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MetaCyc Compound: D-carnitine

Synonyms: S-(+)-3-hydroxy-4-trimethylaminobutyrate, (S)-carnitine

Superclasses: a vitamina D,L-carnitine

Chemical Formula: C7H15NO3

Molecular Weight: 161.2 Daltons

Monoisotopic Molecular Weight: 162.1130183851 Daltons

D-carnitine compound structure

SMILES: C[N+](CC(O)CC(=O)[O-])(C)C

InChI: InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/t6-/m0/s1

InChIKey: InChIKey=PHIQHXFUZVPYII-LURJTMIESA-N

Unification Links: CAS:541-14-0, ChEBI:11060, ChemSpider:2006614, HMDB:HMDB00062, IAF1260:2386130, KEGG:C15025, MetaboLights:MTBLC11060, PubChem:2724480

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 26.8368Inferred by computational analysis [Latendresse13]

Reactions known to produce the compound:

Not in pathways:
D-carnitinyl-CoA + H2O → D-carnitine + coenzyme A + H+

Reactions known to both consume and produce the compound:

D-carnitine degradation I :
D-carnitine + NAD+ ↔ 3-dehydrocarnitine + NADH + H+

D-carnitine degradation II :
D-carnitine ↔ L-carnitine

Enzymes inhibited by D-carnitine, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: L-carnitine dehydrogenase [Hanschmann96]

This compound has been characterized as an alternative substrate of the following enzymes: L-proline:H+ symporter, L-carnitine : γ-butyrobetaine antiporter, carnitine-CoA ligase


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

Kleber97: Kleber HP (1997). "Bacterial carnitine metabolism." FEMS Microbiol Lett 147(1);1-9. PMID: 9037756

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

Rebouche98: Rebouche CJ, Seim H (1998). "Carnitine metabolism and its regulation in microorganisms and mammals." Annu Rev Nutr 18;39-61. PMID: 9706218

Skulachev00: Skulachev VP (2000). "Biological role of carnosine in the functioning of excitable tissues.Centenary of Gulewitsch's discovery." Biochemistry (Mosc) 65(7);749-50. PMID: 11183736


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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