1.0 2011-09-21 01:32:06 UTC 2015-07-21 06:59:17 UTC FDB027927 PE(P-16:0e/0:0) 1-(1Z-hexadecenyl)-sn-glycero-3-phosphoethanolamine is an phospho-ether lipid. Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. 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-(1Z-Hexadecenyl)-sn-glycero-3-oethanolamine 1-(1Z-hexadecenyl)-sn-glycero-3-phosphoethanolamine 2-Azaniumylethyl [(2R)-3-[(e)-hexadec-1-enoxy]-2-hydroxy-propyl] ate 2-azaniumylethyl [(2R)-3-[(E)-hexadec-1-enoxy]-2-hydroxy-propyl] phosphate LysoPE(dm16:0e) C21H44NO6P 437.5509 437.290624657 (2-aminoethoxy)[(2R)-3-(hexadec-1-en-1-yloxy)-2-hydroxypropoxy]phosphinic acid 2-aminoethoxy(2R)-3-(hexadec-1-en-1-yloxy)-2-hydroxypropoxyphosphinic acid [H][C@@](O)(COC=CCCCCCCCCCCCCCC)COP(O)(=O)OCCN InChI=1S/C21H44NO6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17-26-19-21(23)20-28-29(24,25)27-18-16-22/h15,17,21,23H,2-14,16,18-20,22H2,1H3,(H,24,25)/t21-/m1/s1 QYTPGOPLNFESQC-OAQYLSRUSA-N belongs to the class of organic compounds known as 1-(1z-alkenyl)-glycero-3-phosphoethanolamines. These are glycerophosphoglycerophosphates that carry exactly one 1Z-alkenyl chain attached to the glycerol moiety through an ether linkage. 1-(1Z-alkenyl)-glycero-3-phosphoethanolamines Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphoethanolamines Aliphatic acyclic compounds Dialkyl phosphates Glycerol vinyl ethers Hydrocarbon derivatives Monoalkylamines Organic oxides Organopnictogen compounds Phosphoethanolamines Secondary alcohols 1-(1z-alkenyl)-glycero-3-phosphoethanolamine Alcohol Aliphatic acyclic compound Alkyl phosphate Amine Dialkyl phosphate Glycerol vinyl ether Hydrocarbon derivative 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 Secondary alcohol Solid logp 4.63 ALOGPS logs -5.23 ALOGPS solubility 2.57e-03 g/l ALOGPS logp 3.92 ChemAxon pka_strongest_acidic 1.87 ChemAxon pka_strongest_basic 10 ChemAxon iupac (2-aminoethoxy)[(2R)-3-(hexadec-1-en-1-yloxy)-2-hydroxypropoxy]phosphinic acid ChemAxon average_mass 437.5509 ChemAxon mono_mass 437.290624657 ChemAxon smiles [H][C@@](O)(COC=CCCCCCCCCCCCCCC)COP(O)(=O)OCCN ChemAxon formula C21H44NO6P ChemAxon inchi InChI=1S/C21H44NO6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17-26-19-21(23)20-28-29(24,25)27-18-16-22/h15,17,21,23H,2-14,16,18-20,22H2,1H3,(H,24,25)/t21-/m1/s1 ChemAxon inchikey QYTPGOPLNFESQC-OAQYLSRUSA-N ChemAxon polar_surface_area 111.24 ChemAxon refractivity 117.75 ChemAxon polarizability 51.8 ChemAxon rotatable_bond_count 22 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB11152 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