2.0 2012-05-31 14:20:17 -0600 2015-06-03 17:19:01 -0600 ECMDB11145 M2MDB000814 PA(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-phosphate 2-Octadecanoyl-1-hexadecyl-sn-glycero-3-phosphoric acid PA(O-16:0/18:0) C37H75O7P 662.961 662.525041266 [(2R)-3-(hexadecyloxy)-2-(octadecanoyloxy)propoxy]phosphonic acid (2R)-3-(hexadecyloxy)-2-(octadecanoyloxy)propoxyphosphonic acid [H][C@@](COCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCC InChI=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/s1 BIMPCBJDAYKNLD-PSXMRANNSA-N Solid Inner membrane Membrane Outer membrane logp 9.40 ALOGPS logs -6.90 ALOGPS solubility 8.40e-05 g/l ALOGPS logp 13.15 ChemAxon pka_strongest_acidic 1.32 ChemAxon pka_strongest_basic -4.1 ChemAxon iupac [(2R)-3-(hexadecyloxy)-2-(octadecanoyloxy)propoxy]phosphonic acid ChemAxon average_mass 662.961 ChemAxon mono_mass 662.525041266 ChemAxon smiles [H][C@@](COCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCC ChemAxon formula C37H75O7P ChemAxon inchi InChI=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/s1 ChemAxon inchikey BIMPCBJDAYKNLD-PSXMRANNSA-N ChemAxon polar_surface_area 102.29 ChemAxon refractivity 188.02 ChemAxon polarizability 84.19 ChemAxon rotatable_bond_count 38 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::CMs 10105 Specdb::NmrOneD 339048 Specdb::NmrOneD 339049 Specdb::NmrOneD 339050 Specdb::NmrOneD 339051 Specdb::NmrOneD 339052 Specdb::NmrOneD 339053 Specdb::NmrOneD 339054 Specdb::NmrOneD 339055 Specdb::NmrOneD 339056 Specdb::NmrOneD 339057 Specdb::NmrOneD 339058 Specdb::NmrOneD 339059 Specdb::NmrOneD 339060 Specdb::NmrOneD 339061 Specdb::NmrOneD 339062 Specdb::NmrOneD 339063 Specdb::NmrOneD 339064 Specdb::NmrOneD 339065 Specdb::NmrOneD 339066 Specdb::NmrOneD 339067 Specdb::MsMs 23393 Specdb::MsMs 23394 Specdb::MsMs 23395 Specdb::MsMs 30191 Specdb::MsMs 30192 Specdb::MsMs 30193 Specdb::MsMs 3044236 Specdb::MsMs 3044237 Specdb::MsMs 3044238 Specdb::MsMs 3098842 Specdb::MsMs 3098843 Specdb::MsMs 3098844 HMDB11145 24766519 Keseler, 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. 21097882 Kanehisa, 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. 22080510 Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. 22102590 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A 1-acyl-sn-glycerol-3-phosphate acyltransferase P26647 PLSC_ECOLI plsC http://ecmdb.ca/proteins/P26647.xml Protein crcA P37001 CRCA_ECOLI crcA http://ecmdb.ca/proteins/P37001.xml Probable phospholipid ABC transporter-binding protein mlaB P64602 MLAB_ECOLI mlaB http://ecmdb.ca/proteins/P64602.xml Probable phospholipid ABC transporter-binding protein mlaD P64604 MLAD_ECOLI mlaD http://ecmdb.ca/proteins/P64604.xml Probable phospholipid ABC transporter permease protein mlaE P64606 MLAE_ECOLI mlaE http://ecmdb.ca/proteins/P64606.xml