Information on EC 1.14.13.8 - flavin-containing monooxygenase and Organism(s) Homo sapiens and UniProt Accession P31512

for references in articles please use BRENDA:EC1.14.13.8
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
Select one or more organisms in this record:
This record set is specific for:
Homo sapiens
UNIPROT: P31512


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


The taxonomic range for the selected organisms is: Homo sapiens

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
nicotine degradation IV
-
-
Drug metabolism - cytochrome P450
-
-
Microbial metabolism in diverse environments
-
-
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
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
-
mutations in isoform FMO3 are causative of the disorder trimethylaminuria
metabolism
physiological function
additional information
-
although maltose-binding-protein-FMO enzymes afford lower rates of turnover than the corresponding commercial recombinant FMOs, both types of FMO show identical substrate dependencies and similar responses to changes in assay conditions. Comparison of commercial recombinant enzymes with recombinant MBP-FMOs expressed in Escherichia coli, overview
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
L-methionine + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
?
methimazole + NADPH + H+ + O2
?
show the reaction diagram
an thyroperoxidase inhibitor, is converted to the S-oxide
-
-
?
S-allyl-L-cysteine + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
?
(R)-metamphetamine + NADPH + H+ + O2
(R)-metamphetamine N-oxide + NADP+ + H2O
show the reaction diagram
-
substrate of isoform FMO1
-
-
?
(S)-metamphetamine + NADPH + H+ + O2
(S)-metamphetamine N-oxide + NADP+ + H2O
show the reaction diagram
-
substrate of isoforms FMO1 and FMO3
-
-
?
(S)-nicotine + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
(S)-nicotine + NADPH + O2
(S)-nicotine N1-oxide + NADP+ + H2O
show the reaction diagram
-
(S)-nicotine N-1'-oxygenation
-
-
?
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
-
-
?
4-aminobenzoic acid hydrazide + NADPH + O2
?
show the reaction diagram
-
-
-
?
5,6-dimethylxanthenone-4-acetic acid + NADPH + H+ + O2
?
show the reaction diagram
-
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
show the reaction diagram
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
show the reaction diagram
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
show the reaction diagram
-
substrate of isoform FMO3
-
-
?
albendazole + NADPH + H+ + O2
albendazole S-oxide + NADP+ + H2O
show the reaction diagram
-
substrate of isoform FMO3
-
-
?
almotriptan + NADPH + H+ + O2
almotriptan N-oxide + NADP+ + H2O
show the reaction diagram
-
substrate of isoform FMO3
-
-
?
ammonia + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
amphetamine + NADPH + H+ + O2
?
show the reaction diagram
amphetamine + NADPH + H+ + O2
amphetamine N-oxide + NADP+ + H2O
show the reaction diagram
-
substrate of isoform FMO3
-
-
?
amphetamine + NADPH + O2
amphetamine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
benzydamine + NADPH + H+ + O2
?
show the reaction diagram
-
i.e. 3-(1-benzyl-1H-indazol-3-yloxy)-N,N-dimethylpropan-1-amine
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
show the reaction diagram
benzylamine + [reduced NADPH-hemoprotein reductase] + O2
benzylamine N-oxide + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
chlorpromazine + NADPH + H+ + O2
chlorpromazine N-oxide + NADP+ + H2O
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
cimetidine + NADPH + O2
cimetidine S-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
clomiphene + NADPH + H+ + O2
?
show the reaction diagram
-
i.e. 2-[4-[2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethanamine
-
-
?
clozapine + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
show the reaction diagram
clozapine + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
contezolid + NADPH + H+ + O2
contezolid N-oxide + NADP+ + H2O
show the reaction diagram
-
substrate of isoform FMO5
-
-
?
cysteamine + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
danusertib + NADPH + H+ + O2
danusertib N-oxide + NADP+ + H2O
show the reaction diagram
-
substrate of isoform FMO3
-
-
?
dapsone + NADPH + O2
?
