol-4-yl]benzonitrile
-
-
4-[2-(2-cyclopentylidenehydrazinyl)-1,3-thiazol-4-yl]benzonitrile
-
-
4-[2-[(2E)-2-(2-methylcyclohexylidene)hydrazinyl]-1,3-thiazol-4-yl]benzonitrile
-
-
4-[2-[2-(4-methylcyclohexylidene)hydrazinyl]-1,3-thiazol-4-yl]benzonitrile
-
-
4-{[(2-oxo-2H-chromen-3-yl)carbonyl]amino}benzoic acid
-
-
5,7-diethyl-3-methyl-2-[(1E,3E)-4-phenylbuta-1,3-dien-1-yl]-3H-imidazo[4,5-c]pyridine-4,6(5H,7H)-dione
-
-
5-(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3-thiazolidine-2,4-dione
-
-
5-(4-(2-[methyl(pyridin-2-yl)amino]ethoxy)benzyl)-1,3-thiazolidine-2,4-dione
-
i.e. rosiglitazone
5-(4-hydroxy-3,5-dimethylbenzyl)-1,3-thiazolidine-2,4-dione
-
-
5-(4-hydroxybenzyl)-1,3-thiazolidine-2,4-dione
-
-
5-(4-[(1-methylcyclohexyl)methoxy]benzyl)-1,3-thiazolidine-2,4-dione
-
i.e. ciglitazone
5-(4-[(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl)methoxy]benzyl)-1,3-thiazolidine-2,4-dione
-
i.e. troglitazone
5-(4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl)-1,3-thiazolidine-2,4-dione
-
i.e. pioglitazone, docking of R-pioglitazone in the substrate cavity of MAO-B
5-(aminomethyl)-3-aryl-2-oxazolidinones
-
-
5-chloro-2-[(E)-(prop-2-yn-1-ylimino)methyl]phenol
-
-
5-chloro-2-[(prop-2-yn-1-ylamino)methyl]phenol
-
-
5-nitro-1-(pyridin-2-ylmethyl)-1H-indazol-3-ol
-
-
5-nitroindazole
-
inhibits MAO-B by 98.5% at 0.015 mM
5-[(4-acetylcyclohexa-1,4-dien-1-yl)methyl]-1,3-thiazolidine-2,4-dione ammoniate (1:1)
-
-
5-[(4-acetylcyclohexa-1,4-dien-1-yl)methyl]-2-imino-1,3-thiazolidin-4-one
-
-
6-hydroxy-N-propargyl-1(R)-aminoindan
-
the experimentally tested model compound is docked computationally to the active site of the MAO-B enzyme. The AutoDock 3.0.5 program is employed to perform automated molecular docking. The free energies of binding and inhibition constants (Ki) of the docked compounds are calculated by the Lamarckian Genetic Algorithm of AutoDock 3.0.5. Excellent to good correlations between the calculated and experimental Ki values are obtained
6-nitroindazole
-
inhibits MAO-B by 89% at 0.015 mM, also inhibits MAO-A
7-(3-chlorobenzyloxy)-4-(methylamino)methylcoumarin
-
; binds noncovalently to MAO B, occupying both the entrance and the substrate cavities
7-(3-chlorobenzyloxy)-4-carboxaldehydecoumarin
-
; binds noncovalently to MAO B, occupying both the entrance and the substrate cavities
7-(anilinomethyl)-2H-chromen-2-one
-
-
7-(benzylamino)-3,4-dimethyl-2H-chromen-2-one
-
-
7-(benzyloxy)-2H-chromen-2-one
-
-
7-(benzyloxy)-3,4-dimethyl-2H-chromen-2-one
-
-
7-(benzyloxy)-4-methyl-2H-chromen-2-one
-
-
7-(benzyloxy)-4-phenyl-2H-chromen-2-one
-
-
7-nitroindazole
-
inhibits MAO-B by 35% at 0.015 mM
7-[(3-chlorophenyl)methoxy]-4-(methylaminomethyl)chromen-2-one
-
-
8-(3-chloro)styrylcaffeine
-
-
8-(3-chlorostrylyl)caffeine
-
the experimentally tested model compound is docked computationally to the active site of the MAO-B enzyme. The AutoDock 3.0.5 program is employed to perform automated molecular docking. The free energies of binding and inhibition constants (Ki) of the docked compounds are calculated by the Lamarckian Genetic Algorithm of AutoDock 3.0.5. Excellent to good correlations between the calculated and experimental Ki values are obtained
8-(3-chlorostyryl)caffeine
-
monoamine oxidase B
8-(benzyloxy)-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione
