2.0 2012-10-24 09:55:07 -0600 2015-09-16 17:34:55 -0600 ECMDB23722 M2MDB004112 PG(19:iso/16:1(9Z)) PG(19:iso/16:1(9Z)) 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(19:iso/16:1(9Z)), in particular, consists of one 17-methylocatdecanoyl chain to the C-1 atom, and one 9Z-hexadecenoyl 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. 1-17-methylocatdecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phospho-(1'-glycerol) 1-17-methylocatdecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphoglycerol 1-17-methylocatdecanoyl-2-palmitoleoyl-sn-glycero-3-phosphoglycerol GPG(19:0/16:1) GPG(35:1) PG(19:0/16:1) PG(35:1) Phosphatidylglycerol(19:0/16:1) Phosphatidylglycerol(35:1) C41H79O10P 763.0337 762.54108526 (2,3-dihydroxypropoxy)({2-[(9Z)-hexadec-9-enoyloxy]-3-[(17-methyloctadecanoyl)oxy]propoxy})phosphinic acid 2,3-dihydroxypropoxy(2-[(9Z)-hexadec-9-enoyloxy]-3-[(17-methyloctadecanoyl)oxy]propoxy)phosphinic acid CCCCCC\C=C/CCCCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCCC(C)C)COP(O)(=O)OCC(O)CO InChI=1S/C41H79O10P/c1-4-5-6-7-8-9-10-12-17-20-23-26-29-32-41(45)51-39(36-50-52(46,47)49-34-38(43)33-42)35-48-40(44)31-28-25-22-19-16-14-11-13-15-18-21-24-27-30-37(2)3/h9-10,37-39,42-43H,4-8,11-36H2,1-3H3,(H,46,47)/b10-9- KJGSRJJSXMPJRT-KTKRTIGZSA-N Solid Membrane logp 8.21 ALOGPS logs -6.86 ALOGPS solubility 1.06e-04 g/l ALOGPS logp 11.75 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2,3-dihydroxypropoxy)({2-[(9Z)-hexadec-9-enoyloxy]-3-[(17-methyloctadecanoyl)oxy]propoxy})phosphinic acid ChemAxon average_mass 763.0337 ChemAxon mono_mass 762.54108526 ChemAxon smiles CCCCCC\C=C/CCCCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCCC(C)C)COP(O)(=O)OCC(O)CO ChemAxon formula C41H79O10P ChemAxon inchi InChI=1S/C41H79O10P/c1-4-5-6-7-8-9-10-12-17-20-23-26-29-32-41(45)51-39(36-50-52(46,47)49-34-38(43)33-42)35-48-40(44)31-28-25-22-19-16-14-11-13-15-18-21-24-27-30-37(2)3/h9-10,37-39,42-43H,4-8,11-36H2,1-3H3,(H,46,47)/b10-9- ChemAxon inchikey KJGSRJJSXMPJRT-KTKRTIGZSA-N ChemAxon polar_surface_area 148.82 ChemAxon refractivity 210.18 ChemAxon polarizability 93.08 ChemAxon rotatable_bond_count 41 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis (CL(19:0cycv8c/16:1(9Z)/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. PW001385 Metabolic phospholipid biosynthesis (CL(19:0cycv8c/16:1(9Z)/19:0cycv8c/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. PW001388 Metabolic phospholipid biosynthesis (CL(19:0cycv8c/16:1(9Z)/19:0cycv8c/16:1(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. PW001394 Metabolic phospholipid biosynthesis (CL(19:0cycv8c/16:1(9Z)/19:0cycv8c/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. PW001395 Metabolic Specdb::CMs 1087775 Specdb::NmrOneD 256908 Specdb::NmrOneD 256909 Specdb::NmrOneD 256910 Specdb::NmrOneD 256911 Specdb::NmrOneD 256912 Specdb::NmrOneD 256913 Specdb::NmrOneD 256914 Specdb::NmrOneD 256915 Specdb::NmrOneD 256916 Specdb::NmrOneD 256917 Specdb::NmrOneD 256918 Specdb::NmrOneD 256919 Specdb::NmrOneD 256920 Specdb::NmrOneD 256921 Specdb::NmrOneD 256922 Specdb::NmrOneD 256923 Specdb::NmrOneD 256924 Specdb::NmrOneD 256925 Specdb::NmrOneD 256926 Specdb::NmrOneD 256927 Specdb::MsMs 27569 Specdb::MsMs 27570 Specdb::MsMs 27571 Specdb::MsMs 34127 Specdb::MsMs 34128 Specdb::MsMs 34129 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 Casadei MA, Mañas P, Niven G, Needs E, Mackey BM. (2002) "Role of membrane fluidity in pressure resistance of Escherichia coli NCTC 8164." Appl Environ Microbiol. 68(12):5965-72. 12450817 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 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 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 PG(19:iso/16:1(9Z)) + PE(19:0cycw8c/17:0cycw7c) > Ethanolamine + CL(19:0cycv8c/16:1(9Z)/19:0cycv8c/17:0cycw7c) PW_R004982 PG(19:iso/16:1(9Z)) + PE(19:0cycv8c/14:0(3-OH)) > Ethanolamine + CL(19:0cycv8c/16:1(9Z)/19:0cycv8c/14:0) PW_R004983 PE(17:0cycw7c/17:0cycw7c) + PG(19:iso/16:1(9Z)) > Ethanolamine + CL(19:0cycv8c/16:1(9Z)/17:0cycw7c/17:0cycw7c) PW_R004985 PG(19:iso/16:1(9Z)) + PE(19:iso/16:1(9Z)) > Ethanolamine + CL(19:0cycv8c/16:1(9Z)/19:0cycv8c/16:1(9Z)) PW_R005055 2 PGP(19:iso/16:1(9Z)) + Water >2 PG(19:iso/16:1(9Z)) + Phosphate PW_R005758