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MetaCyc Compound: trimethylamine

Systematic Name: N,N-dimethylmethanamine

Synonyms: (CH3)3NH, (CH3)3NH+

Chemical Formula: C3H10N

Molecular Weight: 60.119 Daltons

Monoisotopic Molecular Weight: 60.0813243262 Daltons

trimethylamine compound structure

SMILES: C[N+](C)C

InChI: InChI=1S/C3H9N/c1-4(2)3/h1-3H3/p+1

InChIKey: InChIKey=GETQZCLCWQTVFV-UHFFFAOYSA-O

Unification Links: CAS:75-50-3, ChEBI:58389, ChemSpider:3010173, HMDB:HMDB00906, IAF1260:35366, KEGG:C00565, PubChem:3782034

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 111.29915Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

methanogenesis from trimethylamine :
trimethylamine + a [Co(I) trimethylamine-specific corrinoid protein] + H+ → a [methyl-Co(III) trimethylamine-specific corrinoid protein] + dimethylamine

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

Reactions known to produce the compound:

choline degradation III :
choline → trimethylamine + acetaldehyde

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]

L-carnitine degradation III :
L-carnitine + NAD(P)H + oxygen + H+ → L-malic semialdehyde + trimethylamine + NAD(P)+ + H2O

methanogenesis from tetramethylammonium :
tetramethylammonium + a [Co(I) tetramethylammonium-specific corrinoid protein] + H+ → a [methyl-(Co(III) tetramethylammonium-specific corrinoid protein] + trimethylamine

Not in pathways:
acetyl phosphate + trimethylamine + an oxidized thioredoxin + H2O ← glycine betaine + a reduced thioredoxin + phosphate + H+

In Reactions of unknown directionality:

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

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

Enzymes inhibited by trimethylamine, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: dimethylamine dehydrogenase [Meiberg79] Inhibitor (Mechanism unknown) of: L-carnitine dehydrogenase [Hanschmann96]

References

Hanschmann96: Hanschmann H, Ehricht R, Kleber HP (1996). "Purification and properties of L(-)-carnitine dehydrogenase from Agrobacterium sp." Biochim Biophys Acta 1290(2);177-83. PMID: 8645721

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

Meiberg79: Meiberg, J.B.M., Harder, W. (1979). "Dimethylamine dehydrogenase from Hyphomicrobium X: purification and some properties of a new enzyme that oxidizes secondary amines." J. Gen. Microbiol. 115: 49-58.


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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