2.0 2012-05-31 14:13:40 -0600 2015-09-14 11:19:22 -0600 ECMDB09019 M2MDB000763 PE(18:1(11Z)/14:0) PE(18:1(11Z)/14:0) 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(18:1(11Z)/14:0), in particular, consists of one 11Z-octadecenoyl chain to the C-1 atom, and one tetradecanoyl 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-(11Z-octadecenoyl)-2-tetradecanoyl-sn-glycero-3-phosphoethanolamine 1-phosphatidylethanolamine 1-Vaccenoyl-2-myristoyl-sn-glycero-3-phosphoethanolamine <i>O</i>-(1-β-acyl-2-acyl-<i>sn</i>-glycero-3-phospho)-ethanolamine A 1-phosphatidylethanolamine A phosphatidylethenolamine An L-1-phosphotidylethanolamine Glycerophosphoethanolamine GPEtn(18:1/14:0) GPEtn(18:1n7/14:0) GPEtn(18:1w7/14:0) GPEtn(32:1) L-1-phosphotidylethanolamine O-(1-β-acyl-2-acyl-sn-glycero-3-phospho)-ethanolamine PE(18:1/14:0) PE(18:1n7/14:0) PE(18:1w7/14:0) PE(32:1) Phophatidylethanolamine(18:1/14:0) Phophatidylethanolamine(18:1n7/14:0) Phophatidylethanolamine(18:1w7/14:0) Phophatidylethanolamine(32:1) Phosphatidylethanolamine Phosphatidylethanolamine (ecoli) PtdEtn C37H72NO8P 689.9432 689.499554797 (2-aminoethoxy)[(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-(tetradecanoyloxy)propoxy]phosphinic acid 2-aminoethoxy((2R)-3-[(11Z)-octadec-11-enoyloxy]-2-(tetradecanoyloxy)propoxy)phosphinic acid [H][C@@](COC(=O)CCCCCCCCC\C=C/CCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCC InChI=1S/C37H72NO8P/c1-3-5-7-9-11-13-15-16-17-18-20-21-23-25-27-29-36(39)43-33-35(34-45-47(41,42)44-32-31-38)46-37(40)30-28-26-24-22-19-14-12-10-8-6-4-2/h13,15,35H,3-12,14,16-34,38H2,1-2H3,(H,41,42)/b15-13-/t35-/m1/s1 ONLSYXWRWGUPKV-JUOLSMOWSA-N Solid Inner membrane Membrane Outer membrane logp 7.99 ALOGPS logs -6.84 ALOGPS solubility 9.94e-05 g/l ALOGPS logp 10.09 ChemAxon pka_strongest_acidic 1.87 ChemAxon pka_strongest_basic 10 ChemAxon iupac (2-aminoethoxy)[(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-(tetradecanoyloxy)propoxy]phosphinic acid ChemAxon average_mass 689.9432 ChemAxon mono_mass 689.499554797 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCCC\C=C/CCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCC ChemAxon formula C37H72NO8P ChemAxon inchi InChI=1S/C37H72NO8P/c1-3-5-7-9-11-13-15-16-17-18-20-21-23-25-27-29-36(39)43-33-35(34-45-47(41,42)44-32-31-38)46-37(40)30-28-26-24-22-19-14-12-10-8-6-4-2/h13,15,35H,3-12,14,16-34,38H2,1-2H3,(H,41,42)/b15-13-/t35-/m1/s1 ChemAxon inchikey ONLSYXWRWGUPKV-JUOLSMOWSA-N ChemAxon polar_surface_area 134.38 ChemAxon refractivity 192.12 ChemAxon polarizability 84.09 ChemAxon rotatable_bond_count 38 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis (CL(19:0/18:1(11Z)/14:0/14:0)) Phospholipids are membrane components in E. coli. The major phospholipids of E. coli are phosphatidylethanolamine, phosphatidylglycerol and cardiolipin. All phospholipids contain sn-glycerol-3-phosphate esterified with fatty acids at the sn-1 and sn-2 positions. The reaction starts from a glycerone phosphate (dihydroxyacetone phosphate) produced in glycolysis. The glycerone phosphate is transformed to a sn-glycerol 3-phosphate (glycerol 3 phosphate) by NADPH driven glycerol-3-phosphate dehydrogenase. Sn-glycerol 3-phosphate is transformed to a 1-acyl-sn-glycerol 3-phosphate(1-oleyl-2-lyso-phosphatidate , 1-palmitoylglycerol 3-phosphate , 1-stearoyl-sn-glycerol 3-phosphate). This can be achieve by a sn-glycerol-3-phosphate 1-0-acyltransferase that interacts either with a long-chain acyl-CoA or with an acyl-[acp]. The 1-acyl-sn-glycerol 3-phosphate is transformed into a 1,2-diacyl-sn-glycerol 3-phosphate through a 1-acylglycerol-3-phosphate O-acyltransferase. This compound is then converted into a CPD-diacylglycerol through a CTP (phosphatidate cytididyltransferase. CPD-diacylglycerol can be transformed either to a L-1-phosphatidylserine or a L-1-phosphatidylglycerol-phosphate through a phosphatidylserine synthase or a phosphatidylglycerophosphate synthase respectively. The L-1-phosphatidylserine transforms into L-1-phosphatidylethanolamine through a phosphatidylserine decarboxylase, o the other hand L-1-phosphatidylglycerol-phosphate gets transformed into a L-1-phosphatidyl-glycerol through a phosphatidylglycerophosphatase. These 2 products combines produce a cardiolipin and a ethanolamine. The L-1 phosphatidyl-glycerol can also interact with cardiolipin synthase resulting in a glycerol and a cardiolipin. PW001986 Metabolic phosphatidylethanolamine biosynthesis I PWY-5669 phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::CMs 229693 Specdb::NmrOneD 332238 Specdb::NmrOneD 332239 Specdb::NmrOneD 332240 Specdb::NmrOneD 332241 Specdb::NmrOneD 332242 Specdb::NmrOneD 332243 Specdb::NmrOneD 332244 Specdb::NmrOneD 332245 Specdb::NmrOneD 332246 Specdb::NmrOneD 332247 Specdb::NmrOneD 332248 Specdb::NmrOneD 332249 Specdb::NmrOneD 332250 Specdb::NmrOneD 332251 Specdb::NmrOneD 332252 Specdb::NmrOneD 332253 Specdb::NmrOneD 332254 Specdb::NmrOneD 332255 Specdb::NmrOneD 332256 Specdb::NmrOneD 332257 Specdb::MsMs 27956 Specdb::MsMs 27957 Specdb::MsMs 27958 Specdb::MsMs 34514 Specdb::MsMs 34515 Specdb::MsMs 34516 Specdb::MsMs 2506858 Specdb::MsMs 2506859 Specdb::MsMs 2506860 Specdb::MsMs 2803270 Specdb::MsMs 2803271 Specdb::MsMs 2803272 Specdb::MsMs 2879510 Specdb::MsMs 2879511 Specdb::MsMs 2879512 HMDB09019 24768492 C00350 L-1-PHOSPHATIDYL-ETHANOLAMINE Lecithin 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 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 Phosphatidylserine decarboxylase proenzyme P0A8K1 PSD_ECOLI psd http://ecmdb.ca/proteins/P0A8K1.xml Bifunctional protein aas P31119 AAS_ECOLI aas http://ecmdb.ca/proteins/P31119.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 PS(18:1(11Z)/14:0) + Hydrogen ion > Carbon dioxide + PE(18:1(11Z)/14:0) PW_R003208