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1.14.13.8: flavin-containing monooxygenase

This is an abbreviated version!
For detailed information about flavin-containing monooxygenase, go to the full flat file.

Word Map on EC 1.14.13.8

Reaction

Hypotaurine
+
H2O
+
NAD+
=
taurine
+
NADH
+
H+

Synonyms

class 3 flavin-containing mono-oxygenase, class 3 FMO, dechlorinating flavin-dependent monooxygenase, dimethylaniline monooxygenase (N-oxide-forming), dimethylaniline monooxygenase [N-oxide-forming] 1, dimethylaniline N-oxidase, dimethylaniline oxidase, dimethylsulfone monooxygenase, DMA oxidase, EC 1.13.12.11, EC 1.8.1.3, EtaA, FAD-containing monooxygenase, FAD-containing monooxygenase 3, flavin containing monooxygenase 3, flavin mono-oxygenase, flavin monooxygenase, flavin-containing mono-oxygenase, flavin-containing monooxygenase, flavin-containing monooxygenase 1, flavin-containing monooxygenase 3, flavin-containing monooxygenase 5, flavin-containing monooxygenase-3, flavin-containing-monooxygenase, flavin-dependent monooxygenase, flavoprotein monooxygenase, FMO, FMO 1A1, FMO 1B1, FMO 1C1, FMO 1D1, FMO 1E1, FMO-E, FMO-I, FMO-II, FMO1, FMO2, FMO2.1, FMO3, FMO4, FMO5, FMOGS-OX6, FMOGS-OX7, HadA, hFMO1, hFMO3, hFMO5, Met S-oxidase, mFMO, mixed-function amine oxidase, monooxygenase FMO1, More, MymA, N,N-dimethylaniline monooxygenase, oxygenase, dimethylaniline mono- (N-oxide-forming), oxygenase, methylphenyltetrahydropyridine N-mono-, PtFMO, sfnG, TetX, type II flavin-containing monooxygenase

ECTree

     1 Oxidoreductases
         1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
             1.14.13 With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
                1.14.13.8 flavin-containing monooxygenase

Natural Substrates Products

Natural Substrates Products on EC 1.14.13.8 - flavin-containing monooxygenase

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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(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
-
-
-
-
?
3-hydroxy-nabumetone + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
activation reaction
-
-
?
4-aminobenzoic acid hydrazide + NADPH + 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
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
-
-
-
?
cimetidine + NADPH + O2
cimetidine S-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
clomiphene + NADPH + H+ + O2
clomiphene N-oxide + NADP+ + H2O
show the reaction diagram
clomiphene is used in infertility medication
-
-
?
clomipramine + NADPH + H+ + O2
clomipramine N-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
-
-
-
-
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
show the reaction diagram
dapsone + NADPH + O2
?
show the reaction diagram
bioactivation by isozyme FMO3, not FMO1, results in covalent adduct formation
-
-
?
dasatinib + NADPH + H+ + O2
dasatinib N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
?
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
-
-
-
-
?
GSK5182 + NADPH + H+ + O2
GSK5182 N-oxide + NADP+ + H2O
show the reaction diagram
an antidiabetic lead molecule
-
-
?
hypotaurine + H2O + NAD+
taurine + NADH
show the reaction diagram
-
metabolism of cysteine
-
?
hypotaurine + NADH + H+ + O2
taurine + NAD+ + H2O
show the reaction diagram
hypotaurine + NADPH + H+ + O2
taurine + NADP+ + H2O
show the reaction diagram
imipramine + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
indole + NADPH + H+ + O2
indole 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
-
-
-
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
show the reaction diagram
lipoic acid + NADPH + O2
?
show the reaction diagram
loxapine + NADPH + H+ + O2
loxapine N-oxide + NADP+ + H2O
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
-
-
-
-
?
methylthioalkyl glucosinolate + NADPH + H+ + O2
methylsulfinylalkyl glucosinolate S-oxide + 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
-
-
-
-
?
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
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 + H+ + O2
tamoxifen N-oxide + 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
-
-
?
tozasertib + NADPH + H+ + O2
tozasertib N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
?
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
-
-
?
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
?
-