show the reaction diagram
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
show the reaction diagram
-
substrate of isoform FMO3
-
-
?
demeton-O + NADPH + O2
demeton-O sulfoxide + NADP+ + H2O
show the reaction diagram
deprenyl + NADPH + H+ + O2
?
show the reaction diagram
deprenyl + NADPH + H+ + O2
deprenyl N-oxide + NADP+ + H2O
show the reaction diagram
-
substrate of isoforms FMO1 and FMO3
-
-
?
disulfoton + NADPH + H+ + O2
?
show the reaction diagram
E-7016 + NADPH + H+ + O2
?
show the reaction diagram
-
substrate of isoform FMO5, Bayer Villiger oxidation
-
-
?
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
an antibiotic agent
-
-
?
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
ethylene thiourea + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
ethylenethiourea + NADPH + O2
ethylenethiourea S-oxide + NADP+ + H2O
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
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
show the reaction diagram
-
substrate of isoforms FMO1 and FMO3
-
-
?
imipramine + NADPH + H+ + O2
imipramine N-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
-
-
-
-
?
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
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
show the reaction diagram
-
substrate of isoform FMO3
-
-
?
L-Met-Phe + NADPH + O2
(L-Met-S-oxide)-Phe + NADP+ + H2O
show the reaction diagram
-
isozymes FMO1-FMO4
-
-
?
L-Met-Val + NADPH + O2
(L-Met-S-oxide)-Val + NADP+ + H2O
show the reaction diagram
-
isozymes FMO1-FMO4, low activity by isozyme FMO1
-
-
?
L-methionine + NADPH + H+ + O2
L-methionine S-oxide + NADP+ + H2O
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
-
-
-
-
?
lorcaserin + NADPH + H+ + O2
lorcaserin N-oxide + NADP+ + H2O
show the reaction diagram
-
substrate of isoform FMO1
-
-
?
loxapine + NADPH + H+ + O2
4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)-1-methylpiperazine 1-oxide + NADP+ + H2O
show the reaction diagram
-
substrate of isoform FMO3
-
-
?
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
-
-
?
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 + H+ + O2
methimazole S-oxide + NADPH + H+ + O2
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 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-4-tolyl sulfide + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
methylmercaptan + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
MK-0457 + NADPH + H+ + O2
MK-0457 N-oxide + NADP+ + H2O
show the reaction diagram
-
substrate of isoforms FMO1 and FMO3
-
-
?
MK-0767 methyl sulfide + NADPH + H+ + O2
?
show the reaction diagram
moclobemide + NADPH + H+ + O2
moclobemide N-oxide + NADP+ + H2O
show the reaction diagram
-
substrate of isoform FMO3
-
-
?
N,N,N-trimethylamine + NADPH + H+ + O2
N,N,N-trimethylamine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
N,N-diallyltryptamine + NADPH + H+ + O2
N,N-diallyltryptamine N-oxide + NADP+ + H2O
show the reaction diagram
-
substrate of isoform FMO3
-
-
?
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 + NADH + H+ + O2
N,N-dimethylaniline N-oxide + NAD+ + H2O
show the reaction diagram
-
-
-
-
?
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-(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
show the reaction diagram
-
substrate of isoforms FMO1 and FMO3
-
-
?
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
N-deacetyloxoconazole + NADPH + H+ + O2
N-deacetyl ketoconazole N-oxide + NADP+ + H2O
show the reaction diagram
-
substrate of isoform FMO3
-
-
?
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
-
recombinant protein expressed in E. coli
-
-
?
naphthylthiourea + NADPH + O2
naphthylthiourea S-oxide + NADP+ + H2O
show the reaction diagram
-
isozyme FMO2
-
-
?
nicotine + NADPH + H+ + O2
(S)-nicotine N1-oxide + NADP+ + H2O
show the reaction diagram
-
substrate of isoform FMO3
-
-
?
nicotine + NADPH + H+ + O2
nicotine N-oxide + NADP+ + H2O
show the reaction diagram
a stimulant, is converted to the trans-N-oxide
-
-
?
nomifensine + NADPH + H+ + O2
?
show the reaction diagram
-
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
show the reaction diagram
-
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
show the reaction diagram
-
substrate of isoform FMO3
-
-
?
