2.0 2012-05-31 14:20:20 -0600 2015-06-03 17:19:01 -0600 ECMDB11155 M2MDB000815 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. 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-phosphate 2-(9Z,12Z-Octadecadienoyl)-1-(1Z-hexadecenyl)-sn-glycero-3-phosphoric acid C37H69O7P 656.9133 656.478091074 [(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 acid CCCCCCCCCCCCCC\C=C/OC[C@]([H])(COP(=O)(O)O)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC 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)/b13-11-,19-17-,33-31-/t36-/m1/s1 OLCTYLMZTXKGKH-BBNWHMLASA-N Solid Inner membrane Membrane Outer membrane 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-[(1Z)-hexadec-1-en-1-yloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphonic acid ChemAxon average_mass 656.9133 ChemAxon mono_mass 656.478091074 ChemAxon smiles CCCCCCCCCCCCCC\C=C/OC[C@]([H])(COP(=O)(O)O)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC 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)/b13-11-,19-17-,33-31-/t36-/m1/s1 ChemAxon inchikey OLCTYLMZTXKGKH-BBNWHMLASA-N ChemAxon polar_surface_area 102.29 ChemAxon refractivity 190.35 ChemAxon polarizability 79.89 ChemAxon rotatable_bond_count 35 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 16361 Specdb::NmrOneD 335278 Specdb::NmrOneD 335279 Specdb::NmrOneD 335280 Specdb::NmrOneD 335281 Specdb::NmrOneD 335282 Specdb::NmrOneD 335283 Specdb::NmrOneD 335284 Specdb::NmrOneD 335285 Specdb::NmrOneD 335286 Specdb::NmrOneD 335287 Specdb::NmrOneD 335288 Specdb::NmrOneD 335289 Specdb::NmrOneD 335290 Specdb::NmrOneD 335291 Specdb::NmrOneD 335292 Specdb::NmrOneD 335293 Specdb::NmrOneD 335294 Specdb::NmrOneD 335295 Specdb::NmrOneD 335296 Specdb::NmrOneD 335297 Specdb::MsMs 27023 Specdb::MsMs 27024 Specdb::MsMs 27025 Specdb::MsMs 33581 Specdb::MsMs 33582 Specdb::MsMs 33583 Specdb::MsMs 2456202 Specdb::MsMs 2456203 Specdb::MsMs 2456204 Specdb::MsMs 2478997 Specdb::MsMs 2478998 Specdb::MsMs 2478999 HMDB11155 24766521 C15647 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