1.0 2011-09-21 01:53:26 UTC 2015-07-21 06:59:41 UTC FDB029295 LysoPC(P-18:0) LysoPC(P-18:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(P-18:0), in particular, consists of one chain of plasmalogen 18:0 at the C-1 position. The plasmalogen 18:0 moiety is derived from animal fats, liver and kidney. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins. 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-(1-Enyl-stearoyl)-glycero-3-ocholine 1-(1-enyl-stearoyl)-glycero-3-phosphocholine LysoPC(18:0) PC(P-18:0/0:0) C26H54NO6P 507.6838 507.368874977 (2-{[(2R)-2-hydroxy-3-(octadec-1-en-1-yloxy)propyl phosphonato]oxy}ethyl)trimethylazanium (2-{[(2R)-2-hydroxy-3-(octadec-1-en-1-yloxy)propyl phosphonato]oxy}ethyl)trimethylazanium [H][C@@](O)(COC=CCCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C InChI=1S/C26H54NO6P/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/h20,22,26,28H,5-19,21,23-25H2,1-4H3/t26-/m1/s1 WBOMIOWRFSPZMC-AREMUKBSSA-N belongs to the class of organic compounds known as 1-(1z-alkenyl)-glycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one 1Z-alkenyl chain attached at the O1 position of a glycerol moiety through an ether linkage. 1-(1Z-alkenyl)-glycero-3-phosphocholines Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphocholines Aliphatic acyclic compounds Amines Dialkyl phosphates Glycerol vinyl ethers Hydrocarbon derivatives Organic oxides Organic salts Organopnictogen compounds Phosphocholines Secondary alcohols Tetraalkylammonium salts 1-(1z-alkenyl)-glycero-3-phosphocholine Alcohol Aliphatic acyclic compound Alkyl phosphate Amine Dialkyl phosphate Glycerol vinyl ether Hydrocarbon derivative 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 Solid logp 2.99 ALOGPS logs -6.39 ALOGPS solubility 2.28e-04 g/l ALOGPS logp 2.47 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac (2-{[(2R)-2-hydroxy-3-(octadec-1-en-1-yloxy)propyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon average_mass 507.6838 ChemAxon mono_mass 507.368874977 ChemAxon smiles [H][C@@](O)(COC=CCCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C ChemAxon formula C26H54NO6P ChemAxon inchi InChI=1S/C26H54NO6P/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/h20,22,26,28H,5-19,21,23-25H2,1-4H3/t26-/m1/s1 ChemAxon inchikey WBOMIOWRFSPZMC-AREMUKBSSA-N ChemAxon polar_surface_area 88.05 ChemAxon refractivity 151.81 ChemAxon polarizability 62.16 ChemAxon rotatable_bond_count 25 ChemAxon acceptor_count 4 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB13122 Eosinophil lysophospholipase Q05315 CLC Lysophosphatidylcholine acyltransferase 2 Q7L5N7 LPCAT2 Lysophospholipid acyltransferase 5 Q6P1A2 LPCAT3 Phosphatidylcholine-sterol acyltransferase P04180 LCAT