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-tolyl sulfide + NADPH + O2
p-tolyl sulfoxide + NADP+ + H2O
show the reaction diagram
-
S-oxidase activity
-
-
?
pargyline + NADPH + H+ + O2
pargyline N-oxide + NADP+ + H2O
show the reaction diagram
-
substrate of isoforms FMO1 and FMO3
-
-
?
phenethylamine + NADPH + O2
phenethylamine N-oxide + NADP+ + H2O
show the reaction diagram
-
isozyme FMO3
-
-
?
phenylthiourea + NADPH + O2
phenylthiourea S-oxide + NADP+ + H2O
show the reaction diagram
-
isozyme FMO2
-
-
?
phorate + NADPH + H+ + O2
?
show the reaction diagram
a thioether-containing organophosphate insecticide
-
-
?
phospho-sulindac + NADPH + H+ + O2
?
show the reaction diagram
-
substrate of isoforms FMO1, FMO3, and FMO5
-
-
?
primaquine + NADPH + H+ + O2
?
show the reaction diagram
-
substrate of isoform FMO3
-
-
?
pyrazolacridine + NADPH + H+ + O2
pyrazolacridine N-oxide + NADP+ + H2O
show the reaction diagram
pyrazoloacridine + NADPH + O2
pyrazoloacridine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
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
show the reaction diagram
-
substrate of isoform FMO1
-
-
?
ranitidine + NADPH + H+ + O2
?
show the reaction diagram
ranitidine + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
S-methyl esonarimod + NADPH + H+ + O2
?
show the reaction diagram
a cytokine production inhbitor, is converted to the S-oxide
-
-
?
S-methyl esonarimod + NADPH + H+ + O2
S-methyl esonarimod S-oxide + NADP+ + H2O
show the reaction diagram
S-methyl N,N-diethyldithiocarbamate + NADPH + H+ + O2
(diethylnitroryl)(methylsulfanyl)methanethione + NADP+ + H2O
show the reaction diagram
-
substrate of isoform FMO1 and FMO3
-
-
?
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
-
-
?
selegiline + NADPH + H+ + O2
?
show the reaction diagram
-
i.e. (2R)-N-methyl-1-phenyl-N-prop-2-ynylpropan-2-amine
-
-
?
selenomethionine + NADPH + H+ + O2
seleno-L-methionine Se-oxideoxide + NADP+ + H2O
show the reaction diagram
-
substrate of isoform FMO3
-
-
?
SNI-2011 + NADPH + H+ + O2
?
show the reaction diagram
a muscarinic receptor antagonist, is converted to the N-oxide
-
-
?
SNI-2011 + NADPH + H+ + O2
SNI-2011 N-oxide + NADP+ + H2O
show the reaction diagram
-
substrate of isoform FMO1
-
-
?
sulfamethoxazole + NADPH + O2
?
show the reaction diagram
sulindac sulfide + NADPH + H+ + O2
?
show the reaction diagram
-
substrate of isoforms FMO1 and FMO3
-
-
?
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
-
-
-
-
?
tamoxifen + NADPH + H+ + O2
?
show the reaction diagram
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
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
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
show the reaction diagram
-
substrate of isoform FMO3
-
-
?
