2.02012-05-31 14:20:17 -06002015-06-03 17:19:01 -0600ECMDB11145M2MDB000814PA(16:0e/18:0)2-octadecanoyl-1-hexadecyl-sn-glycero-3-phosphate is an intermediate in ether lipid metabolism. 2-octadecanoyl-1-hexadecyl-sn-glycero-3-phosphate is converted from 1-octadecyl-glycerone-3-phosphate via 1-acylglycerol-3-phosphate O-acyltransferase. (EC: 2.3.1.51) 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. Ether lipids are called plasmalogens (1-O-1'-alkenyl-2-acylglycerophospholipids) if these are glycerol-containing phospholipids with an unsaturated O-(1-alkenyl) (vinyl ether) group at the first position on the glycerol chain. Plasmalogens as well as some 1-O-alkyl lipids are ubiquitous and sometimes major parts of the cell membranes in mammals and anaerobic bacteria. In archaea, ether lipids are the major polar lipids in the cell envelope and their abundance is one of the major characteristics that separate this group of prokaryotes from the bacteria. In these cells, diphytanylglycerolipids or bipolar macrocyclic tetraethers can form covalently linked bilayers.2-Octadecanoyl-1-hexadecyl-sn-glycero-3-phosphate2-Octadecanoyl-1-hexadecyl-sn-glycero-3-phosphoric acidPA(O-16:0/18:0)C37H75O7P662.961662.525041266[(2R)-3-(hexadecyloxy)-2-(octadecanoyloxy)propoxy]phosphonic acid(2R)-3-(hexadecyloxy)-2-(octadecanoyloxy)propoxyphosphonic acid[H][C@@](COCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCCInChI=1S/C37H75O7P/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/h36H,3-35H2,1-2H3,(H2,39,40,41)/t36-/m1/s1BIMPCBJDAYKNLD-PSXMRANNSA-NSolidInner membraneMembraneOuter membranelogp9.40logs-6.90solubility8.40e-05 g/llogp13.15pka_strongest_acidic1.32pka_strongest_basic-4.1iupac[(2R)-3-(hexadecyloxy)-2-(octadecanoyloxy)propoxy]phosphonic acidaverage_mass662.961mono_mass662.525041266smiles[H][C@@](COCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCCformulaC37H75O7PinchiInChI=1S/C37H75O7P/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/h36H,3-35H2,1-2H3,(H2,39,40,41)/t36-/m1/s1inchikeyBIMPCBJDAYKNLD-PSXMRANNSA-Npolar_surface_area102.29refractivity188.02polarizability84.19rotatable_bond_count38acceptor_count5donor_count2physiological_charge-2formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis IPHOSLIPSYN-PWYSpecdb::CMs10105Specdb::NmrOneD339048Specdb::NmrOneD339049Specdb::NmrOneD339050Specdb::NmrOneD339051Specdb::NmrOneD339052Specdb::NmrOneD339053Specdb::NmrOneD339054Specdb::NmrOneD339055Specdb::NmrOneD339056Specdb::NmrOneD339057Specdb::NmrOneD339058Specdb::NmrOneD339059Specdb::NmrOneD339060Specdb::NmrOneD339061Specdb::NmrOneD339062Specdb::NmrOneD339063Specdb::NmrOneD339064Specdb::NmrOneD339065Specdb::NmrOneD339066Specdb::NmrOneD339067Specdb::MsMs23393Specdb::MsMs23394Specdb::MsMs23395Specdb::MsMs30191Specdb::MsMs30192Specdb::MsMs30193Specdb::MsMs3044236Specdb::MsMs3044237Specdb::MsMs3044238Specdb::MsMs3098842Specdb::MsMs3098843Specdb::MsMs3098844HMDB1114524766519Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, 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