2.0 2012-08-13 14:57:48 -0600 2015-09-14 11:19:25 -0600 ECMDB21608 M2MDB002002 PE(12:0/19:1(12Z)) PE(12:0/19:1(12Z)) 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(12:0/19:1(12Z)), in particular, consists of one dodecanoyl chain to the C-1 atom, and one 12Z-nonadecenoyl 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-dodecanoyl-2-(12Z-nonadecenoyl)-sn-glycero-3-phosphoethanolamine 1-dodecanoyl-2-12Z-nonadecenoyl-sn-glycero-3-phosphoethanolamine GPEtn(12:0/19:1) GPEtn(31:1) PE(12:0/19:1) PE(31:1) Phophatidylethanolamine(12:0/19:1) Phophatidylethanolamine(31:1) C36H70NO8P 675.9167 675.483904733 (2-aminoethoxy)[(2R)-3-(dodecanoyloxy)-2-[(12Z)-nonadec-12-enoyloxy]propoxy]phosphinic acid 2-aminoethoxy((2R)-3-(dodecanoyloxy)-2-[(12Z)-nonadec-12-enoyloxy]propoxy)phosphinic acid [H]\C(CCCCCC)=C(/[H])CCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCCCCCC)COP(O)(=O)OCCN InChI=1S/C36H70NO8P/c1-3-5-7-9-11-13-14-15-16-17-18-19-21-23-25-27-29-36(39)45-34(33-44-46(40,41)43-31-30-37)32-42-35(38)28-26-24-22-20-12-10-8-6-4-2/h13-14,34H,3-12,15-33,37H2,1-2H3,(H,40,41)/b14-13-/t34-/m1/s1 WQPDSCRZHOEWHQ-YAGQSAGLSA-N Solid Membrane logp 7.76 ALOGPS logs -6.78 ALOGPS solubility 1.12e-04 g/l ALOGPS logp 9.64 ChemAxon pka_strongest_acidic 1.87 ChemAxon pka_strongest_basic 10 ChemAxon iupac (2-aminoethoxy)[(2R)-3-(dodecanoyloxy)-2-[(12Z)-nonadec-12-enoyloxy]propoxy]phosphinic acid ChemAxon average_mass 675.9167 ChemAxon mono_mass 675.483904733 ChemAxon smiles [H]\C(CCCCCC)=C(/[H])CCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCCCCCC)COP(O)(=O)OCCN ChemAxon formula C36H70NO8P ChemAxon inchi InChI=1S/C36H70NO8P/c1-3-5-7-9-11-13-14-15-16-17-18-19-21-23-25-27-29-36(39)45-34(33-44-46(40,41)43-31-30-37)32-42-35(38)28-26-24-22-20-12-10-8-6-4-2/h13-14,34H,3-12,15-33,37H2,1-2H3,(H,40,41)/b14-13-/t34-/m1/s1 ChemAxon inchikey WQPDSCRZHOEWHQ-YAGQSAGLSA-N ChemAxon polar_surface_area 134.38 ChemAxon refractivity 187.52 ChemAxon polarizability 81.66 ChemAxon rotatable_bond_count 37 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis CDP-DG(12:0/19:1(9Z)) V 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 PS (16:1(9z)/18:1(11z))L-1-phosphatidylserine or a L-1-phosphatidy PE(16:1(9z)/18:1(11z)) (phosphatidylethanolamine) through a phosphatidylserine decarboxylase, on the other hand PGP(16:1(9z)/18:1(11z)) L-1-phosphatidylglycerol-phosphate gets transformed into a PG(16:1(9z)/18:1(11z)) 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. PW001845 Metabolic phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::CMs 1085821 Specdb::NmrOneD 286415 Specdb::NmrOneD 286416 Specdb::NmrOneD 286417 Specdb::NmrOneD 286418 Specdb::NmrOneD 286419 Specdb::NmrOneD 286420 Specdb::NmrOneD 286421 Specdb::NmrOneD 286422 Specdb::NmrOneD 286423 Specdb::NmrOneD 286424 Specdb::NmrOneD 286425 Specdb::NmrOneD 286426 Specdb::NmrOneD 286427 Specdb::NmrOneD 286428 Specdb::NmrOneD 286429 Specdb::NmrOneD 286430 Specdb::NmrOneD 286431 Specdb::NmrOneD 286432 Specdb::NmrOneD 286433 Specdb::NmrOneD 286434 Specdb::MsMs 23687 Specdb::MsMs 23688 Specdb::MsMs 23689 Specdb::MsMs 30485 Specdb::MsMs 30486 Specdb::MsMs 30487 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 De Siervo, A. J. (1969). "Alterations in the phospholipid composition of Escherichia coli B during growth at different temperatures." J Bacteriol 100:1342-1349. 4902814 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(12:0/19:iso) + Hydrogen ion > PE(12:0/19:1(12Z)) + Carbon dioxide PW_R004920