1.0 2011-09-21 01:32:04 UTC 2015-07-21 06:59:16 UTC FDB027924 LysoPC(O-18:0) 1-Octadecyl-sn-glycero-3-phosphocholine is an intermediate in the ether lipid metabolism pathway. 1-Octadecyl-sn-glycero-3-phosphocholine is irreversibly produced from 2-acetyl-1-(9Z-octadecenyl)-sn-glycero-3-phosphocholine via the enzyme 1-alkyl-2-acetylglycerophosphocholine esterase (EC 3.1.1.47). 1-Octadecyl-sn-glycero-3-phosphocholine is an ether phospho-ether lipid. Ether lipids are lipids in which one or more of the carbon atoms on glycerol are bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. [HMDB] 1-O-Octadecyl-sn-glycero-3-ocholine 1-O-Octadecylglycerol-3-atidylcholine 1-Octadecyl-sn-glycero-3-ocholine 1-Octadecyl-sn-glycero-3-phosphocholine LPC (O-18:0) LysoPC(18:0e/0:0) LysoPC(dm18:0) LysoPC(o-18:0)LysoPC(dm18:0) LysoPC(o-18:0/0:0) PC(O-18:0/0:0) C26H56NO6P 509.6997 509.384525041 (2-{[(2R)-2-hydroxy-3-(octadecyloxy)propyl phosphono]oxy}ethyl)trimethylazanium (2-{[(2R)-2-hydroxy-3-(octadecyloxy)propyl phosphono]oxy}ethyl)trimethylazanium [H][C@@](O)(COCCCCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C InChI=1S/C26H56NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-22-31-24-26(28)25-33-34(29,30)32-23-21-27(2,3)4/h26,28H,5-25H2,1-4H3/t26-/m1/s1 XKBJVQHMEXMFDZ-AREMUKBSSA-N belongs to the class of organic compounds known as monoalkylglycerophosphocholines. Monoalkylglycerophosphocholines are compounds containing glycerophosphocholine moiety attached to an fatty acyl chain through an ether bond. Monoalkylglycerophosphocholines Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphocholines Aliphatic acyclic compounds Amines Dialkyl ethers Dialkyl phosphates Glycerol ethers Hydrocarbon derivatives Organic oxides Organic salts Organopnictogen compounds Phosphocholines Secondary alcohols Tetraalkylammonium salts Alcohol Aliphatic acyclic compound Alkyl phosphate Amine Dialkyl ether Dialkyl phosphate Ether Glycerol ether Hydrocarbon derivative Monoalkylglycerophosphocholine Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic salt Organonitrogen compound Organooxygen compound Organopnictogen compound Phosphocholine Phosphoric acid ester Quaternary ammonium salt Secondary alcohol Tetraalkylammonium salt 1-alkyl-sn-glycero-3-phosphocholine Monoalkylglycerophosphocholines organic molecular entity Solid logp 2.98 ALOGPS logs -6.32 ALOGPS solubility 2.67e-04 g/l ALOGPS logp 2.46 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac (2-{[(2R)-2-hydroxy-3-(octadecyloxy)propyl phosphono]oxy}ethyl)trimethylazanium ChemAxon average_mass 509.6997 ChemAxon mono_mass 509.384525041 ChemAxon smiles [H][C@@](O)(COCCCCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C ChemAxon formula C26H56NO6P ChemAxon inchi InChI=1S/C26H56NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-22-31-24-26(28)25-33-34(29,30)32-23-21-27(2,3)4/h26,28H,5-25H2,1-4H3/t26-/m1/s1 ChemAxon inchikey XKBJVQHMEXMFDZ-AREMUKBSSA-N ChemAxon polar_surface_area 88.05 ChemAxon refractivity 151.72 ChemAxon polarizability 62.7 ChemAxon rotatable_bond_count 26 ChemAxon acceptor_count 4 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 20482 Specdb::CMs 39565 Specdb::MsMs 311599 Specdb::MsMs 311600 Specdb::MsMs 311601 Specdb::MsMs 356638 Specdb::MsMs 356639 Specdb::MsMs 356640 Specdb::MsMs 2401205 Specdb::MsMs 2401206 Specdb::MsMs 2401207 Specdb::MsMs 2434867 Specdb::MsMs 2434868 Specdb::MsMs 2434869 Specdb::MsMs 2469451 Specdb::MsMs 2469452 Specdb::MsMs 2469453 Specdb::MsMs 2504549 Specdb::MsMs 2504550 Specdb::MsMs 2504551 HMDB11149 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 60 kDa lysophospholipase Q86U10 ASPG Eosinophil lysophospholipase Q05315 CLC Lysophosphatidylcholine acyltransferase 2 Q7L5N7 LPCAT2 Lysophospholipid acyltransferase 5 Q6P1A2 LPCAT3 Platelet-activating factor acetylhydrolase Q13093 PLA2G7 Platelet-activating factor acetylhydrolase 2, cytoplasmic Q99487 PAFAH2 Platelet-activating factor acetylhydrolase IB subunit beta P68402 PAFAH1B2 Platelet-activating factor acetylhydrolase IB subunit gamma Q15102 PAFAH1B3