1.02011-09-21 01:26:21 UTC2019-11-26 03:21:25 UTCFDB027547LysoPC(20:4(8Z,11Z,14Z,17Z))LysoPC(20:4(8Z,11Z,14Z,17Z)) 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(20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of eicsoatetraenoic acid at the C-1 position. The eicsoatetraenoic acid moiety is derived from fish oils. 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. [HMDB]1-Eicsoatetraenoyl-glycero-3-ocholine1-eicsoatetraenoyl-glycero-3-phosphocholineLPC(20:4n3/0:0)LPC(20:4w3/0:0)LyPC(20:4n3/0:0)LyPC(20:4w3/0:0)Lysoatidylcholine(20:4N3/0:0)Lysoatidylcholine(20:4W3/0:0)LysoPC(20:4n3/0:0)LysoPC(20:4w3/0:0)Lysophosphatidylcholine(20:4n3/0:0)Lysophosphatidylcholine(20:4w3/0:0)C28H50NO7P543.6729543.332489471(2-{[(2R)-2-hydroxy-3-(icosa-8,11,14,17-tetraenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium(2-{[(2R)-2-hydroxy-3-(icosa-8,11,14,17-tetraenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazaniumCCC=CCC=CCC=CCC=CCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)CInChI=1S/C28H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-28(31)34-25-27(30)26-36-37(32,33)35-24-23-29(2,3)4/h6-7,9-10,12-13,15-16,27,30H,5,8,11,14,17-26H2,1-4H3/t27-/m1/s1GOMVPVRDBLLHQC-HHHXNRCGSA-N belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine.1-acyl-sn-glycero-3-phosphocholinesOrganic compoundsLipids and lipid-like moleculesGlycerophospholipidsGlycerophosphocholinesAliphatic acyclic compoundsAminesCarbonyl compoundsCarboxylic acid estersDialkyl phosphatesFatty acid estersHydrocarbon derivativesMonocarboxylic acids and derivativesOrganic oxidesOrganic saltsOrganopnictogen compoundsPhosphocholinesSecondary alcoholsTetraalkylammonium salts1-acyl-sn-glycero-3-phosphocholineAlcoholAliphatic acyclic compoundAlkyl phosphateAmineCarbonyl groupCarboxylic acid derivativeCarboxylic acid esterDialkyl phosphateFatty acid esterFatty acylHydrocarbon derivativeMonocarboxylic acid or derivativesOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganic phosphoric acid derivativeOrganic saltOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPhosphocholinePhosphoric acid esterQuaternary ammonium saltSecondary alcoholTetraalkylammonium saltSolidlogp2.41logs-6.31solubility2.91e-04 g/llogp1.52pka_strongest_acidic1.86pka_strongest_basic-3.4iupac(2-{[(2R)-2-hydroxy-3-(icosa-8,11,14,17-tetraenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazaniumaverage_mass543.6729mono_mass543.332489471smilesCCC=CCC=CCC=CCC=CCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)CformulaC28H50NO7PinchiInChI=1S/C28H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-28(31)34-25-27(30)26-36-37(32,33)35-24-23-29(2,3)4/h6-7,9-10,12-13,15-16,27,30H,5,8,11,14,17-26H2,1-4H3/t27-/m1/s1inchikeyGOMVPVRDBLLHQC-HHHXNRCGSA-Npolar_surface_area105.12refractivity165.14polarizability62.45rotatable_bond_count24acceptor_count4donor_count1physiological_charge0formal_charge0HMDB10396Cow milk, pasteurized, vitamin A + D added, 0% fatType 2specificCow milk, pasteurized, vitamin A + D added, 1% fatType 2specificCow milk, pasteurized, vitamin A + D added, 2% fatType 2specificCow milk, pasteurized, vitamin D added, 3.25% fatType 2specific60 kDa lysophospholipaseQ86U10ASPGAcyl-protein thioesterase 1O75608LYPLA1Acyl-protein thioesterase 2O95372LYPLA2Eosinophil lysophospholipaseQ05315CLCLysophosphatidylcholine acyltransferase 2Q7L5N7LPCAT2Lysophospholipid acyltransferase 5Q6P1A2LPCAT3Phosphatidylcholine-sterol acyltransferaseP04180LCATPlatelet-activating factor acetylhydrolaseQ13093PLA2G7Platelet-activating factor acetylhydrolase 2, cytoplasmicQ99487PAFAH2Platelet-activating factor acetylhydrolase IB subunit betaP68402PAFAH1B2Platelet-activating factor acetylhydrolase IB subunit gammaQ15102PAFAH1B3