TG100435 + NADPH + H+ + O2
?
show the reaction diagram
-
substrate of isoform FMO1
-
-
?
thiacetazone + 2 NADPH + 2 H+ + 2 O2
thiacetazone carbodiimide + 2 NADP+ + 2 H2O
show the reaction diagram
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
thiobenzamide + NADPH + H+ + O2
thiobenzamide N-oxide + NADP+ + H2O
show the reaction diagram
-
N-oxidation
-
-
?
thiourea + NADPH + O2
thiourea S-oxide + NADP+ + H2O
show the reaction diagram
-
isozyme FMO2
-
-
?
tozasertib + NADPH + H+ + O2
?
show the reaction diagram
triethylamine + NADPH + H+ + O2
triethylamine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
trifluoroperazine + NADPH + H+ + O2
2,3,4-trifluoropyridine 1-oxide + NADP+ + H2O
show the reaction diagram
-
substrate of isoform FMO3
-
-
?
trimethylamine + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
show the reaction diagram
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADPH + H+ + O2
show the reaction diagram
-
substrate of isoform FMO3
-
-
?
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
[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
-
-
?
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
-
-
-
-
?
benzylamine + [reduced NADPH-hemoprotein reductase] + O2
benzylamine N-oxide + [oxidized NADPH-hemoprotein reductase] + 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
-
-
-
-
?
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 is a pro-drug requiring bioactivation to exert toxicity
-
-
?
ethionamide + NADPH + O2 + H+
2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O
show the reaction diagram
-
bioactivation by isozymes FMO1 and FMO3
-
-
?
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 + NADH + H+ + O2
N,N-dimethylaniline N-oxide + NAD+ + H2O
show the reaction diagram
-
-
-
-
?
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
-
-
-
-
?
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
-
bioactivation by isozymes FMO1 and FMO3, two-step process
-
-
?
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
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
FAD
binding site structure containing an GXGXXG motif, overview
NADPH
binding site structure containing an GXGXXG motif, overview
NADH
-
-
NADPH
additional information
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
-
-
MgCl2
-
activates activity of mutant N413K by 18%
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1-aminobenzotriazole
3,3'-diindolylmethane
-
competitive inhibition of FMO3
alpha-naphthoflavone
-
-
Benzydamine
-
i.e. 3-(1-benzyl-1H-indazol-3-yloxy)-N,N-dimethylpropan-1-amine, 47% inhibition at 1 mM
clomiphene
-
i.e. 2-[4-[2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethanamine, 60% inhibition at 0.05 mM
dimethyl sulfoxide
-
about 50% inhibition at 0.5 % (v/v)
imipramine
-
a FMO1-specific inhibitor, selectively inhibits N,N-dimethylamphetamine N-oxidation
indole-3-carbinol
ketoconazole
-
-
Methimazole
MgCl2
-
100 mM, 100% inhibition within 6 min
NO
-
overproduced NO in liver causes the suppression of FMO3 activity directly via reversible S-nitrosylation. Overproduced NO may be responsible, at least in part, for the impairment of the detoxification or metabolism by FMOs of xenobiotics, which include a number of therapeutic drugs
Phenylthiourea
-
-
selegiline
-
i.e. (2R)-N-methyl-1-phenyl-N-prop-2-ynylpropan-2-amine, 21% inhibition at 0.1 mM
sodium cholate
-
1%, time-dependent sensitivity, maximum 65-100% inhibition
tamoxifen
-
i.e. (Z)-2-[4-(1,2-diphenylbut-1-enyl)phenoxy]-N,N-dimethylethanamine, 55% inhibition at 1 mM
Thiourea
tozasertib
-
i.e. N-[4-[4-(4-methylpiperazin-1-yl)-6-[(5-methyl-1H-pyrazol-3-yl)amino]pyrimidin2yl]sulfanylphenyl]cyclopropane carboxamide, 41% inhibition at 0.1 mM
trimethylamine
-
a FMO3-specific inhibitor, exhibits anegligible effect on the N,N-dimethylamphetamine N-oxide formation
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cholate
-
activates activity of mutant N413K by 23%
Triton X-100
-
FMO3 enzymes show a 2fold activation of kcat/Km in the presence of Triton X-100. MBP-FMO3 also shows disassociation from a high-order oligomeric form to a monomeric status in the presence of Triton X-100