-
-
8-[(3-bromobenzyl)oxy]-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione
-
-
8-[(3-chlorobenzyl)oxy]-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione
-
-
8-[(3-fluorobenzyl)oxy]-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione
-
-
8-[(3-methoxybenzyl)oxy]-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione
-
-
amitriptyline
-
competive inhibition with 2-phenylethylamine as substrate
amphetamine
befloxatone
-
the inhibitor induces changes in the spectrum of MAO A, consistent with stacking of inhibitor with the flavin in the active site
benzaldehyde (4-methyl-1,3-thiazol-2-yl)hydrazone
-
pKi: 8.14
benzaldehyde (4-phenyl-1,3-thiazol-2-yl)hydrazone
-
pKi: 5.92
benzhydrylidene-prop-2-ynyl-amine
-
-
benzoic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester
-
-
benzylhydrazine
the mode of irreversible MAO inhibition involves covalent modification of the flavin coenzyme, overview; the three-dimensional structures of phenylethylhydrazine- and benzylhydrazine-inhibited MAO B show that alkylation occurs at the N5 position on the re-face of the covalent flavin with loss of the hydrazyl nitrogens, mechanism, the mode of irreversible MAO inhibition involves covalent modification of the flavin coenzyme, overview
beta-carbolines
-
competitive reversible and potent inhibitor
brofaromine
Caffeine
-
a dual-target-directed drug inhibiting MAO-B and antagonizing A2A receptors
ciglitazone
-
-
cinnamyl alcohol
-
compound from Rhodiola rosea extract, inhibits both MAO A and MAO B
cis-2,4,5-trimethoxypropenylbenzene
-
IC50: 0.142 mM, monoamine oxidase A; IC50: 0.362 mM, monoamine oxidase B
Clorgyline
cyanidin
-
competitive interaction of cyanidin with MAO A plus a mixed competitive and non-competitive mode of interaction of cyanidin with MAO B
cyanidin-3,5-diglucoside
-
-
cyanidin-3-O-beta-D-galactoside
-
-
cyanidin-3-O-beta-D-glucoside
-
mixed competitive and non-competitive mode of interaction with both enzyme isozymes
cyanidin-3-O-beta-D-rutinoside
-
-
cyclohexanone (4-phenyl-1,3-thiazol-2-yl)hydrazone
-
pKi: 7.69
cyclopentanone (4-phenyl-1,3-thiazol-2-yl)hydrazone
-
pKi: 6.85
D-amphetamine
delphinidin
-
-
delphinidin-3-O-beta-D-glucoside
-
-
Deprenyl
di(2-hydroxyethyl)methyldodecylammonium
-
reversible competitive inhibitor
di(2-hydroxyethyl)methyldodecylammonium ion
-
a biocide, inhibits MAO-B
epigallocatechin gallate dimer
-
compound from Rhodiola rosea extract, inhibits both MAO A and MAO B
esuprone
-
inhibits MAO-A reversibly
ethyl 4-hydroxy-3-methoxycinnamate
-
IC50: 0.0057 mM, monoamine oxidase B; IC50: 0.0247 mM, monoamine oxidase A
ethyl 4-{[(2-oxo-2H-chromen-3-yl)carbonyl]amino}benzoate
-
-
ethyl-4-hydroxy-3-methoxyphenylacetate
-
IC50: 0.081 mM, monoamine oxidase A
Eugenol
-
IC50: 0.0344 mM, monoamine oxidase A; IC50: 0.288 mM, monoamine oxidase B
eugenol methyl ether
-
IC50: 0.11 mM, monoamine oxidase A; IC50: 0.269 mM, monoamine oxidase B
farnesol
-
-
Harmaline
harmalol
-
identification by HPLC-ESI-mass spectrometry
harman
Harmane
harmine
harmol
-
identification by HPLC-ESI-mass spectrometry
indol -2,3-dione
-
the experimentally tested model compound is docked computationally to the active site of the MAO-B enzyme. The AutoDock 3.0.5 program is employed to perform automated molecular docking. The free energies of binding and inhibition constants (Ki) of the docked compounds are calculated by the Lamarckian Genetic Algorithm of AutoDock 3.0.5. Excellent to good correlations between the calculated and experimental Ki values are obtained
