1.02011-09-21 01:07:21 UTC2015-07-21 06:58:41 UTCFDB026207PE(18:0/P-18:1(11Z))PE(18:0/P-18:1(11Z)) 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(18:0/P-18:1(11Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of plasmalogen 18:1n7 at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the plasmalogen 18:1n7 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-Stearoyl-2-(1-enyl-vaccenoyl)-sn-glycero-3-oethanolamine1-stearoyl-2-(1-enyl-vaccenoyl)-sn-glycero-3-phosphoethanolamineC41H80NO7P730.0502729.567240431(2-aminoethoxy)[(2R)-2-(octadeca-1,11-dien-1-yloxy)-3-(octadecanoyloxy)propoxy]phosphinic acid2-aminoethoxy(2R)-2-(octadeca-1,11-dien-1-yloxy)-3-(octadecanoyloxy)propoxyphosphinic acid[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC=CCCCCCCCCC=CCCCCCCInChI=1S/C41H80NO7P/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/h13,15,33,36,40H,3-12,14,16-32,34-35,37-39,42H2,1-2H3,(H,44,45)/t40-/m1/s1XJRBLUARQNXNQS-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.GlycerophosphoethanolaminesOrganic compoundsLipids and lipid-like moleculesGlycerophospholipidsGlycerophosphoethanolaminesAliphatic acyclic compoundsAmino acids and derivativesCarbonyl compoundsCarboxylic acid estersDialkyl phosphatesFatty acid estersGlycerol vinyl ethersHydrocarbon derivativesMonoalkylaminesMonocarboxylic acids and derivativesOrganic oxidesOrganopnictogen compoundsPhosphoethanolaminesAliphatic acyclic compoundAlkyl phosphateAmineAmino acid or derivativesCarbonyl groupCarboxylic acid derivativeCarboxylic acid esterDialkyl phosphateFatty acid esterFatty acylGlycerol vinyl etherHydrocarbon derivativeMonocarboxylic acid or derivativesOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganic phosphoric acid derivativeOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPhosphoethanolaminePhosphoric acid esterPrimary aliphatic aminePrimary amineSn-glycero-3-phosphoethanolamineSolidlogp9.33logs-7.10solubility5.80e-05 g/llogp12.26pka_strongest_acidic1.87pka_strongest_basic10iupac(2-aminoethoxy)[(2R)-2-(octadeca-1,11-dien-1-yloxy)-3-(octadecanoyloxy)propoxy]phosphinic acidaverage_mass730.0502mono_mass729.567240431smiles[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC=CCCCCCCCCC=CCCCCCCformulaC41H80NO7PinchiInChI=1S/C41H80NO7P/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/h13,15,33,36,40H,3-12,14,16-32,34-35,37-39,42H2,1-2H3,(H,44,45)/t40-/m1/s1inchikeyXJRBLUARQNXNQS-RRHRGVEJSA-Npolar_surface_area117.31refractivity210.86polarizability92.1rotatable_bond_count41acceptor_count5donor_count2physiological_charge0formal_charge0HMDB09017AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823Abhydrolase domain-containing protein 4Q8TB40ABHD4Phosphatidylethanolamine-binding protein 1P30086PEBP1Phosphatidylethanolamine-binding protein 4Q96S96PEBP4Phosphatidylserine decarboxylase proenzymeQ9UG56PISDPhospholipase D2O14939PLD2Phospholipase D3Q8IV08PLD3Phospholipase D4Q96BZ4PLD4