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Record Information
Version1.0
Creation Date2016-07-13 19:42:24 UTC
Update Date2020-03-19 21:19:42 UTC
LmdbLMDB00102
Secondary Accession NumbersNone
Metabolite Identification
Common NameL-Palmitoylcarnitine
DescriptionL-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 ).
Structure
Thumb
Synonyms
ValueSource
(3R)-3-(Hexadecanoyloxy)-4-(trimethylazaniumyl)butanoateChEBI
(3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoateChEBI
Hexadecanoyl-L-carnitineChEBI
HexadecanoylcarnitineChEBI
Hexadecenoyl carnitineChEBI
L-Carnitine palmitoyl esterChEBI
O-Hexadecanoyl-(R)-carnitineChEBI
O-Hexadecanoyl-R-carnitineChEBI
Palmitoyl-L-carnitineChEBI
PalmitoylcarnitineChEBI
(3R)-3-(Hexadecanoyloxy)-4-(trimethylazaniumyl)butanoic acidGenerator
(3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoic acidGenerator
(+)-PalmitoylcarnitineHMDB
3-Carboxy-N,N,N-trimethyl-2-[(1-oxohexadecyl)oxy]-1-propanaminiumHMDB
L(-)-PalmitylcarnitineHMDB
L-Palmitoyl-L-carnitineHMDB
Palmitoyl-(-)-carnitineHMDB
Palmityl-L-carnitineHMDB
PalmitylcarnitineHMDB
(2R)-PalmitoylcarnitineHMDB
C16 CarnitineHMDB
L-PalmitoylcarnitineHMDB
Chemical FormulaC23H45NO4
Average Molecular Weight399.6077
Monoisotopic Molecular Weight399.334858933
IUPAC Name(3R)-3-(hexadecanoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional Namepalmitoylcarnitine
CAS Registry Number2364-67-2
SMILES
CCCCCCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/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
InChI KeyXOMRRQXKHMYMOC-OAQYLSRUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentAcyl carnitines
Alternative Parents
Substituents
  • Acyl-carnitine
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.77ALOGPS
logP2.03ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity137.08 m³·mol⁻¹ChemAxon
Polarizability50.35 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9220000000-890219021b84f6894540Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-1000900000-109f35c9819eb5eed7b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-9d6bb14eddb4cfa8341aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-87b1d0debe4e0cb7bd31Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0139500000-21c36c851939b94d4523Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0029600000-69ebe292c2ce42c8d810Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0f6x-0139600000-197944fd1aa4ac44bdd2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0uxr-0000613900-006582b143e5906e51ccSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0uxr-0000614900-14a5d773f652b71671fbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0f6x-0139600000-b0528be9c13e412551afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000900000-b54b0a7f2164f15f15f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-9000500000-d7434e08a3e0942fa2e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-e9262cbaff8cb4ad0ba6Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
  • Ruminal Fluid
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
Ruminal FluidDetected and Quantified0.03 +/- 0.004 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine
    • Pengcheng Zhou, J...
details
SerumDetected and Quantified0.02 +/- 0.01 uMNot AvailableOvine
    • Candidate serum m...
details
DrugBank IDNot Available
HMDB IDHMDB0000222
FooDB IDFDB021910
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID40966
BioCyc IDCPD-419
METLIN ID5231
PDB IDNot Available
Wikipedia LinkPalmitoylcarnitine
Chemspider ID10128117
ChEBI ID17490
PubChem Compound ID11953816
Kegg Compound IDC02990
YMDB IDYMDB01534
ECMDB IDECMDB24024
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Watanabe H, Kobayashi A, Hayashi H, Yamazaki N: Effects of long-chain acyl carnitine on membrane fluidity of human erythrocytes. Biochim Biophys Acta. 1989 Apr 28;980(3):315-8. [2540838 ]
  2. Nalecz KA, Miecz D, Berezowski V, Cecchelli R: Carnitine: transport and physiological functions in the brain. Mol Aspects Med. 2004 Oct-Dec;25(5-6):551-67. [15363641 ]
  3. Goni FM, Requero MA, Alonso A: Palmitoylcarnitine, a surface-active metabolite. FEBS Lett. 1996 Jul 15;390(1):1-5. [8706815 ]