Information on EC 1.14.13.8 - flavin-containing monooxygenase

New: Word Map on EC 1.14.13.8
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Mark a special word or phrase in this record:
Search Reference ID:
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)


The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
1.14.13.8
-
RECOMMENDED NAME
GeneOntology No.
flavin-containing monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Drug metabolism - cytochrome P450
-
-
Microbial metabolism in diverse environments
-
-
nicotine degradation IV
-
-
SYSTEMATIC NAME
IUBMB Comments
N,N-dimethylaniline,NADPH:oxygen oxidoreductase (N-oxide-forming)
A flavoprotein. A broad spectrum monooxygenase that accepts substrates as diverse as hydrazines, phosphines, boron-containing compounds, sulfides, selenides, iodide, as well as primary, secondary and tertiary amines [3,4]. This enzyme is distinct from other monooxygenases in that the enzyme forms a relatively stable hydroperoxy flavin intermediate [4,5]. This microsomal enzyme generally converts nucleophilic heteroatom-containing chemicals and drugs into harmless, readily excreted metabolites. For example, N-oxygenation is largely responsible for the detoxification of the dopaminergic neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) [2,6]
CAS REGISTRY NUMBER
COMMENTARY hide
117910-56-2
-
148848-55-9
-
37256-73-8
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene tetX
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
silky shark
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
Methylophaga sp.
-
-
-
Manually annotated by BRENDA team
Methylophaga sp. SK1
-
-
-
Manually annotated by BRENDA team
Mus musculus C-57 BL
strain C-57 BL
-
-
Manually annotated by BRENDA team
gene etaA or RV3854c
-
-
Manually annotated by BRENDA team
7-9-months-old Akkaraman sheep, isozyme FMO3
-
-
Manually annotated by BRENDA team
turbot
-
-
Manually annotated by BRENDA team
dogfish shark
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(S)-nicotine + NADPH + O2
(S)-nicotine N1-oxide + NADP+ + H2O
show the reaction diagram
-
(S)-nicotine N-1'-oxygenation
-
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
show the reaction diagram
1,2,3,4-tetrahydroisoquinoline + NADPH + O2
?
show the reaction diagram
1,2-dimethylhydrazine + NADPH + O2
?
show the reaction diagram
1,2-dimethylphenylhydrazine + NADPH + O2
?
show the reaction diagram
1-butanethiol + NADPH + O2
?
show the reaction diagram
1-methyl-1-phenylhydrazine + NADPH + O2
?
show the reaction diagram
1-methyl-2-benzylhydrazine + NADPH + O2
?
show the reaction diagram
1-methyl-2-thioimidazole + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
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
show the reaction diagram
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + O2
?
show the reaction diagram
1-methyl-6,7-dihydroxytetrahydroisoquinoline + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
1-[4-(methylsulfanyl)phenyl]ethanone + NADPH + H+ + O2
(R,S)-1-[4-(methylsulfanyl)phenyl]ethanone S-oxide + NADP+ + H2O
show the reaction diagram
10-(N,N-dimethylaminoalkyl)-2-(trifluoromethyl) phenothiazines + NADPH + O2
?
show the reaction diagram
10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
10-(N,N-dimethylaminopentyl)-2-(trifluoromethyl)phenothiazine + NADPH + O2
?
show the reaction diagram
10-([N,N-dimethylaminopentyl]-2-trifluoromethyl)phenothiazine + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine + NADPH + O2
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine N-oxide + NADP+ + H2O
show the reaction diagram
10-[(N,N-dimethylaminooctyl)-2-(trifluoromethyl)]phenothiazine + NADPH + H+ + O2
10-[(N,N-dimethylaminooctyl)-2-(trifluoromethyl)]phenothiazine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
10-[(N,N-dimethylaminopentyl)-2-(trifluoromethyl)]phenothiazine + NADPH + O2
?
show the reaction diagram
-
i.e. 5-DPT or diethylenetriaminepentaacetic acid
-
-
?
2-(methylsulfanyl)pyridine + NADPH + H+ + O2
2-(methylsulfanyl)pyridine S-oxide + NADP+ + H2O
show the reaction diagram
2-(methylsulfanyl)thiophene + NADPH + H+ + O2
2-(methylsulfanyl)thiophene S-oxide + NADP+ + H2O
show the reaction diagram
2-acetylsulfanylmethyl-4-(4-methoxyphenyl)-4-oxobutyric acid + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
2-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-2-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
show the reaction diagram
2-mercaptobenzimidazole + NADPH + O2
?
show the reaction diagram
2-[(methylsulfanyl)methyl]furan + NADPH + H+ + O2
2-[(methylsulfanyl)methyl]furan S-oxide + NADP+ + H2O
show the reaction diagram
Methylophaga sp.
