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Bovine Rumen Metabolome Database



Showing metabocard for L-Palmitoylcarnitine (RMDB00222)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:46
Accession Number RMDB00222
Common Name L-Palmitoylcarnitine
Description L-Palmitoylcarnitine is a long-chain acyl fatty acid derivative ester of carnitine which facilitates the transfer of long-chain fatty acids from cytoplasm into mitochondria during the oxidation of fatty acids. L-palmitoylcarnitine, due to its amphipatic character is, like detergents, a surface-active molecule and by changing the membrane fluidity and surface charge can change activity of several enzymes and transporters localized in the membrane. L-palmitoylcarnitine has been also reported to change the activity of certain proteins. On the contrary to carnitine, palmitoylcarnitine was shown to stimulate the activity of caspases 3, 7 and 8 and the level of this long-chain acylcarnitine increased during apoptosis. Palmitoylcarnitine was also reported to diminish completely binding of phorbol esters, the protein kinase C activators and to decrease the autophosphorylation of the enzyme. Apart from these isoform nonspecific phenomena, palmitoylcarnitine was also shown to be responsible for retardation in cytoplasm of protein kinase C isoforms β and δ and, in the case of the latter one, to decrease its interaction with GAP-43. Some of the physico-chemical properties of palmitoylcarnitine may help to explain the need for coenzyme A-carnitine-coenzyme A acyl exchange during mitochondrial fatty acid import. The amphiphilic character of palmitoylcarnitine may also explain its proposed involvement in the pathogenesis of myocardial ischemia. L-Palmitoylcarnitine accumulates in ischemic myocardium and potentially contribute to myocardial damage through alterations in membrane molecular dynamics , one mechanism through which could play an important role in ischemic injury. Palmitoylcarnitine is characteristically elevated in carnitine palmitoyltransferase II deficiency, late-onset (OMIM 255110). (PMID 2540838, 15363641, 8706815)
Synonyms
  1. Palmitoyl d-carnitine
  2. (3S)-3-hexadecanoyloxy-4-(trimethylammonio)butanoate
  3. (3S)-3-hexadecanoyloxy-4-(trimethylammonio)butanoic acid
  4. L-carnitine palmitoyl ester
  5. (+)-palmitoylcarnitine
  6. Hexadecanoyl-L-carnitine
  7. (3S)-3-palmitoyloxy-4-(trimethylammonio)butanoate
  8. (3S)-3-palmitoyloxy-4-(trimethylammonio)butanoic acid
  9. Palmityl-L-carnitine
  10. D-palmitylcarnitine
  11. L-palmitoyl-L-carnitine
  12. Hexadecenoyl carnitine
  13. L(-)-Palmitylcarnitine
  14. Palmitoyl-(-)-carnitine
  15. Palmitoyl-L-carnitine
  16. 3-carboxy-N,N,N-trimethyl-2-[(1-oxohexadecyl)oxy]-1-Propanaminium
Chemical IUPAC Name (3R)-3-hexadecanoyloxy-4-trimethylazaniumylbutanoate
Chemical Formula C23H45NO4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Quaternary Amines
Sub Class
  • Long chain acyl carnitines
Family
  • Mammalian_Metabolite
Species
  • cation; anion; quaternary ammonium salt; carboxylic acid salt; carboxylic acid ester
Biofunction
  • Component of Fatty acid metabolism
Application
Source
  • Endogenous
Average Molecular Weight 399.608
Monoisotopic Molecular Weight 399.334869
Isomeric SMILES CCCCCCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C
Canonical SMILES CCCCCCCCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C
KEGG Compound ID C02990 Link Image
BioCyc ID CPD-419 Link Image
BiGG ID 40966 Link Image
Wikipedia Link Not Available
METLIN ID 5231 Link Image
PubChem Compound 11953816 Link Image
PubChem Substance 24701436 Link Image
ChEBI ID 17490 Link Image
CAS Registry Number 2364-67-2
InChI Identifier InChI=1/C23H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h21H,5-20H2,1-4H3/t21-/m1/s1
Synthesis Reference Norum, Kaare R. Palmityl coenzyme A-carnitine palmityltransferase. Purification from calf-liver mitochondria and some properties of the enzyme. Biochimica et Biophysica Acta, Specialized Section on Enzymological Subjects (1964), 89(1), 95-108.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 1.20e-05 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 1.77 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
  • mitochondria
Biofluid Location
  • Rumen
Tissue Location Not Available
Concentrations (Normal)
Biofluid Rumen
Value 0.02 +/- 0.012 uM
Age N/A
Sex N/A
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
  • The rumen metabolome (in preparation)
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References Not Available