Iproniazid
-
-
Iproniazide
isatin
isocarboxazide
isoproniazid
-
inhibits MAO-A and MAO-B irreversibly
KF-17837
-
a dual-target-directed drug inhibiting MAO-B and antagonizing A2A receptors
KW-6002
-
a dual-target-directed drug inhibiting MAO-B and antagonizing A2A receptors
L-deprenyl
-
inhibition of MAO A and MAO B
ladostigil
-
-
lamotrigine
-
its in vivo MAO-B inhibiting effect might contribute in part to its antidepressant activity
lazabemide
LU-53439
-
inhibits MAO-B reversibly
malvidin
-
-
malvidin 3-O,5-O-di-beta-D-glucoside
-
-
malvidin-3-O-beta-D-galactoside
-
-
malvidin-3-O-beta-D-glucoside
-
-
metanephrine
-
IC50: 0.252 mM, monoamine oxidase A
methyl (2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoate
-
;
methyl 4'-[(E)-(prop-2-yn-1-ylimino)methyl]biphenyl-4-carboxylate
-
-
methylene blue
-
-
moclobemide
mofegiline
N'-(2-cyanoethyl)-4-ethylbenzohydrazide
-
-
N'-(nonan-5-yl)-2-naphthohydrazide
-
-
N'-(nonan-5-yl)benzo[d][1,3]dioxole-5-carbohydrazide
-
-
N'-phenyl-7-benzyloxy-2-oxo-2H-chromene-3-carbohydrazide
-
-
N,N'-bis[[(5S)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]butanediamide
-
IC50: 0.09 mM, at 0.15 mM kynuramine
N,N'-[(1,5-dioxopentane-1,5-diyl)bis[piperazine-4,1-diyl(3-fluorobenzene-4,1-diyl)[(5R)-2-oxo-1,3-oxazolidine-3,5-diyl]methanediyl]]diacetamide
-
IC50: 0.0005 mM, at 0.15 mM kynuramine
N-((4-isopropylphenyl)-2-oxo-2H-chromene-3-carboxamide)-amide
-
-
N-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)-2-(4-[[methyl(prop-2-yn-1-yl)amino]methyl]phenyl)acetamide
N-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)-3-[[methyl(prop-2-yn-1-yl)amino]methyl]benzamide
-
i.e. ParSL-3, a TEMPO-conjugated pargyline analogue, specifically inhibits MAO-A
N-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)-4-[[methyl(prop-2-yn-1-yl)amino]methyl]benzamide
-
i.e. ParSL-2, a TEMPO-conjugated pargyline analogue, specifically inhibits MAO-B
N-(2,3-dimethylphenyl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(2,4-dimethylphenyl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(2,6-difluorophenyl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(2,6-dimethylphenyl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(2-aminoethyl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(2-aminoethyl)-4-chlorobenzamide
-
-
N-(2-aminoethyl)-aryl-carboxamide
-
-
N-(2-aminoethyl)-p-chlorobenzamide
N-(2-benzylphenyl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(2-benzylphenyl)-7-(4-fluorobenzyloxy)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(2-benzylphenyl)-7-benzyloxy-2-oxo-2H-chromene-3-carboxamide
-
-
N-(2-chloro-6-methylphenyl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(2-methyl-1H-indol-5-yl)benzamide
-
-
N-(2-methyl-1H-indol-5-yl)cyclohexanecarboxamide
-
-
N-(2-methyl-6-chlorophenyl)-7-(4-fluorobenzyloxy)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(2-methyl-6-chlorophenyl)-7-benzyloxy-2-oxo-2H-chromene-3-carboxamide
-
-
N-(3,4-dichlorophenyl)-1-(2-methoxyethyl)-1H-indazole-5-carboxamide
-
;
N-(3,4-dichlorophenyl)-1-methyl-1H-indazole-5-carboxamide
-
;
N-(3,4-dichlorophenyl)-1H-indazole-5-carboxamide
