Record Information
Version1.0
Creation date2011-09-21 00:05:00 UTC
Update date2015-10-09 22:33:40 UTC
Primary IDFDB021910
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number2364-67-2
Structure
Thumb
Synonyms
SynonymSource
(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
(+)-palmitoylcarnitinehmdb
(3S)-3-hexadecanoyloxy-4-(trimethylammonio)butanoatehmdb
(3S)-3-hexadecanoyloxy-4-(trimethylammonio)butanoic acidhmdb
(3S)-3-palmitoyloxy-4-(trimethylammonio)butanoatehmdb
(3S)-3-palmitoyloxy-4-(trimethylammonio)butanoic acidhmdb
3-carboxy-N,N,N-trimethyl-2-[(1-oxohexadecyl)oxy]-1-Propanaminiumhmdb
D-palmitylcarnitinehmdb
L-carnitine palmitoyl esterhmdb
L-palmitoyl-L-carnitinehmdb
Palmitoyl d-carnitinehmdb
Predicted Properties
PropertyValueSource
Water Solubility1.2e-05 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC23H45NO4
IUPAC name(3R)-3-(hexadecanoyloxy)-4-(trimethylazaniumyl)butanoate
InChI IdentifierInChI=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
Isomeric SMILESCCCCCCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C
Average Molecular Weight399.6077
Monoisotopic Molecular Weight399.334858933
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9220000000-890219021b84f6894540JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-1000900000-109f35c9819eb5eed7b7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-9d6bb14eddb4cfa8341aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-87b1d0debe4e0cb7bd31JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0139500000-21c36c851939b94d4523JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0029600000-69ebe292c2ce42c8d810JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0f6x-0139600000-197944fd1aa4ac44bdd2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0uxr-0000613900-006582b143e5906e51ccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0uxr-0000614900-14a5d773f652b71671fbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0f6x-0139600000-b0528be9c13e412551afJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID10128117
ChEMBL IDNot Available
KEGG Compound IDC02990
Pubchem Compound ID11953816
Pubchem Substance IDNot Available
ChEBI ID17490
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00222
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID40966
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Carnitine O-palmitoyltransferase 1, muscle isoformCPT1BQ92523
Carnitine O-palmitoyltransferase 1, liver isoformCPT1AP50416
Carnitine O-palmitoyltransferase 2, mitochondrialCPT2P23786
Carnitine O-palmitoyltransferase 1, brain isoformCPT1CQ8TCG5
Pathways
NameSMPDB LinkKEGG Link
Fatty acid MetabolismSMP00051 map00071
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference