1.0 2011-09-21 01:32:08 UTC 2015-07-21 06:59:17 UTC FDB027929 LPA(P-16:0e/0:0) 1-(1Z-hexadecenyl)-sn-glycero-3-phosphate is an intermediate of ether lipid metabolism. 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. 1-(1Z-hexadecenyl)-sn-glycero-3-phosphate is irreversibly produced from 1-(1Z-hexadecenyl)-sn-glycero-3-phosphoethanolamine via the enzyme alkylglycerophosphoethanolamine phosphodiesterase (EC: 3.1.4.39). 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-ate 1-(1Z-hexadecenyl)-sn-glycero-3-phosphate LysoPA(dm16:0e) C19H39O6P 394.4831 394.248425492 [(2R)-3-(hexadec-1-en-1-yloxy)-2-hydroxypropoxy]phosphonic acid (2R)-3-(hexadec-1-en-1-yloxy)-2-hydroxypropoxyphosphonic acid [H][C@@](O)(COC=CCCCCCCCCCCCCCC)COP(O)(O)=O InChI=1S/C19H39O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-24-17-19(20)18-25-26(21,22)23/h15-16,19-20H,2-14,17-18H2,1H3,(H2,21,22,23)/t19-/m1/s1 LBGSRVIXIVDRQM-LJQANCHMSA-N This compound belongs to the class of organic compounds known as glycerophospholipids. These are derivatives of glycerophosphoric acid that contains at least one O-acyl, or O-alkyl, or O-(1-alkenyl) group attached to the glycerol residue. Glycerophospholipids Organic compounds Lipids and lipid-like molecules Glycerophospholipids Aliphatic acyclic compounds Glycerol vinyl ethers Glycerophosphates Hydrocarbon derivatives Monoalkyl phosphates Organic phosphoric acids Secondary alcohols Alcohol Aliphatic acyclic compound Alkyl phosphate Glycerol vinyl ether Glycerophospholipid Hydrocarbon derivative Monoalkyl phosphate Organic phosphate Organic phosphoric acid derivative Organooxygen compound Phosphoric acid ester Secondary alcohol Sn-glycerol-3-phosphate Solid logp 4.81 ALOGPS logs -5.08 ALOGPS solubility 3.26e-03 g/l ALOGPS logp 5.35 ChemAxon pka_strongest_acidic 1.51 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [(2R)-3-(hexadec-1-en-1-yloxy)-2-hydroxypropoxy]phosphonic acid ChemAxon average_mass 394.4831 ChemAxon mono_mass 394.248425492 ChemAxon smiles [H][C@@](O)(COC=CCCCCCCCCCCCCCC)COP(O)(O)=O ChemAxon formula C19H39O6P ChemAxon inchi InChI=1S/C19H39O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-24-17-19(20)18-25-26(21,22)23/h15-16,19-20H,2-14,17-18H2,1H3,(H2,21,22,23)/t19-/m1/s1 ChemAxon inchikey LBGSRVIXIVDRQM-LJQANCHMSA-N ChemAxon polar_surface_area 96.22 ChemAxon refractivity 105.32 ChemAxon polarizability 46.5 ChemAxon rotatable_bond_count 19 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon HMDB11154 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 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