-
;
N-(3,4-dichlorophenyl)-2-methyl-2H-indazole-5-carboxamide
-
;
N-(3,4-difluorophenyl)-1-methyl-1H-indazole-5-carboxamide
-
;
N-(3,4-difluorophenyl)-1H-indazole-5-carboxamide
-
;
N-(3,4-difluorophenyl)-2-methyl-2H-indazole-5-carboxamide
-
;
N-(3,4-dimethoxyphenyl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(3,4-dimethoxyphenyl)-7-(4-fluorobenzyloxy)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(3,4-dimethoxyphenyl)-7-benzyloxy-2-oxo-2H-chromene-3-carboxamide
-
-
N-(3,4-dimethoxyphenyl)-7-benzyloxy-8-methyl-2-oxo-2H-chromene-3-carboxamide
-
-
N-(3,4-dimethoxyphenyl)-8-methyl-2-oxo-7-(2-phenylethyl)-2H-chromene-3-carboxamide
-
-
N-(3,4-dimethyl-2-oxo-2H-chromen-7-yl)benzamide
-
-
N-(3,4-dimethylphenyl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(3,5-dimethoxyphenyl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(3,5-dimethoxyphenyl)-7-(4-fluorobenzyloxy)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(3,5-dimethoxyphenyl)-7-benzyloxy-2-oxo-2H-chromene-3-carboxamide
-
-
N-(3,5-dimethylphenyl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(3-chloro-4-fluorophenyl)-1-methyl-1H-indazole-5-carboxamide
-
NTZ-1441; NTZ-1441
-
N-(3-chloro-4-fluorophenyl)-1H-indazole-5-carboxamide
-
;
N-(3-chloro-4-fluorophenyl)-2-methyl-2H-indazole-5-carboxamide
-
NTZ-1442; NTZ-1442
-
N-(3-fluorophenyl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(3-methylphenyl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(3-trifluoromethylphenyl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(3-{[(3,4-dimethyl-2-oxo-2H-chromen-7-yl)oxy]methyl}phenyl)acetamide
-
-
N-(4-cyano-2,3,5,6-tetrafluorophenyl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(4-cyano-2,3,5,6-tetrafluorophenyl)-7-(4-fluorobenzyloxy)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(4-cyano-2,3,5,6-tetrafluorophenyl)-7-benzyloxy-2-oxo-2H-chromene-3-carboxamide
-
-
N-(4-ethylphenyl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(4-fluorophenyl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(4-isopropylphenyl)-7-(4-fluorobenzyloxy)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(4-isopropylphenyl)-7-benzyloxy-2-oxo-2H-chromene-3-carboxamide
-
-
N-(4-methanesulfonylphenyl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(4-methoxyphenyl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(biphenyl-2-yl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(butan-2-yl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-(cycloheptylidenemethyl)-4-(3-methoxyphenyl)-1,3-thiazol-2-amine
-
-
N-(prop-2-ynyl)-2-oxo-2H-chromene-3-carboxamide
-
-
N-([(5S)-3-[3-fluoro-4-(4-pyrazin-2-ylpiperazin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl)acetamide
-
-
N-([(5S)-3-[4-(4-bromo-1H-imidazol-1-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl)acetamide
-
-
N-benzyl-12-isothiocyanato-N-methyldodecan-1-amine
-
irreversible inhibition with respect to isoform MAO-A, competitive inhibition with respect to isoform MAO-B; irreversible inhibition with respect to isoform MAO-A, competitive inhibition with respect to isoform MAO-B
N-benzyl-2-oxo-2H-chromene-3-carboxamide
-
-
N-benzyl-7-benzyloxy-2-oxo-2H-chromene-3-carboxamide
-
-
N-benzyl-N-methyl-2-oxo-2H-chromene-3-carboxamide
-
-
N-benzyl-N-methylprop-2-yn-1-amine
-
i.e. pargyline
N-benzylprop-2-yn-1-amine
-
-
