KEGG   ENZYME: 1.14.13.8Help
Entry
EC 1.14.13.8                Enzyme                                 

Name
flavin-containing monooxygenase;
dimethylaniline oxidase;
dimethylaniline N-oxidase;
FAD-containing monooxygenase;
N,N-dimethylaniline monooxygenase;
DMA oxidase;
flavin mixed function oxidase;
Ziegler's enzyme;
mixed-function amine oxidase;
FMO;
FMO-I;
FMO-II;
FMO1;
FMO2;
FMO3;
FMO4;
FMO5;
flavin monooxygenase;
methylphenyltetrahydropyridine N-monooxygenase;
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine:oxygen N-oxidoreductase;
dimethylaniline monooxygenase (N-oxide-forming)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy
Sysname
N,N-dimethylaniline,NADPH:oxygen oxidoreductase (N-oxide-forming)
Reaction(IUBMB)
N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O [RN:R03344]
Reaction(KEGG)
R03344;
(other) R04523 R08266
Show
Substrate
N,N-dimethylaniline [CPD:C02846];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007]
Product
N,N-dimethylaniline N-oxide [CPD:C01183];
NADP+ [CPD:C00006];
H2O [CPD:C00001]
Comment
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]
History
EC 1.14.13.8 created 1972 (EC 1.13.12.11 created 1992, part-incorporated 2006), modified 2006
Pathway
Drug metabolism - cytochrome P450
Microbial metabolism in diverse environments
Orthology
K00485  
dimethylaniline monooxygenase (N-oxide forming)
Genes
HSA: 
2326(FMO1) 2327(FMO2) 2328(FMO3) 2329(FMO4) 2330(FMO5)
PTR: 
449587(FMO2) 456443(FMO4) 456444(FMO1) 457505(FMO3) 469472(FMO5) 469579
PPS: 
GGO: 
PON: 
100171678(FMO3) 100171693(FMO2) 100173722(FMO1) 100174599(FMO4) 100437586(FMO5)
NLE: 
MCC: 
574244(FMO3) 703639(FMO2) 703743(FMO1) 704074(FMO4) 706438(FMO6P) 709691(FMO5)
MCF: 
CJC: 
100406306(FMO5) 100408861(FMO4) 100409221(FMO1) 100409812(FMO2) 100410172(FMO3)
MMU: 
14261(Fmo1) 14262(Fmo3) 14263(Fmo5) 226564(Fmo4) 226565(Fmo6) 226601(Gm4846) 226604(Gm4847) 240894(Fmo9) 55990(Fmo2)
RNO: 
246245(Fmo2) 246247(Fmo4) 246248(Fmo5) 25256(Fmo1) 289193(Fmo13) 304922(Fmo6) 685351 685365(Fmo9) 84493(Fmo3)
CGE: 
NGI: 
HGL: 
OCU: 
TUP: 
CFA: 
403603(FMO3) 403604(FMO1) 475819(FMO5) 478994 480076(FMO2) 490345(FMO4) 490346
AML: 
UMR: 
FCA: 
PTG: 
BTA: 
100849673 281167(FMO3) 504401(FMO2) 508781(FMO1) 517828 539356(FMO4) 788719(FMO5)
BOM: 
PHD: 
CHX: 
OAS: 
SSC: 
CFR: 
BACU: 
LVE: 
ECB: 
100052022(FMO3) 100052080(FMO4) 100059647(FMO2) 100059719(FMO1) 100065455(FMO5)
MYB: 
MYD: 
PALE: 
MDO: 
SHR: 
OAA: 
GGA: 
100857724 395267(FMO6P) 770587(FMO4)
MGP: 
APLA: 
TGU: 
FAB: 
PHI: 
FPG: 
FCH: 
CLV: 
102083528(FMO4) 102096840(FMO5) 102098872(FMO1)
ASN: 
AMJ: 
PSS: 
CMY: 
ACS: 
PBI: 
XLA: 
398813(fmo5) 398930(fmo2) 447211
XTR: 
DRE: 
557628(fc14c11) 794311(fmo5)
