Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
(R)-metamphetamine + NADPH + H+ + O2
(R)-metamphetamine N-oxide + NADP+ + H2O
-
substrate of isoform FMO1
-
-
?
(S)-metamphetamine + NADPH + H+ + O2
(S)-metamphetamine N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
(S)-nicotine + NADPH + H+ + O2
?
-
-
-
-
?
(S)-nicotine + NADPH + O2
(S)-nicotine N1-oxide + NADP+ + H2O
-
(S)-nicotine N-1'-oxygenation
-
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
1,2,3,4-tetrahydroisoquinoline + NADPH + O2
?
1,2-dimethylhydrazine + NADPH + H+ + O2
1,2-dimethylhydrazine N-oxide + NADP+ + H2O
-
-
-
-
r
1,2-dimethylhydrazine + NADPH + O2
?
1,2-dimethylphenylhydrazine + NADPH + O2
?
1-butanethiol + NADPH + O2
?
1-methyl-1-phenylhydrazine + NADPH + O2
?
1-methyl-2-benzylhydrazine + NADPH + H+ + O2
1-methyl-2-benzylhydrazine N-oxide + NADP+ + H2O
-
-
-
-
r
1-methyl-2-benzylhydrazine + NADPH + O2
?
1-methyl-2-thioimidazole + NADPH + O2
?
-
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + O2
?
1-methyl-6,7-dihydroxytetrahydroisoquinoline + NADPH + O2
?
-
-
-
-
?
1-[4-(methylsulfanyl)phenyl]ethanone + NADPH + H+ + O2
(R,S)-1-[4-(methylsulfanyl)phenyl]ethanone S-oxide + NADP+ + H2O
10-(N,N-dimethylaminoalkyl)-2-(trifluoromethyl) phenothiazines + NADPH + O2
?
10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene + NADPH + H+ + O2
? + NADP+ + H2O
10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazine + NADPH + H+ + O2
10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazine N-oxide + NADP+ + H2O
-
-
-
r
10-(N,N-dimethylaminopentyl)-2-(trifluoromethyl)phenothiazine + NADPH + O2
?
10-([N,N-dimethylaminopentyl]-2-trifluoromethyl)phenothiazine + NADPH + O2
?
-
-
-
-
?
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine + NADPH + O2
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine N-oxide + NADP+ + H2O
10-[(N,N-dimethylaminooctyl)-2-(trifluoromethyl)]phenothiazine + NADPH + H+ + O2
10-[(N,N-dimethylaminooctyl)-2-(trifluoromethyl)]phenothiazine N-oxide + NADP+ + H2O
-
-
-
-
?
10-[(N,N-dimethylaminopentyl)-2-(trifluoromethyl)]phenothiazine + NADPH + O2
?
-
i.e. 5-DPT or diethylenetriaminepentaacetic acid
-
-
?
2 bicyclo[4.2.0]octan-7-one + 2 NADH + 2 H+ + 2 O2
(3aS,7aS)-hexahydro-1-benzofuran-2(3H)-one + (3aR,7aS)-hexahydro-2-benzofuran-1(3H)-one + 2 NAD+ + 2 H2O
-
-
-
-
?
2,4,5-trichlorphenol + O2
2,5-dichlorohydroquinone + H2O + Cl-
2,4,6-trichlorphenol + O2
2,6-dichlorohydroquinone + H2O + Cl-
2,4-dichlorphenol + O2
chlorohydroquinone + H2O + Cl-
2-(methylsulfanyl)pyridine + NADPH + H+ + O2
2-(methylsulfanyl)pyridine S-oxide + NADP+ + H2O
2-(methylsulfanyl)thiophene + NADPH + H+ + O2
2-(methylsulfanyl)thiophene S-oxide + NADP+ + H2O
2-acetylsulfanylmethyl-4-(4-methoxyphenyl)-4-oxobutyric acid + NADPH + H+ + O2
?
-
-
-
-
?
2-chlorophenol + O2
chlorohydroquinone + H2O
2-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-2-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
2-mercaptobenzimidazole + NADPH + O2
?
2-[(methylsulfanyl)methyl]furan + NADPH + H+ + O2
2-[(methylsulfanyl)methyl]furan S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
2-[2-(4-methoxyphenyl)-2-oxoethyl]-acrylic acid + NADPH + H+ + O2
?
-
a synthetic 10-(N,N-dimethylaminoalkyl)-2-(trifluoromethyl)phenothiazine analogue
-
-
?
3-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-3-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 15% R-enantiomer as product
-
-
?
3-hydroxy-nabumetone + NADPH + H+ + O2
? + NADP+ + H2O
activation reaction
-
-
?
4-(4-methoxyphenyl)-2-methylsulfanylmethyl-4-oxobutyric acid + NADPH + H+ + O2
?
-
FMO1, poor activity with FMO3 and FMO5
-
-
?
4-(4-methylphenyl)-2-methylsulfanylmethyl-4-oxobutyric acid + NADPH + H+ + O2
?
-
FMO1 and FMO5, no activity with FMO3
-
-
?
4-(methylsulfanyl)benzonitrile + NADPH + H+ + O2
(R,S)-4-(methylsulfanyl)benzonitrile S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 22% S-enantiomer as product
-
-
?
4-(methylsulfanyl)phenol + NADPH + H+ + O2
(R,S)-4-(methylsulfanyl)phenol S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 81% S-enantiomer as product
-
-
?
4-aminobenzoic acid hydrazide + NADPH + O2
?
-
-
-
?
4-chlorophenol + O2
hydroquinone + H2O + Cl-
4-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-4-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 95% S-enantiomer as product
-
-
?
5,6-dimethylxanthenone-4-acetic acid + NADPH + H+ + O2
?
-
substrate of isoform FMO3, methyl hydroxylation
-
-
?
5-[[3-(dimethylamino)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
5-[[3-(dimethylamino)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
9-hydroxy-5,6-dimethyl-N-(2-(dimethylamino)ethyl)-6H-pyrido(4,3-B)-carbazole-1-carboxamide + NADPH + H+ + O2
2-(9-hydroxy-5,6-dimethyl-6H-pyrido[4,3-b]carbazole-1-carboxamido)-N,N-dimethylethan-1-amine oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
albendazole + NADPH + H+ + O2
albendazole S-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
aldicarb + NADPH + O2
?
-
-
-
-
?
almotriptan + NADPH + H+ + O2
almotriptan N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
alpha-naphthylthiourea + NADPH + O2
?
aminopyrine + NADPH + O2
?
ammonia + NADPH + H+ + O2
? + NADP+ + H2O
-
-
-
-
?
amphetamine + NADPH + H+ + O2
?
amphetamine + NADPH + H+ + O2
amphetamine N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
amphetamine + NADPH + O2
amphetamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
?
-
i.e. 3-(1-benzyl-1H-indazol-3-yloxy)-N,N-dimethylpropan-1-amine
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
benzydamine + NADPH + O2
benzydamine N-oxide + NADP+ + H2O
benzyl ethyl sulfide + NADPH + H+ + O2
benzyl ethyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
benzyl methyl sulfide + NADPH + H+ + O2
benzyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
benzylamine + [reduced NADPH-hemoprotein reductase] + O2
benzylamine N-oxide + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
benzylhydrazine + NADPH + H+ + O2
benzylhydrazine N-oxide + NADP+ + H2O
-
-
-
-
r
benzylhydrazine + NADPH + O2
?
beta-ethylphenylhydrazine + NADPH + H+ + O2
beta-ethylphenylhydrazine N-oxide + NADP+ + H2O
-
-
-
-
r
beta-ethylphenylhydrazine + NADPH + O2
?
bicyclo[3.2.0]hept-2-en-6-one + NADH + H+ + O2
?
-
-
-
-
?
bicyclo[3.2.0]hept-2-en-6-one + NADPH + H+ + O2
?
-
-
-
-
?
bupivacaine + NADPH + O2
bupivacaine-oxide + NADP+
-
-
-
-
?
butyl ethyl sulfide + NADPH + H+ + O2
butyl ethyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
butyl methyl sulfide + NADPH + H+ + O2
butyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
butylhydrazine + NADPH + H+ + O2
butylhydrazine N-oxide + NADP+ + H2O
-
-
-
-
r
butylhydrazine + NADPH + O2
?
chlorpromazine + NADPH + H+ + O2
chlorpromazine N-oxide + NADP+ + H2O
chlorpromazine + NADPH + H+ + O2
chlorpromazine oxide + NADP+ + H2O
-
-
-
-
?
chlorpromazine + NADPH + O2
?
chlorpromazine + NADPH + O2
chlorpromazine N-oxide + NADP+ + H2O
-
-
-
-
?
cimetidine + NADPH + H+ + O2
cimetidine S-oxide + NADP+ + H2O
cimetidine + NADPH + O2
cimetidine S-oxide + NADP+ + H2O
-
-
-
-
?
clomiphene + NADPH + H+ + O2
?
-
i.e. 2-[4-[2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethanamine
-
-
?
clomiphene + NADPH + H+ + O2
clomiphene N-oxide + NADP+ + H2O
clomipramine + NADPH + H+ + O2
clomipramine N-oxide + NADP+ + H2O
-
-
-
?
clozapine + NADPH + H+ + O2
?
-
-
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
clozapine + NADPH + O2
?
-
-
-
-
?
contezolid + NADPH + H+ + O2
contezolid N-oxide + NADP+ + H2O
-
substrate of isoform FMO5
-
-
?
cyclobutanone + NADH + H+ + O2
gamma-butyrolactone + NAD+ + H2O
-
-
-
-
?
cyclohexyl methyl sulfide + NADPH + H+ + O2
cyclohexyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
cysteamine + NADPH + H+ + O2
?
cysteamine + NADPH + O2
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
danusertib + NADPH + H+ + O2
danusertib N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
dasatinib + NADPH + H+ + O2
4-(6-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)-2-methylpyrimidin-4-yl)-1-(2-hydroxyethyl)piperazine 1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
dasatinib + NADPH + H+ + O2
dasatinib N-oxide + NADP+ + H2O
-
-
-
?
demeton-O + NADPH + O2
demeton-O sulfoxide + NADP+ + H2O
deprenyl + NADPH + H+ + O2
?
deprenyl + NADPH + H+ + O2
deprenyl N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
dibenzylamine + NADPH + O2
?
dihydrolipoic acid + NADPH + O2
?
-
-
-
-
?
dimethylsulfone + NADH + H+ + O2
methanesulfinate + NAD+ + H2O
disulfoton + NADPH + H+ + O2
?
E-7016 + NADPH + H+ + O2
?
-
substrate of isoform FMO5, Bayer Villiger oxidation
-
-
?
esonarimod + NADPH + H+ + O2
S-methyl esonarimod + NADP+ + H2O
a antirheumatic drug, is converted to the S-oxide
-
-
?
ethiofencarb + NADPH + O2
ethiofencarb sulfoxide + NADP+ + H2O
ethionamide + NADPH + H+ + O2
?
ethionamide + NADPH + H+ + O2
ethionamide N-oxide + NADP+ + H2O
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
ethionamide + NADPH + O2 + H+
2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O
ethyl phenyl sulfide + NADPH + H+ + O2
ethyl phenyl sulfoxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
ethylene sulfide + NADPH + O2
?
ethylene thiourea + NADPH + H+ + O2
?
