1.0 2011-09-21 00:52:06 UTC 2015-07-21 06:58:18 UTC FDB025044 LPA(0:0/18:1(9Z)) LPA(0:0/18:1(9Z)) 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. 1-Palmitoyl lysophosphatidic acid is the major component of lysophosphatidic acid (LPA) in plasma, and is in a reduced ratio in individuals with gynecological cancers (PMID 11585410). 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-oleoyl-atidate 1-Lyso-2-oleoyl-atidic acid 1-Lyso-2-oleoyl-sn-glycero-3-ate 1-Lyso-2-oleoyl-sn-glycero-3-ic acid 2-(9Z-Octadecenoyl)-atidate 2-(9Z-Octadecenoyl)-atidic acid 2-(9Z-octadecenoyl)-phosphatidic acid 2-(9Z-Octadecenoyl)-sn-glycero-3-ate 2-(9Z-Octadecenoyl)-sn-glycero-3-ic acid 2-(9Z)-Octadecenoyl-sn-glycero-3-ate 2-(9Z)-Octadecenoyl-sn-glycero-3-ic acid 2-Oleoyl-glycero-3-ate 2-Oleoyl-glycero-3-ic acid 2-oleoyl-glycero-3-phosphate LPA(0:0/18:1) LPA(0:0/18:1n9) LPA(0:0/18:1omega9) LPA(0:0/18:1w9) LPA(18:1) Lysoatidate(0:0/18:1) Lysoatidate(0:0/18:1N9) Lysoatidate(0:0/18:1omega9) Lysoatidate(18:1) Lysoatidic acid(0:0/18:1) Lysoatidic acid(0:0/18:1N9) Lysoatidic acid(0:0/18:1omega9) Lysoatidic acid(0:0/18:1W9) Lysoatidic acid(18:1) Lysophosphatidic acid(0:0/18:1) Lysophosphatidic acid(0:0/18:1n9) Lysophosphatidic acid(0:0/18:1w9) C21H41O7P 436.5198 436.258990178 [(2R)-3-hydroxy-2-(octadec-9-enoyloxy)propoxy]phosphonic acid (2R)-3-hydroxy-2-(octadec-9-enoyloxy)propoxyphosphonic acid [H][C@@](CO)(COP(O)(O)=O)OC(=O)CCCCCCCC=CCCCCCCCC InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)28-20(18-22)19-27-29(24,25)26/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26)/t20-/m1/s1 ZOOLJLSXNRZLDH-HXUWFJFHSA-N This compound belongs to the class of chemical entities 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 Chemical entities Organic compounds Lipids and lipid-like molecules Glycerophospholipids Aliphatic acyclic compounds Carbonyl compounds Carboxylic acid esters Fatty acid esters Hydrocarbon derivatives Monoalkyl phosphates Monocarboxylic acids and derivatives 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 Monoalkyl phosphate Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organooxygen compound Phosphoric acid ester Primary alcohol Solid logp 4.70 ALOGPS logs -5.40 ALOGPS solubility 1.74e-03 g/l ALOGPS logp 5.49 ChemAxon pka_strongest_acidic 1.32 ChemAxon pka_strongest_basic -3 ChemAxon iupac [(2R)-3-hydroxy-2-(octadec-9-enoyloxy)propoxy]phosphonic acid ChemAxon average_mass 436.5198 ChemAxon mono_mass 436.258990178 ChemAxon smiles [H][C@@](CO)(COP(O)(O)=O)OC(=O)CCCCCCCC=CCCCCCCCC ChemAxon formula C21H41O7P ChemAxon inchi InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)28-20(18-22)19-27-29(24,25)26/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26)/t20-/m1/s1 ChemAxon inchikey ZOOLJLSXNRZLDH-HXUWFJFHSA-N ChemAxon polar_surface_area 113.29 ChemAxon refractivity 115.3 ChemAxon polarizability 50.18 ChemAxon rotatable_bond_count 21 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon HMDB07851 #<Reference:0x000055ce318c5258> #<Reference:0x000055ce318c50a0> #<Reference:0x000055ce318c4ee8> 1-acyl-sn-glycerol-3-phosphate acyltransferase alpha Q99943 AGPAT1 1-acyl-sn-glycerol-3-phosphate acyltransferase beta O15120 AGPAT2 1-acyl-sn-glycerol-3-phosphate acyltransferase delta Q9NRZ5 AGPAT4 1-acyl-sn-glycerol-3-phosphate acyltransferase epsilon Q9NUQ2 AGPAT5 1-acyl-sn-glycerol-3-phosphate acyltransferase gamma Q9NRZ7 AGPAT3 Acyl-CoA:lysophosphatidylglycerol acyltransferase 1 Q92604 LPGAT1 Diacylglycerol kinase, epsilon 64kDa A1L4Q0 DGKE Focal adhesion kinase 1 Q05397 PTK2 Glycerol-3-phosphate acyltransferase 3 Q53EU6 AGPAT9 Glycerol-3-phosphate acyltransferase 4 Q86UL3 AGPAT6 Lipid phosphate phosphatase-related protein type 4 Q7Z2D5 LPPR4 Lysocardiolipin acyltransferase 1 Q6UWP7 LCLAT1 Lysophosphatidic acid phosphatase type 6 Q9NPH0 ACP6 Lysophosphatidic acid receptor 1 Q92633 LPAR1 Lysophosphatidic acid receptor 2 Q9HBW0 LPAR2 Lysophosphatidic acid receptor 3 Q9UBY5 LPAR3 Lysophosphatidic acid receptor 5 Q9H1C0 LPAR5 Lysophosphatidylcholine acyltransferase 2 Q7L5N7 LPCAT2 Lysophospholipid acyltransferase LPCAT4 Q643R3 LPCAT4 Phosphatidate cytidylyltransferase 2 O95674 CDS2 Phosphatidylinositol-glycan-specific phospholipase D P80108 GPLD1 Phospholipase D2 O14939 PLD2