1.02011-09-21 00:05:00 UTC2015-10-09 22:33:40 UTCFDB021910L-PalmitoylcarnitineL-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](+)-palmitoylcarnitine(3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoate(3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoic acid(3S)-3-hexadecanoyloxy-4-(trimethylammonio)butanoate(3S)-3-hexadecanoyloxy-4-(trimethylammonio)butanoic acid(3S)-3-palmitoyloxy-4-(trimethylammonio)butanoate(3S)-3-palmitoyloxy-4-(trimethylammonio)butanoic acid3-carboxy-N,N,N-trimethyl-2-[(1-oxohexadecyl)oxy]-1-PropanaminiumD-palmitylcarnitineHexadecanoyl-L-carnitineHexadecanoylcarnitineHexadecenoyl carnitineL-carnitine palmitoyl esterL-palmitoyl-L-carnitineL(-)-PalmitylcarnitineO-Hexadecanoyl-(R)-carnitineO-Hexadecanoyl-R-carnitinePalmitoyl d-carnitinePalmitoyl-(-)-carnitinePalmitoyl-L-carnitinePalmitoylcarnitinePalmityl-L-carnitineC23H45NO4399.6077399.3348589332364-67-2CCCCCCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)CInChI=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/s1XOMRRQXKHMYMOC-OAQYLSRUSA-NSolidaverage_mass399.6077mono_mass399.334858933smilesCCCCCCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)CformulaC23H45NO4inchiInChI=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/s1inchikeyXOMRRQXKHMYMOC-OAQYLSRUSA-NFatty acid MetabolismSMP00051map00071Specdb::NmrTwoD1217Specdb::CMs3336Specdb::CMs131920Specdb::CMs139654Specdb::CMs1055060Specdb::CMs1055062Specdb::NmrOneD1221Specdb::NmrOneD269658Specdb::NmrOneD269659Specdb::NmrOneD269660Specdb::NmrOneD269661Specdb::NmrOneD269662Specdb::NmrOneD269663Specdb::NmrOneD269664Specdb::NmrOneD269665Specdb::NmrOneD269666Specdb::NmrOneD269667Specdb::NmrOneD269668Specdb::NmrOneD269669Specdb::NmrOneD269670Specdb::NmrOneD269671Specdb::NmrOneD269672Specdb::NmrOneD269673Specdb::NmrOneD269674Specdb::NmrOneD269675Specdb::NmrOneD269676Specdb::NmrOneD269677Specdb::MsMs364Specdb::MsMs365Specdb::MsMs366Specdb::MsMs439588Specdb::MsMs439589Specdb::MsMs449652Specdb::MsMs449653Specdb::MsMs449654Specdb::MsMs449655Specdb::MsMs2915558Specdb::MsMs2915559Specdb::MsMs2915560HMDB0022217490#<Reference:0x000055567557f9b0>#<Reference:0x000055567557f758>#<Reference:0x000055567557f5a0>#<Reference:0x000055567557f398>#<Reference:0x000055567557f1e0>#<Reference:0x000055567557efb0>#<Reference:0x000055567557ed30>#<Reference:0x000055567557eb00>#<Reference:0x000055567557e920>#<Reference:0x000055567557e768>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823Carnitine O-palmitoyltransferase 1, brain isoformQ8TCG5CPT1CCarnitine O-palmitoyltransferase 1, liver isoformP50416CPT1ACarnitine O-palmitoyltransferase 1, muscle isoformQ92523CPT1BCarnitine O-palmitoyltransferase 2, mitochondrialP23786CPT2