1.0 2011-09-21 00:36:57 UTC 2015-07-21 06:57:56 UTC FDB023928 Linoleyl carnitine Linoleyl carnitine is a long-chain acyl fatty acid derivative ester of carnitine. Long-chain acyl fatty acid derivatives accumulate in the cytosol and serum of patients suffering of mitochondrial carnitine palmitoyltransferase II (CPT II, EC 2.3.1.12) deficiency, the most common inherited disorder of lipid metabolism in adults. carnitine palmitoyltransferase II deficiency is an autosomal recessive disorder of fatty acid metabolism presenting as two clinical phenotypes: (i) a severe infantile hepatocardiomuscular form and (ii) a milder adult muscular form. Energy production from long-chain fatty acids (LCFAs) requires the transport of LCFAs into the mitochondrial matrix. This transport is carnitine-dependent and involves translocation machinery. mitochondrial fatty acid oxidation disorders cause hypoglycaemia, hepatic dysfunction, myopathy, cardiomyopathy and encephalopathy. Patients with end-stage renal disease (ESRD) undergoing long-term haemodialysis exhibit elevated acylcarnitine concentrations. (PMID: 11999976, 10682306, 15025677, 16168195) [HMDB] 3-carboxy-N,N,N-trimethyl-2-[(1-oxo-9,12-octadecadienyl)oxy]-1-Propanaminium 3-carboxy-N,N,N-trimethyl-2-[[(9Z,12Z)-1-oxo-9,12-octadecadienyl]oxy]-1-Propanaminium 9,12-octadecadienoylcarnitine 9,12-octadecadienylcarnitine alpha-Linoleoylcarnitine Decadienylcarnitine Linoleic acid carnitine Linoleoyl carnitine Octadecadienyl-L-carnitine C25H45NO4 423.6291 423.334858933 (3R)-3-(octadeca-9,12-dienoyloxy)-4-(trimethylazaniumyl)butanoate (3R)-3-(octadeca-9,12-dienoyloxy)-4-(trimethylammonio)butanoate 36816-10-1 [H][C@@](CC([O-])=O)(C[N+](C)(C)C)OC(=O)CCCCCCCC=CCC=CCCCCC InChI=1S/C25H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h9-10,12-13,23H,5-8,11,14-22H2,1-4H3/t23-/m1/s1 MJLXQSQYKZWZCB-HSZRJFAPSA-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 Solid logp 1.46 ALOGPS logs -7.74 ALOGPS solubility 8.62e-06 g/l ALOGPS logp 2.2 ChemAxon pka_strongest_acidic 4.22 ChemAxon pka_strongest_basic -7.1 ChemAxon iupac (3R)-3-(octadeca-9,12-dienoyloxy)-4-(trimethylazaniumyl)butanoate ChemAxon average_mass 423.6291 ChemAxon mono_mass 423.334858933 ChemAxon smiles [H][C@@](CC([O-])=O)(C[N+](C)(C)C)OC(=O)CCCCCCCC=CCC=CCCCCC ChemAxon formula C25H45NO4 ChemAxon inchi InChI=1S/C25H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h9-10,12-13,23H,5-8,11,14-22H2,1-4H3/t23-/m1/s1 ChemAxon inchikey MJLXQSQYKZWZCB-HSZRJFAPSA-N ChemAxon polar_surface_area 66.43 ChemAxon refractivity 148.51 ChemAxon polarizability 51.43 ChemAxon rotatable_bond_count 20 ChemAxon acceptor_count 3 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB06469 #<Reference:0x000055ce302a1a58> #<Reference:0x000055ce302a1850> #<Reference:0x000055ce302a15d0> #<Reference:0x000055ce302a1418> 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