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
2-[2-(4-methoxyphenyl)-2-oxoethyl]-acrylic acid + NADPH + H+ + O2
?
show the reaction diagram
-
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
show the reaction diagram
Methylophaga sp.
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 15% R-enantiomer as product
-
-
?
4-(4-methoxyphenyl)-2-methylsulfanylmethyl-4-oxobutyric acid + NADPH + H+ + O2
?
show the reaction diagram
-
FMO1, poor activity with FMO3 and FMO5
-
-
?
4-(4-methylphenyl)-2-methylsulfanylmethyl-4-oxobutyric acid + NADPH + H+ + O2
?
show the reaction diagram
-
FMO1 and FMO5, no activity with FMO3
-
-
?
4-(methylsulfanyl)benzonitrile + NADPH + H+ + O2
(R,S)-4-(methylsulfanyl)benzonitrile S-oxide + NADP+ + H2O
show the reaction diagram
Methylophaga sp.
-
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
show the reaction diagram
Methylophaga sp.
-
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
?
show the reaction diagram
-
-
-
?
4-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-4-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
show the reaction diagram
Methylophaga sp.
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 95% S-enantiomer as product
-
-
?
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
show the reaction diagram
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
show the reaction diagram
aldicarb + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
alpha-naphthylthiourea + NADPH + O2
?
show the reaction diagram
aminopyrine + NADPH + O2
?
show the reaction diagram
ammonia + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
amphetamine + NADPH + H+ + O2
?
show the reaction diagram
amphetamine + NADPH + O2
amphetamine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
show the reaction diagram
benzydamine + NADPH + O2
benzydamine N-oxide + NADP+ + H2O
show the reaction diagram
benzyl ethyl sulfide + NADPH + H+ + O2
benzyl ethyl sulfide S-oxide + NADP+ + H2O
show the reaction diagram
Methylophaga sp.
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
benzyl methyl sulfide + NADPH + H+ + O2
benzyl methyl sulfide S-oxide + NADP+ + H2O
show the reaction diagram
Methylophaga sp.
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
benzylamine + NADPH + O2
benzylamine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
benzylhydrazine + NADPH + O2
?
show the reaction diagram
beta-ethylphenylhydrazine + NADPH + O2
?
show the reaction diagram
bupivacaine + NADPH + O2
bupivacaine-oxide + NADP+
show the reaction diagram
-
-
-
-
?
butyl ethyl sulfide + NADPH + H+ + O2
butyl ethyl sulfide S-oxide + NADP+ + H2O
show the reaction diagram
Methylophaga sp.
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
butyl methyl sulfide + NADPH + H+ + O2
butyl methyl sulfide S-oxide + NADP+ + H2O
show the reaction diagram
Methylophaga sp.
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
butylhydrazine + NADPH + O2
?
show the reaction diagram
chlorpromazine + NADPH + H+ + O2
chlorpromazine N-oxide + NADP+ + H2O
show the reaction diagram
chlorpromazine + NADPH + H+ + O2
chlorpromazine oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
chlorpromazine + NADPH + O2
?
show the reaction diagram
chlorpromazine + NADPH + O2
chlorpromazine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
cimetidine + NADPH + H+ + O2
cimetidine S-oxide + NADP+ + H2O
show the reaction diagram
-
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 + O2
cimetidine S-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
show the reaction diagram
clozapine + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
cyclohexyl methyl sulfide + NADPH + H+ + O2
cyclohexyl methyl sulfide S-oxide + NADP+ + H2O
show the reaction diagram
Methylophaga sp.
