2.0 2012-10-24 09:54:27 -0600 2015-09-14 11:19:52 -0600 ECMDB23495 M2MDB003885 PE(15:0/14:0(3-OH)) PE(15:0/14:0(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(15:0/14:0(3-OH)), in particular, consists of one pentadecanoyl chain to the C-1 atom, and one 3-hydroxytetradecanoyl 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-pentadecanoyl-2-3-hydroxytetradecanoyl-sn-glycero-3-phosphoethanolamine 1-pentadecanoyl-2-3-hydroxytetradecanoyl-sn-glycero-3-phosphoethanolamine GPEtn(15:0/14:0) GPEtn(29:0) PE(15:0/14:0) PE(29:0) Phophatidylethanolamine(15:0/14:0) Phophatidylethanolamine(29:0) C34H68NO9P 665.8788 665.463169291 (2-aminoethoxy)[(2R)-2-[(3-hydroxytetradecanoyl)oxy]-3-(pentadecanoyloxy)propoxy]phosphinic acid 2-aminoethoxy((2R)-2-[(3-hydroxytetradecanoyl)oxy]-3-(pentadecanoyloxy)propoxy)phosphinic acid CCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CC(O)CCCCCCCCCCC InChI=1S/C34H68NO9P/c1-3-5-7-9-11-13-14-15-17-19-21-23-25-33(37)41-29-32(30-43-45(39,40)42-27-26-35)44-34(38)28-31(36)24-22-20-18-16-12-10-8-6-4-2/h31-32,36H,3-30,35H2,1-2H3,(H,39,40)/t31?,32-/m1/s1 BMXKYOFPEDXCRN-IADGFXSZSA-N Solid Membrane logp 6.46 ALOGPS logs -6.46 ALOGPS solubility 2.28e-04 g/l ALOGPS logp 7.89 ChemAxon pka_strongest_acidic 1.87 ChemAxon pka_strongest_basic 10 ChemAxon iupac (2-aminoethoxy)[(2R)-2-[(3-hydroxytetradecanoyl)oxy]-3-(pentadecanoyloxy)propoxy]phosphinic acid ChemAxon average_mass 665.8788 ChemAxon mono_mass 665.463169291 ChemAxon smiles CCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CC(O)CCCCCCCCCCC ChemAxon formula C34H68NO9P ChemAxon inchi InChI=1S/C34H68NO9P/c1-3-5-7-9-11-13-14-15-17-19-21-23-25-33(37)41-29-32(30-43-45(39,40)42-27-26-35)44-34(38)28-31(36)24-22-20-18-16-12-10-8-6-4-2/h31-32,36H,3-30,35H2,1-2H3,(H,39,40)/t31?,32-/m1/s1 ChemAxon inchikey BMXKYOFPEDXCRN-IADGFXSZSA-N ChemAxon polar_surface_area 154.61 ChemAxon refractivity 178.72 ChemAxon polarizability 79.34 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 CL(15:0cyclo/15:0cyclo/16:0/14:0) "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." PW001066 Metabolic phospholipid biosynthesis (CL(15:0/14:0(3-OH)/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. PW001947 Metabolic Specdb::CMs 1083809 Specdb::NmrOneD 267408 Specdb::NmrOneD 267409 Specdb::NmrOneD 267410 Specdb::NmrOneD 267411 Specdb::NmrOneD 267412 Specdb::NmrOneD 267413 Specdb::NmrOneD 267414 Specdb::NmrOneD 267415 Specdb::NmrOneD 267416 Specdb::NmrOneD 267417 Specdb::NmrOneD 267418 Specdb::NmrOneD 267419 Specdb::NmrOneD 267420 Specdb::NmrOneD 267421 Specdb::NmrOneD 267422 Specdb::NmrOneD 267423 Specdb::NmrOneD 267424 Specdb::NmrOneD 267425 Specdb::NmrOneD 267426 Specdb::NmrOneD 267427 Specdb::MsMs 28742 Specdb::MsMs 28743 Specdb::MsMs 28744 Specdb::MsMs 35300 Specdb::MsMs 35301 Specdb::MsMs 35302 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 Yuan Y, Leeds JA, Meredith TC (2012). "Pseudomonas aeruginosa Directly Shunts β-Oxidation Degradation Intermediates into De Novo Fatty Acid Biosynthesis." J Bacteriol. 194(19):5185-96 22753057 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 Cardiolipin synthase C P75919 CLSC_ECOLI clsC http://ecmdb.ca/proteins/P75919.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 PE(15:0/14:0(3-OH)) + PG(15:0/16:1) > Ethanolamine + CL(15:0cyclo/15:0cyclo/16:0/14:0) PW_R003923 PS(15:0/14:0(3-OH)) + Hydrogen ion > PE(15:0/14:0(3-OH)) + Carbon dioxide PW_R005477 PE(15:0/14:0(3-OH)) + PG(14:0/14:0) > Ethanolamine + CL(15:0/14:0(3-OH)/14:0/14:0) PW_R005478