2.0 2012-10-24 09:55:06 -0600 2015-09-16 17:34:55 -0600 ECMDB23716 M2MDB004106 PG(19:iso/12:0(3-OH)) PG(19:iso/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(19:iso/12:0(3-OH)), in particular, consists of one 17-methylocatdecanoyl 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. 1-17-methylocatdecanoyl-2-3-hydroxydodecanoyl-sn-glycero-3-phospho-(1'-glycerol) 1-17-methylocatdecanoyl-2-3-hydroxydodecanoyl-sn-glycero-3-phosphoglycerol 1-17-methylocatdecanoyl-2-3-hydroxydodecanoyl-sn-glycero-3-phosphoglycerol GPG(19:0/12:0) GPG(31:0) PG(19:0/12:0) PG(31:0) Phosphatidylglycerol(19:0/12:0) Phosphatidylglycerol(31:0) C37H73O11P 724.9427 724.48904969 (2,3-dihydroxypropoxy)({2-[(3-hydroxydodecanoyl)oxy]-3-[(17-methyloctadecanoyl)oxy]propoxy})phosphinic acid 2,3-dihydroxypropoxy(2-[(3-hydroxydodecanoyl)oxy]-3-[(17-methyloctadecanoyl)oxy]propoxy)phosphinic acid CCCCCCCCCC(O)CC(=O)OC(COC(=O)CCCCCCCCCCCCCCCC(C)C)COP(O)(=O)OCC(O)CO InChI=1S/C37H73O11P/c1-4-5-6-7-15-19-22-25-33(39)27-37(42)48-35(31-47-49(43,44)46-29-34(40)28-38)30-45-36(41)26-23-20-17-14-12-10-8-9-11-13-16-18-21-24-32(2)3/h32-35,38-40H,4-31H2,1-3H3,(H,43,44) UOPWRRQJYQWUOE-UHFFFAOYSA-N Solid Membrane logp 6.44 ALOGPS logs -6.38 ALOGPS solubility 2.99e-04 g/l ALOGPS logp 9.1 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac (2,3-dihydroxypropoxy)({2-[(3-hydroxydodecanoyl)oxy]-3-[(17-methyloctadecanoyl)oxy]propoxy})phosphinic acid ChemAxon average_mass 724.9427 ChemAxon mono_mass 724.48904969 ChemAxon smiles CCCCCCCCCC(O)CC(=O)OC(COC(=O)CCCCCCCCCCCCCCCC(C)C)COP(O)(=O)OCC(O)CO ChemAxon formula C37H73O11P ChemAxon inchi InChI=1S/C37H73O11P/c1-4-5-6-7-15-19-22-25-33(39)27-37(42)48-35(31-47-49(43,44)46-29-34(40)28-38)30-45-36(41)26-23-20-17-14-12-10-8-9-11-13-16-18-21-24-32(2)3/h32-35,38-40H,4-31H2,1-3H3,(H,43,44) ChemAxon inchikey UOPWRRQJYQWUOE-UHFFFAOYSA-N ChemAxon polar_surface_area 169.05 ChemAxon refractivity 192.17 ChemAxon polarizability 86.83 ChemAxon rotatable_bond_count 38 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis (CL(19:iso/12:0(3-OH)/12:0/12:0)) 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. PW001999 Metabolic phospholipid biosynthesis (CL(19:iso/12:0(3-OH)/19:iso/12:0(3-OH))) 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. PW002000 Metabolic Specdb::CMs 1085627 Specdb::NmrOneD 268308 Specdb::NmrOneD 268309 Specdb::NmrOneD 268310 Specdb::NmrOneD 268311 Specdb::NmrOneD 268312 Specdb::NmrOneD 268313 Specdb::NmrOneD 268314 Specdb::NmrOneD 268315 Specdb::NmrOneD 268316 Specdb::NmrOneD 268317 Specdb::NmrOneD 268318 Specdb::NmrOneD 268319 Specdb::NmrOneD 268320 Specdb::NmrOneD 268321 Specdb::NmrOneD 268322 Specdb::NmrOneD 268323 Specdb::NmrOneD 268324 Specdb::NmrOneD 268325 Specdb::NmrOneD 268326 Specdb::NmrOneD 268327 Specdb::MsMs 29273 Specdb::MsMs 29274 Specdb::MsMs 29275 Specdb::MsMs 35831 Specdb::MsMs 35832 Specdb::MsMs 35833 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 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 2 PGP(19:iso/12:0(3-OH)) + Water >2 PG(19:iso/12:0(3-OH)) + Phosphate PW_R005631 PG(19:iso/12:0(3-OH)) + PE(12:0/12:0) > Ethanolamine + CL(19:iso/12:0(3-OH)/12:0/12:0) PW_R005632 2 PG(19:iso/12:0(3-OH)) > Glycerol + CL(19:iso/12:0(3-OH)/19:iso/12:0(3-OH)) PW_R005633