2.02012-08-13 14:57:50 -06002015-09-17 16:24:41 -0600ECMDB21622M2MDB002016PE(17:0cycw7c/10:0)PE(17:0cycw7c/10:0) is a phosphatidylethanolamine. It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms. PE(17:0cycw7c/10:0), in particular, consists of one heptadec-9-10-cyclo-anoyl chain to the C-1 atom, and one decanoyl to the C-2 atom. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.1-heptadec-9-10-cyclo-anoyl-2-decanoyl-sn-glycero-3-phosphoethanolamine1-heptadec-cyclopropanol-2-decanoyl-sn-glycero-3-phosphoethanolamine1-NULL-2-decanoyl-sn-glycero-3-phosphoethanolamineGPEtn(17:0/10:0)GPEtn(27:0)PE(17:0/10:0)PE(27:0)Phophatidylethanolamine(17:0/10:0)Phophatidylethanolamine(27:0)C32H62NO8P619.8103619.421304477(2-aminoethoxy)[(2R)-2-(decanoyloxy)-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy]phosphinic acid2-aminoethoxy((2R)-2-(decanoyloxy)-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy)phosphinic acidCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCCCC)COP(O)(=O)OCCNInChI=1S/C32H62NO8P/c1-3-5-7-9-10-13-18-22-32(35)41-30(27-40-42(36,37)39-24-23-33)26-38-31(34)21-17-14-11-12-16-20-29-25-28(29)19-15-8-6-4-2/h28-30H,3-27,33H2,1-2H3,(H,36,37)/t28?,29?,30-/m1/s1PRTXIECJQSCAGA-QGVFFIPKSA-NSolidMembranelogp6.49logs-6.48solubility2.05e-04 g/llogp7.45pka_strongest_acidic1.87pka_strongest_basic10iupac(2-aminoethoxy)[(2R)-2-(decanoyloxy)-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy]phosphinic acidaverage_mass619.8103mono_mass619.421304477smilesCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCCCC)COP(O)(=O)OCCNformulaC32H62NO8PinchiInChI=1S/C32H62NO8P/c1-3-5-7-9-10-13-18-22-32(35)41-30(27-40-42(36,37)39-24-23-33)26-38-31(34)21-17-14-11-12-16-20-29-25-28(29)19-15-8-6-4-2/h28-30H,3-27,33H2,1-2H3,(H,36,37)/t28?,29?,30-/m1/s1inchikeyPRTXIECJQSCAGA-QGVFFIPKSA-Npolar_surface_area134.38refractivity166.09polarizability72.7rotatable_bond_count32acceptor_count5donor_count2physiological_charge0formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis IPHOSLIPSYN-PWYSpecdb::CMs1087330Specdb::EiMs2174Specdb::NmrOneD320751Specdb::NmrOneD320752Specdb::NmrOneD320753Specdb::NmrOneD320754Specdb::NmrOneD320755Specdb::NmrOneD320756Specdb::NmrOneD320757Specdb::NmrOneD320758Specdb::NmrOneD320759Specdb::NmrOneD320760Specdb::NmrOneD320761Specdb::NmrOneD320762Specdb::NmrOneD320763Specdb::NmrOneD320764Specdb::NmrOneD320765Specdb::NmrOneD320766Specdb::NmrOneD320767Specdb::NmrOneD320768Specdb::NmrOneD320769Specdb::NmrOneD320770Specdb::MsMs27527Specdb::MsMs27528Specdb::MsMs27529Specdb::MsMs34085Specdb::MsMs34086Specdb::MsMs34087Keseler, 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-D114.22080510De Siervo, A. J. (1969). "Alterations in the phospholipid composition of Escherichia coli B during growth at different temperatures." J Bacteriol 100:1342-1349.4902814Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.APhosphatidylserine decarboxylase proenzymeP0A8K1PSD_ECOLIpsdhttp://ecmdb.ca/proteins/P0A8K1.xmlBifunctional protein aasP31119AAS_ECOLIaashttp://ecmdb.ca/proteins/P31119.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