-
-
-
-
?
ethylenethiourea + NADPH + O2
ethylenethiourea S-oxide + NADP+ + H2O
-
-
-
-
?
ethylenthiourea + NADPH + O2
?
-
-
-
-
?
ethylhydrazine + NADPH + H+ + O2
ethylhydrazine N-oxide + NADP+ + H2O
-
-
-
-
r
etionamide + NADPH + H+ + O2
etionamide S-oxide + NADP+ + H2O
substrate of FMO1, FMO3, and FMO2.1
-
-
?
fenthion + NADPH + O2
fenthion sulfoxide + NADP+
-
-
74% (+)-sulfoxide
-
?
fenthion + NADPH + O2
fenthion sulfoxide + NADP+ + H2O
GSK5182 + NADPH + H+ + O2
(Z)-2-(4-(5-hydroxy-1-(4-hydroxyphenyl)-2-phenylpent-1-en-1-yl)phenoxy)-N,N-dimethylethan-1-amine oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
GSK5182 + NADPH + H+ + O2
GSK5182 N-oxide + NADP+ + H2O
hypotaurine + H2O + NAD+
taurine + NADH
hypotaurine + NADH + H+ + O2
taurine + NAD+ + H2O
hypotaurine + NADPH + H+ + O2
taurine + NADP+ + H2O
hypotaurine + O2 + NADH + H+
taurine + NAD+ + H2O
-
-
-
?
hypotaurine + O2 + NADPH + H+
taurine + NADP+ + H2O
-
-
-
?
imipramine + NADPH + H+ + O2
imipramine N-oxide + NADP+ + H2O
imipramine + NADPH + H+ + O2
imipramine oxide + NADP+ + H2O
-
-
-
-
?
imipramine + NADPH + O2
?
imipramine + NADPH + O2
imipramine N-oxide + NADP+ + H2O
indole + NADPH + H+ + O2
indole N-oxide + NADP+ + H2O
indole + NADPH + H+ + O2
indoxyl + NADP+ + H2O
isopropylhydrazine + NADPH + H+ + O2
isopropylhydrazine N-oxide + NADP+ + H2O
-
-
-
-
r
isopropylhydrazine + NADPH + O2
?
itopride + NADPH + H+ + O2
itopride N-oxide + NADP+ + H2O
itopride + NADPH + O2
?
-
-
-
-
?
K11777 + NADPH + H+ + O2
K11777 N-oxide + NADP+ + H2O
L-775,606 + NADPH + H+ + O2
4-(3-(5-(4H-1,2,4-triazol-4-yl)-1H-indol-3-yl)propyl)-1-(3-fluorophenethyl)piperazine 1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
L-Met-Phe + NADPH + O2
(L-Met-S-oxide)-Phe + NADP+ + H2O
L-Met-Val + NADPH + O2
(L-Met-S-oxide)-Val + NADP+ + H2O
L-methionine + NADPH + H+ + O2
?
-
-
-
?
L-methionine + NADPH + H+ + O2
L-methionine S-oxide + NADP+ + H2O
-
-
-
-
?
L-methionine + NADPH + H+ + O2
methionine S-oxide + NADP+ + H2O
stereochemistry, overview
formation of 80% D-isomer
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
L-Phe-Met + NADPH + O2
(L-Met-S-oxide)-Phe + NADP+ + H2O
-
liver microsomes
-
-
?
L-seleno-methionine + NADPH + O2
L-methionine seleno-oxide + NADP+ + H2O
lidocaine + NADPH + O2
lidocaine-oxide + NADP+
-
-
-
-
?
lipoic acid + NADPH + O2
?
lorcaserin + NADPH + H+ + O2
lorcaserin N-oxide + NADP+ + H2O
-
substrate of isoform FMO1
-
-
?
loxapine + NADPH + H+ + O2
4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)-1-methylpiperazine 1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
loxapine + NADPH + H+ + O2
loxapine N-oxide + NADP+ + H2O
-
-
-
?
mercaptoimidazole + NADPH + H+ + O2
?
-
FMO1 and FMO3, no activity with FMO5
-
-
?
mercaptoimidazole + NADPH + O2
mercaptoimidazole S-oxide + NADP+ + H2O
-
-
-
-
?
methamphetamine + NADPH + H+ + O2
?
methamphetamine + NADPH + H+ + O2
methamphetamine N-oxide + NADP+ + H2O
a psychostimulant, is converted to the hydroxylamine
-
-
?
methamphetamine + NADPH + O2
?
methimazole + NADH + H+
?
-
-
-
?
methimazole + NADPH + H+
?
-
-
-
?
methimazole + NADPH + H+ + O2
?
methimazole + NADPH + H+ + O2
methimazole N-oxide + NADP+ + H2O
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADP+ + H2O
methimazole + NADPH + O2
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
methiocarb + NADPH + O2
methiocarb sulfoxide + NADP+ + H2O
methyl 2-phenylethyl sulfide + NADPH + H+ + O2
methyl 2-phenylethyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
methyl 4-(methylsulfanyl)phenyl ether + NADPH + H+ + O2
(R,S)-methyl 4-(methylsulfanyl)phenyl ether S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 70% S-enantiomer as product
-
-
?
methyl 4-methylphenyl sulfide + NADPH + H+ + O2
(R,S)-methyl 4-methylphenyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 92% S-enantiomer as product
-
-
?
methyl 4-nitrophenyl sulfide + NADPH + H+ + O2
(R,S)-methyl 4-nitrophenyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 37% S-enantiomer as product
-
-
?
methyl 4-tolyl sulfide + NADPH + O2
methyl 4-tolyl sulfoxide + NADP+ + H2O
methyl p-tolyl sulfide + NADPH + H+ + O2
?
methyl p-tolyl sulfide + NADPH + O2
methyl p-tolyl sulfoxide + NADP+ + H2O
methyl phenyl sulfide + NADPH + H+ + O2
(R,S)-methyl phenyl sulfoxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 35% S-enantiomer as product
-
-
?
methyl-4-tolyl sulfide + NADPH + H+ + O2
?
-
-
-
-
?
methylmercaptan + NADPH + H+ + O2
? + NADP+ + H2O
-
-
-
-
?
methylphenylsulfide + NADPH + O2
?
methylthioalkyl glucosinolate + NADPH + H+ + O2
methylsulfinylalkyl glucosinolate S-oxide + NADP+ + H2O
-
-
-
-
?
MK-0457 + NADPH + H+ + O2
MK-0457 N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
MK-0767 methyl sulfide + NADPH + H+ + O2
?
moclobemide + NADPH + H+ + O2
moclobemide N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
N,N,N-trimethylamine + NADPH + H+ + O2
N,N,N-trimethylamine N-oxide + NADP+ + H2O
-
-
-
?
N,N-diallyltryptamine + NADPH + H+ + O2
N,N-diallyltryptamine N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
N,N-dimethyl-3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propan-1-amine + NADPH + H+ + O2
?
-
3-DPT, a phenothiazine analogue, N-oxygenation by FMO1 and FMO3, no activity with FMO5
-
-
?
N,N-dimethyl-5-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]pentan-1-amine + NADPH + H+ + O2
?
-
5-DPT, a phenothiazine analogue, N-oxygenation by FMO1, FMO3, and FMO5
-
-
?
N,N-dimethyl-8-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]octan-1-amine + NADPH + H+ + O2
?
-
8-DPT, a phenothiazine analogue, N-oxygenation by FMO1, FMO3, and FMO5
-
-
?
N,N-dimethylamphetamine + NADPH + H+ + O2
N,N-dimethylamphetamine N-oxide + NADP+ + H2O
N-oxygenation mainly by isozyme FMO1, low activity with isozyme FMO3
-
-
?
N,N-dimethylaniline + NADH + H+ + O2
N,N-dimethylaniline N-oxide + NAD+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
N-(3R)-1-azabicyclo[2.2.2]oct-3-ylfuro[2,3-c]pyridine-5-carboxamide + NADPH + H+ + O2
(R)-3-(furo[2,3-c]pyridine-5-carboxamido)quinuclidine 1-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
N-aminohomopiperidine + NADPH + O2
?
N-aminomorpholine + NADPH + H+ + O2
N-aminomorpholine N-oxide + NADP+ + H2O
-
-
-
-
r
N-aminomorpholine + NADPH + O2
?
N-aminopiperidine + NADPH + O2
?
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
N-aminopyrrolidine + NADPH + H+ + O2
N-aminopyrrolidine N-oxide + NADP+ + H2O
-
-
-
-
r
N-aminopyrrolidone + NADPH + O2
?
N-deacetyl ketoconazole + NADPH + H+ + O2
?
an antifungal agent, is converted to the N-hydroxyl
-
-
?
N-deacetyl ketoconazole + NADPH + H+ + O2
N-deacetyl ketoconazole N-oxide + NADP+ + H2O
n-decylamine + NADPH + O2
1-nitrosodecane + NADP+ + H2O
N-methyl-1,2,3,4-tetrahydroisoquinoline + NADPH + O2
?
-
-
-
-
?
N-methyl-tamoxifen + NADPH + O2
N-methyl-tamoxifen N-oxide + NADP+ + H2O
-
recombinant isozymes FMO1 and FMO3
-
-
?
n-octylamine + NADPH + O2
1-nitrosooctane + NADP+ + H2O
n-propylhydrazine + NADPH + H+ + O2
N-propylhydrazine N-oxide + NADP+ + H2O
-
-
-
-
r
naphthylthiourea + NADPH + O2
naphthylthiourea S-oxide + NADP+ + H2O
nicotine + NADPH + H+ + O2
(S)-nicotine N1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
nicotine + NADPH + H+ + O2
nicotine N-oxide + NADP+ + H2O
nomifensine + NADPH + H+ + O2
?
-
substrate of isoforms FMO3 and FMO5
-
-
?
NSC645809 + NADPH + H+ + O2
N,N-diethyl-2-((8-hydroxy-6-oxo-6H-imidazo[4,5,1-de]acridin-5-yl)amino)ethan-1-amine oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
olanzapine + NADPH + H+ + O2
1-methyl-4-(2-methyl-10H-benzo[b]thieno[2,3-e][1,4]diazepin-4-yl)piperazine 1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
olopatadine + NADPH + H+ + O2
olopatadine N-oxide + NADP+ + H2O
orphenadrine + NADPH + H+ + O2
orphenadrine N-oxide + NADP+ + H2O
an anticholinergic drug
-
-
?
p-chloro-N-methylaniline + NADPH + O2
?
p-tolyl sulfide + NADPH + O2
p-tolyl sulfoxide + NADP+ + H2O
pargyline + NADPH + H+ + O2
pargyline N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
pargyline + NADPH + O2
?
-
inhibitor of monoaminoxidase B
-
-
?
pentoxifylline + NADPH + H+ + O2
pentoxifylline N-oxide + NADP+ + H2O
phenethylamine + NADPH + O2
phenethylamine N-oxide + NADP+ + H2O
-
isozyme FMO3
-
-
?
phenyl propyl sulfide + NADPH + H+ + O2
phenyl propyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
phenylhydrazine + NADPH + H+ + O2
phenylhydrazine N-oxide + NADP+ + H2O
-
-
-
-
r
phenylhydrazine + NADPH + O2
?
phenylthiourea + NADPH + O2
?
phenylthiourea + NADPH + O2
phenylthiourea S-oxide + NADP+ + H2O
phorate + NADPH + H+ + O2
?
a thioether-containing organophosphate insecticide
-
-
?
phospho-sulindac + NADPH + H+ + O2
?
