1.0 2011-09-21 00:05:00 UTC 2025-11-19 02:40:22 UTC FDB021910 L-Palmitoylcarnitine 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 &#946; and &#948; 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 acid 3-carboxy-N,N,N-trimethyl-2-[(1-oxohexadecyl)oxy]-1-Propanaminium D-palmitylcarnitine Hexadecanoyl-L-carnitine Hexadecanoylcarnitine Hexadecenoyl carnitine L-carnitine palmitoyl ester L-palmitoyl-L-carnitine L(-)-Palmitylcarnitine O-Hexadecanoyl-(R)-carnitine O-Hexadecanoyl-R-carnitine Palmitoyl d-carnitine Palmitoyl-(-)-carnitine Palmitoyl-L-carnitine Palmitoylcarnitine Palmityl-L-carnitine C23H45NO4 399.6077 399.334858933 (3R)-3-(hexadecanoyloxy)-4-(trimethylazaniumyl)butanoate palmitoylcarnitine 2364-67-2 CCCCCCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C 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 XOMRRQXKHMYMOC-OAQYLSRUSA-N 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. Acyl carnitines Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acid esters Aliphatic acyclic compounds Amines Carbonyl compounds Carboxylic acid esters Carboxylic acid salts Carboxylic acids Dicarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides Organic salts Organopnictogen compounds Tetraalkylammonium salts Acyl-carnitine Aliphatic acyclic compound Amine Carbonyl group Carboxylic acid Carboxylic acid derivative Carboxylic acid ester Carboxylic acid salt Dicarboxylic acid or derivatives Hydrocarbon derivative Organic nitrogen compound Organic oxide Organic oxygen compound Organic salt Organonitrogen compound Organooxygen compound Organopnictogen compound Quaternary ammonium salt Tetraalkylammonium salt Fatty acyl carnitines Fatty acyl carnitines O-acyl-L-carnitine O-palmitoylcarnitine Solid logp 1.77 ALOGPS logs -7.58 ALOGPS solubility 1.20e-05 g/l ALOGPS logp 2.03 ChemAxon pka_strongest_acidic 4.22 ChemAxon pka_strongest_basic -7.1 ChemAxon iupac (3R)-3-(hexadecanoyloxy)-4-(trimethylazaniumyl)butanoate ChemAxon average_mass 399.6077 ChemAxon mono_mass 399.334858933 ChemAxon smiles CCCCCCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C ChemAxon formula C23H45NO4 ChemAxon inchi 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 ChemAxon inchikey XOMRRQXKHMYMOC-OAQYLSRUSA-N ChemAxon polar_surface_area 66.43 ChemAxon refractivity 137.08 ChemAxon polarizability 50.35 ChemAxon rotatable_bond_count 20 ChemAxon acceptor_count 3 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Fatty acid Metabolism SMP00051 map00071 Specdb::CMs 3336 Specdb::CMs 131920 Specdb::CMs 139654 Specdb::CMs 1055060 Specdb::CMs 1055062 Specdb::MsMs 364 Specdb::MsMs 365 Specdb::MsMs 366 Specdb::MsMs 439588 Specdb::MsMs 439589 Specdb::MsMs 449652 Specdb::MsMs 449653 Specdb::MsMs 449654 Specdb::MsMs 449655 Specdb::MsMs 2915558 Specdb::MsMs 2915559 Specdb::MsMs 2915560 Specdb::NmrOneD 1221 Specdb::NmrOneD 269658 Specdb::NmrOneD 269659 Specdb::NmrOneD 269660 Specdb::NmrOneD 269661 Specdb::NmrOneD 269662 Specdb::NmrOneD 269663 Specdb::NmrOneD 269664 Specdb::NmrOneD 269665 Specdb::NmrOneD 269666 Specdb::NmrOneD 269667 Specdb::NmrOneD 269668 Specdb::NmrOneD 269669 Specdb::NmrOneD 269670 Specdb::NmrOneD 269671 Specdb::NmrOneD 269672 Specdb::NmrOneD 269673 Specdb::NmrOneD 269674 Specdb::NmrOneD 269675 Specdb::NmrOneD 269676 Specdb::NmrOneD 269677 Specdb::NmrTwoD 1217 HMDB00222 17490 #<Reference:0x000055ce31cbbc90> #<Reference:0x000055ce31cbbad8> #<Reference:0x000055ce31cbb8f8> #<Reference:0x000055ce31cbb740> #<Reference:0x000055ce31cbb560> #<Reference:0x000055ce31cbb380> #<Reference:0x000055ce31cbb1c8> #<Reference:0x000055ce31cbb010> #<Reference:0x000055ce31cbae30> #<Reference:0x000055ce31cbac78> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Carnitine O-palmitoyltransferase 1, brain isoform Q8TCG5 CPT1C Carnitine O-palmitoyltransferase 1, liver isoform P50416 CPT1A Carnitine O-palmitoyltransferase 1, muscle isoform Q92523 CPT1B Carnitine O-palmitoyltransferase 2, mitochondrial P23786 CPT2