1.0 2011-09-21 00:52:14 UTC 2015-07-21 06:58:18 UTC FDB025055 PA(18:1(11Z)/18:1(9Z)) PA(18:1(11Z)/18:1(9Z)) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(18:1(11Z)/18:1(9Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of oleic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. Indeed, the concentration of phosphatidic acids is often over-estimated in tissues and biofluids as it can arise by inadvertent enzymatic hydrolysis during inappropriate storage or extraction conditions during analysis. The main biosynthetic route of phosphatidic acid in animal tissues involves sequential acylation of alpha-glycerophosphate by acyl-coA derivatives of fatty acids. PAs are biologically active lipids that can stimulate a large range of responses in many different cell types, such as platelet aggregation, smooth muscle contraction, in vivo vasoactive effects, chemotaxis, expression of adhesion molecules, increased tight junction permeability of endothelial cells, induction of stress fibres, modulation of cardiac contractility, and many others. Diacylglycerols (DAGs) can be converted to PAs by DAG kinases and indirect evidence supports the notion that PAs alter the excitability of neurons. Phospholipase Ds (PLDs), which catalyze the conversion of glycerolphospholipids, particularly phosphatidylcholine, to PAs and the conversion of N-arachidonoyl-phosphatidylethanolamine (NAPE) to anandamide and PAs are activated by several inflammatory mediators including bradykinin, ATP and glutamate. PAs activate downstream signaling pathways such as PKCs and mitogen-activated protein kinases (MAPKs), which are linked to an increase in sensitivity of sensory neurons either during inflammation or in chronic pain models. Circumstantial evidence that PAs are converted to DAGs. (PMID: 12618218, 16185776). [HMDB] 1-(11Z-Octadecenoyl)-2-(9Z-octadecenoyl)-sn-atidic acid 1-(11Z-octadecenoyl)-2-(9Z-octadecenoyl)-sn-phosphatidic acid 1-Vaccenoyl-2-oleoyl-sn-glycero-3-ate 1-vaccenoyl-2-oleoyl-sn-glycero-3-phosphate Atidic acid(18:1N7/18:1N9) Atidic acid(18:1W7/18:1W9) PA(18:1n7/18:1n9) PA(18:1w7/18:1w9) Phosphatidic acid(18:1n7/18:1n9) Phosphatidic acid(18:1w7/18:1w9) C39H73O8P 700.9659 700.504305824 [(2R)-3-(octadec-11-enoyloxy)-2-(octadec-9-enoyloxy)propoxy]phosphonic acid (2R)-3-(octadec-11-enoyloxy)-2-(octadec-9-enoyloxy)propoxyphosphonic acid [H][C@@](COC(=O)CCCCCCCCCC=CCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCC=CCCCCCCCC InChI=1S/C39H73O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(40)45-35-37(36-46-48(42,43)44)47-39(41)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13,15,18,20,37H,3-12,14,16-17,19,21-36H2,1-2H3,(H2,42,43,44)/t37-/m1/s1 IIMFLKINUHKKSA-DIPNUNPCSA-N belongs to the class of organic compounds known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages. 1,2-diacylglycerol-3-phosphates Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acid esters Dicarboxylic acids and derivatives Fatty acid esters Hydrocarbon derivatives Monoalkyl phosphates Organic oxides 1,2-diacylglycerol-3-phosphate Aliphatic acyclic compound Alkyl phosphate Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dicarboxylic acid or derivatives Fatty acid ester Fatty acyl Hydrocarbon derivative Monoalkyl phosphate Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organooxygen compound Phosphoric acid ester Solid logp 9.12 ALOGPS logs -7.02 ALOGPS solubility 6.67e-05 g/l ALOGPS logp 12.93 ChemAxon pka_strongest_acidic 1.32 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac [(2R)-3-(octadec-11-enoyloxy)-2-(octadec-9-enoyloxy)propoxy]phosphonic acid ChemAxon average_mass 700.9659 ChemAxon mono_mass 700.504305824 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCCCC=CCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCC=CCCCCCCCC ChemAxon formula C39H73O8P ChemAxon inchi InChI=1S/C39H73O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(40)45-35-37(36-46-48(42,43)44)47-39(41)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13,15,18,20,37H,3-12,14,16-17,19,21-36H2,1-2H3,(H2,42,43,44)/t37-/m1/s1 ChemAxon inchikey IIMFLKINUHKKSA-DIPNUNPCSA-N ChemAxon polar_surface_area 119.36 ChemAxon refractivity 199.21 ChemAxon polarizability 85.8 ChemAxon rotatable_bond_count 38 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon HMDB07863 #<Reference:0x000055ce31f8be98> #<Reference:0x000055ce31f8bce0> 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 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 2-acylglycerol O-acyltransferase 2 Q3SYC2 MOGAT2 Diacylglycerol kinase, epsilon 64kDa A1L4Q0 DGKE Lipid phosphate phosphatase-related protein type 4 Q7Z2D5 LPPR4 Lipid phosphate phosphatase-related protein type 5 Q32ZL2 LPPR5 Lysocardiolipin acyltransferase 1 Q6UWP7 LCLAT1 Phosphatidate cytidylyltransferase 2 O95674 CDS2 Phosphatidate phosphatase PPAPDC1A Q5VZY2 PPAPDC1A Phosphatidate phosphatase PPAPDC1B Q8NEB5 PPAPDC1B Phosphatidylinositol-glycan-specific phospholipase D P80108 GPLD1 Phospholipase D2 O14939 PLD2 Phospholipase DDHD1 Q8NEL9 DDHD1 Phospholipase DDHD2 O94830 DDHD2 Presqualene diphosphate phosphatase Q8IY26 PPAPDC2 Probable lipid phosphate phosphatase PPAPDC3 Q8NBV4 PPAPDC3