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
15 - 38
10-[(N,N-dimethylaminooctyl)-2-(trifluoromethyl)]phenothiazine
0.0229
5-[[3-(dimethylamino)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
isozyme FMO1, in 0.1 M potassium phosphate buffer (pH 8.4) at 37C
0.05903 - 0.4314
5-[[3-(dimethylamino)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
0.0426 - 0.056
Benzydamine
0.022 - 0.08
chlorpromazine
4.31 - 4.56
cimetidine
0.018
clomiphene
-
pH and temperature not specified in the publication
0.013 - 0.25
demeton-O
0.101 - 1.45
ethiofencarb
0.105 - 0.336
Ethionamide
0.0502 - 0.0761
ethylenethiourea
0.145 - 0.351
fenthion
0.0078 - 0.02
imipramine
6.5 - 10
L-methionine
0.018 - 0.046
mercaptoimidazole
0.007 - 0.5758
Methimazole
0.079
methiocarb
-
pH 9.0, isozyme FMO1
0.0048 - 0.3
methyl p-tolyl sulfide
0.0445 - 0.261
N,N-dimethylamphetamine
0.0068 - 0.132
NADPH
0.0871
p-tolyl sulfide
-
37C
0.147
pyrazoloacridine
-
-
0.314
selegiline
-
pH and temperature not specified in the publication
0.0665 - 0.2071
sulindac
0.005 - 0.121
tamoxifen
0.0058 - 0.007
thiacetazone
0.023
tozasertib
-
pH and temperature not specified in the publication
0.0209 - 0.0373
trimethylamine
3 - 3.4
voriconazole
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.18 - 0.72
10-[(N,N-dimethylaminooctyl)-2-(trifluoromethyl)]phenothiazine
0.15
Benzydamine
-
pH and temperature not specified in the publication
0.0017
clomiphene
-
pH and temperature not specified in the publication
0.805 - 1.5
Ethionamide
0.036 - 0.05
ethylenethiourea
0.004 - 0.525
Methimazole
10 - 71.1
methyl p-tolyl sulfide
0.1 - 0.33
N-methyl-tamoxifen
15.2 - 94.4
NADPH
0.023
selegiline
-
pH and temperature not specified in the publication
0.003 - 0.068
sulindac
0.273 - 3.18
tamoxifen
0.023 - 1.335
thiacetazone
0.155
tozasertib
-
pH and temperature not specified in the publication
0.034 - 0.065
trimethylamine
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.005 - 0.027
10-[(N,N-dimethylaminooctyl)-2-(trifluoromethyl)]phenothiazine
0.0028 - 0.014
Ethionamide
0.0091 - 0.0469
Methimazole
0.0022 - 0.0149
methyl p-tolyl sulfide
0.00014 - 0.0144
NADPH
0.0033 - 0.238
thiacetazone
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.008 - 0.013
indole-3-carbinol
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0046 - 0.0073
-
recombinant wild-type and mutant His6-tagged MBT-fusion-FMO3s
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.4 - 9
7.4
-
assay at
8.3
-
assay at
8.8
-
imipramine N-oxidase activity
9 - 10
-
-
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 10
-
isozyme FMO1, pH profile
7.4 - 8.4
the activity is approximately twice as high at pH 8.4 as at pH 7.4
7.5 - 10
-
isozyme FMO3, pH profile
7.5 - 9.5
-
-
7.6 - 9
-
pH 7.6: about 70% of maximal activity, pH 9.0: about 65% of maximal activity, p-tolyl sulfide S-oxidase activity
8.5 - 9.5
-
-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
3
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
-
Manually annotated by BRENDA team
-
recombinant enzymes expressed in insect cells
Manually annotated by BRENDA team
FMO1, expression profiling in tissue from patients with atrial fibrillation
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
-
reduced expression in amyotrophic lateral sclerosis
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
PDB
SCOP
CATH
UNIPROT
ORGANISM
-
-
-
-
-
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
63338
x * 63338, sequence calculation
60000
-
recombinant protein expressed in E. coli
60047
x * 60047, sequence calcualtion
100000
-
x * 100000, recombinant MBP-FMO3 and MBP-FMO5, SDS-PAGE, x * 102000, about, MBP-FMO3, sequence calculation, x * 104000, about, MBP-FMO5, sequence calculation
102000
-
x * 100000, recombinant MBP-FMO3 and MBP-FMO5, SDS-PAGE, x * 102000, about, MBP-FMO3, sequence calculation, x * 104000, about, MBP-FMO5, sequence calculation
104000
-
x * 100000, recombinant MBP-FMO3 and MBP-FMO5, SDS-PAGE, x * 102000, about, MBP-FMO3, sequence calculation, x * 104000, about, MBP-FMO5, sequence calculation
