1.0 2011-09-21 01:09:37 UTC 2015-07-21 06:58:44 UTC FDB026373 PE(18:3(9Z,12Z,15Z)/P-18:1(9Z)) PE(18:3(9Z,12Z,15Z)/P-18:1(9Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines 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. PE(18:3(9Z,12Z,15Z)/P-18:1(9Z)), in particular, consists of one chain of a-linolenic acid at the C-1 position and one chain of plasmalogen 18:1n9 at the C-2 position. The a-linolenic acid moiety is derived from seed oils, especially canola and soybean oil, while the plasmalogen 18:1n9 moiety is derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. [HMDB] 1-a-Linolenoyl-2-(1-enyl-oleoyl)-sn-glycero-3-oethanolamine 1-a-linolenoyl-2-(1-enyl-oleoyl)-sn-glycero-3-phosphoethanolamine 1-alpha-Linolenoyl-2-(1-enyl-oleoyl)-sn-glycero-3-oethanolamine 1-alpha-linolenoyl-2-(1-enyl-oleoyl)-sn-glycero-3-phosphoethanolamine C41H74NO7P 724.0025 723.520290239 (2-aminoethoxy)[(2R)-2-(octadeca-1,9-dien-1-yloxy)-3-(octadeca-9,12,15-trienoyloxy)propoxy]phosphinic acid 2-aminoethoxy(2R)-2-(octadeca-1,9-dien-1-yloxy)-3-(octadeca-9,12,15-trienoyloxy)propoxyphosphinic acid [H][C@@](COC(=O)CCCCCCCC=CCC=CCC=CCC)(COP(O)(=O)OCCN)OC=CCCCCCCC=CCCCCCCCC InChI=1S/C41H74NO7P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-36-46-40(39-49-50(44,45)48-37-35-42)38-47-41(43)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h6,8,12,14,17-20,33,36,40H,3-5,7,9-11,13,15-16,21-32,34-35,37-39,42H2,1-2H3,(H,44,45)/t40-/m1/s1 WMZLOYMIIRLLCB-RRHRGVEJSA-N belongs to the class of organic compounds known as glycerophosphoethanolamines. These are glycerolipids characterized by an ethanolamine ester of glycerophosphoric acid. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms. Glycerophosphoethanolamines Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphoethanolamines Aliphatic acyclic compounds Amino acids and derivatives Carbonyl compounds Carboxylic acid esters Dialkyl phosphates Fatty acid esters Glycerol vinyl ethers Hydrocarbon derivatives Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Phosphoethanolamines Aliphatic acyclic compound Alkyl phosphate Amine Amino acid or derivatives Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dialkyl phosphate Fatty acid ester Fatty acyl Glycerol vinyl ether Hydrocarbon derivative Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organonitrogen compound Organooxygen compound Organopnictogen compound Phosphoethanolamine Phosphoric acid ester Primary aliphatic amine Primary amine Sn-glycero-3-phosphoethanolamine Solid logp 9.02 ALOGPS logs -6.95 ALOGPS solubility 8.11e-05 g/l ALOGPS logp 11.17 ChemAxon pka_strongest_acidic 1.87 ChemAxon pka_strongest_basic 10 ChemAxon iupac (2-aminoethoxy)[(2R)-2-(octadeca-1,9-dien-1-yloxy)-3-(octadeca-9,12,15-trienoyloxy)propoxy]phosphinic acid ChemAxon average_mass 724.0025 ChemAxon mono_mass 723.520290239 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCC=CCC=CCC=CCC)(COP(O)(=O)OCCN)OC=CCCCCCCC=CCCCCCCCC ChemAxon formula C41H74NO7P ChemAxon inchi InChI=1S/C41H74NO7P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-36-46-40(39-49-50(44,45)48-37-35-42)38-47-41(43)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h6,8,12,14,17-20,33,36,40H,3-5,7,9-11,13,15-16,21-32,34-35,37-39,42H2,1-2H3,(H,44,45)/t40-/m1/s1 ChemAxon inchikey WMZLOYMIIRLLCB-RRHRGVEJSA-N ChemAxon polar_surface_area 117.31 ChemAxon refractivity 214.21 ChemAxon polarizability 89.63 ChemAxon rotatable_bond_count 38 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB09183 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 Abhydrolase domain-containing protein 4 Q8TB40 ABHD4 Phosphatidylethanolamine-binding protein 1 P30086 PEBP1 Phosphatidylethanolamine-binding protein 4 Q96S96 PEBP4 Phosphatidylserine decarboxylase proenzyme Q9UG56 PISD Phospholipase D2 O14939 PLD2 Phospholipase D3 Q8IV08 PLD3 Phospholipase D4 Q96BZ4 PLD4