2.0 2012-05-31 13:02:02 -0600 2015-09-13 15:15:20 -0600 ECMDB00906 M2MDB000200 Trimethylamine Trimethylamine, 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+ Dimethylmethaneamine N,N-Dimethyl-Methanamine N,N-Dimethyl-Methanamine (9CI) N,N-Dimethyl-Methylamine N,N-Dimethylmethanamine N-Trimethylamine TMA TMeAla Trimethylamine Trimethylamine (8CI) Trimethylamine (anhydrous) Trimethylamine anhydrous Trimethylamine anhydrous [UN1083] [Flammable gas] Trimethylamine aqueous solution Trimethylamine aqueous solutions not >50% trimethylamine by mass [UN1297] [Flammable liquid] Trimethylamine for synthesis Trimethylamine HCL Trimethylamine hydrochloride Trimethylamine in aqueous solution Trimethylamine solution Trimethylamine solution (30% or less) Trimethylammonium chloride C3H9N 59.1103 59.073499293 trimethylamine trimethylamine 75-50-3 CN(C)C InChI=1S/C3H9N/c1-4(2)3/h1-3H3 GETQZCLCWQTVFV-UHFFFAOYSA-N Liquid Cytosol Extra-organism Periplasm logp -0.14 ALOGPS logs 1.04 ALOGPS solubility 6.54e+02 g/l ALOGPS melting_point -117.1 oC logp 0.19 ChemAxon pka_strongest_basic 9.57 ChemAxon iupac trimethylamine ChemAxon average_mass 59.1103 ChemAxon mono_mass 59.073499293 ChemAxon smiles CN(C)C ChemAxon formula C3H9N ChemAxon inchi InChI=1S/C3H9N/c1-4(2)3/h1-3H3 ChemAxon inchikey GETQZCLCWQTVFV-UHFFFAOYSA-N ChemAxon polar_surface_area 3.24 ChemAxon refractivity 19.99 ChemAxon polarizability 7.64 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Methane metabolism ec00680 Microbial metabolism in diverse environments ec01120 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 5676 Specdb::CMs 29402 Specdb::CMs 99629 Specdb::CMs 163727 Specdb::EiMs 286 Specdb::NmrOneD 1284 Specdb::NmrOneD 1598 Specdb::NmrOneD 2619 Specdb::NmrOneD 21022 Specdb::NmrOneD 21023 Specdb::NmrOneD 21024 Specdb::NmrOneD 21025 Specdb::NmrOneD 21026 Specdb::NmrOneD 21027 Specdb::NmrOneD 21028 Specdb::NmrOneD 21029 Specdb::NmrOneD 21030 Specdb::NmrOneD 21031 Specdb::NmrOneD 21032 Specdb::NmrOneD 21033 Specdb::NmrOneD 21034 Specdb::NmrOneD 21035 Specdb::NmrOneD 21036 Specdb::NmrOneD 21037 Specdb::NmrOneD 21038 Specdb::NmrOneD 21039 Specdb::NmrOneD 21040 Specdb::NmrOneD 21041 Specdb::NmrOneD 166464 Specdb::MsMs 1292 Specdb::MsMs 1293 Specdb::MsMs 1294 Specdb::MsMs 4872 Specdb::MsMs 240160 Specdb::MsMs 240161 Specdb::MsMs 240162 Specdb::MsMs 242215 Specdb::MsMs 242216 Specdb::MsMs 242217 Specdb::MsMs 2226564 Specdb::MsMs 2228136 Specdb::MsMs 2230536 Specdb::MsMs 2766674 Specdb::MsMs 2766675 Specdb::MsMs 2766676 Specdb::MsMs 2911898 Specdb::MsMs 2911899 Specdb::MsMs 2911900 Specdb::NmrTwoD 1046 Specdb::NmrTwoD 1539 HMDB00906 1114 C00565 18139 TRIMETHYLAMINE KEN Trimethylamine Keseler, 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. 21097882 Kanehisa, 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. 22080510 Winder, 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. 18331064 Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. 12097436 Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. 7762816 Sweatman BC, Farrant RD, Holmes E, Ghauri FY, Nicholson JK, Lindon JC: 600 MHz 1H-NMR spectroscopy of human cerebrospinal fluid: effects of sample manipulation and assignment of resonances. J Pharm Biomed Anal. 1993 Aug;11(8):651-64. 8257730 Maschke S, Wahl A, Azaroual N, Boulet O, Crunelle V, Imbenotte M, Foulard M, Vermeersch G, Lhermitte M: 1H-NMR analysis of trimethylamine in urine for the diagnosis of fish-odour syndrome. Clin Chim Acta. 1997 Jul 25;263(2):139-46. 9246418 Hillier SL: Diagnostic microbiology of bacterial vaginosis. Am J Obstet Gynecol. 1993 Aug;169(2 Pt 2):455-9. 8357044 Chao CK, Zeisel SH: Formation of trimethylamine from dietary choline by Streptococcus sanguis I, which colonizes the mouth. J Nutr Biochem. 1990 Feb;1(2):89-97. 15539190 Dzik-Jurasz AS, Prescot AP, Leach MO, Collins DJ: Non-invasive study of human gall bladder bile in vivo using (1)H-MR spectroscopy. Br J Radiol. 2003 Jul;76(907):483-6. 12857709 Leys D, Basran J, Talfournier F, Chohan KK, Munro AW, Sutcliffe MJ, Scrutton NS: Flavin radicals, conformational sampling and robust design principles in interprotein electron transfer: the trimethylamine dehydrogenase-electron-transferring flavoprotein complex. Biochem Soc Symp. 2004;(71):1-14. 15777008 Zeisel SH, daCosta KA, LaMont JT: Mono-, di- and trimethylamine in human gastric fluid: potential substrates for nitrosodimethylamine formation. Carcinogenesis. 1988 Jan;9(1):179-81. 3335043 Mitchell SC, Zhang AQ, Barrett T, Ayesh R, Smith RL: Studies on the discontinuous N-oxidation of trimethylamine among Jordanian, Ecuadorian and New Guinean populations. Pharmacogenetics. 1997 Feb;7(1):45-50. 9110361 Al-Waiz M, Ayesh R, Mitchell SC, Idle JR, Smith RL: A genetic polymorphism of the N-oxidation of trimethylamine in humans. Clin Pharmacol Ther. 1987 Nov;42(5):588-94. 3677545 Kenyon S, Carmichael PL, Khalaque S, Panchal S, Waring R, Harris R, Smith RL, Mitchell SC: The passage of trimethylamine across rat and human skin. Food Chem Toxicol. 2004 Oct;42(10):1619-28. 15304308 Thithapandha A: A pharmacogenetic study of trimethylaminuria in Orientals. Pharmacogenetics. 1997 Dec;7(6):497-501. 9429235 Hirohata, Saneo; Tanba, Kiyonobu; Inoue, Kenichi. Preparation of trimethylamine by zeolite-catalyzed reaction of methanol and ammonia. Jpn. Kokai Tokkyo Koho (2006), 5pp. http://hmdb.ca/system/metabolites/msds/000/000/818/original/HMDB00906.pdf?1358462318 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