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 63338, sequence calculation
additional information
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
-
FMO1 is selectively N-glycosylated at Asn120, N-glycosylation is not essential for functional activity
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40
-
in absence of NADPH, residue 360 is important for thermal stability, half-lives of wild-type and mutant isozymes FMO1 and FMO3, overview
45
-
the benzydamine N-oxygenation activity of the enzyme is reduced by approximately 70% by preheating at 45C for 5 min. Benzydamine N-oxygenation is suppressed by 30% and 50% after preincubation of liver microsomes at 37C for 5 and 10 min, respectively
50
-
the enzyme is unstable in absence of NADPH
60
-
90 s, inactivation of FMO in liver microsomes
additional information
-
loss of about 30% of activity after heat treatment of mutant enzyme N413K, activity is preservable by NADPH
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
NADPH stabilizes the enzyme
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
nickel affinity column chromatography
-
recombinant MBP-fusion FMO3 and FMO5 from Escherichia coli strain DH5alpha to about 90% purity by amylose affinity chromatography, and for FMO3 also further by anion exchange chromatography
-
recombinant protein
recombinant wild-type and mutant FMO3 from Escherichia coli strain JM109 in a multistep process
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
FMO isozyme expression patterns, expression analysis
FMO4, DNA and amino acid sequence determination and analysis, phylogenetic analysis, the gene maps to the long arm of chromosome 1, genotyping and alternative splicing variants, overview
DNA and amino acid sequence determination and analysis of multiple samples of gene FMO3, expression of clones in Spodoptera frugiperda Sf9 insect cell microsomes via baculovirus transfection system, the FMO multigene family consists of a five-gene cluster at 1q24.3, comprising FMO1-4 and FMO6p, and a second cluster of five genes at 1q24.2, comprising FMO7p-11p, and a single gene, FMO5, at 1q21.1, encoding a total of five active proteins in humans
-
DNA sequence determination and analysis, and genotyping
-
expressed in Escherichia coli JM109 cells
-
expressed in Sf9 insect cell microsomes
-
expressed in Sf9 insect cells
-
expressed in Trichoplusia ni cells using a baculovirus expression vector system
-
expression as maltose-binding fusion proteins in Escherichia coli
expression of FMO1, FMO2.1, and FMO3 in Spodoptera frugiperda Sf9 cell microsomes
-
expression of FMO3 and FMO5 as N-terminal maltose-binding protein fusion proteins, MBP-FMOs, in Escherichia coli strain DH5alpha
-
expression of isozyme FMO genetic variants in Spodoptera frugiperda Sf9 insect cell microsomes via baculovirus transfection system
-
expression of isozymes FMO1-FMO5, optimized for heterologous expression, in Escherichia coli, isozymes FMO1-FMO4 are active with peptide-bound methionine, while FMO5 is inactive
-
expression of wild-type and mutant FMO3 in Escherichia coli strain JM109
-
expression of wild-type and mutant isozymes FMO1 and FMO3 as N-terminally maltose-binding-protein fusion and C-terminally His6-tagged proteins in Escherichia coli strain JM109
-
expression of wild-type enzyme and mutants M66I and R492W in Spodoptera frugiperda Sf9 cell membranes
-
five genes encoding isozymes FMO1-FMO5 and 1 pseudogene organized in a gene cluster
-
FMO isozyme expression patterns, expression analysis
FMO1, DNA and amino acid sequence determination and analysis, phylogenetic analysis
FMO2, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis
FMO3 cDNA from liver, expression in Spodoptera frugiperda Sf9 insect cells
-
FMO3, DNA and amino acid sequence determination and analysis, genotyping
-
FMO3, DNA and amino acid sequence determination and analysis, the gene maps to the long arm of chromosome 1, phylogenetic analysis
FMO3, genotyping in relation to gender, age, race/ethnic, and FMO3 expression in response to administration of the anti-schizophrenia drug olanzapine
