2.02012-05-31 14:06:52 -06002015-06-03 15:54:48 -0600ECMDB04161M2MDB000643Trimethylamine N-OxideTrimethylamine N-oxide (TMAO) is found at high concentrations in the tissues of fish, and the bacterial reduction of this compound to foul-smelling trimethylamine is a major process in the spoilage of fish. Trimethylamine N-oxide reductase (TOR or TMAO reductase, EC 1.7.2.3) is a microbial enzyme that can reduce TMAO into trimethylamine (TMA), as part of the electron transport chain. The enzyme has been purified from E. coli. It can accept electrons from cytochromes. (Wikipedia; PMID: 1337081; PMID: 11056172)N,N-Dimethylmethanamine N-oxideTMA-oxideTMAOTMeAla-oxideTrimethylamine N-oxideTrimethylamine oxideTrimethylamine-N-oxideTrioxC3H9NO75.109775.068413915N,N-dimethylmethanamine oxidetrimethylamine-n-oxide1184-78-7C[N+](C)(C)[O-]InChI=1S/C3H9NO/c1-4(2,3)5/h1-3H3UYPYRKYUKCHHIB-UHFFFAOYSA-NSolidCytosolExtra-organismPeriplasmlogp-2.01logs-0.11solubility5.78e+01 g/lmelting_point95-99 oClogp-0.93pka_strongest_basic4.66iupacN,N-dimethylmethanamine oxideaverage_mass75.1097mono_mass75.068413915smilesC[N+](C)(C)[O-]formulaC3H9NOinchiInChI=1S/C3H9NO/c1-4(2,3)5/h1-3H3inchikeyUYPYRKYUKCHHIB-UHFFFAOYSA-Npolar_surface_area23.06refractivity22.03polarizability8.4rotatable_bond_count0acceptor_count1donor_count0physiological_charge0formal_charge0Methane metabolismec00680Microbial metabolism in diverse environmentsec01120Two-component systemec02020Collection of Reactions without pathwaysPW001891MetabolicN-oxide electron transferThe pathway can start in various spots. First step in this case starts with NADH interacting with a menaquinone oxidoreductase resulting in the release of a NADH and a hydrogen Ion, at the same time in the inner membrane a menaquinone interacts with 2 electrons and 2 hydrogen ions thus releasing a menaquinol. This allows for 4 hydrogen ions to be transferred from the cytosol to the periplasmic space. The menaquinol then interacts with a trimethylamine N-oxide reductase resulting in the release of 2 hydrogen ion and 2 electrons. At the same time trimethylamine N-oxide and 3 hydrogen ions interact with the enzyme trimethylamine N-oxide reductase resulting in the release of a trimethylamine and a water molecule, this reaction happening in the periplasmic space.
The second set of reactions starts with a hydrogen interacting with a menaquinone oxidoreductase resulting in the release of two electrons being released into the inner membrane which then react with with 2 hydrogen ion and a menaquinone to produce a menaquinol. This menaquinol then reacts with a trimethylamine N-oxide reductase following the same steps as mentioned before.
