2.0 2012-05-31 14:58:02 -0600 2015-12-09 12:07:31 -0700 ECMDB21084 M2MDB001500 PG(16:0/19:0) PG(16:0/19:0) 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(16:0/19:0), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one nonadecanoyl 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-hexadecanoyl-2-nonadecanoyl-glycero-3-phospho-(1'-sn-glycerol) 1-hexadecanoyl-2-nonadecanoyl-sn-glycero-3-phospho-(1'-glycerol) 1-hexadecanoyl-2-nonadecanoyl-sn-glycero-3-phosphoglycerol 1-palmitoyl-2--sn-glycero-3-phosphoglycerol 1-palmitoyl-2-nonadecanoyl-sn-glycero-3-phosphoglycerol GPG(16:0/19:0) GPG(35:0) PG(35:0) Phosphatidylglycerol(16:0/19:0) Phosphatidylglycerol(35:0) C41H81O10P 765.0496 764.556735324 [(2S)-2,3-dihydroxypropoxy][(2R)-2-(hexadecanoyloxy)-3-(nonadecanoyloxy)propoxy]phosphinic acid (2S)-2,3-dihydroxypropoxy(2R)-2-(hexadecanoyloxy)-3-(nonadecanoyloxy)propoxyphosphinic acid [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC InChI=1S/C41H81O10P/c1-3-5-7-9-11-13-15-17-18-19-21-22-24-26-28-30-32-40(44)48-36-39(37-50-52(46,47)49-35-38(43)34-42)51-41(45)33-31-29-27-25-23-20-16-14-12-10-8-6-4-2/h38-39,42-43H,3-37H2,1-2H3,(H,46,47)/t38-,39+/m0/s1 WXDNYCHHTCISSS-ZESVVUHVSA-N Inner membrane Membrane Outer membrane logp 8.43 ALOGPS logs -6.90 ALOGPS solubility 9.69e-05 g/l ALOGPS logp 12.27 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -3 ChemAxon iupac [(2S)-2,3-dihydroxypropoxy][(2R)-2-(hexadecanoyloxy)-3-(nonadecanoyloxy)propoxy]phosphinic acid ChemAxon average_mass 765.0496 ChemAxon mono_mass 764.556735324 ChemAxon smiles [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC ChemAxon formula C41H81O10P ChemAxon inchi InChI=1S/C41H81O10P/c1-3-5-7-9-11-13-15-17-18-19-21-22-24-26-28-30-32-40(44)48-36-39(37-50-52(46,47)49-35-38(43)34-42)51-41(45)33-31-29-27-25-23-20-16-14-12-10-8-6-4-2/h38-39,42-43H,3-37H2,1-2H3,(H,46,47)/t38-,39+/m0/s1 ChemAxon inchikey WXDNYCHHTCISSS-ZESVVUHVSA-N ChemAxon polar_surface_area 148.82 ChemAxon refractivity 209.11 ChemAxon polarizability 93.74 ChemAxon rotatable_bond_count 43 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis (CL(19:0/16:1(9Z)/16:0/16:0)) 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. PW001984 Metabolic phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::CMs 1085884 Specdb::NmrOneD 301385 Specdb::NmrOneD 301386 Specdb::NmrOneD 301387 Specdb::NmrOneD 301388 Specdb::NmrOneD 301389 Specdb::NmrOneD 301390 Specdb::NmrOneD 301391 Specdb::NmrOneD 301392 Specdb::NmrOneD 301393 Specdb::NmrOneD 301394 Specdb::NmrOneD 301395 Specdb::NmrOneD 301396 Specdb::NmrOneD 301397 Specdb::NmrOneD 301398 Specdb::NmrOneD 301399 Specdb::NmrOneD 301400 Specdb::NmrOneD 301401 Specdb::NmrOneD 301402 Specdb::NmrOneD 301403 Specdb::NmrOneD 301404 Specdb::MsMs 24941 Specdb::MsMs 24942 Specdb::MsMs 24943 Specdb::MsMs 31499 Specdb::MsMs 31500 Specdb::MsMs 31501 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 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 2 PGP(16:0/19:0) + Water >2 PG(16:0/19:0) + Phosphate PW_R005854