FMO5, the gene encoding the enzyme is located at 1q21.1, not in the FMO gene cluster at 1q24.3, DNA and amino acid sequence determination and analysis, phylogenetic analysis
gene FMO1, DNA and amino acid sequence determination and analysis, the gene contains five long interspersed nuclear element-1-like elements, i.e. LINE elements, expression analysis, silencing of FMO1 in adult human liver is due apparently to the presence upstream of the proximal P0 of LINE-1 elements rather than the absence of retrotransposons, expression in Hep-G2 cells
gene FMO1, genes FMO1 to FMO4 are clustered on chromosome 1 at q24.3, along with a pseudogene FMO6P
-
gene FMO2, genes FMO1 to FMO4 are clustered on chromosome 1 at q24.3, along with a pseudogene FMO6P
-
gene fMO3, DNA and amino acid sequence determination and analysis of wild-type and natural mutant enzymes, overview
-
gene FMO3, DNA and amino acid sequence determination and analysis, transient expression in Hep-G2 cells
-
gene FMO3, genes FMO1 to FMO4 are clustered on chromosome 1 at q24.3, along with a pseudogene FMO6P
-
genes FMO1-FMO6, FMO6 is a pseudogene, the genes are organized in two clusters chromosome 1, one of which resides on the long arm of chromosome 1 at q23 25, the second cluster is composed of 5 pseudogenes
-
independent expression of isozymes FMO1 and FMO3 in Spodoptera frugiperda Sf9 insect cell microsomes via baculovirus transfection system
-
missense mutations causing fish-odour syndrome
-
using a baculovuirus expression system in Sf-9 insect cells, dFMO1 is expressed to protein levels of 0.4 nM/mg
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
FMO3 expression in response to administration of the anti-schizophrenia drug olanzapine, allele frequencies and phenotypes, overview
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
E339Q
naturally occuring single nucleotide polymorphism of FMO4
I37T
naturally occuring single nucleotide polymorphism of FMO4
P457L
naturally occuring single nucleotide polymorphism of FMO4
R506S
naturally occuring single nucleotide polymorphism of FMO4
T308S
naturally occuring single nucleotide polymorphism of FMO4
V323A
naturally occuring single nucleotide polymorphism of FMO4
A52T
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
C530L
naturally occuring single nucleotide polymorphism of FMO2
D198E
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
D227K
pKa value 7.3 for N-oxygenation of 10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene, compared with 6.9 for wild-type
D36G
naturally occuring single nucleotide polymorphism of FMO2
down
-
FMO5 is downregulated in type II diabetes in liver. FMO1 downregulation and inhibition by 3,3'-diindolylmethane
E132H
-
natural genetic variant of isozyme FMO2, substrate specificity, overview
E132H/E158K
-
natural genetic variant of isozyme FMO2, substrate specificity, overview
E158K/E308G
E158K/T201K/E308G
-
naturally occuring genetic variant of isozyme FMO3, and site-directed mutagenesis, the mutant shows reduced activity with sulindac and methyl 4-toyl sulfide compared to the wild-type FMO3
E158K/V257M
-
the naturally occuring polymorphisms reduce the oxidation and clearance of FMO3 substrates such as tyramine, and TMA in vitro, and mutations are highly likely to eliminate the enzyme function in vivo
E305X
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
E314G
naturally occuring single nucleotide polymorphism of FMO2
E314X
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
E32K
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
E362Q
naturally occuring single nucleotide polymorphism of FMO3
F182S
naturally occuring single nucleotide polymorphism of FMO2
F510X
-
natural genetic variant of isozyme FMO2, substrate specificity, overview
F69Y
naturally occuring single nucleotide polymorphism of FMO2
F81S
naturally occuring single nucleotide polymorphism of FMO2
G148X
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
G180V
naturally occuring single nucleotide polymorphism of FMO3, the mutant is similar to the wild-type enzyme
