2.02012-05-31 13:02:02 -06002015-09-13 15:15:20 -0600ECMDB00906M2MDB000200TrimethylamineTrimethylamine, also known as NMe3, N(CH3)3, and TMA, is a colorless, hygroscopic, and flammable simple amine with a typical fishy odor in low concentrations and an ammonia-like odor in higher concentrations. Trimethylamine has a boiling point of 2.9 (CH3)3N(CH3)3NH(CH3)3NH+DimethylmethaneamineN,N-Dimethyl-MethanamineN,N-Dimethyl-Methanamine (9CI)N,N-Dimethyl-MethylamineN,N-DimethylmethanamineN-TrimethylamineTMATMeAlaTrimethylamineTrimethylamine (8CI)Trimethylamine (anhydrous)Trimethylamine anhydrousTrimethylamine anhydrous [UN1083] [Flammable gas]Trimethylamine aqueous solutionTrimethylamine aqueous solutions not >50% trimethylamine by mass [UN1297] [Flammable liquid]Trimethylamine for synthesisTrimethylamine HCLTrimethylamine hydrochlorideTrimethylamine in aqueous solutionTrimethylamine solutionTrimethylamine solution (30% or less)Trimethylammonium chlorideC3H9N59.110359.073499293trimethylaminetrimethylamine75-50-3CN(C)CInChI=1S/C3H9N/c1-4(2)3/h1-3H3GETQZCLCWQTVFV-UHFFFAOYSA-NLiquidCytosolExtra-organismPeriplasmlogp-0.14logs1.04solubility6.54e+02 g/lmelting_point-117.1 oClogp0.19pka_strongest_basic9.57iupactrimethylamineaverage_mass59.1103mono_mass59.073499293smilesCN(C)CformulaC3H9NinchiInChI=1S/C3H9N/c1-4(2)3/h1-3H3inchikeyGETQZCLCWQTVFV-UHFFFAOYSA-Npolar_surface_area3.24refractivity19.99polarizability7.64rotatable_bond_count0acceptor_count1donor_count0physiological_charge1formal_charge0Methane metabolismec00680Microbial metabolism in diverse environmentsec01120Collection 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::CMs5676Specdb::CMs29402Specdb::CMs99629Specdb::CMs163727Specdb::EiMs286Specdb::NmrOneD1284Specdb::NmrOneD1598Specdb::NmrOneD2619Specdb::NmrOneD21022Specdb::NmrOneD21023Specdb::NmrOneD21024Specdb::NmrOneD21025Specdb::NmrOneD21026Specdb::NmrOneD21027Specdb::NmrOneD21028Specdb::NmrOneD21029Specdb::NmrOneD21030Specdb::NmrOneD21031Specdb::NmrOneD21032Specdb::NmrOneD21033Specdb::NmrOneD21034Specdb::NmrOneD21035Specdb::NmrOneD21036Specdb::NmrOneD21037Specdb::NmrOneD21038Specdb::NmrOneD21039Specdb::NmrOneD21040Specdb::NmrOneD21041Specdb::NmrOneD166464Specdb::MsMs1292Specdb::MsMs1293Specdb::MsMs1294Specdb::MsMs4872Specdb::MsMs240160Specdb::MsMs240161Specdb::MsMs240162Specdb::MsMs242215Specdb::MsMs242216Specdb::MsMs242217Specdb::MsMs2226564Specdb::MsMs2228136Specdb::MsMs2230536Specdb::MsMs2766674Specdb::MsMs2766675Specdb::MsMs2766676Specdb::MsMs2911898Specdb::MsMs2911899Specdb::MsMs2911900Specdb::NmrTwoD1046Specdb::NmrTwoD1539HMDB009061114C0056518139TRIMETHYLAMINEKENTrimethylamineKeseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.18331064Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. 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Kokai Tokkyo Koho (2006), 5pp.http://hmdb.ca/system/metabolites/msds/000/000/818/original/HMDB00906.pdf?1358462318Probable 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