1.0 2011-09-21 01:26:19 UTC 2019-11-26 03:21:25 UTC FDB027546 LysoPC(20:4(5Z,8Z,11Z,14Z)) LysoPC(20:4(5Z,8Z,11Z,14Z)) 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(5Z,8Z,11Z,14Z)), in particular, consists of one chain of arachidonic acid at the C-1 position. The arachidonic acid moiety is derived from animal fats and eggs. 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-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-sn-glycero-3-ocholine 1-Arachidonoyl-glycero-3-ocholine 1-arachidonoyl-glycero-3-phosphocholine LPC 20:4(5Z,8Z,11Z,14Z)/0:0 LPC(20:4(5Z,8Z,11Z,14Z)/0:0) LPC(20:4) LPC(20:4/0:0) LPC(20:4n6/0:0) LPC(20:4w6/0:0) LyPC(20:4) LyPC(20:4/0:0) LyPC(20:4n6/0:0) LyPC(20:4w6/0:0) Lysoatidylcholine(20:4(5Z,8Z,11Z,14Z)/0:0) Lysoatidylcholine(20:4) Lysoatidylcholine(20:4/0:0) Lysoatidylcholine(20:4N6/0:0) Lysoatidylcholine(20:4W6/0:0) LysoPC 20:4(5Z,8Z,11Z,14Z)/0:0 LysoPC a C20:4 LysoPC(20:4(5Z,8Z,11Z,14Z)/0:0) LysoPC(20:4) LysoPC(20:4/0:0) LysoPC(20:4n6/0:0) LysoPC(20:4w6/0:0) Lysophosphatidylcholine(20:4n6/0:0) Lysophosphatidylcholine(20:4w6/0:0) PC 20:4(5Z,8Z,11Z,14Z)/0:0 PC(20:4(5Z,8Z,11Z,14Z)/0:0) C28H50NO7P 543.6729 543.332489471 (2-{[(2R)-2-hydroxy-3-(icosa-5,8,11,14-tetraenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium (2-{[(2R)-2-hydroxy-3-(icosa-5,8,11,14-tetraenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C InChI=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/h9-10,12-13,15-16,18-19,27,30H,5-8,11,14,17,20-26H2,1-4H3/t27-/m1/s1 LAXQYRRMGGEGOH-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-phosphocholines Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphocholines Aliphatic acyclic compounds Amines Carbonyl compounds Carboxylic acid esters Dialkyl phosphates Fatty acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Organic salts Organopnictogen compounds Phosphocholines Secondary alcohols Tetraalkylammonium salts 1-acyl-sn-glycero-3-phosphocholine Alcohol Aliphatic acyclic compound Alkyl phosphate Amine Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dialkyl phosphate Fatty acid ester Fatty acyl Hydrocarbon derivative Monocarboxylic acid or derivatives 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 2.45 ALOGPS logs -6.31 ALOGPS solubility 2.89e-04 g/l ALOGPS logp 1.52 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac (2-{[(2R)-2-hydroxy-3-(icosa-5,8,11,14-tetraenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon average_mass 543.6729 ChemAxon mono_mass 543.332489471 ChemAxon smiles CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C ChemAxon formula C28H50NO7P ChemAxon inchi InChI=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/h9-10,12-13,15-16,18-19,27,30H,5-8,11,14,17,20-26H2,1-4H3/t27-/m1/s1 ChemAxon inchikey LAXQYRRMGGEGOH-HHHXNRCGSA-N ChemAxon polar_surface_area 105.12 ChemAxon refractivity 165.14 ChemAxon polarizability 61.4 ChemAxon rotatable_bond_count 24 ChemAxon acceptor_count 4 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 266968 Specdb::NmrOneD 266969 Specdb::NmrOneD 266970 Specdb::NmrOneD 266971 Specdb::NmrOneD 266972 Specdb::NmrOneD 266973 Specdb::NmrOneD 266974 Specdb::NmrOneD 266975 Specdb::NmrOneD 266976 Specdb::NmrOneD 266977 Specdb::NmrOneD 266978 Specdb::NmrOneD 266979 Specdb::NmrOneD 266980 Specdb::NmrOneD 266981 Specdb::NmrOneD 266982 Specdb::NmrOneD 266983 Specdb::NmrOneD 266984 Specdb::NmrOneD 266985 Specdb::NmrOneD 266986 Specdb::NmrOneD 266987 HMDB10395 Cow milk, pasteurized, vitamin A + D added, 0% fat Type 2 specific Cow milk, pasteurized, vitamin A + D added, 1% fat Type 2 specific Cow milk, pasteurized, vitamin A + D added, 2% fat Type 2 specific Cow milk, pasteurized, vitamin D added, 3.25% fat Type 2 specific 60 kDa lysophospholipase Q86U10 ASPG Acyl-protein thioesterase 1 O75608 LYPLA1 Acyl-protein thioesterase 2 O95372 LYPLA2 Eosinophil lysophospholipase Q05315 CLC Lysophosphatidylcholine acyltransferase 2 Q7L5N7 LPCAT2 Lysophospholipid acyltransferase 5 Q6P1A2 LPCAT3 Phosphatidylcholine-sterol acyltransferase P04180 LCAT 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