TRU: 
MZE: 
OLA: 
XMA: 
LCM: 
CMK: 
BFO: 
CIN: 
SPU: 
DME: 
ISC: 
CEL: 
CBR: 
CBG04445(Cbr-fmo-2) CBG11527(Cbr-fmo-4) CBG18329(Cbr-fmo-3)
BMY: 
LOA: 
TSP: 
LGI: 
NVE: 
HMG: 
TAD: 
AQU: 
ALY: 
CRB: 
EUS: 
CIT: 
CIC: 
TCC: 
GMX: 
PVU: 
MTR: 
CAM: 
FVE: 
PPER: 
PMUM: 
MDM: 
CSV: 
CMO: 
RCU: 
POP: 
POPTR_0001s36280g(POPTRDRAFT_752663) POPTR_0005s27200g(POPTRDRAFT_864734) POPTR_0006s05920g POPTR_0006s05930g POPTR_0006s13990g POPTR_0009s14570g(POPTRDRAFT_200388) POPTR_0018s12360g(POPTRDRAFT_779640)
VVI: 
SLY: 
SOT: 
DOSA: 
Os03t0182000-00(Os03g0182000) Os04t0223901-00(Os04g0223901) Os09t0548400-01(Os09g0548400)
OBR: 
BDI: 
SBI: 
SORBI_01g045120(SORBIDRAFT_01g045120) SORBI_02g004310(SORBIDRAFT_02g004310) SORBI_06g001960(SORBIDRAFT_06g001960)
SITA: 
PDA: 
ATR: 
s00001p00055460(AMTR_s00001p00055460) s00001p00064470(AMTR_s00001p00064470) s00007p00261040(AMTR_s00007p00261040)
SMO: 
CRE: 
MIS: 
MPP: 
PAN: 
TMN: 
NHE: 
TRE: 
MAW: 
MAJ: 
CMT: 
VAL: 
MBE: 
ACT: 
PBL: 
ABE: 
TVE: 
AJE: 
PNO: 
PTE: 
BZE: 
BSC: 
BOR: 
PFJ: 
TMS: 
SHS: 
PSQ: 
ADL: 
GTR: 
SCM: 
DPP: 
DFA: 
ACAN: 
TET: 
EHX: 
GTT: 
NGR: 
MME: 
TMO: 
SGU: 
RIV: 
 » show all
Taxonomy
Reference
1  [PMID:4381353]
  Authors
Ziegler DM, Pettit FH.
  Title
Microsomal oxidases. I. The isolation and dialkylarylamine oxygenase activity of pork liver microsomes.
  Journal
Biochemistry. 5 (1966) 2932-8.
Reference
2  [PMID:3262153]
  Authors
Chiba K, Kubota E, Miyakawa T, Kato Y, Ishizaki T.
  Title
Characterization of hepatic microsomal metabolism as an in vivo detoxication pathway of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in mice.
  Journal
J. Pharmacol. Exp. Ther. 246 (1988) 1108-15.
Reference
3
  Authors
Cashman, J.R.
  Title
Structural and catalytic properties of the mammalian flavin-containing monooxygenase.
  Journal
Chem. Res. Toxicol. 8 (1995) 165-181.
Reference
4  [PMID:16402899]
  Authors
Cashman JR, Zhang J.
  Title
Human flavin-containing monooxygenases.
  Journal
Annu. Rev. Pharmacol. Toxicol. 46 (2006) 65-100.
Reference
5  [PMID:3949735]
  Authors
Jones KC, Ballou DP.
  Title
Reactions of the 4a-hydroperoxide of liver microsomal flavin-containing monooxygenase with nucleophilic and electrophilic substrates.
  Journal
J. Biol. Chem. 261 (1986) 2553-9.
Reference
6  [PMID:7672012]
  Authors
Chiba K, Kobayashi K, Itoh K, Itoh S, Chiba T, Ishizaki T, Kamataki T.
  Title
N-oxygenation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine by the rat liver flavin-containing monooxygenase expressed in yeast cells.
  Journal
Eur. J. Pharmacol. 293 (1995) 97-100.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 
CAS: 
37256-73-8

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