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MetaCyc Compound: trimethylamine N-oxide

Synonyms: TMAO

Trimethylamine N-oxide is an important constituent of fish muscle and body fluids. It is believed to promote atherogenesis through its interaction with macrophages and lipid metabolism [Koeth13, Bennett13, Wang11d, Tang13a].

Chemical Formula: C3H9NO

Molecular Weight: 75.11 Daltons

Monoisotopic Molecular Weight: 75.0684139162 Daltons

trimethylamine <i>N</i>-oxide compound structure


InChI: InChI=1S/C3H9NO/c1-4(2,3)5/h1-3H3


Unification Links: CAS:1184-78-7, ChEBI:15724, ChemSpider:1113, HMDB:HMDB00925, IAF1260:36816, KEGG:C01104, MetaboLights:MTBLC15724, NCI:408426, PubChem:1145

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 48.69009Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

formate to trimethylamine N-oxide electron transfer , hydrogen to trimethylamine N-oxide electron transfer , NADH to trimethylamine N-oxide electron transfer :
trimethylamine N-oxide[periplasm] + a menaquinol[inner membrane] + H+[periplasm] → trimethylamine[periplasm] + a menaquinone[inner membrane] + H2O[periplasm]

trimethylamine degradation :
trimethylamine N-oxide + H+ → dimethylamine + formaldehyde

Reactions known to produce the compound:

trimethylamine degradation :
trimethylamine + NADPH + oxygen → trimethylamine N-oxide + NADP+ + H2O

In Reactions of unknown directionality:

Not in pathways:
trimethylamine + 2 an oxidized c-type cytochrome + H2O = trimethylamine N-oxide + 2 a reduced c-type cytochrome + 3 H+
trimethylamine N-oxide + NADH + 2 H+ = trimethylamine + NAD+ + H2O

In Redox half-reactions:
trimethylamine N-oxide[out] + 3 H+[out] + 2 e-[membrane] → trimethylamine[out] + H2O[out]

This compound has been characterized as an alternative substrate of the following enzymes: biotin sulfoxide reductase, dimethyl sulfoxide reductase

Revised 19-Mar-2014 by Caspi R, SRI International


Bennett13: Bennett BJ, de Aguiar Vallim TQ, Wang Z, Shih DM, Meng Y, Gregory J, Allayee H, Lee R, Graham M, Crooke R, Edwards PA, Hazen SL, Lusis AJ (2013). "Trimethylamine-N-oxide, a metabolite associated with atherosclerosis, exhibits complex genetic and dietary regulation." Cell Metab 17(1);49-60. PMID: 23312283

Koeth13: Koeth RA, Wang Z, Levison BS, Buffa JA, Org E, Sheehy BT, Britt EB, Fu X, Wu Y, Li L, Smith JD, DiDonato JA, Chen J, Li H, Wu GD, Lewis JD, Warrier M, Brown JM, Krauss RM, Tang WH, Bushman FD, Lusis AJ, Hazen SL (2013). "Intestinal microbiota metabolism of L-carnitine, a nutrient in red meat, promotes atherosclerosis." Nat Med 19(5);576-85. PMID: 23563705

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Tang13a: Tang WH, Wang Z, Levison BS, Koeth RA, Britt EB, Fu X, Wu Y, Hazen SL (2013). "Intestinal microbial metabolism of phosphatidylcholine and cardiovascular risk." N Engl J Med 368(17);1575-84. PMID: 23614584

Wang11d: Wang Z, Klipfell E, Bennett BJ, Koeth R, Levison BS, Dugar B, Feldstein AE, Britt EB, Fu X, Chung YM, Wu Y, Schauer P, Smith JD, Allayee H, Tang WH, DiDonato JA, Lusis AJ, Hazen SL (2011). "Gut flora metabolism of phosphatidylcholine promotes cardiovascular disease." Nature 472(7341);57-63. PMID: 21475195

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Sat Feb 13, 2016, biocyc12.