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
cysteamine + NADPH + O2
?
show the reaction diagram
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
show the reaction diagram
dapsone + NADPH + O2
?
show the reaction diagram
demeton-O + NADPH + O2
demeton-O sulfoxide + NADP+ + H2O
show the reaction diagram
deprenyl + NADPH + H+ + O2
?
show the reaction diagram
dibenzylamine + NADPH + O2
?
show the reaction diagram
dihydrolipoic acid + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
disulfoton + NADPH + H+ + O2
?
show the reaction diagram
a thioether-containing organophosphate insecticide
-
-
?
ephedrine + NADPH + O2
?
show the reaction diagram
esonarimod + NADPH + H+ + O2
S-methyl esonarimod + NADP+ + H2O
show the reaction diagram
a antirheumatic drug, is converted to the S-oxide
-
-
?
ethiofencarb + NADPH + O2
ethiofencarb sulfoxide + NADP+ + H2O
show the reaction diagram
ethionamide + NADPH + H+ + O2
?
show the reaction diagram
ethionamide + NADPH + H+ + O2
ethionamide N-oxide + NADP+ + H2O
show the reaction diagram
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
show the reaction diagram
ethionamide + NADPH + O2 + H+
2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O
show the reaction diagram
ethyl phenyl sulfide + NADPH + H+ + O2
ethyl phenyl sulfoxide + NADP+ + H2O
show the reaction diagram
Methylophaga sp.
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
ethylene sulfide + NADPH + O2
?
show the reaction diagram
ethylenethiourea + NADPH + O2
ethylenethiourea S-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
ethylenthiourea + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
etionamide + NADPH + H+ + O2
etionamide S-oxide + NADP+ + H2O
show the reaction diagram
-
substrate of FMO1, FMO3, and FMO2.1
-
-
?
fenthion + NADPH + O2
fenthion sulfoxide + NADP+
show the reaction diagram
-
-
74% (+)-sulfoxide
-
?
fenthion + NADPH + O2
fenthion sulfoxide + NADP+ + H2O
show the reaction diagram
imipramine + NADPH + H+ + O2
imipramine N-oxide + NADP+ + H2O
show the reaction diagram
imipramine + NADPH + H+ + O2
imipramine oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
imipramine + NADPH + O2
?
show the reaction diagram
imipramine + NADPH + O2
imipramine N-oxide + NADP+ + H2O
show the reaction diagram
indole + NADPH + H+ + O2
indole N-oxide + NADP+ + H2O
show the reaction diagram
isopropylhydrazine + NADPH + O2
?
show the reaction diagram
itopride + NADPH + H+ + O2
itopride N-oxide + NADP+ + H2O
show the reaction diagram
itopride + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
K11777 + NADPH + H+ + O2
K11777 N-oxide + NADP+ + H2O
show the reaction diagram
a cysteine protease inhibitor against Trypanosoma cruzi, is converted to the N-oxide
-
-
?
L-Met-Phe + NADPH + O2
(L-Met-S-oxide)-Phe + NADP+ + H2O
show the reaction diagram
L-Met-Val + NADPH + O2
(L-Met-S-oxide)-Val + NADP+ + H2O
show the reaction diagram
L-methionine + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
?
L-methionine + NADPH + H+ + O2
L-methionine S-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
L-methionine + NADPH + H+ + O2
methionine S-oxide + NADP+ + H2O
show the reaction diagram
stereochemistry, overview
formation of 80% D-isomer
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
show the reaction diagram
L-Phe-Met + NADPH + O2
(L-Met-S-oxide)-Phe + NADP+ + H2O
show the reaction diagram
-
liver microsomes
-
-
?
L-seleno-methionine + NADPH + O2
L-methionine seleno-oxide + NADP+ + H2O
show the reaction diagram
lidocaine + NADPH + O2
lidocaine-oxide + NADP+
show the reaction diagram
-
-
-
-
?
lipoic acid + NADPH + O2
?
show the reaction diagram
mercaptoimidazole + NADPH + H+ + O2
?
show the reaction diagram
-
FMO1 and FMO3, no activity with FMO5
-
-
?
mercaptoimidazole + NADPH + O2
mercaptoimidazole S-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
methamphetamine + NADPH + H+ + O2
?
show the reaction diagram
methamphetamine + NADPH + H+ + O2
methamphetamine N-oxide + NADP+ + H2O
show the reaction diagram
a psychostimulant, is converted to the hydroxylamine
-
-
?
methamphetamine + NADPH + O2
?
show the reaction diagram
methimazole + NADPH + H+ + O2
?
show the reaction diagram
methimazole + NADPH + H+ + O2
methimazole N-oxide + NADP+ + H2O
show the reaction diagram
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADP+ + H2O
show the reaction diagram
methimazole + NADPH + O2
?
show the reaction diagram
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
show the reaction diagram
methiocarb + NADPH + O2
methiocarb sulfoxide + NADP+ + H2O
show the reaction diagram
methyl 2-phenylethyl sulfide + NADPH + H+ + O2
methyl 2-phenylethyl sulfide S-oxide + NADP+ + H2O
show the reaction diagram
Methylophaga sp.