-
substrate of isoforms FMO1, FMO3, and FMO5
-
-
?
primaquine + NADPH + H+ + O2
?
-
substrate of isoform FMO3
-
-
?
procarbazine + NADPH + H+ + O2
procarbazine N-oxide + NADP+ + H2O
-
-
-
-
r
procarbazine + NADPH + O2
?
propranolol + NADPH + O2
propranolol-hydroxylamine + NADP+
-
-
-
-
?
pyrazolacridine + NADPH + H+ + O2
pyrazolacridine N-oxide + NADP+ + H2O
pyrazoloacridine + NADPH + O2
pyrazoloacridine N-oxide + NADP+ + H2O
-
-
-
-
?
quazepam + NADPH + H+ + O2
7-chloro-5-(2-fluorophenyl)-1-(2,2,2-trifluoroethyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one + NADP+ + H2O
-
substrate of isoform FMO1
-
-
?
R(-)-deprenyl + NADPH + O2
?
-
inhibitor of monoaminoxidase B
-
-
?
ranitidine + NADPH + H+ + O2
?
ranitidine + NADPH + O2
?
-
-
-
-
?
S-allyl-L-cysteine + NADPH + H+ + O2
?
-
-
-
?
S-allyl-L-cysteine + NADPH + H+ + O2
? + NADP+ + H2O
stereochemmistry, overview
-
-
?
S-benzyl-L-cysteine + NADPH + O2
S-benzyl-L-cysteine S-oxide + NADP+ + H2O
-
isozyme FMO1
-
-
?
S-farnesylcysteine + NADPH + O2
S-farnesylcysteine S-oxide + NADP+ + H2O
-
-
-
-
?
S-farnesylcysteine methyl ester + NADPH + O2
?
-
-
-
-
?
S-farnesylcysteine methyl ester + NADPH + O2
S-farnesylcysteine S-oxide methyl ester + NADP+ + H2O
-
-
-
-
?
S-methyl esonarimod + NADPH + H+ + O2
?
S-methyl esonarimod + NADPH + H+ + O2
S-methyl esonarimod S-oxide + NADP+ + H2O
S-methyl N,N-diethyldithiocarbamate + NADPH + H+ + O2
(diethylnitroryl)(methylsulfanyl)methanethione + NADP+ + H2O
-
substrate of isoform FMO1 and FMO3
-
-
?
S16020 + NADPH + H+ + O2
S16020 N-oxide + NADP+ + H2O
a topoisomerase II inhibitor and antitumor drug, is converted to the N-oxide
-
-
?
secondary amine + NADPH + O2
secondary nitrone + NADP+ + H2O
-
-
first oxidation to the N-hydroxy amine and then to the corresponding nitrone
?
selegiline + NADPH + H+ + O2
?
-
i.e. (2R)-N-methyl-1-phenyl-N-prop-2-ynylpropan-2-amine
-
-
?
selegiline + NADPH + O2
selegiline N-oxide + NADP+
-
-
-
-
?
seleno-L-methionine + NADPH + H+ + O2
seleno-L-methionine Se-oxide + NADP+ + H2O
-
-
-
?
selenomethionine + NADPH + H+ + O2
seleno-L-methionine Se-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
SNI-2011 + NADPH + H+ + O2
?
a muscarinic receptor antagonist, is converted to the N-oxide
-
-
?
SNI-2011 + NADPH + H+ + O2
SNI-2011 N-oxide + NADP+ + H2O
-
substrate of isoform FMO1
-
-
?
sulfamethoxazole + NADPH + O2
?
sulindac sulfide + NADPH + H+ + O2
?
-
substrate of isoforms FMO1 and FMO3
-
-
?
sulindac sulfide + NADPH + H+ + O2
sulindac + NADP+ + H2O
sulindac sulfide + NADPH + H+ + O2
sulindac sulfide S-oxide + NADP+ + H2O
-
-
-
?
sulindac sulfide + NADPH + O2
(S,R)-sulindac + NADP+ + H2O
-
-
-
-
?
sulindac sulfide + NADPH + O2
sulindac + NADP+ + H2O
-
-
-
-
?
tamoxifen + NADPH + H+ + O2
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
tamoxifen + NADPH + O2
?
-
-
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
tazarotenic acid + NADPH + H+ + O2
?
a retinoic acid receptor modulator, is converted to the S-oxide
-
-
?
tazarotenic acid + NADPH + H+ + O2
tazarotenate N-oxide + NADP+ + H2O
tertiary amine + NADPH + O2
tertiary N-oxide + NADP+ + H2O
-
-
-
-
?
TG100435 + NADPH + H+ + O2
1-(2-(4-((7-(2,6-dichlorophenyl)-5-methylbenzo[e][1,2,4]triazin-3-yl)amino)phenoxy)ethyl)pyrrolidine 1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
TG100435 + NADPH + H+ + O2
?
-
substrate of isoform FMO1
-
-
?
thiacetazone + 2 NADPH + 2 H+ + 2 O2
thiacetazone carbodiimide + 2 NADP+ + 2 H2O
thiacetazone + 2 NADPH + 2 O2
(E)-{(2E)-[4-(acetylamino)benzylidene]hydrazinylidene}(amino)methanesulfinic acid + 2 NADP+ + H2O
-
bioactivation by EtaA
-
-
?
thiacetazone + NADPH + H+ + O2
?
thiacetazone + NADPH + H+ + O2
thiacetazone N-oxide + NADP+ + H2O
thiacetazone + NADPH + H+ + O2
thiacetazone S-oxide + NADP+ + H2O
thioacetamide + NADPH + O2
?
thiobenzamide + NADPH + H+ + O2
thiobenzamide N-oxide + NADP+ + H2O
-
N-oxidation
-
-
?
thiobenzamide + NADPH + O2
?
thiocarbanilide + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + H+ + O2
?
thiourea + NADPH + O2
thiourea S-oxide + NADP+ + H2O
tigecycline + NADPH + O2
11a-hydroxytigecycline + NADP+ + H2O
tozasertib + NADPH + H+ + O2
?
tozasertib + NADPH + H+ + O2
tozasertib N-oxide + NADP+ + H2O
-
-
-
?
triethylamine + NADPH + H+ + O2
triethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trifluoperazine + NADPH + O2
?
-
-
-
-
?
trifluoroperazine + NADPH + H+ + O2
2,3,4-trifluoropyridine 1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
trifluoroperazine + NADPH + O2
?
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
trimethylamine + NADPH + O2
?
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
tyramine + NADPH + O2
tyramine N-oxide + NADP+ + H2O
-
-
-
-
?
voriconazole + NADPH + H+ + O2
?
xanomeline + NADPH + H+ + O2
xanomeline N-oxide + NADP+ + H2O
[7-(2,6-dichloro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine + NADPH + H+ + O2
[7-(2,6-dichlorophenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-(4-[2-(1-oxy-pyrrolidin-1-yl)-ethoxy]-phenyl)-amine + NADP+ + H2O
-
i.e. TG100435, a multitargeted Src family kinase inhibitor with anticancer activity, FMO3 is the primary enzyme responsible for TG100855 formation, enzyme-mediated retroreduction of TG100855 back to TG100435 is observed catalyzed by a cytochrome P450 reductase, overview
i.e. TG100855, the N-oxide product is also a multitargeted Src family kinase inhibitor with anticancer activity
-
?
additional information
?
-
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
-
-
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
-
possibly, and other 1,1-disubstituted hydrazines
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
-
-
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
-
possibly, and other 1,1-disubstituted hydrazines
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
-
-
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
-
possibly, and other 1,1-disubstituted hydrazines
-
?
1,2,3,4-tetrahydroisoquinoline + NADPH + O2
?
-
-
-
-
?
1,2,3,4-tetrahydroisoquinoline + NADPH + O2
?
-
-
-
-
?
1,2-dimethylhydrazine + NADPH + O2
?
-
-
-
-
?
1,2-dimethylhydrazine + NADPH + O2
?
-
-
-
-
?
1,2-dimethylphenylhydrazine + NADPH + O2
?
-
-
-
-
?
1,2-dimethylphenylhydrazine + NADPH + O2
?
-
-
-
-
?
1-butanethiol + NADPH + O2
?
-
-
-
-
?
1-butanethiol + NADPH + O2
?
-
-
-
-
?
1-butanethiol + NADPH + O2
?
-
-
-
-
?
1-butanethiol + NADPH + O2
?
-
-
-
-
?
1-methyl-1-phenylhydrazine + NADPH + O2
?
-
-
-
-
?
1-methyl-1-phenylhydrazine + NADPH + O2
?
-
-
-
-
?
1-methyl-1-phenylhydrazine + NADPH + O2
?
-
-
-
-
?
1-methyl-2-benzylhydrazine + NADPH + O2
?
-
-
-
-
?
1-methyl-2-benzylhydrazine + NADPH + O2
?
-
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
reaction in microsomal detoxification pathway of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, a neurotoxin to nigrostriatal dopaminergic neurons
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
reaction in microsomal detoxification pathway of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, a neurotoxin to nigrostriatal dopaminergic neurons
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
one of the predominant enzmyes responsible for the oxygenation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + O2
?
-
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + O2
?
-
-
-
-
?
1-[4-(methylsulfanyl)phenyl]ethanone + NADPH + H+ + O2
(R,S)-1-[4-(methylsulfanyl)phenyl]ethanone S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 21% R-enantiomer as product
-
-
?
1-[4-(methylsulfanyl)phenyl]ethanone + NADPH + H+ + O2
(R,S)-1-[4-(methylsulfanyl)phenyl]ethanone S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 21% R-enantiomer as product
-
-
?
10-(N,N-dimethylaminoalkyl)-2-(trifluoromethyl) phenothiazines + NADPH + O2
?
-
with the alkyl side chain varying in length from 5 to 7 carbons, no activity with shorter side chains by isozyme FMO2
-
-
?
10-(N,N-dimethylaminoalkyl)-2-(trifluoromethyl) phenothiazines + NADPH + O2
?
-
with the alkyl side chain varying in length from 2 to 7 carbons, liver isozyme FMO1
-
-
?
10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene + NADPH + H+ + O2
? + NADP+ + H2O
-
-
-
?
10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene + NADPH + H+ + O2
? + NADP+ + H2O
-
-
-
?
10-(N,N-dimethylaminopentyl)-2-(trifluoromethyl)phenothiazine + NADPH + O2
?
-
-
-
-
?
10-(N,N-dimethylaminopentyl)-2-(trifluoromethyl)phenothiazine + NADPH + O2
?
-
isozyme FMO3
-
-
?
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine + NADPH + O2
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine N-oxide + NADP+ + H2O
-
-
-
-
?
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine + NADPH + O2
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine N-oxide + NADP+ + H2O
-
formation of the cis-oxime
-
-
?
2,4,5-trichlorphenol + O2
2,5-dichlorohydroquinone + H2O + Cl-
-
100% conversion
-
-
?
2,4,5-trichlorphenol + O2
2,5-dichlorohydroquinone + H2O + Cl-
-
100% conversion
-
-
?
2,4,6-trichlorphenol + O2
2,6-dichlorohydroquinone + H2O + Cl-
-
72% conversion
-
-
?
