Metabolic Modeling Tutorial
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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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: 59.073499294099996 Daltons

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 Change Formation (ΔfG in kcal/mol): 111.29915 Inferred 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 , NADH to trimethylamine N-oxide electron transfer :
trimethylamine N-oxide[periplasmic space] + a menaquinol[inner membrane] + H+[periplasmic space]trimethylamine[periplasmic space] + a menaquinone[inner membrane] + H2O[periplasmic space]

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

In Reactions of unknown directionality:

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

In Redox half-reactions:
trimethylamine N-oxide[out] + 3 H+[out] + 2 e-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
Page generated by SRI International Pathway Tools version 18.5 on Mon Nov 24, 2014, BIOCYC14B.