-
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
show the reaction diagram
Methylophaga sp.
-
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
show the reaction diagram
Methylophaga sp.
-
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
show the reaction diagram
Methylophaga sp.
-
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
show the reaction diagram
methyl p-tolyl sulfide + NADPH + H+ + O2
?
show the reaction diagram
methyl p-tolyl sulfide + NADPH + O2
methyl p-tolyl sulfoxide + NADP+ + H2O
show the reaction diagram
methyl phenyl sulfide + NADPH + H+ + O2
(R,S)-methyl phenyl sulfoxide + NADP+ + H2O
show the reaction diagram
Methylophaga sp.
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 35% S-enantiomer as product
-
-
?
methylmercaptan + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
methylphenylsulfide + NADPH + O2
?
show the reaction diagram
MK-0767 methyl sulfide + NADPH + H+ + O2
?
show the reaction diagram
a peroxisome proliferator receptor activator, is converted to the S-oxide
-
-
?
N,N,N-trimethylamine + NADPH + H+ + O2
N,N,N-trimethylamine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
N,N-dimethyl-3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propan-1-amine + NADPH + H+ + O2
?
show the reaction diagram
-
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
?
show the reaction diagram
-
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
?
show the reaction diagram
-
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
show the reaction diagram
-
N-oxygenation mainly by isozyme FMO1, low activity with isozyme FMO3
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
show the reaction diagram
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
show the reaction diagram
N-aminohomopiperidine + NADPH + O2
?
show the reaction diagram
N-aminomorpholine + NADPH + O2
?
show the reaction diagram
N-aminopiperidine + NADPH + O2
?
show the reaction diagram
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
show the reaction diagram
N-aminopyrrolidone + NADPH + O2
?
show the reaction diagram
N-deacetyl ketoconazole + NADPH + H+ + O2
?
show the reaction diagram
an antifungal agent, is converted to the N-hydroxyl
-
-
?
N-deacetyl ketoconazole + NADPH + H+ + O2
N-deacetyl ketoconazole N-oxide + NADP+ + H2O
show the reaction diagram
an antifungal agent, is converted to the N-hydroxyl
-
-
?
n-decylamine + NADPH + O2
1-nitrosodecane + NADP+ + H2O
show the reaction diagram
N-methyl-1,2,3,4-tetrahydroisoquinoline + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
N-methyl-tamoxifen + NADPH + O2
N-methyl-tamoxifen N-oxide + NADP+ + H2O
show the reaction diagram
-
recombinant isozymes FMO1 and FMO3
-
-
?
n-octylamine + NADPH + O2
1-nitrosooctane + NADP+ + H2O
show the reaction diagram
naphthylthiourea + NADPH + O2
naphthylthiourea S-oxide + NADP+ + H2O
show the reaction diagram
nicotine + NADPH + H+ + O2
nicotine N-oxide + NADP+ + H2O
show the reaction diagram
olopatadine + NADPH + H+ + O2
olopatadine N-oxide + NADP+ + H2O
show the reaction diagram
orphenadrine + NADPH + H+ + O2
orphenadrine N-oxide + NADP+ + H2O
show the reaction diagram
an anticholinergic drug
-
-
?
p-chloro-N-methylaniline + NADPH + O2
?
show the reaction diagram
p-tolyl sulfide + NADPH + O2
p-tolyl sulfoxide + NADP+ + H2O
show the reaction diagram
pargyline + NADPH + O2
?
show the reaction diagram
-
inhibitor of monoaminoxidase B
-
-
?
phenethylamine + NADPH + O2
phenethylamine N-oxide + NADP+ + H2O
show the reaction diagram
-
isozyme FMO3
-
-
?
phenyl propyl sulfide + NADPH + H+ + O2
phenyl propyl sulfide S-oxide + NADP+ + H2O
show the reaction diagram
Methylophaga sp.