The third set of reactions starts with with formate interacting with a formate dehydrogenase-O resulting in a release of carbon dioxide and a hydrogen ion, this releases 2 electrons that interact with a menaquinone and two hydrogen ions. This releases a menaquinol which then reacts with a trimethylamine N-oxide reductase following the same steps as mentioned beforePW001889Metabolicformate to trimethylamine N-oxide electron transferPWY0-1355NADH to trimethylamine N-oxide electron transferPWY0-1347Specdb::CMs17537Specdb::CMs169443Specdb::EiMs705Specdb::NmrOneD1286Specdb::NmrOneD1605Specdb::NmrOneD2177Specdb::NmrOneD2865Specdb::NmrOneD145790Specdb::NmrOneD145791Specdb::NmrOneD145792Specdb::NmrOneD145793Specdb::NmrOneD145794Specdb::NmrOneD145795Specdb::NmrOneD145796Specdb::NmrOneD145797Specdb::NmrOneD145798Specdb::NmrOneD145799Specdb::NmrOneD145800Specdb::NmrOneD145801Specdb::NmrOneD145802Specdb::NmrOneD145803Specdb::NmrOneD145804Specdb::NmrOneD145805Specdb::NmrOneD145806Specdb::NmrOneD145807Specdb::NmrOneD145808Specdb::NmrOneD145809Specdb::NmrOneD166485Specdb::MsMs1312Specdb::MsMs1313Specdb::MsMs1314Specdb::MsMs4875Specdb::MsMs4876Specdb::MsMs4877Specdb::MsMs4878Specdb::MsMs4879Specdb::MsMs4880Specdb::MsMs304822Specdb::MsMs304823Specdb::MsMs304824Specdb::MsMs348115Specdb::MsMs348116Specdb::MsMs348117Specdb::MsMs447109Specdb::MsMs447110Specdb::MsMs447111Specdb::MsMs447112Specdb::MsMs447113Specdb::MsMs448169Specdb::MsMs2235697Specdb::MsMs2237658Specdb::MsMs2237863Specdb::MsMs2239724Specdb::NmrTwoD1546HMDB0092511451113C0110415724TRIMENTHLAMINE-N-OTMOTrimethylamine oxideKeseler, I. 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Epub 2013 Apr 7.23563705Hazard, Rene; Cheymol, Jean; Chabrier, Pierre. Trimethylamine oxide. (1962), 1 p.Probable anaerobic dimethyl sulfoxide reductase chain ynfGP0AAJ1YNFG_ECOLIynfGhttp://ecmdb.ca/proteins/P0AAJ1.xmlAnaerobic dimethyl sulfoxide reductase chain AP18775DMSA_ECOLIdmsAhttp://ecmdb.ca/proteins/P18775.xmlAnaerobic dimethyl sulfoxide reductase chain BP18776DMSB_ECOLIdmsBhttp://ecmdb.ca/proteins/P18776.xmlPutative dimethyl sulfoxide reductase chain ynfEP77374YNFE_ECOLIynfEhttp://ecmdb.ca/proteins/P77374.xmlProbable dimethyl sulfoxide reductase chain ynfFP77783YNFF_ECOLIynfFhttp://ecmdb.ca/proteins/P77783.xmlTrimethylamine-N-oxide reductase 2P46923TORZ_ECOLItorZhttp://ecmdb.ca/proteins/P46923.xmlCytochrome c-type protein torYP52005TORY_ECOLItorYhttp://ecmdb.ca/proteins/P52005.xmlAnaerobic dimethyl sulfoxide reductase chain CP18777DMSC_ECOLIdmsChttp://ecmdb.ca/proteins/P18777.xmlTrimethylamine-N-oxide reductase 1P33225TORA_ECOLItorAhttp://ecmdb.ca/proteins/P33225.xmlCytochrome c-type protein torCP33226TORC_ECOLItorChttp://ecmdb.ca/proteins/P33226.xmlAnaerobic dimethyl sulfoxide reductase chain ynfHP76173YNFH_ECOLIynfHhttp://ecmdb.ca/proteins/P76173.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlHydrogen ion + Menaquinol 8 + Trimethylamine N-Oxide > Water + Menaquinone 8 + Trimethylamine2-Demethylmenaquinol 8 + Hydrogen ion + Trimethylamine N-Oxide > 2-Demethylmenaquinone 8 + Water + Trimethylaminea menaquinol + Hydrogen ion + Trimethylamine N-Oxide > a menaquinone + Water + TrimethylamineRXN0-5264Trimethylamine N-Oxide + NADH + Hydrogen ion > Trimethylamine + NAD + WaterTMAOREDUCT-RXNTrimethylamine + 2 (ferricytochrome c)-subunit + Water > Trimethylamine N-Oxide +2 (ferrocytochrome c)-subunit +2 Hydrogen ionTrimethylamine N-Oxide + 3 Hydrogen ion + Menaquinol 8 + 2 Electron > Trimethylamine + Water +2 Hydrogen ion + menaquinone-8PW_RCT000173Trimethylamine N-Oxide + NADH + 2 Hydrogen ion > Trimethylamine + NAD + WaterPW_R005885