N-cyclohexyl-2-oxo-2H-chromene-3-carboxamide
-
-
N-cyclohexyl-7-benzyloxy-2-oxo-2H-chromene-3-carboxamide
-
-
N-isobutyl-7-benzyloxy-2-oxo-2H-chromene-3-carboxamide
-
-
N-isopropyl-7-benzyloxy-2-oxo-2H-chromene-3-carboxamide
-
-
N-methyl-N-benzyl-2-oxo-2H-chromene-3-carboxamide
-
-
N-methyl-N-phenyl-2-oxo-2H-chromene-3-carboxamide
-
-
N-methyl-N-phenyl-7-benzyloxy-2-oxo-2H-chromene-3-carboxamide
-
-
N-methyl-N-propargyl-1(R)-aminoindan
-
the experimentally tested model compound is docked computationally to the active site of the MAO-B enzyme. The AutoDock 3.0.5 program is employed to perform automated molecular docking. The free energies of binding and inhibition constants (Ki) of the docked compounds are calculated by the Lamarckian Genetic Algorithm of AutoDock 3.0.5. Excellent to good correlations between the calculated and experimental Ki values are obtained
N-phenyl-1H-indazole-5-carboxamide
-
;
N-propargyl-1(R)-aminoindan
-
the experimentally tested model compound is docked computationally to the active site of the MAO-B enzyme. The AutoDock 3.0.5 program is employed to perform automated molecular docking. The free energies of binding and inhibition constants (Ki) of the docked compounds are calculated by the Lamarckian Genetic Algorithm of AutoDock 3.0.5. Excellent to good correlations between the calculated and experimental Ki values are obtained
N-propargyl-l(R)-aminoindan
-
i.e. rasagiline. N-Propargyl-l(R)-aminoindan is well tolerated and effective in the treatment of early Parkinson's disease and as adjunctive treatment in levodopa-treated patients with Parkinson's disease experiencing motor fluctuations
N-[3-(2,4-dichlorophenoxy)propyl]-N-methyl-prop-2-yn-1-amine
-
i.e. clorgiline
N-[4-(methylsulfonyl)phenyl]-2-oxo-2H-chromene-3-carboxamide
-
-
N-[[(5S)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
-
-
N1,N12-dibenzyldodecane-1,12-diamine
-
;
-
N1-(3-aminopropyl)-N4-(3-((naphthalen-2-ylmethyl)amino)propyl)butane-1,4-diamine
-
;
-
N1-(3-aminopropyl)-N4-(3-((pyridin-3-ylmethyl)amino)propyl)butane-1,4-diamine
-
;
N1-(3-aminopropyl)-N4-(3-((thiophen-2-ylmethyl)amino)propyl)butane-1,4-diamine
-
mixed-type reversible inhibition with respect to isoform MAO-A and MAO-B; mixed-type reversible inhibition with respect to isoform MAO-A and MAO-B
N1-benzyl-spermine
-
;
-
norharman
o-eugenol
-
IC50: 0.101 mM, monoamine oxidase A; IC50: above 0.5 mM, monoamine oxidase B
oleamide
-
inhibits MAO B
p-(propylthio)-phenylisopropylamine
-
-
p-nitrobenzylamine
-
substrate for wild-type enzyme, competitive inhibitor for mutant enzyme Y435L
Pargyline
ParSL
a pargyline based nitroxide spin labeled irreversible inhibitor, active site binding, structure, overview; a pargyline based nitroxide spin labeled irreversible inhibitor, active site binding, structure, overview
pelargonidin
-
-
pelargonidin 3-O,5-O-di-beta-D-glucoside
-
-
peonidin
-
-
peonidin-3-O-beta-D-glucoside
-
-
petunidin
-
-
Phenelzine
phentermine
Phenylethylhydrazine
the mode of irreversible MAO inhibition involves covalent modification of the flavin coenzyme, overview; the three-dimensional structures of phenylethylhydrazine- and benzylhydrazine-inhibited MAO B show that alkylation occurs at the N5 position on the re-face of the covalent flavin with loss of the hydrazyl nitrogens, mechanism, the mode of irreversible MAO inhibition involves covalent modification of the flavin coenzyme, overview