2,4,6-trichlorphenol + O2
2,6-dichlorohydroquinone + H2O + Cl-
-
72% conversion
-
-
?
2,4-dichlorphenol + O2
chlorohydroquinone + H2O + Cl-
-
100% conversion
-
-
?
2,4-dichlorphenol + O2
chlorohydroquinone + H2O + Cl-
-
100% conversion
-
-
?
2-(methylsulfanyl)pyridine + NADPH + H+ + O2
2-(methylsulfanyl)pyridine S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
2-(methylsulfanyl)pyridine + NADPH + H+ + O2
2-(methylsulfanyl)pyridine S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
2-(methylsulfanyl)thiophene + NADPH + H+ + O2
2-(methylsulfanyl)thiophene S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
2-(methylsulfanyl)thiophene + NADPH + H+ + O2
2-(methylsulfanyl)thiophene S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
2-chlorophenol + O2
chlorohydroquinone + H2O
-
-
-
-
?
2-chlorophenol + O2
chlorohydroquinone + H2O
-
-
-
-
?
2-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-2-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 75% R-enantiomer as product
-
-
?
2-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-2-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 75% R-enantiomer as product
-
-
?
2-mercaptobenzimidazole + NADPH + O2
?
-
-
-
-
?
2-mercaptobenzimidazole + NADPH + O2
?
-
-
-
-
?
2-mercaptobenzimidazole + NADPH + O2
?
-
-
-
-
?
2-mercaptobenzimidazole + NADPH + O2
?
-
-
-
-
?
4-chlorophenol + O2
hydroquinone + H2O + Cl-
-
100% conversion
-
-
?
4-chlorophenol + O2
hydroquinone + H2O + Cl-
-
100% conversion
-
-
?
5-[[3-(dimethylamino)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
i.e. C-1305
-
-
?
5-[[3-(dimethylamino)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
-
i.e. C-1305
-
-
?
5-[[3-(dimethylamino)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
i.e. C-1299
-
-
?
5-[[3-(dimethylamino)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
i.e. C-1305
-
-
?
5-[[3-(dimethylamino)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
-
i.e. C-1299
-
-
?
alpha-naphthylthiourea + NADPH + O2
?
-
-
-
-
?
alpha-naphthylthiourea + NADPH + O2
?
-
-
-
-
?
alpha-naphthylthiourea + NADPH + O2
?
-
-
-
-
?
alpha-naphthylthiourea + NADPH + O2
?
-
-
-
-
?
aminopyrine + NADPH + O2
?
-
-
-
-
?
aminopyrine + NADPH + O2
?
-
-
-
-
?
aminopyrine + NADPH + O2
?
-
-
-
-
?
aminopyrine + NADPH + O2
?
-
-
-
-
?
amphetamine + NADPH + H+ + O2
?
an antipsychotic agent, is converted to the hydroxylamine
-
-
?
amphetamine + NADPH + H+ + O2
?
an antipsychotic agent, is converted to the hydroxylamine
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
N-oxidation
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
high activity
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
a nonsteroidal antiinflammatory drug, is converted to the N-oxide
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
N-oxidation
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
N-oxygenation of benzydamine by the wild-type and N61S mutant variant of FMO3
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + O2
benzydamine N-oxide + NADP+ + H2O
KC734478, KC734481, KC734482, KC734486
-
-
-
?
benzydamine + NADPH + O2
benzydamine N-oxide + NADP+ + H2O
KC734478, KC734481, KC734482, KC734486
highest activity of all isoforms tested
-
-
?
benzydamine + NADPH + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzylhydrazine + NADPH + O2
?
-
-
-
-
?
benzylhydrazine + NADPH + O2
?
-
-
-
-
?
beta-ethylphenylhydrazine + NADPH + O2
?
-
-
-
-
?
beta-ethylphenylhydrazine + NADPH + O2
?
-
-
-
-
?
butylhydrazine + NADPH + O2
?
-
-
-
-
?
butylhydrazine + NADPH + O2
?
-
-
-
-
?
chlorpromazine + NADPH + H+ + O2
chlorpromazine N-oxide + NADP+ + H2O
-
-
-
?
chlorpromazine + NADPH + H+ + O2
chlorpromazine N-oxide + NADP+ + H2O
a dopemaine D2 antagonist
-
-
?
chlorpromazine + NADPH + H+ + O2
chlorpromazine N-oxide + NADP+ + H2O
a dopemaine D2 antagonist
-
-
?
chlorpromazine + NADPH + O2
?
-
-
-
-
?
chlorpromazine + NADPH + O2
?
-
liver microsomes
-
-
?
chlorpromazine + NADPH + O2
?
-
liver isozyme FMO1
-
-
?
cimetidine + NADPH + H+ + O2
cimetidine S-oxide + NADP+ + H2O
-
S-oxygenation of cimetidine, i.e. CIM, a histamine H2-receptor antagonist of therapeutic utility in the treatment of peptic ulcer disease and gastric hypersecretory syndromes. Development of in-line screening and an off-line chiral CE method for determination of the stereoselectivity of flavin-containing monooxygenase isoforms FMO1, FMO3, and FMO5 using chiral specific selectors, overview
-
-
?
cimetidine + NADPH + H+ + O2
cimetidine S-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
clomiphene + NADPH + H+ + O2
clomiphene N-oxide + NADP+ + H2O
-
-
-
?
clomiphene + NADPH + H+ + O2
clomiphene N-oxide + NADP+ + H2O
clomiphene is used in infertility medication
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
-
N-oxidation
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
-
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
an antipsychotic agent, is converted to the N-oxide
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
an antipsychotic agent, is converted to the N-oxide
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
-
N-oxidation
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
cysteamine + NADPH + H+ + O2
?
-
-
-
-
?
cysteamine + NADPH + H+ + O2
?
-
-
-
-
?
cysteamine + NADPH + H+ + O2
?
-
-
-
-
?
cysteamine + NADPH + O2
?
-
-
-
-
?
cysteamine + NADPH + O2
?
-
-
-
-
?
cysteamine + NADPH + O2
?
-
-
-
-
?
cysteamine + NADPH + O2
?
-
-
-
-
?
cysteamine + NADPH + O2
?
-
-
-
-
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
-
-
-
-
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
-
-
-
-
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
-
-
-
-
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
-
-
-
-
?
dapsone + NADPH + O2
?
bioactivation by isozyme FMO3, not FMO1, results in covalent adduct formation
-
-
?
dapsone + NADPH + O2
?
isozyme FMO3, not FMO1
-
-
?
demeton-O + NADPH + O2
demeton-O sulfoxide + NADP+ + H2O
-
-
-
-
?
demeton-O + NADPH + O2
demeton-O sulfoxide + NADP+ + H2O
-
i.e. O,O-diethyl O-2-ethylthioethyl phosphorothioate, isozymes FMO1 and FMO3, higher activity by FMO1
-
-
?
deprenyl + NADPH + H+ + O2
?
a monoamine oxidase type B inhibitor, is converted to the hydroxylamine
-
-
?
deprenyl + NADPH + H+ + O2
?
a monoamine oxidase type B inhibitor, is converted to the hydroxylamine
-
-
?
deprenyl + NADPH + H+ + O2
?
-
-
-
-
?
dibenzylamine + NADPH + O2
?
-
-
-
-
?
dibenzylamine + NADPH + O2
?
-
-
-
-
?
dibenzylamine + NADPH + O2
?
-
-
-
-
?
dibenzylamine + NADPH + O2
?
-
-
-
-
?
dimethylsulfone + NADH + H+ + O2
methanesulfinate + NAD+ + H2O
-
-
-
-
?
dimethylsulfone + NADH + H+ + O2
methanesulfinate + NAD+ + H2O
-
-
-
-
?
disulfoton + NADPH + H+ + O2
?
-
-
-
-
?
disulfoton + NADPH + H+ + O2
?
a thioether-containing organophosphate insecticide
-
-
?
ephedrine + NADPH + O2
?
-
-
-
-
?
ephedrine + NADPH + O2
?
-
-
-
-
?
ephedrine + NADPH + O2
?
-
-
-
-
?
ephedrine + NADPH + O2
?
-
-
-
-
?
ethiofencarb + NADPH + O2
ethiofencarb sulfoxide + NADP+ + H2O
-
-
-
-
?
ethiofencarb + NADPH + O2
ethiofencarb sulfoxide + NADP+ + H2O
-
i.e. alpha-ethylthio-o-tolyl methylcarbamate, isozymes FMO1 and FMO3, higher activity by FMO1
-
-
?
ethionamide + NADPH + H+ + O2
?
an antibiotic agent
-
-
?
ethionamide + NADPH + H+ + O2
?
an antibiotic agent
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide N-oxide + NADP+ + H2O
an antibiotic agent
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide N-oxide + NADP+ + H2O
-
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
-
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
ethionamide is a pro-drug requiring bioactivation to exert toxicity
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
i.e. ETA, S-oxygenation by isozymes FMO1, FMO2, and FMO3
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
-
substrate of isoforms FMO1, FMO2, and FMO3
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
-
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
ethionamide is a pro-drug requiring bioactivation to exert toxicity
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
i.e. ETA, S-oxygenation by isozymes FMO1, FMO2, and FMO3
-
-
?
ethionamide + NADPH + O2 + H+
2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O
-
bioactivation by isozymes FMO1 and FMO3
-
-
?
ethionamide + NADPH + O2 + H+
2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O
-
a thioamide-containing second line antitubercular prodrug
-
-
?
ethionamide + NADPH + O2 + H+
2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O
-
bioactivation by EtaA
-
-
?
ethionamide + NADPH + O2 + H+
2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O
-
a thioamide-containing second line antitubercular prodrug
-
-
?
ethylene sulfide + NADPH + O2
?
-
-
-
-
?
ethylene sulfide + NADPH + O2
?
-
-
-
-
?
ethylene sulfide + NADPH + O2
?
-
-
-
-
?
ethylene sulfide + NADPH + O2
?
-
-
-
-
?
fenthion + NADPH + O2
fenthion sulfoxide + NADP+ + H2O
-
-
-
-
?
fenthion + NADPH + O2
fenthion sulfoxide + NADP+ + H2O
-
-
more than 95% (+)-sulfoxide
-
?
fenthion + NADPH + O2
fenthion sulfoxide + NADP+ + H2O
-
i.e. O,O-dimethyl O-4-methylthio-m-tolyl phosphorothioate, isozymes FMO1 and FMO3, stereospecifc product formation, overview
-
-
?
GSK5182 + NADPH + H+ + O2
GSK5182 N-oxide + NADP+ + H2O
-
-
-
?
GSK5182 + NADPH + H+ + O2
GSK5182 N-oxide + NADP+ + H2O
an antidiabetic lead molecule
-
-
?
hypotaurine + H2O + NAD+
taurine + NADH
-
-
-
?
hypotaurine + H2O + NAD+
taurine + NADH
-
metabolism of cysteine
-
?
hypotaurine + NADH + H+ + O2
taurine + NAD+ + H2O
S-oxygenation
-
-
?
hypotaurine + NADH + H+ + O2
taurine + NAD+ + H2O
S-oxygenation
-
-
?
hypotaurine + NADPH + H+ + O2
taurine + NADP+ + H2O
S-oxygenation
-
-
?
hypotaurine + NADPH + H+ + O2
taurine + NADP+ + H2O
S-oxygenation
-
-
?
imipramine + NADPH + H+ + O2
imipramine N-oxide + NADP+ + H2O
an antidepressant, is converted to the N-oxide
-
-
?
imipramine + NADPH + H+ + O2
imipramine N-oxide + NADP+ + H2O
an antidepressant, is converted to the N-oxide
-
-
?
imipramine + NADPH + H+ + O2
imipramine N-oxide + NADP+ + H2O
-
substrate of isoform FMO1
-
-
?
imipramine + NADPH + H+ + O2
imipramine N-oxide + NADP+ + H2O
-
substrate of isoform FMO1
-
-
?
imipramine + NADPH + O2
?
