2.0 2012-10-24 09:55:02 -0600 2015-12-09 12:07:39 -0700 ECMDB23698 M2MDB004088 PG(16:1(9Z)/12:0(3-OH)) PG(16:1(9Z)/12:0(3-OH)) 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(16:1(9Z)/12:0(3-OH)), in particular, consists of one 9Z-hexadecenoyl chain to the C-1 atom, and one 3-hydroxydodecanoyl 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-(9Z-hexadecenoyl)-2-3-hydroxydodecanoyl-sn-glycero-3-phospho-(1'-glycerol) 1-(9Z-hexadecenoyl)-2-3-hydroxydodecanoyl-sn-glycero-3-phosphoglycerol 1-palmitoleoyl-2-3-hydroxydodecanoyl-sn-glycero-3-phosphoglycerol GPG(16:1/12:0) GPG(28:1) PG(16:1/12:0) PG(28:1) Phosphatidylglycerol(16:1/12:0) Phosphatidylglycerol(28:1) C34H65O11P 680.857 680.426449911 [(2S)-2,3-dihydroxypropoxy][(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(3-hydroxydodecanoyl)oxy]propoxy]phosphinic acid (2S)-2,3-dihydroxypropoxy((2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(3-hydroxydodecanoyl)oxy]propoxy)phosphinic acid [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC InChI=1S/C34H65O11P/c1-3-5-7-9-11-12-13-14-15-16-18-20-22-24-33(38)45-32(29-44-46(40,41)43-27-31(37)26-35)28-42-34(39)25-30(36)23-21-19-17-10-8-6-4-2/h12-13,30-32,35-37H,3-11,14-29H2,1-2H3,(H,40,41)/b13-12-/t30?,31-,32+/m0/s1 DYLWWUHLOZGLPM-KVRHGVBDSA-N Solid Membrane logp 5.72 ALOGPS logs -6.04 ALOGPS solubility 6.16e-04 g/l ALOGPS logp 7.57 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac [(2S)-2,3-dihydroxypropoxy][(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(3-hydroxydodecanoyl)oxy]propoxy]phosphinic acid ChemAxon average_mass 680.857 ChemAxon mono_mass 680.426449911 ChemAxon smiles [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC ChemAxon formula C34H65O11P ChemAxon inchi InChI=1S/C34H65O11P/c1-3-5-7-9-11-12-13-14-15-16-18-20-22-24-33(38)45-32(29-44-46(40,41)43-27-31(37)26-35)28-42-34(39)25-30(36)23-21-19-17-10-8-6-4-2/h12-13,30-32,35-37H,3-11,14-29H2,1-2H3,(H,40,41)/b13-12-/t30?,31-,32+/m0/s1 ChemAxon inchikey DYLWWUHLOZGLPM-KVRHGVBDSA-N ChemAxon polar_surface_area 169.05 ChemAxon refractivity 179.54 ChemAxon polarizability 78.34 ChemAxon rotatable_bond_count 35 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/14:0/15:0cyclo) 5) 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. PW001717 Metabolic Specdb::CMs 1085150 Specdb::NmrOneD 344728 Specdb::NmrOneD 344729 Specdb::NmrOneD 344730 Specdb::NmrOneD 344731 Specdb::NmrOneD 344732 Specdb::NmrOneD 344733 Specdb::NmrOneD 344734 Specdb::NmrOneD 344735 Specdb::NmrOneD 344736 Specdb::NmrOneD 344737 Specdb::NmrOneD 344738 Specdb::NmrOneD 344739 Specdb::NmrOneD 344740 Specdb::NmrOneD 344741 Specdb::NmrOneD 344742 Specdb::NmrOneD 344743 Specdb::NmrOneD 344744 Specdb::NmrOneD 344745 Specdb::NmrOneD 344746 Specdb::NmrOneD 344747 Specdb::MsMs 1235776 Specdb::MsMs 1235777 Specdb::MsMs 1235778 Specdb::MsMs 1351249 Specdb::MsMs 1351250 Specdb::MsMs 1351251 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 Taylor SS, Heath EC. (1969) "The incorporation of beta-hydroxy fatty acids into a phospholipid of Escherichia coli B." J Biol Chem. 244(24):6605-16. 4902888 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 Lysophospholipase L2 P07000 PLDB_ECOLI pldB http://ecmdb.ca/proteins/P07000.xml Phosphatidylglycerophosphatase B P0A924 PGPB_ECOLI pgpB http://ecmdb.ca/proteins/P0A924.xml Phosphatidylglycerophosphatase A P18200 PGPA_ECOLI pgpA http://ecmdb.ca/proteins/P18200.xml Lipid A export ATP-binding/permease protein msbA P60752 MSBA_ECOLI msbA http://ecmdb.ca/proteins/P60752.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 Lipid A export ATP-binding/permease protein msbA P60752 MSBA_ECOLI msbA http://ecmdb.ca/proteins/P60752.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 PGP(14:0/14:0) + Water > PG(16:1(9Z)/12:0(3-OH)) + Phosphate PW_R004649 2 PG(16:1(9Z)/12:0(3-OH)) > Glycerol + CL(18:1(9Z)/15:0cyclo/14:0/15:0cyclo) PW_R004650 2 PGP(16:1(9Z)/12:0(3-OH)) + Water >2 PG(16:1(9Z)/12:0(3-OH)) + Phosphate PW_R005741