2.0 2015-09-08 17:49:29 -0600 2015-09-14 11:20:00 -0600 ECMDB24120 M2MDB006237 PE(18:0/18:0) PE(18:0/18:0) 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 positions. PE(18:0/18:0), in particular, consists of two octadecanoyl chains at positions C-1 and C-2. 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. C41H82NO8P 748.0654 747.577805117 (2-aminoethoxy)[(2R)-2,3-bis(octadecanoyloxy)propoxy]phosphinic acid L-β,gamm [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCCCC InChI=1S/C41H82NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(43)47-37-39(38-49-51(45,46)48-36-35-42)50-41(44)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h39H,3-38,42H2,1-2H3,(H,45,46)/t39-/m1/s1 LVNGJLRDBYCPGB-LDLOPFEMSA-N logp 8.91 ALOGPS logs -7.14 ALOGPS solubility 5.43e-05 g/l ALOGPS logp 12.23 ChemAxon pka_strongest_acidic 1.87 ChemAxon pka_strongest_basic 10 ChemAxon iupac (2-aminoethoxy)[(2R)-2,3-bis(octadecanoyloxy)propoxy]phosphinic acid ChemAxon average_mass 748.0654 ChemAxon mono_mass 747.577805117 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCCCC ChemAxon formula C41H82NO8P ChemAxon inchi InChI=1S/C41H82NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(43)47-37-39(38-49-51(45,46)48-36-35-42)50-41(44)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h39H,3-38,42H2,1-2H3,(H,45,46)/t39-/m1/s1 ChemAxon inchikey LVNGJLRDBYCPGB-LDLOPFEMSA-N ChemAxon polar_surface_area 134.38 ChemAxon refractivity 209.41 ChemAxon polarizability 93.58 ChemAxon rotatable_bond_count 43 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (PE(18:0/18:0)) 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. PW001772 Metabolic phospholipid biosynthesis I (18:0, 18:0) PW001001 Metabolic Specdb::CMs 236884 Specdb::NmrOneD 341268 Specdb::NmrOneD 341269 Specdb::NmrOneD 341270 Specdb::NmrOneD 341271 Specdb::NmrOneD 341272 Specdb::NmrOneD 341273 Specdb::NmrOneD 341274 Specdb::NmrOneD 341275 Specdb::NmrOneD 341276 Specdb::NmrOneD 341277 Specdb::NmrOneD 341278 Specdb::NmrOneD 341279 Specdb::NmrOneD 341280 Specdb::NmrOneD 341281 Specdb::NmrOneD 341282 Specdb::NmrOneD 341283 Specdb::NmrOneD 341284 Specdb::NmrOneD 341285 Specdb::NmrOneD 341286 Specdb::NmrOneD 341287 Specdb::MsMs 688594 Specdb::MsMs 688595 Specdb::MsMs 688596 Specdb::MsMs 691057 Specdb::MsMs 691058 Specdb::MsMs 691059 Specdb::MsMs 1471298 Specdb::MsMs 1473371 Specdb::MsMs 1476196 Specdb::MsMs 2231593 Specdb::MsMs 2232582 Specdb::MsMs 2234044 Specdb::MsMs 2234913 Specdb::MsMs 2308356 Specdb::MsMs 2308357 Specdb::MsMs 2308358 Specdb::MsMs 2351038 Specdb::MsMs 2351039 Specdb::MsMs 2351040 Specdb::MsMs 2583923 Specdb::MsMs 2583924 Specdb::MsMs 2583925 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 Cardiolipin synthase C P75919 CLSC_ECOLI clsC http://ecmdb.ca/proteins/P75919.xml Hydrogen ion + PS(18:0/18:0) > PE(18:0/18:0) + Carbon dioxide PW_R003742 PG(18:0/18:0) + PE(18:0/18:0) + PG(18:0/18:0) > CL(16:0/16:0/16:0/16:1(9Z)) + Ethanolamine PW_R003744