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Literature summary for 1.14.13.8 extracted from

  • Cashman, J.R.
    Some distinctions between flavin-containing and cytochrome P450 monooxygenases (2005), Biochem. Biophys. Res. Commun., 338, 599-604.
    View publication on PubMed
Search for more literature for 1.14.13.8

Activating Compound

Activating Compound Comment Organism Structure
additional information FMO is not induced or readily inhibited by drugs in general in contrast to cytochrome P450 monooxygenases Homo sapiens

Application

Application Comment Organism
drug development the enzyme is not affected by drugs in contrast to cytochrome P450 monooxygenases, EC 1.14.14.1, by incorporating FMO detoxication pathways into drug candidates, more drug-like materials may emerge Homo sapiens

Protein Variants

Protein Variants Comment Organism
additional information occuring single nucleotide polymorphisms are associated with dramatic functional differences in selective functional enzyme activity, overview Homo sapiens

General Stability

General Stability Organism
NADPH stabilizes the enzyme Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
additional information FMO is not induced or readily inhibited by drugs in general in contrast to cytochrome P450 monooxygenases Homo sapiens

Localization

Localization Comment Organism GeneOntology No. Textmining
microsome the highly hydrophobic FMO shows multiple internal sites of membrane association Homo sapiens
-
-

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(S)-nicotine + NADPH + O2 Homo sapiens (S)-nicotine N-1'-oxygenation (S)-nicotine N1-oxide + NADP+ + H2O
-
 ?
benzylamine + [reduced NADPH-hemoprotein reductase] + O2 Homo sapiens
-
 benzylamine N-oxide + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
cimetidine + NADPH + O2 Homo sapiens
-
 cimetidine S-oxide + NADP+ + H2O
-
 ?
clozapine + NADPH + O2 Homo sapiens
-
 ?
-
 ?
itopride + NADPH + O2 Homo sapiens
-
 ?
-
 ?
additional information Homo sapiens enzyme regulation, overview ?
-
 ?
N,N-dimethylaniline + NADPH + O2 Homo sapiens
-
 N,N-dimethylaniline N-oxide + NADP+ + H2O
-
 ?
ranitidine + NADPH + O2 Homo sapiens
-
 ?
-
 ?
trimethylamine + NADPH + O2 Homo sapiens
-
 trimethylamine N-oxide + NADP+ + H2O
-
 ?

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
 isozymes FMO1-FMO5
-

Posttranslational Modification

Posttranslational Modification Comment Organism
glycoprotein FMO1 is selectively N-glycosylated at Asn120, N-glycosylation is not essential for functional activity Homo sapiens

Reaction

Reaction Comment Organism Reaction ID
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 Homo sapiens
a

Source Tissue

Source Tissue Comment Organism Textmining
liver
-
 Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(S)-nicotine + NADPH + O2 (S)-nicotine N-1'-oxygenation Homo sapiens (S)-nicotine N1-oxide + NADP+ + H2O
-
 ?
benzylamine + [reduced NADPH-hemoprotein reductase] + O2
-
 Homo sapiens benzylamine N-oxide + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
cimetidine + NADPH + O2
-
 Homo sapiens cimetidine S-oxide + NADP+ + H2O
-
 ?
clozapine + NADPH + O2
-
 Homo sapiens ?
-
 ?
itopride + NADPH + O2
-
 Homo sapiens ?
-
 ?
additional information enzyme regulation, overview Homo sapiens ?
-
 ?
additional information FMO oxygenates soft nucleophiles, and converts lipophilic compounds into more hydrophilic metabolites, potential adverse drug-drug interactions are minimized for drugs prominently metabolized by FMO, substrate specificities of isozmes, overview Homo sapiens ?
-
 ?
N,N-dimethylaniline + NADPH + O2
-
 Homo sapiens N,N-dimethylaniline N-oxide + NADP+ + H2O
-
 ?
ranitidine + NADPH + O2
-
 Homo sapiens ?
-
 ?
trimethylamine + NADPH + O2
-
 Homo sapiens trimethylamine N-oxide + NADP+ + H2O
-
 ?

Synonyms

Synonyms Comment Organism
flavin-containing-monooxygenase
-
 Homo sapiens
FMO
-
 Homo sapiens

Temperature Stability [°C]

Temperature Stability Minimum [°C] Temperature Stability Maximum [°C] Comment Organism
50
-
 the enzyme is unstable in absence of NADPH Homo sapiens

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
9 10
-
 Homo sapiens

Cofactor

Cofactor Comment Organism Structure
FAD
-
 Homo sapiens
NADPH
-
 Homo sapiens