2.0 2012-05-31 14:56:11 -0600 2015-12-09 17:00:57 -0700 ECMDB21048 M2MDB001464 PG(14:0/18:1(11Z)) PG(14:0/18:1(11Z)) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PG(14:0/18:1(11Z)), in particular, consists of one tetradecanoyl chain to the C-1 atom, and one 11Z-octadecenoyl to the C-2 atom. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes. 1-myristoyl-2-vaccenoyl-sn-glycero-3-phosphoglycerol 1-tetradecanoyl-2-(11Z-octadecenoyl)-sn-glycero-3-phospho-(1'-glycerol) 1-tetradecanoyl-2-(11Z-octadecenoyl)-sn-glycero-3-phosphoglycerol GPG(14:0/18:1) GPG(32:1) PG(14:0/18:1) PG(32:1) Phosphatidylglycerol(14:0/18:1) Phosphatidylglycerol(32:1) C38H73O10P 720.966 720.494135549 [(2R)-2,3-dihydroxypropoxy][(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-(tetradecanoyloxy)propoxy]phosphinic acid (2R)-2,3-dihydroxypropoxy((2R)-3-[(11Z)-octadec-11-enoyloxy]-2-(tetradecanoyloxy)propoxy)phosphinic acid [H][C@@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCC InChI=1S/C38H73O10P/c1-3-5-7-9-11-13-15-16-17-18-20-21-23-25-27-29-37(41)45-33-36(34-47-49(43,44)46-32-35(40)31-39)48-38(42)30-28-26-24-22-19-14-12-10-8-6-4-2/h13,15,35-36,39-40H,3-12,14,16-34H2,1-2H3,(H,43,44)/b15-13-/t35-,36-/m1/s1 RLKNQCBSMHWYDB-YNJXHKFOSA-N Inner membrane Membrane Outer membrane logp 7.72 ALOGPS logs -6.73 ALOGPS solubility 1.35e-04 g/l ALOGPS logp 10.58 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -3 ChemAxon iupac [(2R)-2,3-dihydroxypropoxy][(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-(tetradecanoyloxy)propoxy]phosphinic acid ChemAxon average_mass 720.966 ChemAxon mono_mass 720.494135549 ChemAxon smiles [H][C@@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCC ChemAxon formula C38H73O10P ChemAxon inchi InChI=1S/C38H73O10P/c1-3-5-7-9-11-13-15-16-17-18-20-21-23-25-27-29-37(41)45-33-36(34-47-49(43,44)46-32-35(40)31-39)48-38(42)30-28-26-24-22-19-14-12-10-8-6-4-2/h13,15,35-36,39-40H,3-12,14,16-34H2,1-2H3,(H,43,44)/b15-13-/t35-,36-/m1/s1 ChemAxon inchikey RLKNQCBSMHWYDB-YNJXHKFOSA-N ChemAxon polar_surface_area 148.82 ChemAxon refractivity 196.43 ChemAxon polarizability 85.7 ChemAxon rotatable_bond_count 39 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis (CL(18:1(9Z)/14:0/17:0cycw7c/17:0cycw7c)) 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. PW001499 Metabolic phospholipid biosynthesis (CL(19:0cycv8c/19:0cycv8c/14:0/18:1(9Z))) 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. PW001438 Metabolic phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::CMs 1085040 Specdb::NmrOneD 307911 Specdb::NmrOneD 307912 Specdb::NmrOneD 307913 Specdb::NmrOneD 307914 Specdb::NmrOneD 307915 Specdb::NmrOneD 307916 Specdb::NmrOneD 307917 Specdb::NmrOneD 307918 Specdb::NmrOneD 307919 Specdb::NmrOneD 307920 Specdb::NmrOneD 307921 Specdb::NmrOneD 307922 Specdb::NmrOneD 307923 Specdb::NmrOneD 307924 Specdb::NmrOneD 307925 Specdb::NmrOneD 307926 Specdb::NmrOneD 307927 Specdb::NmrOneD 307928 Specdb::NmrOneD 307929 Specdb::NmrOneD 307930 Specdb::MsMs 1271899 Specdb::MsMs 1271900 Specdb::MsMs 1271901 Specdb::MsMs 1386901 Specdb::MsMs 1386902 Specdb::MsMs 1386903 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 Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. 22102590 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 Phosphatidylglycerophosphatase B P0A924 PGPB_ECOLI pgpB http://ecmdb.ca/proteins/P0A924.xml Phosphatidylglycerophosphatase A P18200 PGPA_ECOLI pgpA http://ecmdb.ca/proteins/P18200.xml Protein crcA P37001 CRCA_ECOLI crcA http://ecmdb.ca/proteins/P37001.xml Cardiolipin synthase P0A6H8 CLS_ECOLI cls http://ecmdb.ca/proteins/P0A6H8.xml Putative cardiolipin synthase ybhO P0AA84 YBHO_ECOLI ybhO http://ecmdb.ca/proteins/P0AA84.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(17:0cycw7c/17:0cycw7c) + PG(14:0/18:1(11Z)) > CL(18:1(9Z)/14:0/17:0cycw7c/17:0cycw7c) + Ethanolamine PW_R005008 PE(19:iso/19:iso) + PG(14:0/18:1(11Z)) > Ethanolamine + CL(19:0cycv8c/19:0cycv8c/14:0/18:1(9Z)) PW_R005129 2 PGP(14:0/18:1(11Z)) + Water >2 PG(14:0/18:1(11Z)) + Phosphate PW_R005735