1.0 2011-09-21 01:50:07 UTC 2017-04-03 05:02:19 UTC FDB029101 1-Lyso-2-arachidonoyl-phosphatidate LPA(0:0/20:4n6) is a lysophosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. Fatty acids containing 16 and 18 carbons are the most common. Lysophosphatidic acid is the simplest possible glycerophospholipid. It is the biosynthetic precursor of phosphatidic acid. Although it is present at very low levels only in animal tissues, it is extremely important biologically, influencing many biochemical processes. In particular, lysophosphatidic acid is an intercellular lipid mediator with growth factor-like activities, and is rapidly produced and released from activated platelets to influence target cells.LPA is a pluripotent lipid mediator controlling growth, motility, and differentiation, that has a strong influence on the chemotaxis and ultrastructure of human neutrophils (PMID 7416233). In serum and plasma, LPA is mainly converted from lysophospholipids, whereas in platelets and some cancer cells it is converted from phosphatidic acid. In each pathway, at least two phospholipase activities are required: phospholipase A1 (PLA1)/PLA2 plus lysophospholipase D (lysoPLD) activities are involved in the first pathway and phospholipase D (PLD) plus PLA1/PLA2 activities are involved in the second pathway. (PMID 15271293) [HMDB] 1-Lyso-2-all-cis-5,8,11,14-eicosatetraenoyl-sn-glycero-3-atidic acid 1-lyso-2-all-cis-5,8,11,14-eicosatetraenoyl-sn-glycero-3-phosphatidic acid 2-(5Z,8Z,11Z,14Z)-Eicosatetraenoyl-sn-glycero-3-ate 2-(5Z,8Z,11Z,14Z)-Eicosatetraenoyl-sn-glycero-3-ic acid 2-(5Z,8Z,11Z,14Z)-Icosatetraenoyl-sn-glycero-3-ate(2-) 2-(5Z,8Z,11Z,14Z)-Icosatetraenoyl-sn-glycero-3-ic acid(2-) 2-all-cis-5,8,11,14-Eicosatetraenoyl-lysoatidic acid 2-all-cis-5,8,11,14-eicosatetraenoyl-lysophosphatidic acid 2-Arachidonoyl-lysoatidic acid 2-arachidonoyl-lysophosphatidic acid 2-Arachidonoyl-sn-glycero-3-ate 2-arachidonoyl-sn-glycero-3-phosphate L-beta-Arachidonoyl-alpha-lysoatidic acid L-beta-arachidonoyl-alpha-lysophosphatidic acid C23H37O7P 456.5094 456.22769005 (2R)-1-hydroxy-3-(phosphonatooxy)propan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate (2R)-1-hydroxy-3-(phosphonatooxy)propan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate 95-01-2 CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)O[C@H](CO)COP([O-])([O-])=O InChI=1S/C23H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(25)30-22(20-24)21-29-31(26,27)28/h6-7,9-10,12-13,15-16,22,24H,2-5,8,11,14,17-21H2,1H3,(H2,26,27,28)/p-2/b7-6-,10-9-,13-12-,16-15-/t22-/m1/s1 BDCFJMBXZCIVRH-NZRYSPDRSA-L belongs to the class of organic compounds known as 2-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-2 position. 2-acylglycerol-3-phosphates Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphates Aliphatic acyclic compounds Alkyl phosphates Carbonyl compounds Carboxylic acid esters Fatty acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic anions Organic oxides Primary alcohols 2-acylglycerol-3-phosphate Alcohol Aliphatic acyclic compound Alkyl phosphate Carbonyl group Carboxylic acid derivative Carboxylic acid ester Fatty acid ester Fatty acyl Hydrocarbon derivative Monocarboxylic acid or derivatives Organic anion Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organooxygen compound Phosphoric acid ester Primary alcohol 2-acyl-sn-glycero-3-phosphate(2-) Solid logp 5.57 ALOGPS logs -5.16 ALOGPS solubility 3.45e-03 g/l ALOGPS logp 5.29 ChemAxon pka_strongest_acidic 1.32 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R)-1-hydroxy-3-(phosphonatooxy)propan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate ChemAxon average_mass 456.5094 ChemAxon mono_mass 456.22769005 ChemAxon smiles CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)O[C@H](CO)COP([O-])([O-])=O ChemAxon formula C23H37O7P ChemAxon inchi InChI=1S/C23H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(25)30-22(20-24)21-29-31(26,27)28/h6-7,9-10,12-13,15-16,22,24H,2-5,8,11,14,17-21H2,1H3,(H2,26,27,28)/p-2/b7-6-,10-9-,13-12-,16-15-/t22-/m1/s1 ChemAxon inchikey BDCFJMBXZCIVRH-NZRYSPDRSA-L ChemAxon polar_surface_area 118.95 ChemAxon refractivity 125.61 ChemAxon polarizability 49.07 ChemAxon rotatable_bond_count 20 ChemAxon acceptor_count 5 ChemAxon donor_count 1 ChemAxon physiological_charge -2 ChemAxon formal_charge -2 ChemAxon HMDB12496 #<Reference:0x000055ce3206d168> #<Reference:0x000055ce3206cfb0>