G182E
pKa value 6.6 for N-oxygenation of 10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene, compared with 6.9 for wild-type
G475D
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
G503R
naturally occuring single nucleotide polymorphism of FMO3
H360P
-
site-directed mutagenesis of isozyme FMO1, the mutant shows altered thermal stability and highly increased activity with mercaptoimidazole and chlorpromazine compared to the wild-type FMO1
I199T
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
I37T
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
I468M
naturally occuring single nucleotide polymorphism of FMO3
K158L
-
Km-value for fenthion is 1.4fold higher than the wild-type value, Vmax for fenthion is nearly identical to the wild-type value, mutant of FMO3
K158L/D132H
-
Km-value for fenthion is 1.5fold higher than the wild-type value, Vmax for fenthion is 1.5fold higher than the wild-type value, mutant of FMO3
L360A
-
site-directed mutagenesis of isozyme FMO3, the mutant shows altered thermal stability and reduced activity with mercaptoimidazole, chlorpromazine, and 10-[(N,N-dimethylaminopentyl)-2-(trifluoromethyl)]phenothiazine compared to the wild-type FMO3
L360H
-
site-directed mutagenesis of isozyme FMO3, the mutant shows altered thermal stability and reduced activity with mercaptoimidazole, chlorpromazine, and 10-[(N,N-dimethylaminopentyl)-2-(trifluoromethyl)]phenothiazine compared to the wild-type FMO3
L360Q
-
site-directed mutagenesis of isozyme FMO3, the mutant shows altered thermal stability and reduced activity with mercaptoimidazole, chlorpromazine, and 10-[(N,N-dimethylaminopentyl)-2-(trifluoromethyl)]phenothiazine compared to the wild-type FMO3
M260V
naturally occuring single nucleotide polymorphism of FMO3
M434I
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
M82T
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
N114S
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
Q170K
pKa value 6.6 for N-oxygenation of 10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene, compared with 6.9 for wild-type
Q206H
pKa value 6.5 for N-oxygenation of 10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene, compared with 6.9 for wild-type
Q470X
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
R238P
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
R238Q
naturally occuring single nucleotide polymorphism of FMO2
R249X
naturally occuring single nucleotide polymorphism of FMO2, probably inactive mutant
R378L
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
R391T
naturally occuring single nucleotide polymorphism of FMO2
R492W
-
naturally occuring mutation involved in trimethylaminuria, the mutant fails to incorporate/retain the FAD cofactor
R500X
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
R502V
-
no activity with methimazole, KM-value for methyl p-tolyl sulfide is 70% of the wild-type value, Vmax with methyl p-tolyl sulfide is 70% of the wild-type value, KM-value for imipramine is is nearly identical to the the wild-type value, Vmax with imipramine is 49% of the wild-type value, KM-value for fenthion is 88% of the wild-type value, Vmax with fenthion is 55% of wild-type value, mutant of FMO1
R51G
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
T201K
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
V143E
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
V257M/E308G
-
naturally occuring polymorphism, the substitutions do not affect enzyme activity in vitro
V257M/M260V
-
naturally occuring genetic variant of isozyme FMO3, and site-directed mutagenesis, the mutant shows reduced activity with sulindac and methyl 4-toyl sulfide compared to the wild-type FMO3
V277A
naturally occuring single nucleotide polymorphism of FMO3
V58I
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
W388X
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
Y228H
pKa value 7.9 for N-oxygenation of 10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene, compared with 6.9 for wild-type
additional information