-
-
-
-
?
imipramine + NADPH + O2
?
-
-
-
-
?
imipramine + NADPH + O2
?
-
-
-
-
?
imipramine + NADPH + O2
?
-
liver microsomes
-
-
?
imipramine + NADPH + O2
?
-
-
-
-
?
imipramine + NADPH + O2
?
-
-
-
-
?
imipramine + NADPH + O2
?
-
liver isozyme FMO1
-
-
?
imipramine + NADPH + O2
imipramine N-oxide + NADP+ + H2O
-
-
-
-
?
imipramine + NADPH + O2
imipramine N-oxide + NADP+ + H2O
-
-
-
-
?
indole + NADPH + H+ + O2
indole N-oxide + NADP+ + H2O
-
-
-
-
?
indole + NADPH + H+ + O2
indole N-oxide + NADP+ + H2O
-
-
-
-
?
indole + NADPH + H+ + O2
indoxyl + NADP+ + H2O
-
-
-
-
?
indole + NADPH + H+ + O2
indoxyl + NADP+ + H2O
-
-
-
-
?
indole + NADPH + H+ + O2
indoxyl + NADP+ + H2O
-
-
-
-
?
indole + NADPH + H+ + O2
indoxyl + NADP+ + H2O
-
-
-
?
indole + NADPH + H+ + O2
indoxyl + NADP+ + H2O
-
-
-
-
?
indole + NADPH + H+ + O2
indoxyl + NADP+ + H2O
-
-
-
?
isopropylhydrazine + NADPH + O2
?
-
-
-
-
?
isopropylhydrazine + NADPH + O2
?
-
-
-
-
?
itopride + NADPH + H+ + O2
itopride N-oxide + NADP+ + H2O
-
-
-
?
itopride + NADPH + H+ + O2
itopride N-oxide + NADP+ + H2O
-
-
-
-
?
itopride + NADPH + H+ + O2
itopride N-oxide + NADP+ + H2O
a dopamine D2 receptor antagonist, is converted to the N-oxide
-
-
?
itopride + NADPH + H+ + O2
itopride N-oxide + NADP+ + H2O
a dopamine D2 receptor antagonist, is converted to the N-oxide
-
-
?
itopride + NADPH + H+ + O2
itopride N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
K11777 + NADPH + H+ + O2
K11777 N-oxide + NADP+ + H2O
a cysteine protease inhibitor against Trypanosoma cruzi, is converted to the N-oxide
-
-
?
K11777 + NADPH + H+ + O2
K11777 N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
L-Met-Phe + NADPH + O2
(L-Met-S-oxide)-Phe + NADP+ + H2O
-
isozymes FMO1-FMO4
-
-
?
L-Met-Phe + NADPH + O2
(L-Met-S-oxide)-Phe + NADP+ + H2O
-
liver microsomes
-
-
?
L-Met-Val + NADPH + O2
(L-Met-S-oxide)-Val + NADP+ + H2O
-
isozymes FMO1-FMO4, low activity by isozyme FMO1
-
-
?
L-Met-Val + NADPH + O2
(L-Met-S-oxide)-Val + NADP+ + H2O
-
liver microsomes
-
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
-
-
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
free and N-terminally peptide-bound L-methionine, no activity with modified peptide-bound methionine and with N-acetyl-L-methionine, isozymes FMO1-FMO4
stereospecificity for formation of the D-isomer, especially by isozyme FMO3
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
-
-
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
free and N-terminally peptide-bound L-methionine, no activity with modified peptide-bound methionine and with N-acetyl-L-methionine, isozymes FMO1-FMO4
stereospecificity for formation of the D-isomer, especially by isozyme FMO3
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
-
-
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
free and N-terminally peptide-bound L-methionine, no activity with modified peptide-bound methionine and with N-acetyl-L-methionine, isozymes FMO1-FMO4
stereospecificity for formation of the D-isomer, especially by isozyme FMO3
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
-
-
-
?
L-seleno-methionine + NADPH + O2
L-methionine seleno-oxide + NADP+ + H2O
-
liver microsomes
-
-
?
L-seleno-methionine + NADPH + O2
L-methionine seleno-oxide + NADP+ + H2O
-
purified liver isozymes FMO1 and FMO3
-
-
?
lipoic acid + NADPH + O2
?
-
-
-
-
?
lipoic acid + NADPH + O2
?
-
-
-
-
?
methamphetamine + NADPH + H+ + O2
?
a psychostimulant, is converted to the hydroxylamine
-
-
?
methamphetamine + NADPH + H+ + O2
?
a psychostimulant, is converted to the hydroxylamine
-
-
?
methamphetamine + NADPH + O2
?
-
-
-
-
?
methamphetamine + NADPH + O2
?
-
-
-
-
?
methamphetamine + NADPH + O2
?
-
-
-
-
?
methamphetamine + NADPH + O2
?
-
-
-
-
?
methamphetamine + NADPH + O2
?
-
-
-
-
?
methimazole + NADPH + H+ + O2
?
a thyroperoxidase inhibitor
-
-
?
methimazole + NADPH + H+ + O2
?
a thyroperoxidase inhibitor, is converted to the S-oxide
-
-
?
methimazole + NADPH + H+ + O2
?
an thyroperoxidase inhibitor, is converted to the S-oxide
-
-
?
methimazole + NADPH + H+ + O2
?
-
-
-
-
?
methimazole + NADPH + H+ + O2
?
-
-
-
-
?
methimazole + NADPH + H+ + O2
?
-
FMO1, FMO2, and FMO3
-
-
?
methimazole + NADPH + H+ + O2
methimazole N-oxide + NADP+ + H2O
an thyroperoxidase inhibitor, is converted to the S-oxide
-
-
?
methimazole + NADPH + H+ + O2
methimazole N-oxide + NADP+ + H2O
-
N-oxidation
-
-
?
methimazole + NADPH + H+ + O2
methimazole N-oxide + NADP+ + H2O
KC734478, KC734481, KC734482, KC734486
-
-
-
?
methimazole + NADPH + H+ + O2
methimazole N-oxide + NADP+ + H2O
KC734478, KC734481, KC734482, KC734486
about 25% of the activityy with substrate benzydamine
-
-
?
methimazole + NADPH + H+ + O2
methimazole N-oxide + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + H+ + O2
methimazole N-oxide + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADP+ + H2O
low activity with FMO2.1, moderate activity with FMO3, high activity with FMO1
-
-
?
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADP+ + H2O
-
substrate of isoforms FMO1, FMO2, and FMO3
-
-
?
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADP+ + H2O
S-oxygenation
-
-
?
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADP+ + H2O
S-oxygenation
-
-
?
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADP+ + H2O
i.e. N-methyl-2-mercaptoimidazole
-
-
?
methimazole + NADPH + O2
?
-
-
-
-
?
methimazole + NADPH + O2
?
-
-
-
?
methimazole + NADPH + O2
?
-
isozyme FMO3
-
-
?
methimazole + NADPH + O2
?
-
liver microsomes
-
-
?
methimazole + NADPH + O2
?
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
recombinant protein expressed in E. coli
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
recombinant protein expressed in E. coli
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
FMO3 5000 times more efficient than FMO5
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
recombinant protein expressed in E. coli
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methiocarb + NADPH + O2
methiocarb sulfoxide + NADP+ + H2O
-
-
-
-
?
methiocarb + NADPH + O2
methiocarb sulfoxide + NADP+ + H2O
-
i.e. 4-methylthio-3,5-xylyl methylcarbamate, isozyme FMO1 acts stereospecifically, no activity by isozyme FMO3
-
-
?
methyl 4-tolyl sulfide + NADPH + O2
methyl 4-tolyl sulfoxide + NADP+ + H2O
-
-
-
-
?
methyl 4-tolyl sulfide + NADPH + O2
methyl 4-tolyl sulfoxide + NADP+ + H2O
-
-
-
-
?
methyl p-tolyl sulfide + NADPH + H+ + O2
?
-
-
-
?
methyl p-tolyl sulfide + NADPH + H+ + O2
?
-
FMO1, FMO2, but poor substrate of FMO3
-
-
?
methyl p-tolyl sulfide + NADPH + O2
methyl p-tolyl sulfoxide + NADP+ + H2O
-
-
-
-
?
methyl p-tolyl sulfide + NADPH + O2
methyl p-tolyl sulfoxide + NADP+ + H2O
-
-
stereochemistry: product 49% R-enantiomer
?
methyl p-tolyl sulfide + NADPH + O2
methyl p-tolyl sulfoxide + NADP+ + H2O
-
-
26% R
-
?
methylphenylsulfide + NADPH + O2
?
-
-
-
-
?
methylphenylsulfide + NADPH + O2
?
-
-
-
-
?
methylphenylsulfide + NADPH + O2
?
-
-
-
-
?
methylphenylsulfide + NADPH + O2
?
-
-
-
-
?
MK-0767 methyl sulfide + NADPH + H+ + O2
?
a peroxisome proliferator receptor activator, is converted to the S-oxide
-
-
?
MK-0767 methyl sulfide + NADPH + H+ + O2
?
-
substrate of isoforms FMO1 and FMO3
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
r
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
r
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
348485, 348486, 348487, 348488, 348490, 348491, 348492, 348494, 348497, 348498, 348499, 348505, 676315 -
-
?
N-aminohomopiperidine + NADPH + O2
?
-
-
-
-
?
N-aminohomopiperidine + NADPH + O2
?
-
-
-
-
?
N-aminohomopiperidine + NADPH + O2
?
-
-
-
-
?
N-aminomorpholine + NADPH + O2
?
-
-
-
-
?
N-aminomorpholine + NADPH + O2
?
-
-
-
-
?
N-aminopiperidine + NADPH + O2
?
-
-
-
-
?
N-aminopiperidine + NADPH + O2
?
-
-
-
-
?
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
-
-
-
?
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
-
-
-
-
?
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
-
-
-
?
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
-
-
-
-
?
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
-
-
-
?
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
-
-
-
-
?
N-aminopyrrolidone + NADPH + O2
?
-
-
-
-
?
N-aminopyrrolidone + NADPH + O2
?
-
-
-
-
?
N-deacetyl ketoconazole + NADPH + H+ + O2
N-deacetyl ketoconazole N-oxide + NADP+ + H2O
an antifungal agent, is converted to the N-hydroxyl
-
-
?
N-deacetyl ketoconazole + NADPH + H+ + O2
N-deacetyl ketoconazole N-oxide + NADP+ + H2O
-
substrate of isoform FMO1
-
-
?
