2.0 2012-10-24 09:55:01 -0600 2015-09-16 17:34:54 -0600 ECMDB23692 M2MDB004082 PG(15:0cyclo/19:iso) PG(15:0cyclo/19:iso) 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(15:0cyclo/19:iso), in particular, consists of one cis-9,10-Methylenetetradecanoic acid chain to the C-1 atom, and one 17-methylocatdecanoyl 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-(cis-9,10-Methylenetetradecanoyl)-2-17-methylocatdecanoyl-sn-glycero-3-phospho-(1'-glycerol) 1-(cis-9,10-Methylenetetradecanoyl)-2-17-methylocatdecanoyl-sn-glycero-3-phosphoglycerol 1-(cis-9,10-Methylenetetradecanoyl)-2-17-methylocatdecanoyl-sn-glycero-3-phosphoglycerol GPG(15:0/19:0) GPG(34:0) PG(15:0/19:0) PG(34:0) Phosphatidylglycerol(15:0/19:0) Phosphatidylglycerol(34:0) C40H77O10P 749.0071 748.525435196 (3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(17-methyloctadecanoyl)oxy]propoxy)(2,3-dihydroxypropoxy)phosphinic acid 3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(17-methyloctadecanoyl)oxy]propoxy(2,3-dihydroxypropoxy)phosphinic acid CCCCC1CC1CCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCCCCC(C)C InChI=1S/C40H77O10P/c1-4-5-25-35-29-36(35)26-21-17-15-19-22-27-39(43)47-32-38(33-49-51(45,46)48-31-37(42)30-41)50-40(44)28-23-18-14-12-10-8-6-7-9-11-13-16-20-24-34(2)3/h34-38,41-42H,4-33H2,1-3H3,(H,45,46) ZGAFCCPBGJRBLI-UHFFFAOYSA-N Solid Membrane logp 7.61 ALOGPS logs -6.83 ALOGPS solubility 1.10e-04 g/l ALOGPS logp 10.89 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -3 ChemAxon iupac (3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(17-methyloctadecanoyl)oxy]propoxy)(2,3-dihydroxypropoxy)phosphinic acid ChemAxon average_mass 749.0071 ChemAxon mono_mass 748.525435196 ChemAxon smiles CCCCC1CC1CCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCCCCC(C)C ChemAxon formula C40H77O10P ChemAxon inchi InChI=1S/C40H77O10P/c1-4-5-25-35-29-36(35)26-21-17-15-19-22-27-39(43)47-32-38(33-49-51(45,46)48-31-37(42)30-41)50-40(44)28-23-18-14-12-10-8-6-7-9-11-13-16-20-24-34(2)3/h34-38,41-42H,4-33H2,1-3H3,(H,45,46) ChemAxon inchikey ZGAFCCPBGJRBLI-UHFFFAOYSA-N ChemAxon polar_surface_area 148.82 ChemAxon refractivity 202.55 ChemAxon polarizability 90.99 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)/15:0cyclo/15:0cyclo/19:0cycv8c)) 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. PW001517 Metabolic phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/19:0cycv8c/15:0cyclo) "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." PW001088 Metabolic Specdb::CMs 1087682 Specdb::NmrOneD 344708 Specdb::NmrOneD 344709 Specdb::NmrOneD 344710 Specdb::NmrOneD 344711 Specdb::NmrOneD 344712 Specdb::NmrOneD 344713 Specdb::NmrOneD 344714 Specdb::NmrOneD 344715 Specdb::NmrOneD 344716 Specdb::NmrOneD 344717 Specdb::NmrOneD 344718 Specdb::NmrOneD 344719 Specdb::NmrOneD 344720 Specdb::NmrOneD 344721 Specdb::NmrOneD 344722 Specdb::NmrOneD 344723 Specdb::NmrOneD 344724 Specdb::NmrOneD 344725 Specdb::NmrOneD 344726 Specdb::NmrOneD 344727 Specdb::MsMs 24938 Specdb::MsMs 24939 Specdb::MsMs 24940 Specdb::MsMs 31496 Specdb::MsMs 31497 Specdb::MsMs 31498 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 PE(15:0/15:0) + PG(15:0cyclo/19:iso) > Ethanolamine + CL(15:0cyclo/15:0cyclo/19:0cycv8c/15:0cyclo) PW_R003951 PG(15:0cyclo/19:iso) + PE(15:0/18:1(9Z)) > CL(18:1(9Z)/15:0cyclo/15:0cyclo/19:0cycv8c) + Ethanolamine PW_R004802 2 PGP(15:0cyclo/19:iso) + Water >2 PG(15:0cyclo/19:iso) + Phosphate PW_R005738