1.0 2010-04-08 22:09:07 UTC 2024-11-29 22:26:13 UTC FDB010413 Trimethylamine oxide Trimethylamine N-oxide (TMAO) is an oxidation product of trimethylamine and a common metabolite in animals and humans. TMAO decomposes to trimethylamine (TMA), which is the main odorant that is characteristic of degrading seafood. TMAO is an osmolyte that the body will use to counter-act the effects of increased concentrations of urea (due to kidney failure) and can be used as a biomarker for kidney problems. Fish odor syndrome or trimethylaminuria is a defect in the production of the enzyme flavin containing monooxygenase 3 (FMO3) causing incomplete breakdown of trimethylamine from choline-containing food into trimethylamine oxide. Trimethylamine then builds up and is released in the person's sweat, urine, and breath, giving off a strong fishy odor.; Trimethylamine N-oxide, also known by several other names and acronyms, is the organic compound with the formula (CH3)3NO. This colorless solid is usually encountered as the dihydrate. It is an oxidation product of trimethylamine and a common metabolite in animals. It is an osmolyte found in saltwater fish, sharks and rays, molluscs, and crustaceans. Along with free amino acids, it reduces the 3% salinity of seawater to about 1% of dissolved solids inside cells. TMAO decomposes to trimethylamine (TMA), which is the main odorant that is characteristic of degrading seafood.; Trimethylaminuria is a defect in the production of the enzyme flavin containing monooxygenase 3 (FMO3),, causing incomplete breakdown of trimethylamine from choline-containing food into trimethylamine oxide. Trimethylamine then builds up and is released in the person's sweat, urine, and breath, giving off a strong fishy odor. Urinary TMAO is a biomarker for the consumption of fish, especially cold-water fish. (CH3)3NO Me3N(+)O(-) Me3N(O) Methanamine, n,n-dimethyl-, n-oxide N,n-dimethylmethanamine n-oxide N,n-dimethylmethanamine oxide N,n-dimethylmethanamine oxide (iupac) N(CH3)3O Tma-oxide Tmano TMAO Trimenthlamine-n-o Trimethylamine n-oxide Trimethylamine n-oxide dihydrate Trimethylamine-n-oxide Trimethylamine, n-oxide Trimethylamine, N-oxide (8CI) Trimethylaminoxid Trimethylammonium oxide Trimethyloxamine 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 belongs to the class of organic compounds known as trialkyl amine oxides. These are hydrocarbyl derivatives of the aminoxide anion, with the general formula R3N+[O-] or R3N=O, where R is an alkyl group. Trialkyl amine oxides Organic compounds Organic nitrogen compounds Organonitrogen compounds Aminoxides Aliphatic acyclic compounds Hydrocarbon derivatives Organic oxides Organopnictogen compounds Trisubstituted amine oxides and derivatives Aliphatic acyclic compound Hydrocarbon derivative N-oxide Organic oxide Organic oxygen compound Organopnictogen compound Trialkyl amine oxide Trisubstituted n-oxide N-oxide a small molecule Solid 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 Metabolism and Physiological Effects of Trimethylamine N-oxide (TMAO) SMP0123192 Metabolism and Physiological Effects of Oxalic acid SMP0124875 Specdb::EiMs 705 Specdb::MsIr 966 Specdb::NmrTwoD 1546 Specdb::CMs 17537 Specdb::CMs 169443 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::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 HMDB00925 15724 TMO #<Reference:0x000055ce32c91700> #<Reference:0x000055ce32c91520> #<Reference:0x000055ce32c912f0> #<Reference:0x000055ce32c91048> #<Reference:0x000055ce32c90dc8> #<Reference:0x000055ce32c90b20> #<Reference:0x000055ce32c908a0> #<Reference:0x000055ce32c906e8> #<Reference:0x000055ce32c904b8> #<Reference:0x000055ce32c902d8> #<Reference:0x000055ce32c900d0> #<Reference:0x000055ce32c8fec8> #<Reference:0x000055ce32c8fba8> #<Reference:0x000055ce32c8f8d8> #<Reference:0x000055ce32c8f720> #<Reference:0x000055ce32c8f540> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Milk (Cow) Type 2 specific 44.5 44.5 44.5 uM Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 odorless