2.0 2012-10-24 09:54:30 -0600 2015-09-14 11:19:53 -0600 ECMDB23514 M2MDB003904 PE(18:1(9Z)/12:0(3-OH)) PE(18:1(9Z)/12:0(3-OH)) 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(9Z)/12:0(3-OH)), in particular, consists of one 9Z-octadecenoyl chain to the C-1 atom, and one 3-hydroxydodecanoyl 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-(9Z-octadecenoyl)-2-3-hydroxydodecanoyl-sn-glycero-3-phosphoethanolamine 1-oleoyl-2-3-hydroxydodecanoyl-sn-glycero-3-phosphoethanolamine GPEtn(18:1/12:0) GPEtn(30:1) PE(18:1/12:0) PE(30:1) Phophatidylethanolamine(18:1/12:0) Phophatidylethanolamine(30:1) C35H68NO9P 677.8895 677.463169291 (2-aminoethoxy)[(2R)-2-[(3-hydroxydodecanoyl)oxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid 2-aminoethoxy((2R)-2-[(3-hydroxydodecanoyl)oxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy)phosphinic acid CCCCCCCCCC(O)CC(=O)O[C@H](COC(=O)CCCCCCC\C=C/CCCCCCCC)COP(O)(=O)OCCN InChI=1S/C35H68NO9P/c1-3-5-7-9-11-12-13-14-15-16-17-18-20-22-24-26-34(38)42-30-33(31-44-46(40,41)43-28-27-36)45-35(39)29-32(37)25-23-21-19-10-8-6-4-2/h14-15,32-33,37H,3-13,16-31,36H2,1-2H3,(H,40,41)/b15-14-/t32?,33-/m1/s1 OONWHZRHFUDHLM-OTWFKUADSA-N Solid Membrane logp 6.54 ALOGPS logs -6.51 ALOGPS solubility 2.09e-04 g/l ALOGPS logp 7.97 ChemAxon pka_strongest_acidic 1.87 ChemAxon pka_strongest_basic 10 ChemAxon iupac (2-aminoethoxy)[(2R)-2-[(3-hydroxydodecanoyl)oxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid ChemAxon average_mass 677.8895 ChemAxon mono_mass 677.463169291 ChemAxon smiles CCCCCCCCCC(O)CC(=O)O[C@H](COC(=O)CCCCCCC\C=C/CCCCCCCC)COP(O)(=O)OCCN ChemAxon formula C35H68NO9P ChemAxon inchi InChI=1S/C35H68NO9P/c1-3-5-7-9-11-12-13-14-15-16-17-18-20-22-24-26-34(38)42-30-33(31-44-46(40,41)43-28-27-36)45-35(39)29-32(37)25-23-21-19-10-8-6-4-2/h14-15,32-33,37H,3-13,16-31,36H2,1-2H3,(H,40,41)/b15-14-/t32?,33-/m1/s1 ChemAxon inchikey OONWHZRHFUDHLM-OTWFKUADSA-N ChemAxon polar_surface_area 154.61 ChemAxon refractivity 184.43 ChemAxon polarizability 79.88 ChemAxon rotatable_bond_count 36 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis (PE(18:1(9Z)/12:0(3-OH))) 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. PW001780 Metabolic Specdb::CMs 1087904 Specdb::NmrOneD 288155 Specdb::NmrOneD 288156 Specdb::NmrOneD 288157 Specdb::NmrOneD 288158 Specdb::NmrOneD 288159 Specdb::NmrOneD 288160 Specdb::NmrOneD 288161 Specdb::NmrOneD 288162 Specdb::NmrOneD 288163 Specdb::NmrOneD 288164 Specdb::NmrOneD 288165 Specdb::NmrOneD 288166 Specdb::NmrOneD 288167 Specdb::NmrOneD 288168 Specdb::NmrOneD 288169 Specdb::NmrOneD 288170 Specdb::NmrOneD 288171 Specdb::NmrOneD 288172 Specdb::NmrOneD 288173 Specdb::NmrOneD 288174 Specdb::MsMs 25667 Specdb::MsMs 25668 Specdb::MsMs 25669 Specdb::MsMs 32225 Specdb::MsMs 32226 Specdb::MsMs 32227 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 Taylor SS, Heath EC. (1969) "The incorporation of beta-hydroxy fatty acids into a phospholipid of Escherichia coli B." J Biol Chem. 244(24):6605-16. 4902888 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(9Z)/12:0(3-OH)) + Hydrogen ion > PE(18:1(9Z)/12:0(3-OH)) + Carbon dioxide PW_R004780