2.02012-05-31 14:20:20 -06002015-06-03 17:19:01 -0600ECMDB11155M2MDB000815PA(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. 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.2-(9Z,12Z-Octadecadienoyl)-1-(1Z-hexadecenyl)-sn-glycero-3-phosphate2-(9Z,12Z-Octadecadienoyl)-1-(1Z-hexadecenyl)-sn-glycero-3-phosphoric acidC37H69O7P656.9133656.478091074[(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphonic acid(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphonic acidCCCCCCCCCCCCCC\C=C/OC[C@]([H])(COP(=O)(O)O)OC(=O)CCCCCCC\C=C/C\C=C/CCCCCInChI=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)/b13-11-,19-17-,33-31-/t36-/m1/s1OLCTYLMZTXKGKH-BBNWHMLASA-NSolidInner membraneMembraneOuter membranelogp9.27logs-6.90solubility8.32e-05 g/llogp12.44pka_strongest_acidic1.32pka_strongest_basic-4.7iupac[(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphonic acidaverage_mass656.9133mono_mass656.478091074smilesCCCCCCCCCCCCCC\C=C/OC[C@]([H])(COP(=O)(O)O)OC(=O)CCCCCCC\C=C/C\C=C/CCCCCformulaC37H69O7PinchiInChI=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)/b13-11-,19-17-,33-31-/t36-/m1/s1inchikeyOLCTYLMZTXKGKH-BBNWHMLASA-Npolar_surface_area102.29refractivity190.35polarizability79.89rotatable_bond_count35acceptor_count5donor_count2physiological_charge-2formal_charge0Specdb::CMs16361Specdb::NmrOneD335278Specdb::NmrOneD335279Specdb::NmrOneD335280Specdb::NmrOneD335281Specdb::NmrOneD335282Specdb::NmrOneD335283Specdb::NmrOneD335284Specdb::NmrOneD335285Specdb::NmrOneD335286Specdb::NmrOneD335287Specdb::NmrOneD335288Specdb::NmrOneD335289Specdb::NmrOneD335290Specdb::NmrOneD335291Specdb::NmrOneD335292Specdb::NmrOneD335293Specdb::NmrOneD335294Specdb::NmrOneD335295Specdb::NmrOneD335296Specdb::NmrOneD335297Specdb::MsMs27023Specdb::MsMs27024Specdb::MsMs27025Specdb::MsMs33581Specdb::MsMs33582Specdb::MsMs33583Specdb::MsMs2456202Specdb::MsMs2456203Specdb::MsMs2456204Specdb::MsMs2478997Specdb::MsMs2478998Specdb::MsMs2478999HMDB1115524766521C15647Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75.22102590Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A1-acyl-sn-glycerol-3-phosphate acyltransferaseP26647PLSC_ECOLIplsChttp://ecmdb.ca/proteins/P26647.xmlProtein crcAP37001CRCA_ECOLIcrcAhttp://ecmdb.ca/proteins/P37001.xmlProbable phospholipid ABC transporter-binding protein mlaBP64602MLAB_ECOLImlaBhttp://ecmdb.ca/proteins/P64602.xmlProbable phospholipid ABC transporter-binding protein mlaDP64604MLAD_ECOLImlaDhttp://ecmdb.ca/proteins/P64604.xmlProbable phospholipid ABC transporter permease protein mlaEP64606MLAE_ECOLImlaEhttp://ecmdb.ca/proteins/P64606.xml