N-deacetyl ketoconazole + NADPH + H+ + O2
N-deacetyl ketoconazole N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
n-decylamine + NADPH + O2
1-nitrosodecane + NADP+ + H2O
-
lung enzyme active, liver enzyme not
-
-
?
n-decylamine + NADPH + O2
1-nitrosodecane + NADP+ + H2O
-
lung enzyme active, liver enzyme not
-
-
?
n-octylamine + NADPH + O2
1-nitrosooctane + NADP+ + H2O
-
recombinant protein expressed in E. coli
-
-
?
n-octylamine + NADPH + O2
1-nitrosooctane + NADP+ + H2O
-
recombinant protein expressed in E. coli
-
-
?
n-octylamine + NADPH + O2
1-nitrosooctane + NADP+ + H2O
-
lung enzyme active, liver enzyme not
-
-
?
n-octylamine + NADPH + O2
1-nitrosooctane + NADP+ + H2O
-
lung enzyme active, liver enzyme not
-
-
?
naphthylthiourea + NADPH + O2
naphthylthiourea S-oxide + NADP+ + H2O
-
isozyme FMO2
-
-
?
naphthylthiourea + NADPH + O2
naphthylthiourea S-oxide + NADP+ + H2O
-
isozyme FMO2
-
-
?
nicotine + NADPH + H+ + O2
nicotine N-oxide + NADP+ + H2O
a stimulant, is converted to the trans-N-oxide
-
-
?
nicotine + NADPH + H+ + O2
nicotine N-oxide + NADP+ + H2O
-
-
-
-
?
olopatadine + NADPH + H+ + O2
olopatadine N-oxide + NADP+ + H2O
an antihistamininc drug, is converted to the N-oxide
-
-
?
olopatadine + NADPH + H+ + O2
olopatadine N-oxide + NADP+ + H2O
an antihistamininc drug, is converted to the N-oxide
-
-
?
olopatadine + NADPH + H+ + O2
olopatadine N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
p-chloro-N-methylaniline + NADPH + O2
?
-
-
-
-
?
p-chloro-N-methylaniline + NADPH + O2
?
-
-
-
-
?
p-chloro-N-methylaniline + NADPH + O2
?
-
-
-
-
?
p-chloro-N-methylaniline + NADPH + O2
?
-
-
-
-
?
p-tolyl sulfide + NADPH + O2
p-tolyl sulfoxide + NADP+ + H2O
-
S-oxidase activity
-
-
?
p-tolyl sulfide + NADPH + O2
p-tolyl sulfoxide + NADP+ + H2O
-
S-oxidase activity
-
-
?
pentoxifylline + NADPH + H+ + O2
pentoxifylline N-oxide + NADP+ + H2O
-
-
-
?
pentoxifylline + NADPH + H+ + O2
pentoxifylline N-oxide + NADP+ + H2O
-
-
-
?
phenylhydrazine + NADPH + O2
?
-
-
-
-
?
phenylhydrazine + NADPH + O2
?
-
-
-
-
?
phenylthiourea + NADPH + O2
?
-
-
-
-
?
phenylthiourea + NADPH + O2
?
-
-
-
-
?
phenylthiourea + NADPH + O2
?
-
-
-
-
?
phenylthiourea + NADPH + O2
?
-
-
-
-
?
phenylthiourea + NADPH + O2
?
-
-
-
-
?
phenylthiourea + NADPH + O2
phenylthiourea S-oxide + NADP+ + H2O
-
isozyme FMO2
-
-
?
phenylthiourea + NADPH + O2
phenylthiourea S-oxide + NADP+ + H2O
-
isozyme FMO2
-
-
?
procarbazine + NADPH + O2
?
-
-
-
-
?
procarbazine + NADPH + O2
?
-
-
-
-
?
pyrazolacridine + NADPH + H+ + O2
pyrazolacridine N-oxide + NADP+ + H2O
an antitumor drug, is converted to the N-oxide
-
-
?
pyrazolacridine + NADPH + H+ + O2
pyrazolacridine N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
ranitidine + NADPH + H+ + O2
?
an antihistamininc drug, is converted to the N-oxide and/or S-oxide
-
-
?
ranitidine + NADPH + H+ + O2
?
-
substrate of isoforms FMO3 and FMO5, S-oxygenation and N-oxygenation
-
-
?
S-methyl esonarimod + NADPH + H+ + O2
?
a cytokine production inhibitor, is converted to the S-oxide
-
-
?
S-methyl esonarimod + NADPH + H+ + O2
?
-
-
-
-
?
S-methyl esonarimod + NADPH + H+ + O2
S-methyl esonarimod S-oxide + NADP+ + H2O
an cytokine production inhibitor, is converted to the S-oxide
-
-
?
S-methyl esonarimod + NADPH + H+ + O2
S-methyl esonarimod S-oxide + NADP+ + H2O
-
substrate of isoforms FMO1, FMO3, and FMO5
-
-
?
sulfamethoxazole + NADPH + O2
?
bioactivation by isozyme FMO3, not FMO1, results in covalent adduct formation
-
-
?
sulfamethoxazole + NADPH + O2
?
isozyme FMO3, not FMO1
-
-
?
sulindac sulfide + NADPH + H+ + O2
sulindac + NADP+ + H2O
-
S-oxidation, low activity
-
-
?
sulindac sulfide + NADPH + H+ + O2
sulindac + NADP+ + H2O
a nonsteroidal antiinflammatory drug, is converted to the S-oxide
-
-
?
sulindac sulfide + NADPH + H+ + O2
sulindac + NADP+ + H2O
-
S-oxidation
-
-
?
sulindac sulfide + NADPH + H+ + O2
sulindac + NADP+ + H2O
-
-
-
?
tamoxifen + NADPH + H+ + O2
?
-
-
-
-
?
tamoxifen + NADPH + H+ + O2
?
-
i.e. (Z)-2-[4-(1,2-diphenylbut-1-enyl)phenoxy]-N,N-dimethylethanamine
-
-
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
-
-
-
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
-
-
-
-
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
-
-
-
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
an estrogen receptor modulator, is converted to the N-oxide
-
-
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
an estrogen receptor modulator, is converted to the N-oxide
-
-
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
tamoxifen is used in breast cancer medication
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
tamoxifen metabolism pathways involving FMOs and CYP450s, tamoxifen N-oxide is reconverted into tamoxifen by reduced hemoglobin and NADPH-P450 oxidoreductase, a metabolic cycle in vivo, overview
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
tamoxifen N-oxygenation represents a detoxication pathway, low level of tamoxifen N-oxide production in human liver microsomes may be explained by the kinetics of FMO1 versus FMO3
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
i.e. (Z)-(1-[4-(2-dimethyl-aminoethoxy)phenyl]-1,2-diphenyl-1-butene), a drug used in breast cancer therapy, isozymes FMO1 and FMO3
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
i.e. Z-(1-[4-(2-dimethyl-aminoethoxy)phenyl]-1,2-diphenyl-1-butene)
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
tamoxifen N-oxygenation represents a detoxication pathway, high activity by isozyme FMO1
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
i.e. Z-(1-[4-(2-dimethyl-aminoethoxy)phenyl]-1,2-diphenyl-1-butene)
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
tamoxifen N-oxygenation represents a detoxication pathway
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
i.e. Z-(1-[4-(2-dimethyl-aminoethoxy)phenyl]-1,2-diphenyl-1-butene)
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
tamoxifen N-oxygenation represents a detoxication pathway
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
i.e. (Z)-(1-[4-(2-dimethyl-aminoethoxy)phenyl]-1,2-diphenyl-1-butene)
-
-
?
tazarotenic acid + NADPH + H+ + O2
tazarotenate N-oxide + NADP+ + H2O
an retinoic acid receptor modulator, is converted to the S-oxide
-
-
?
tazarotenic acid + NADPH + H+ + O2
tazarotenate N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
thiacetazone + 2 NADPH + 2 H+ + 2 O2
thiacetazone carbodiimide + 2 NADP+ + 2 H2O
-
bioactivation by isozymes FMO1 and FMO3, two-step process
-
-
?
thiacetazone + 2 NADPH + 2 H+ + 2 O2
thiacetazone carbodiimide + 2 NADP+ + 2 H2O
-
a thiourea-containing second line antitubercular prodrug
-
-
?
thiacetazone + 2 NADPH + 2 H+ + 2 O2
thiacetazone carbodiimide + 2 NADP+ + 2 H2O
-
bioactivation by EtaA
-
-
?
thiacetazone + 2 NADPH + 2 H+ + 2 O2
thiacetazone carbodiimide + 2 NADP+ + 2 H2O
-
a thiourea-containing second line antitubercular prodrug
-
-
?
thiacetazone + NADPH + H+ + O2
?
-
-
-
-
?
thiacetazone + NADPH + H+ + O2
?
a anti-tubercular drug, high activity
-
-
?
thiacetazone + NADPH + H+ + O2
?
an antibiotic agent, is converted to the sulfinic acid/carbodiimide
-
-
?
thiacetazone + NADPH + H+ + O2
?
an antibiotic agent, is converted to the sulfinic acid/carbodiimide
-
-
?
thiacetazone + NADPH + H+ + O2
thiacetazone N-oxide + NADP+ + H2O
an antibiotic agent, is converted to the sulfinic acid/carbodiimide
-
-
?
thiacetazone + NADPH + H+ + O2
thiacetazone N-oxide + NADP+ + H2O
an antibiotic agent, is converted to the sulfinic acid/carbodiimide
-
-
?
thiacetazone + NADPH + H+ + O2
thiacetazone S-oxide + NADP+ + H2O
low activity with FMO1 and FMO3, high activity with FMO2.1
-
-
?
thiacetazone + NADPH + H+ + O2
thiacetazone S-oxide + NADP+ + H2O
-
substrate of isoforms FMO1, FMO2, and FMO3
-
-
?
thioacetamide + NADPH + O2
?
-
-
-
-
?
thioacetamide + NADPH + O2
?
-
-
-
-
?
thioacetamide + NADPH + O2
?
-
-
-
-
?
thioacetamide + NADPH + O2
?
-
-
-
-
?
thiobenzamide + NADPH + O2
?
-
-
-
-
?
thiobenzamide + NADPH + O2
?
-
-
-
-
?
thiobenzamide + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + H+ + O2
?
-
-
-
-
?
thiourea + NADPH + H+ + O2
?
-
-
-
-
?
thiourea + NADPH + H+ + O2
?
-
-
-
-
?
thiourea + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + O2
thiourea S-oxide + NADP+ + H2O
-
isozyme FMO2
-
-
?
thiourea + NADPH + O2
thiourea S-oxide + NADP+ + H2O
-
-
-
-
?
tigecycline + NADPH + O2
11a-hydroxytigecycline + NADP+ + H2O
-
detoxification, the organism is resistant against the antibiotic
-
-
?
tigecycline + NADPH + O2
11a-hydroxytigecycline + NADP+ + H2O
-
a glycylcycline derivative containing a 9-tert-butylglycylamido group belonging to the tetracyline antibiotic compounds
product identification by LC-MS
-
?
tozasertib + NADPH + H+ + O2
?
-
-
-
-
?
tozasertib + NADPH + H+ + O2
?
-
i.e. N-[4-[4-(4-methylpiperazin-1-yl)-6-[(5-methyl-1H-pyrazol-3-yl)amino]pyrimidin2yl]sulfanylphenyl]cyclopropane carboxamide
-
-
?
trimethylamine + NADPH + H+ + O2
?
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
?
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
?
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
?
