2.0 2012-05-31 14:06:52 -0600 2015-06-03 15:54:48 -0600 ECMDB04161 M2MDB000643 Trimethylamine N-Oxide Trimethylamine 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-oxide TMA-oxide TMAO TMeAla-oxide Trimethylamine N-oxide Trimethylamine oxide Trimethylamine-N-oxide Triox C3H9NO 75.1097 75.068413915 N,N-dimethylmethanamine oxide trimethylamine-n-oxide 1184-78-7 C[N+](C)(C)[O-] InChI=1S/C3H9NO/c1-4(2,3)5/h1-3H3 UYPYRKYUKCHHIB-UHFFFAOYSA-N Solid Cytosol Extra-organism Periplasm logp -2.01 ALOGPS logs -0.11 ALOGPS solubility 5.78e+01 g/l ALOGPS melting_point 95-99 oC logp -0.93 ChemAxon pka_strongest_basic 4.66 ChemAxon iupac N,N-dimethylmethanamine oxide ChemAxon average_mass 75.1097 ChemAxon mono_mass 75.068413915 ChemAxon smiles C[N+](C)(C)[O-] ChemAxon formula C3H9NO ChemAxon inchi InChI=1S/C3H9NO/c1-4(2,3)5/h1-3H3 ChemAxon inchikey UYPYRKYUKCHHIB-UHFFFAOYSA-N ChemAxon polar_surface_area 23.06 ChemAxon refractivity 22.03 ChemAxon polarizability 8.4 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Methane metabolism ec00680 Microbial metabolism in diverse environments ec01120 Two-component system ec02020 Collection of Reactions without pathways PW001891 Metabolic N-oxide electron transfer The 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 before PW001889 Metabolic formate to trimethylamine N-oxide electron transfer PWY0-1355 NADH to trimethylamine N-oxide electron transfer PWY0-1347 Specdb::CMs 17537 Specdb::CMs 169443 Specdb::EiMs 705 Specdb::NmrOneD 1286 Specdb::NmrOneD 1605 Specdb::NmrOneD 2177 Specdb::NmrOneD 2865 Specdb::NmrOneD 145790 Specdb::NmrOneD 145791 Specdb::NmrOneD 145792 Specdb::NmrOneD 145793 Specdb::NmrOneD 145794 Specdb::NmrOneD 145795 Specdb::NmrOneD 145796 Specdb::NmrOneD 145797 Specdb::NmrOneD 145798 Specdb::NmrOneD 145799 Specdb::NmrOneD 145800 Specdb::NmrOneD 145801 Specdb::NmrOneD 145802 Specdb::NmrOneD 145803 Specdb::NmrOneD 145804 Specdb::NmrOneD 145805 Specdb::NmrOneD 145806 Specdb::NmrOneD 145807 Specdb::NmrOneD 145808 Specdb::NmrOneD 145809 Specdb::NmrOneD 166485 Specdb::MsMs 1312 Specdb::MsMs 1313 Specdb::MsMs 1314 Specdb::MsMs 4875 Specdb::MsMs 4876 Specdb::MsMs 4877 Specdb::MsMs 4878 Specdb::MsMs 4879 Specdb::MsMs 4880 Specdb::MsMs 304822 Specdb::MsMs 304823 Specdb::MsMs 304824 Specdb::MsMs 348115 Specdb::MsMs 348116 Specdb::MsMs 348117 Specdb::MsMs 447109 Specdb::MsMs 447110 Specdb::MsMs 447111 Specdb::MsMs 447112 Specdb::MsMs 447113 Specdb::MsMs 448169 Specdb::MsMs 2235697 Specdb::MsMs 2237658 Specdb::MsMs 2237863 Specdb::MsMs 2239724 Specdb::NmrTwoD 1546 HMDB00925 1145 1113 C01104 15724 TRIMENTHLAMINE-N-O TMO Trimethylamine oxide Keseler, I. 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Probable anaerobic dimethyl sulfoxide reductase chain ynfG P0AAJ1 YNFG_ECOLI ynfG http://ecmdb.ca/proteins/P0AAJ1.xml Anaerobic dimethyl sulfoxide reductase chain A P18775 DMSA_ECOLI dmsA http://ecmdb.ca/proteins/P18775.xml Anaerobic dimethyl sulfoxide reductase chain B P18776 DMSB_ECOLI dmsB http://ecmdb.ca/proteins/P18776.xml Putative dimethyl sulfoxide reductase chain ynfE P77374 YNFE_ECOLI ynfE http://ecmdb.ca/proteins/P77374.xml Probable dimethyl sulfoxide reductase chain ynfF P77783 YNFF_ECOLI ynfF http://ecmdb.ca/proteins/P77783.xml Trimethylamine-N-oxide reductase 2 P46923 TORZ_ECOLI torZ http://ecmdb.ca/proteins/P46923.xml Cytochrome c-type protein torY P52005 TORY_ECOLI torY http://ecmdb.ca/proteins/P52005.xml Anaerobic dimethyl sulfoxide reductase chain C P18777 DMSC_ECOLI dmsC http://ecmdb.ca/proteins/P18777.xml Trimethylamine-N-oxide reductase 1 P33225 TORA_ECOLI torA http://ecmdb.ca/proteins/P33225.xml Cytochrome c-type protein torC P33226 TORC_ECOLI torC http://ecmdb.ca/proteins/P33226.xml Anaerobic dimethyl sulfoxide reductase chain ynfH P76173 YNFH_ECOLI ynfH http://ecmdb.ca/proteins/P76173.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Hydrogen ion + Menaquinol 8 + Trimethylamine N-Oxide > Water + Menaquinone 8 + Trimethylamine 2-Demethylmenaquinol 8 + Hydrogen ion + Trimethylamine N-Oxide > 2-Demethylmenaquinone 8 + Water + Trimethylamine a menaquinol + Hydrogen ion + Trimethylamine N-Oxide > a menaquinone + Water + Trimethylamine RXN0-5264 Trimethylamine N-Oxide + NADH + Hydrogen ion > Trimethylamine + NAD + Water TMAOREDUCT-RXN Trimethylamine + 2 (ferricytochrome c)-subunit + Water > Trimethylamine N-Oxide +2 (ferrocytochrome c)-subunit +2 Hydrogen ion Trimethylamine N-Oxide + 3 Hydrogen ion + Menaquinol 8 + 2 Electron > Trimethylamine + Water +2 Hydrogen ion + menaquinone-8 PW_RCT000173 Trimethylamine N-Oxide + NADH + 2 Hydrogen ion > Trimethylamine + NAD + Water PW_R005885