phenylhydrazine
weak binding; weak binding
pirlindole
-
an MAO A specific reversible inhibitor
R-(-)-deprenyl
R-deprenyl
-
-
R-rasagiline
-
-
raisin extract
-
;
-
rasagiline
rhodiocyanoside A
-
compound from Rhodiola rosea extract, inhibits MAO B, not MAO A
rhodioloside B
-
compound from Rhodiola rosea extract, inhibits MAO B, not MAO A
Ro 19-6327
-
-
Ro 41-1049
-
-
rosiglitazone
-
-
rosiridin
-
compound from Rhodiola rosea extract, inhibits both MAO A and MAO B
safinamide
salidroside
-
compound from Rhodiola rosea extract, inhibits MAO B, not MAO A
selegiline
syringic acid
-
-
tetrahydroharmine
-
identification by HPLC-ESI-mass spectrometry
tetrindole
toloxatone
trans,trans-farnesol
-
monoamine oxidase B
trans-2,4,5-trimethoxypropenylbenzene
-
IC50: 0.124 mM, monoamine oxidase A; IC50: 0.338 mM, monoamine oxidase B
trans-2-phenylcyclopropylamine
trans-trans-1,4-diphenyl-1,3-butadiene
-
-
Tranylcypromine
triandrin
-
compound from Rhodiola rosea extract, inhibits MAO B, not MAO A
troglitazone
-
-
tyrosol
-
compound from Rhodiola rosea extract, inhibits MAO B, not MAO A
vanillic acid
-
-
[(2E)-3-fluoro-2-phenylprop-2-en-1-yl]hydrazine
-
;
[(5E)-2,4-dioxo-5-(phenylimino)-1,3-thiazolidin-3-yl]acetonitrile
-
R598119
[(E)-1,3-dipropyl-7-methyl-8-(2-(3-thienyl)ethenyl)]xanthine
-
a dual-target-directed drug inhibiting MAO-B and antagonizing A2A receptors
[2-(2-methylphenyl)prop-2-en-1-yl]hydrazine
-
;
[2-(4-chlorophenyl)prop-2-en-1-yl]hydrazine
-
;
[2-(4-fluorophenyl)prop-2-en-1-yl]hydrazine
-
;
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
SRY protein
-
SRY and Sp1 form a transcriptional complex and synergistically activate MAO A transcription, overview
-
transcription factor Sp1
-
SRY and Sp1 form a transcriptional complex and synergistically activate MAO A transcription, overview
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.221
(1R,6S)-3-methyl-6-phenyl-3-aza-bicyclo[4.1.0]heptane
-
pH 7.0, 37C
0.753
(1S,6R)-3-methyl-6-phenyl-3-aza-bicyclo[4.1.0]heptane
-
pH 7.0, 37C
0.033 - 0.04
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
0.016 - 0.68
2-Phenylethylamine
0.401 - 1.2
3-(4-(3-aminopropoxy)butoxy)-N-(thiophen-2-ylmethyl)propan-1-amine
0.19
5-hydroxytryptamine
-
-
0.0109 - 8.8
benzylamine
1.7
benzylamine hydrobromide
-
-
0.111 - 1.36
dopamine
0.0161 - 5.123
kynuramine
0.018 - 0.08
N1-(thiophen-2-ylmethyl)dodecane-1,12-diamine
0.012 - 0.044
N1-benzyl-N1-methyldodecane-1,12-diamine
0.043 - 0.05
N1-benzyldodecane-1,12-diamine
0.33
O2
-
-
0.09 - 0.76
p-nitrobenzylamine
0.005 - 0.22
p-nitrophenylethylamine
0.05 - 2
p-trifluoromethyl-benzylamine
0.19
p-tyramine
-
-
0.89
phenethylamine
-
11C
0.0089 - 0.055
phenylbutylamine
0.0022 - 1.48
Phenylethylamine
0.0863 - 2.92
serotonin
0.066
tryptamine
-
-
0.079
tyramine
-
-
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.16 - 0.29
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
0.012 - 3.82
2-Phenylethylamine
0.028 - 10
benzylamine
0.249
dopamine
-
11C
1.07 - 2.5
kynuramine
0.185 - 0.38
p-nitrobenzylamine
1.8 - 2.24
p-nitrophenylethylamine
0.455 - 2.85
p-trifluoromethyl-benzylamine
1.481
phenethylamine
-
11C
1.83 - 2.34
phenylbutylamine
0.897 - 3.1
Phenylethylamine
0.426 - 18.6
serotonin
5.3
tyramine
-
-
additional information
additional information
-