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
phenylhydrazine + NADPH + O2
?
show the reaction diagram
phenylthiourea + NADPH + O2
?
show the reaction diagram
phenylthiourea + NADPH + O2
phenylthiourea S-oxide + NADP+ + H2O
show the reaction diagram
phorate + NADPH + H+ + O2
?
show the reaction diagram
a thioether-containing organophosphate insecticide
-
-
?
procarbazine + NADPH + O2
?
show the reaction diagram
propranolol + NADPH + O2
propranolol-hydroxylamine + NADP+
show the reaction diagram
-
-
-
-
?
pyrazolacridine + NADPH + H+ + O2
pyrazolacridine N-oxide + NADP+ + H2O
show the reaction diagram
an antitumor drug, is converted to the N-oxide
-
-
?
pyrazoloacridine + NADPH + O2
pyrazoloacridine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
R(-)-deprenyl + NADPH + O2
?
show the reaction diagram
-
inhibitor of monoaminoxidase B
-
-
?
ranitidine + NADPH + H+ + O2
?
show the reaction diagram
an antihistamininc drug, is converted to the N-oxide and/or S-oxide
-
-
?
ranitidine + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
S-allyl-L-cysteine + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
?
S-allyl-L-cysteine + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
stereochemmistry, overview
-
-
?
S-benzyl-L-cysteine + NADPH + O2
S-benzyl-L-cysteine S-oxide + NADP+ + H2O
show the reaction diagram
-
isozyme FMO1
-
-
?
S-farnesylcysteine + NADPH + O2
S-farnesylcysteine S-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
S-farnesylcysteine methyl ester + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
S-farnesylcysteine methyl ester + NADPH + O2
S-farnesylcysteine S-oxide methyl ester + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
S-methyl esonarimod + NADPH + H+ + O2
?
show the reaction diagram
S-methyl esonarimod + NADPH + H+ + O2
S-methyl esonarimod S-oxide + NADP+ + H2O
show the reaction diagram
an cytokine production inhbitor, is converted to the S-oxide
-
-
?
S16020 + NADPH + H+ + O2
S16020 N-oxide + NADP+ + H2O
show the reaction diagram
a topoisomerase II inhibitor and antitumor drug, is converted to the N-oxide
-
-
?
secondary amine + NADPH + O2
secondary nitrone + NADP+ + H2O
show the reaction diagram
-
-
first oxidation to the N-hydroxy amine and then to the corresponding nitrone
?
selegiline + NADPH + O2
selegiline N-oxide + NADP+
show the reaction diagram
-
-
-
-
?
seleno-L-methionine + NADPH + H+ + O2
seleno-L-methionine Se-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
?
SNI-2011 + NADPH + H+ + O2
?
show the reaction diagram
a muscarinic receptor antagonist, is converted to the N-oxide
-
-
?
sulfamethoxazole + NADPH + O2
?
show the reaction diagram
sulindac sulfide + NADPH + H+ + O2
sulindac + NADP+ + H2O
show the reaction diagram
sulindac sulfide + NADPH + O2
(S,R)-sulindac + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
sulindac sulfide + NADPH + O2
sulindac + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
show the reaction diagram
tamoxifen + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
show the reaction diagram
tazarotenic acid + NADPH + H+ + O2
?
show the reaction diagram
a retinoic acid receptor modulator, is converted to the S-oxide
-
-
?
tazarotenic acid + NADPH + H+ + O2
tazarotenate N-oxide + NADP+ + H2O
show the reaction diagram
an retinoic acid receptor modulator, is converted to the S-oxide
-
-
?
tertiary amine + NADPH + O2
tertiary N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
thiacetazone + 2 NADPH + 2 H+ + 2 O2
thiacetazone carbodiimide + 2 NADP+ + 2 H2O
show the reaction diagram
thiacetazone + 2 NADPH + 2 O2
(E)-{(2E)-[4-(acetylamino)benzylidene]hydrazinylidene}(amino)methanesulfinic acid + 2 NADP+ + H2O
show the reaction diagram
-
bioactivation by EtaA
-
-
?
thiacetazone + NADPH + H+ + O2
?
show the reaction diagram
thiacetazone + NADPH + H+ + O2
thiacetazone N-oxide + NADP+ + H2O
show the reaction diagram
thiacetazone + NADPH + H+ + O2
thiacetazone S-oxide + NADP+ + H2O
show the reaction diagram
-
low activity with FMO1 and FMO3, high activity with FMO2.1
-
-
?
thioacetamide + NADPH + O2
?
show the reaction diagram
thiobenzamide + NADPH + H+ + O2
thiobenzamide N-oxide + NADP+ + H2O
show the reaction diagram
-
N-oxidation
-
-
?
thiobenzamide + NADPH + O2
?
show the reaction diagram
thiocarbanilide + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
thiourea + NADPH + O2
?
