1.0 2011-09-21 01:32:09 UTC 2015-07-21 06:59:17 UTC FDB027930 PA(P-16:0e/18:2(9Z,12Z)) 2-(9Z,12Z-octadecadienoyl)-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. 2-(9Z,12Z-octadecadienoyl)-1-(1Z-hexadecenyl)-sn-glycero-3-phosphate is irreversibly produced from 2-(9Z,12Z-octadecadienoyl)-1-(1Z-hexadecenyl))-sn-glycero-3-phosphoethanolamine via the enzyme phospholipase D (EC: 3.1.4.4). 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] 2-(9Z,12Z-Octadecadienoyl)-1-(1Z-hexadecenyl)-sn-glycero-3-ate 2-(9Z,12Z-octadecadienoyl)-1-(1Z-hexadecenyl)-sn-glycero-3-phosphate C37H69O7P 656.9133 656.478091074 [(2R)-3-(hexadec-1-en-1-yloxy)-2-(octadeca-9,12-dienoyloxy)propoxy]phosphonic acid (2R)-3-(hexadec-1-en-1-yloxy)-2-(octadeca-9,12-dienoyloxy)propoxyphosphonic acid [H][C@@](COC=CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCC=CCC=CCCCCC InChI=1S/C37H69O7P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-37(38)44-36(35-43-45(39,40)41)34-42-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11,13,17,19,31,33,36H,3-10,12,14-16,18,20-30,32,34-35H2,1-2H3,(H2,39,40,41)/t36-/m1/s1 OLCTYLMZTXKGKH-PSXMRANNSA-N belongs to the class of organic compounds known as 1-(1z-alkenyl),2-acyl-glycerophosphates. These are glycerophosphates that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one 1Z-alkenyl chain attached through an ether linkage at the O1-position. 1-(1Z-alkenyl),2-acyl-glycerophosphates Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acid esters Fatty acid esters Glycerol vinyl ethers Hydrocarbon derivatives Monoalkyl phosphates Monocarboxylic acids and derivatives Organic oxides 1-(1z-alkenyl),2-acyl-glycerol-3-phosphate Aliphatic acyclic compound Alkyl phosphate Carbonyl group Carboxylic acid derivative Carboxylic acid ester Fatty acid ester Fatty acyl Glycerol vinyl ether Hydrocarbon derivative Monoalkyl phosphate Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organooxygen compound Phosphoric acid ester Solid logp 9.27 ALOGPS logs -6.90 ALOGPS solubility 8.32e-05 g/l ALOGPS logp 12.44 ChemAxon pka_strongest_acidic 1.32 ChemAxon pka_strongest_basic -4.7 ChemAxon iupac [(2R)-3-(hexadec-1-en-1-yloxy)-2-(octadeca-9,12-dienoyloxy)propoxy]phosphonic acid ChemAxon average_mass 656.9133 ChemAxon mono_mass 656.478091074 ChemAxon smiles [H][C@@](COC=CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCC=CCC=CCCCCC ChemAxon formula C37H69O7P ChemAxon inchi InChI=1S/C37H69O7P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-37(38)44-36(35-43-45(39,40)41)34-42-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11,13,17,19,31,33,36H,3-10,12,14-16,18,20-30,32,34-35H2,1-2H3,(H2,39,40,41)/t36-/m1/s1 ChemAxon inchikey OLCTYLMZTXKGKH-PSXMRANNSA-N ChemAxon polar_surface_area 102.29 ChemAxon refractivity 190.35 ChemAxon polarizability 82.48 ChemAxon rotatable_bond_count 35 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon HMDB11155 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 Lipid phosphate phosphatase-related protein type 4 Q7Z2D5 LPPR4 Lipid phosphate phosphatase-related protein type 5 Q32ZL2 LPPR5 Lysocardiolipin acyltransferase 1 Q6UWP7 LCLAT1 Phosphatidate phosphatase PPAPDC1A Q5VZY2 PPAPDC1A Phosphatidate phosphatase PPAPDC1B Q8NEB5 PPAPDC1B Phospholipase D2 O14939 PLD2 Phospholipase DDHD1 Q8NEL9 DDHD1 Phospholipase DDHD2 O94830 DDHD2 Presqualene diphosphate phosphatase Q8IY26 PPAPDC2 Probable lipid phosphate phosphatase PPAPDC3 Q8NBV4 PPAPDC3