1.0 2011-09-21 01:26:12 UTC 2018-05-28 18:37:56 UTC FDB027541 LysoPC(20:0) LysoPC(20:0) 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(20:0), in particular, consists of one chain of arachidic acid at the C-1 position. The arachidic acid moiety is derived from peanut oil. 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-Arachidonyl-glycero-3-ocholine 1-arachidonyl-glycero-3-phosphocholine 1-Arachidoyl-sn-glycero-3-ocholine 1-Eicosanoyl-sn-glycero-3-ocholine LPC(20:0) LPC(20:0/0:0) LyPC(20:0) LyPC(20:0/0:0) Lysoatidylcholine(20:0) Lysoatidylcholine(20:0/0:0) LysoPC(20:0) LysoPC(20:0/0:0) Lysophosphatidylcholine(20:0) Lysophosphatidylcholine(20:0/0:0) PC(20:0/0:0) C28H58NO7P 551.7364 551.395089727 (2-{[(2R)-2-hydroxy-3-(icosanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium (2-{[(2R)-2-hydroxy-3-(icosanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium 108341-80-6 [H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C InChI=1S/C28H58NO7P/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/h27,30H,5-26H2,1-4H3/t27-/m1/s1 UATOAILWGVYRQS-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 1-O-acyl-sn-glycero-3-phosphocholine Monoacylglycerophosphocholines Solid logp 3.14 ALOGPS logs -6.64 ALOGPS solubility 1.38e-04 g/l ALOGPS logp 2.97 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac (2-{[(2R)-2-hydroxy-3-(icosanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium ChemAxon average_mass 551.7364 ChemAxon mono_mass 551.395089727 ChemAxon smiles [H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C ChemAxon formula C28H58NO7P ChemAxon inchi InChI=1S/C28H58NO7P/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/h27,30H,5-26H2,1-4H3/t27-/m1/s1 ChemAxon inchikey UATOAILWGVYRQS-HHHXNRCGSA-N ChemAxon polar_surface_area 105.12 ChemAxon refractivity 160.68 ChemAxon polarizability 66.62 ChemAxon rotatable_bond_count 28 ChemAxon acceptor_count 4 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 12500 Specdb::CMs 39499 Specdb::CMs 281770 Specdb::CMs 334284 Specdb::MsMs 293524 Specdb::MsMs 293525 Specdb::MsMs 293526 Specdb::MsMs 334009 Specdb::MsMs 334010 Specdb::MsMs 334011 Specdb::MsMs 2376137 Specdb::MsMs 2376138 Specdb::MsMs 2376139 Specdb::MsMs 2542772 Specdb::MsMs 2542773 Specdb::MsMs 2542774 Specdb::MsMs 2562099 Specdb::MsMs 2562100 Specdb::MsMs 2562101 Specdb::MsMs 2757459 Specdb::MsMs 2757460 Specdb::MsMs 2757461 Specdb::MsMs 2802922 Specdb::MsMs 2802923 Specdb::MsMs 2802924 HMDB10390 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 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