show the reaction diagram
thiourea + NADPH + O2
thiourea S-oxide + NADP+ + H2O
show the reaction diagram
tigecycline + NADPH + O2
11a-hydroxytigecycline + NADP+ + H2O
show the reaction diagram
triethylamine + NADPH + H+ + O2
triethylamine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
trifluoperazine + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
trifluoroperazine + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
?
show the reaction diagram
-
FMO1, no activity with FMO3 and FMO5
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
show the reaction diagram
trimethylamine + NADPH + O2
?
show the reaction diagram
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
show the reaction diagram
tyramine + NADPH + O2
tyramine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
voriconazole + NADPH + H+ + O2
?
show the reaction diagram
xanomeline + NADPH + H+ + O2
xanomeline N-oxide + NADP+ + H2O
show the reaction diagram
a muscarinic receptor antagonist, is converted to the N-oxide
-
-
?
[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
show the reaction diagram
-
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
?
-
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
(S)-nicotine + NADPH + O2
(S)-nicotine N1-oxide + NADP+ + H2O
show the reaction diagram
-
(S)-nicotine N-1'-oxygenation
-
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
show the reaction diagram
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
show the reaction diagram
10-(N,N-dimethylaminopentyl)-2-(trifluoromethyl)phenothiazine + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine + NADPH + O2
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
4-aminobenzoic acid hydrazide + NADPH + O2
?
show the reaction diagram
Q01740
-
-
-
?
amphetamine + NADPH + O2
amphetamine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
show the reaction diagram
benzylamine + NADPH + O2
benzylamine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
cimetidine + NADPH + O2
cimetidine S-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
clozapine + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
show the reaction diagram
dapsone + NADPH + O2
?
show the reaction diagram
Q01740
bioactivation by isozyme FMO3, not FMO1, results in covalent adduct formation
-
-
?
demeton-O + NADPH + O2
demeton-O sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
dihydrolipoic acid + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
ethiofencarb + NADPH + O2
ethiofencarb sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
show the reaction diagram
ethionamide + NADPH + O2 + H+
2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O
show the reaction diagram
fenthion + NADPH + O2
fenthion sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
imipramine + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
itopride + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
show the reaction diagram
lipoic acid + NADPH + O2
?
show the reaction diagram
methimazole + NADPH + O2
?
show the reaction diagram
methiocarb + NADPH + O2
methiocarb sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
methyl 4-tolyl sulfide + NADPH + O2
methyl 4-tolyl sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
N,N-dimethylamphetamine + NADPH + H+ + O2
N,N-dimethylamphetamine N-oxide + NADP+ + H2O
show the reaction diagram
-
N-oxygenation mainly by isozyme FMO1, low activity with isozyme FMO3
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
show the reaction diagram
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
show the reaction diagram
phenethylamine + NADPH + O2
phenethylamine N-oxide + NADP+ + H2O
show the reaction diagram
-
isozyme FMO3
-
-
?
ranitidine + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
S-farnesylcysteine + NADPH + O2
S-farnesylcysteine S-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
S-farnesylcysteine methyl ester + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
selegiline + NADPH + O2
selegiline N-oxide + NADP+
show the reaction diagram
-
-
-
-
?
sulfamethoxazole + NADPH + O2
?
show the reaction diagram
Q01740
bioactivation by isozyme FMO3, not FMO1, results in covalent adduct formation
-
-
?
sulindac sulfide + NADPH + O2
(S,R)-sulindac + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
show the reaction diagram
thiacetazone + 2 NADPH + 2 H+ + 2 O2
thiacetazone carbodiimide + 2 NADP+ + 2 H2O
show the reaction diagram
thiacetazone + 2 NADPH + 2 O2
(E)-{(2E)-[4-(acetylamino)benzylidene]hydrazinylidene}(amino)methanesulfinic acid + 2 NADP+ + H2O
show the reaction diagram
-
bioactivation by EtaA
-
-
?
tigecycline + NADPH + O2
11a-hydroxytigecycline + NADP+ + H2O
show the reaction diagram
-
detoxification, the organism is resistant against the antibiotic
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
show the reaction diagram
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
show the reaction diagram
tyramine + NADPH + O2
tyramine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
voriconazole + NADPH + H+ + O2
?
show the reaction diagram
-
liver microsomes, a potent second-generation triazole antifungal agent with broad-spectrum activity against clinically important fungi
-
-
?
[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
show the reaction diagram
-
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
?
-