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Information on EC 1.14.13.8 - flavin-containing monooxygenase
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1.14.13.8 flavin-containing monooxygenaseIUBMB Comments
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]
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Word Map
- 1.14.13.8
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orbit
- methimazole
- trimethylamine
- xenobiotics
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fenna-matthews-olson
- sulfoxide
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n-oxygenation
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excitonic
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s-oxidation
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initio
- bacteriochlorophyll
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frontier
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n-demethylation
- antenna
- tepidum
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drug-metabolizing
- thioureas
- n-octylamine
- phenobarbital
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cdna-expressed
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light-harvesting
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pigment-protein
- imipramine
- metyrapone
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yucca
- chlorobium
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baeyer-villiger
- cyp2c19
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n-hydroxylation
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diels-alder
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hamiltonians
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monooxygenation
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sulfenic
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p-450-dependent
- trimethylamine-n-oxide
- aestuarii
- cyp2a6
- nitrone
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malodor
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hartree-fock
- 1-aminobenzotriazole
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ifies
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piperonyl
- drug development
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
fmo, flavin-containing monooxygenase, flavin monooxygenase, flavin-dependent monooxygenase, flavin-containing monooxygenase 3, fad-containing monooxygenase, flavoprotein monooxygenase, hfmo3, flavin-containing mono-oxygenase, flavin-containing monooxygenase 1, 
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topREACTION 
REACTION DIAGRAM
COMMENTARY 
ORGANISM
UNIPROT
LITERATURE
hypotaurine + H2O + NAD+ = taurine + NADH + H+
a molybdohemoprotein
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
ordered ter-bi mechanism with an irreversible step between the second and third substrate, NADPH is added first, followed by O2 and the oxidizable organic substrate last
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
reaction mechanism of S-oxygenation of N-substituted thioureas
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
reaction mechanism of S-oxygenation of N-substituted thioureas
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic cycle and catalytic reaction mechanism, structure-function relationship, FMO oxygenates 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, substrate binding has no effect on velocity, formation of a peroxyflavin intermediate
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic cycle and catalytic reaction mechanism, structure-function relationship, FMO oxygenates 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, substrate binding has no effect on velocity, formation of a peroxyflavin intermediate
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic cycle and catalytic reaction mechanism, structure-function relationship, FMO oxygenates 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, substrate binding has no effect on velocity, formation of a peroxyflavin intermediate
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic cycle and catalytic reaction mechanism, structure-function relationship, FMO oxygenates 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, substrate binding has no effect on velocity, formation of a peroxyflavin intermediate
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic reaction mechanism via 4alpha-hydroperoxyflavin transient intermediate
N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic reaction mechanism, structure-function relationship, FMO oxygenates soft nucleophiles, and converts lipophilic compounds into more hydrophilic metabolites, the first step for FMO is reduction of the FAD by NADPH, the next step is formation of a C4a-hydroperoxy flavin by addition of molecular oxygen to the reduced FAD, when the substrate is accepted by FMO the enzyme is already in an active form, the protein environment of FMO apparently protects the hydroperoxy flavin from decomposing, conserving NADPH, and affording an effcient two-electron oxygenating agent for nucleophiles with the appropriate size and shape
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic cycle, reaction mechanism and structure-function relationship, overview
N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic cycle, reaction mechanism via C4a-hydroperoxyflavin intermediate and structure-function relationship, overview
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
formation of a highly stable C4a-hydroperoxyflavin intermediate of hFMO1 upon reduction by NADPH in presence of O2
N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic cycle, reaction mechanism via C4a-hydroperoxyflavin intermediate and structure-function relationship, overview
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
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PATHWAY SOURCE
PATHWAYS