-
FMO1, no activity with FMO3 and FMO5
-
-
?
trimethylamine + NADPH + H+ + O2
?
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
mutations of FMO3 are involved in trimethylaminuria, primary trimethylaminuria is multifactorial in origin in that enzyme dysfunction can result from kinetic incompetencies as well as impaired assembly of holoprotein, overview
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
KC734478, KC734481, KC734482, KC734486
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + O2
?
-
-
-
-
?
trimethylamine + NADPH + O2
?
-
-
-
-
?
trimethylamine + NADPH + O2
?
-
-
-
-
?
trimethylamine + NADPH + O2
?
-
-
-
-
?
trimethylamine + NADPH + O2
?
-
-
-
-
?
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
-
isozyme FMO3
-
-
?
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
-
preferred substrate of isozyme FMO3
-
-
?
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
voriconazole + NADPH + H+ + O2
?
-
-
-
-
?
voriconazole + NADPH + H+ + O2
?
-
liver microsomes, a potent second-generation triazole antifungal agent with broad-spectrum activity against clinically important fungi
-
-
?
voriconazole + NADPH + H+ + O2
?
-
recombinant FMO1 and FMO3, no activity with FMO5, N-oxidation of the fluoropyrimidine ring, its hydroxylation, and hydroxylation of the adjacent methyl group
-
-
?
voriconazole + NADPH + H+ + O2
?
-
substrate of isoforms FMO1 and FMO3
-
-
?
voriconazole + NADPH + H+ + O2
?
-
-
-
-
?
xanomeline + NADPH + H+ + O2
xanomeline N-oxide + NADP+ + H2O
-
-
-
?
xanomeline + NADPH + H+ + O2
xanomeline N-oxide + NADP+ + H2O
a muscarinic receptor antagonist, is converted to the N-oxide
-
-
?
xanomeline + NADPH + H+ + O2
xanomeline N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
additional information
?
-
enhanced disease susceptibility1, EDS1, controls defense activation and programmed cell death conditioned by intracellular Toll-related immune receptors that recognize specific pathogen effectors in Arabidopsis thaliana, EDS1 is also needed for basal resistance to invasive pathogens by restricting the progression of disease, EDS1 with phytoalexin-deficient 4, PAD4, regulates accumulation of the phenolic defense molecule salicylic acid, EDS1 is regulated by FMO and the Nudix hydrolase NUDT7
-
-
?
additional information
?
-
-
enhanced disease susceptibility1, EDS1, controls defense activation and programmed cell death conditioned by intracellular Toll-related immune receptors that recognize specific pathogen effectors in Arabidopsis thaliana, EDS1 is also needed for basal resistance to invasive pathogens by restricting the progression of disease, EDS1 with phytoalexin-deficient 4, PAD4, regulates accumulation of the phenolic defense molecule salicylic acid, EDS1 is regulated by FMO and the Nudix hydrolase NUDT7
-
-
?
additional information
?
-
-
isozyme FMO1 is an essential component of biologically induced systemic acquired resistance, e.g. versus the bacterial pathogen Pseudomonas syringae pv maculicola, resistance is accompanied by accumulation of salicylic acid, overview
-
-
?
additional information
?
-
-
the enzyme is important for pathogen defense and resistance participating in the detoxification of virulence factors produced by pathogens, overview
-
-
?
additional information
?
-
-
tigecycline displays a broad spectrum of antibacterial activity and circumvents the efflux and ribosomal protection resistance mechanisms, Mg2+-complexing is required for ribosome binding, 11a-hydroxytigecycline forms a weaker complex with magnesium than tigecycline, structure, overview
-
-
?
additional information
?
-
-
benzydamine is a weak base and an indazole derivative with analgesic and antipyretic properties used in human and veterinary medicine, it is metabolized to a wide range of metabolites. One of the main metabolites, benzydamine N-oxide is produced in the liver and brain by flavin-containing monooxygenases
-
-
?
additional information
?
-
-
specificity of FMO-I and FMO-II
-
-
?
additional information
?
-
-
the enzyme does not oxidize glutathione or cysteine
-
-
?
additional information
?
-
-
the enzyme does not oxidize glutathione or cysteine
-
-
?
additional information
?
-
-
comparison of FMO3 and FMO5
-
-
?
additional information
?
-
-
modulation of activity by site directed mutagenesis
-
-
?
additional information
?
-
-
overview on substrate specifities and requirements of FMO1, FMO3
-
-
?
additional information
?
-
-
enzyme regulation, overview
-
-
?
additional information
?
-
arylamine compounds, such as sulfamethoxazole and dapsone, are metabolized in epidermal keratinocytes to arylhydroxylamine metabolites that autooxidize to arylnitroso derivatives, which in turn bind to cellular proteins and can act as antigens/immunogens, methimazole and 4-aminobenzoic acid hydrazide attenuate the protein haptenation, overview
-
-
?
additional information
?
-
-
effects of genetic variants of isozyme FMO3 on N- and S-oxygenation activities, FMO3 polymorphisms are responsible for the genetic disorder trimethylaminuria, or fish-like odor syndrome, overview
-
-
?
additional information
?
-
-
FMO oxygenates a number of drugs and xenobiotics containing a soft-nucleophile heteroatom, mostly sulfur- and nitrogen-containing xenobiotics, isozymes FMO1-FMO3 are involved in detoxication and drug metabolism, FMO3 deficiency causes the disease trimethylaminuria
-
-
?
additional information
?
-
-
FMOs are, together with cytochrome P450 monooxygenases, the major oxidative enzymes in phase I metabolism, extrahepatic metabolism of carbamate and organophosphate thioether compounds, isozyme FMO1 shows higher turnover numbers than isozyme FMO3 for all pesticides studies, overview
-
-
?
additional information
?
-
-
FMOs catalyze NADPH-dependent monooxygenation of soft-nucleophilic nitrogen, sulfur, and phosphorous atoms contained within various drugs, pesticides, and xenobiotics, isozyme FMO3 is responsible for the majority of FMO-mediated xenobiotic metabolism in the adult human liver, FMO3 mutations causing defects in trimethylamine N-oxygenation, result in the disorder known as trimethylaminuria, TMAU, or fish-odour syndrome, overview, interindividual variability in the expression of FMO3 affect drug and exogenous chemical metabolism in the liver and other tissues
-
-
?
additional information
?
-
-
nitrogen- and sulfur-containing endogenous substrates and physiologic functions, FMO is not induced by xenobiotics, isozyme FMO3 mutant alleles contribute to the disease known as trimethylaminuria, the enzyme is involved in detoxification and drug metabolism, overview, expression of FMO5 is markedly down-regulated in the liver of humans with type II diabetes, patients diagnosed with atrial fibrillation document a significant increase in the expression of FMO1, FMO may be associated with sideroblastic anemia, FMO3 mutations lead to trimethylaminuria, detailed overview
-
-
?
additional information
?
-
-
the enzyme catalyzes the NADPH-dependent N-and S-oxidation of a variety of therapeutics, environmental toxicants, carcinogens, and nutrients
-
-
?
additional information
?
-
-
carbophenothion, i.e. S-4-chlorophenylthiomethyl O,O-diethyl phosphorodithioate, and fonofos, i.e. O-ethyl S-phenyl (RS)-ethylphosphonodithioate, are poor substrates
-
-
?
additional information
?
-
-
FMO oxygenates drugs and xenobiotics containing a soft nucleophile, usually nitrogen or sulfur, isozyme substrate specificity, detailed overview, no activity with 1,3-diphenylthiourea
-
-
?
additional information
?
-
-
FMO oxygenates soft nucleophiles, and converts lipophilic compounds into more hydrophilic metabolites, potential adverse drug-drug interactions are minimized for drugs prominently metabolized by FMO, substrate specificities of isozmes, overview
-
-
?
additional information
?
-
-
stereoselectivity of male and female liver microsomes, and of recombinant isozymes FMO1, FMO3, and FMO4, overview
-
-
?
additional information
?
-
drug metabolism, overview, enzyme mutations are involved in development of trimethylaminuria or fish-odor-syndrome, overview
-
-
?
additional information
?
-
drug metabolism, overview, enzyme mutations are involved in development of trimethylaminuria or fish-odor-syndrome, overview
-
-
?
additional information
?
-
drug metabolism, overview, enzyme mutations are involved in development of trimethylaminuria or fish-odor-syndrome, overview
-
-
?
additional information
?
-
-
drug metabolism, overview, enzyme mutations are involved in development of trimethylaminuria or fish-odor-syndrome, overview
-
-
?
additional information
?
-
drug metabolism, overview, most humans are homozygous for a nonsense mutation that inactivates FMO2. But a substantial proportion of sub-Saharan Africans express functional FMO2 and, thus, are predicted to respond differently to drugs and other foreign chemicals
-
-
?
additional information
?
-
drug metabolism, overview, most humans are homozygous for a nonsense mutation that inactivates FMO2. But a substantial proportion of sub-Saharan Africans express functional FMO2 and, thus, are predicted to respond differently to drugs and other foreign chemicals
-
-
?
additional information
?
-
drug metabolism, overview, most humans are homozygous for a nonsense mutation that inactivates FMO2. But a substantial proportion of sub-Saharan Africans express functional FMO2 and, thus, are predicted to respond differently to drugs and other foreign chemicals
-
-
?
additional information
?
-
-
drug metabolism, overview, most humans are homozygous for a nonsense mutation that inactivates FMO2. But a substantial proportion of sub-Saharan Africans express functional FMO2 and, thus, are predicted to respond differently to drugs and other foreign chemicals
-
-
?
additional information
?
-
drug metabolism, overview, the FMO1 gene is downregulated in the spinal cord of patients with the neurodegenerative disease amyotrophic lateral sclerosis, but is upregulated in the myocardial tissue of patients with atrial fibrillation
-
-
?
additional information
?
-
drug metabolism, overview, the FMO1 gene is downregulated in the spinal cord of patients with the neurodegenerative disease amyotrophic lateral sclerosis, but is upregulated in the myocardial tissue of patients with atrial fibrillation
-
-
?
additional information
?
-
drug metabolism, overview, the FMO1 gene is downregulated in the spinal cord of patients with the neurodegenerative disease amyotrophic lateral sclerosis, but is upregulated in the myocardial tissue of patients with atrial fibrillation
-
-
?
additional information
?
-
-
drug metabolism, overview, the FMO1 gene is downregulated in the spinal cord of patients with the neurodegenerative disease amyotrophic lateral sclerosis, but is upregulated in the myocardial tissue of patients with atrial fibrillation
-
-
?
additional information
?
-
FMO2 catalyzes the S-oxygenation of organophosphates representing a detoxification pathway
-
-
?
additional information
?
-
FMO2 catalyzes the S-oxygenation of organophosphates representing a detoxification pathway
-
-
?
additional information
?
-
FMO2 catalyzes the S-oxygenation of organophosphates representing a detoxification pathway
-
-
?
additional information
?
-
FMO2 catalyzes the S-oxygenation of organophosphates representing a detoxification pathway
-
-
?
additional information
?
-
FMO2 catalyzes the S-oxygenation of organophosphates representing a detoxification pathway
-
-
?
additional information
?
-
human FMO3 regulatory elements, overview
-
-
?
additional information
?
-
-
human FMO3 regulatory elements, overview
-
-
?
additional information
?
-
-
the enzyme is regulated by hormones, e.g. testosterone
-
-
?
additional information
?
-
-
FMO1 mediates the formation of a reactive intermediate of 4-fluoro-N-methylaniline. FMO1 catalyzes a carbon oxidation reaction coupled with defluorination that leads to the formation of 4-N-methylaminophenol, mechanism, overview. A labile 1-fluoro-4-(methylimino)cyclohexa-2,5-dienol intermediate is formed leading to an electrophilic quinoneimine intermediate
-
-
?
additional information
?
-
isoform FMO5 exhibits a low catalytic activity only for sulfoxidation of methyl 4-tolyl sulfide
-
-
?
additional information
?
-
-
isoform FMO5 exhibits a low catalytic activity only for sulfoxidation of methyl 4-tolyl sulfide
-
-
?
additional information
?
-
isozyme FMO5 does not metabolize C-1305
-
-
?
additional information
?
-
isozyme FMO5 does not metabolize C-1305
-
-
?
additional information
?
-
-
isozyme FMO5 does not metabolize C-1305
-
-
?
additional information
?
-
comparison of in vivo activity of FMO enzyme with P450 enzme in N-oxygenation of drugs at different pH values, overview
-
-
-
additional information
?
-
-
comparison of in vivo activity of FMO enzyme with P450 enzme in N-oxygenation of drugs at different pH values, overview
-
-
-
additional information
?
-
analysis of the uncoupling reactions in the catalytic cycle of enzyme FMO3, overview. The level of uncoupling varies between 50% and 70% (wild-type) and 90-98% (mutant N61S) for incubations with NADPH and benzydamine over a period of 5 or 20 min, respectively. The substrate lowers the level of uncoupling only related to the H2O2 and not the superoxide radical. In the absence of the substrate benzydamine (BZD), mutant N61S produces higher amounts of H2O2 compared to wild-type
-
-
-
additional information
?
-
-
analysis of the uncoupling reactions in the catalytic cycle of enzyme FMO3, overview. The level of uncoupling varies between 50% and 70% (wild-type) and 90-98% (mutant N61S) for incubations with NADPH and benzydamine over a period of 5 or 20 min, respectively. The substrate lowers the level of uncoupling only related to the H2O2 and not the superoxide radical. In the absence of the substrate benzydamine (BZD), mutant N61S produces higher amounts of H2O2 compared to wild-type
-
-
-
additional information
?
-
formation of a highly stable C4a-hydroperoxyflavin intermediate of hFMO1 upon reduction by NADPH in presence of O2, the intermediate is not fully re-oxidized after 30 min at 15°C in the absence of substrate. The enzyme is below 1% uncoupled in the presence of substrate. Higher stability of the hFMO1 intermediate compared to the stability of the intermediate of isozyme hFMO3
-
-
-
additional information
?
-
-
formation of a highly stable C4a-hydroperoxyflavin intermediate of hFMO1 upon reduction by NADPH in presence of O2, the intermediate is not fully re-oxidized after 30 min at 15°C in the absence of substrate. The enzyme is below 1% uncoupled in the presence of substrate. Higher stability of the hFMO1 intermediate compared to the stability of the intermediate of isozyme hFMO3
-
-
-
additional information
?
-
-
human FMO1 catalyzes the oxygenation of hypotaurine in vitro. Ability of hypotaurine to act as a competitor substrate of FMO1 is assessed by measuring the effect of various concentrations of hypotaurine on FMO1-catalyzed S-oxygenation of methimazole
-
-
-
additional information
?
-
human FMO1 catalyzes the oxygenation of hypotaurine in vitro. Ability of hypotaurine to act as a competitor substrate of FMO1 is assessed by measuring the effect of various concentrations of hypotaurine on FMO1-catalyzed S-oxygenation of methimazole
-
-
-
additional information
?
-
identification of GSK5182 N-oxide products by mass spectrometry
-
-
-
additional information
?
-
-
identification of GSK5182 N-oxide products by mass spectrometry
-
-
-
additional information
?
-
N- and S-oxygenation activity of truncated wild-type human flavin-containing monooxygenase 3 and its common polymorphic variants, overview. The enzyme binds noncovalently one molecule of FAD and is reduced by NADPH before exerting its catalysis
-
-
-
additional information
?
-
-
N- and S-oxygenation activity of truncated wild-type human flavin-containing monooxygenase 3 and its common polymorphic variants, overview. The enzyme binds noncovalently one molecule of FAD and is reduced by NADPH before exerting its catalysis
-
-
-
additional information
?
-
-
S-oxygenation of N-substituted thioureas
-
-
?
additional information
?
-
-
substrate specificity, the ability to stabilize the hydroperoxyflavin intermediate in substrate oxygenation is crucial involving NADP(H), overview
-
-
?
additional information
?
-
-
substrate specificity, the ability to stabilize the hydroperoxyflavin intermediate in substrate oxygenation is crucial involving NADP(H), overview
-
-
?
additional information
?
-
-
substrate specificity of the recombinant PTDH-mFMO fusion enzyme, overview
-
-
?
additional information
?
-
-
substrate specificity of the recombinant PTDH-mFMO fusion enzyme, overview
-
-
?
additional information
?
-
-
overview on specificity
-
-
?
additional information
?
-
-
FMO oxygenates a number of drugs and xenobiotics containing a soft-nucleophile heteroatom, mostly sulfur- and nitrogen-containing xenobiotics, and is involved in detoxication
-
-
?
additional information
?
-
-
nitrogen- and sulfur-containing endogenous substrates and physiologic functions, the enzyme is involved in detoxification and drug metabolism, overview, hepatic total FMO activity is enhanced in mouse models of type I and type II diabetes
-
-
?
additional information
?
-
-
the enzyme is involved in fatty acid oxidation in the liver, as well as in drug detoxification
-
-
?
additional information
?
-
-
regulation of hepatic Fmo isozymes, overview
-
-
?
additional information
?
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
in vitro microsomal Baeyer-Villiger oxidation of pentoxifylline (PTX) by Fmo5
-
-
-
additional information
?
-
-
in vitro microsomal Baeyer-Villiger oxidation of pentoxifylline (PTX) by Fmo5
-
-
-
additional information
?
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
in vitro microsomal Baeyer-Villiger oxidation of pentoxifylline (PTX) by Fmo5
-
-
-
additional information
?
-
-
no activity with glutathione
-
-
?
additional information
?
-
regulation of the enzyme expression by hypersaline conditions and the osmoregulatory hormonecortisol, overview
-
-
?
additional information
?
-
-
regulation of the enzyme expression by hypersaline conditions and the osmoregulatory hormonecortisol, overview
-
-
?
additional information
?
-
-
overview on specificity
-
-
?
additional information
?
-
-
nitrogen- and sulfur-containing endogenous substrates and physiologic functions, the enzyme is involved in detoxification and drug metabolism, overview
-
-
?
additional information
?
-
the enzyme is involved in oxidative metabolism of drugs and other chemicals
-
-
?
additional information
?
-
-
the enzyme is involved in oxidative metabolism of drugs and other chemicals
-
-
?
additional information
?
-
-
stereoselectivity of recombinant isozymes FMO1, FMO2, and FMO3
-
-
?
additional information
?
-
-
the lung isozyme is distinct from the liver isozyme in having high activity toward primary alkyl amines, restricted substrate specificity related to steric properties, resistance to detergent inhibition and enhanced thermal stability, and restricted substrate access, no activity of the lung isozyme with 1,3-diphenylthiourea, chlorpromazine and imipramine by isozyme FMO2, isozyme substrate specificity, detailed overview
-
-
?
additional information
?
-
-
benzydamine is a weak base and an indazole derivative with analgesic and antipyretic properties used in human and veterinary medicine, it is metabolized to a wide range of metabolites. One of the main metabolites, benzydamine N-oxide is produced in the liver and brain by flavin-containing monooxygenases
-
-
?
additional information
?
-
-
the enzyme is involved in detoxification, generally, metabolites produced by FMO-catalysed reactions are more hydrophilic and less toxic, and are easily excreted from the body
-
-
?
additional information
?
-
-
substrates are a wide range of nucleophilic nitrogen-, sulfur-, phosphorus-, and selenium heteroatom-containing chemicals, drugs, and agricultural agents
-
-
?
additional information
?
-
-
overview on specificity
-
-
?
additional information
?
-
-
FMO oxygenates a number of drugs and xenobiotics containing a soft-nucleophile heteroatom, mostly sulfur- and nitrogen-containing xenobiotics, and is involved in detoxication
-
-
?
additional information
?
-
-
the enzyme plays an important role in drug metabolism, insulin itself has no effect on FMO1 activity in non-diabetic animals, but hepatic isozyme FMO1 and intestinal CYP3A activity are correlated with average blood glucose concentration in untreated diabetic rats, and insulin reduces CYP3A activity, thus also regulates FMO1 indirectly
-
-
?
additional information
?
-
-
stereoselectivity of purified isozymes FMO1 and FMO3, overview
-
-
?
additional information
?
-
-
isozyme FMO5 does not metabolize 5-[[3-(dimethylamino)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one (C-1305)
-
-
?
additional information
?
-
-
the substrate specificity of Saccharomyces cerevisiae FMO is more restricted than that of mammalian FMOs, reflecting its role in maintaining redox balance in the cell
-
-
?
additional information
?
-
-
-
-
-
?
additional information
?
-
-
reaction can be functionally separated into 2 partial reactions: 1. a reduced pyridine nucleotide and oxygen-dependent N-oxide synthase, 2. an N-oxide dealkylase
-
-
?
additional information
?
-
-
catalyzes NADPH- and O2-dependent N-oxidation of N-substituted amines and hydrazines and the S-oxidation of thioureylenes and thiols
-
-
?
additional information
?
-
-
catalyzes NADPH- and O2-dependent N-oxidation of N-substituted amines and hydrazines and the S-oxidation of thioureylenes and thiols
-
-
?
additional information
?
-
-
S-oxygenation of N-substituted thioureas
-
-
?
additional information
?
-
-
study of oxidative half-reaction
-
-
?
additional information
?
-
-
study of reductive half-reaction
-
-
?
additional information
?
-
-
FMO oxygenates a number of drugs and xenobiotics containing a soft-nucleophile heteroatom, mostly sulfur- and nitrogen-containing xenobiotics, and is involved in detoxication
-
-
?
additional information
?
-
-
nitrogen- and sulfur-containing endogenous substrates and physiologic functions, the enzyme is involved in detoxification and drug metabolism, overview
-
-
?
additional information
?
-
-
FMO oxygenates oxygenates a wide range of sulfur- and nitrogen-containing xenobiotics and, in some cases, also oxygenates selenium, iodine, boron, phosphorus and even carbon, it oxidizes drugs and xenobiotics containing a soft nucleophile, usually nitrogen or sulfur, utilizing the reducing equivalents of NADPH to reduce 1 atom of molecular oxygen to water, while the other atom is used to oxidize the substrate, FMO does not require a reductase to transfer electrons from NADPH, liver isozyme FMO1 shows a very promiscuous substrate specificity, isozyme substrate specificity, detailed overview
-
-
?
additional information
?
-
-
benzydamine is a weak base and an indazole derivative with analgesic and antipyretic properties used in human and veterinary medicine, it is metabolized to a wide range of metabolites. One of the main metabolites, benzydamine N-oxide is produced in the liver and brain by flavin-containing monooxygenases
-
-
?