2.0 2012-10-24 09:54:59 -0600 2015-12-09 12:06:50 -0700 ECMDB23677 M2MDB004067 PG(14:0(3-OH)/17:0cycw7c) PG(14:0(3-OH)/17:0cycw7c) 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(14:0(3-OH)/17:0cycw7c), in particular, consists of one 3-hydroxytetradecanoyl chain to the C-1 atom, and one heptadec-9-10-cyclo-anoyl 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. 1-3-hydroxytetradecanoyl-2-heptadec-9-10-cyclo-anoyl-sn-glycero-3-phospho-(1'-glycerol) 1-3-hydroxytetradecanoyl-2-heptadec-9-10-cyclo-anoyl-sn-glycero-3-phosphoglycerol 1-3-hydroxytetradecanoyl-2-heptadec-9-10-cyclo-anoyl-sn-glycero-3-phosphoglycerol GPG(14:0/17:0) GPG(31:0) PG(14:0/17:0) PG(31:0) Phosphatidylglycerol(14:0/17:0) Phosphatidylglycerol(31:0) C37H71O11P 722.938 722.473400104 [(2S)-2,3-dihydroxypropoxy][(2R)-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxytetradecanoyl)oxy]propoxy]phosphinic acid (2S)-2,3-dihydroxypropoxy((2R)-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxytetradecanoyl)oxy]propoxy)phosphinic acid [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCCCC)OC(=O)CC(O)CCCCCCCCCCC InChI=1S/C37H71O11P/c1-3-5-7-9-10-11-12-15-19-23-33(39)26-37(42)48-35(30-47-49(43,44)46-28-34(40)27-38)29-45-36(41)24-20-16-13-14-18-22-32-25-31(32)21-17-8-6-4-2/h31-35,38-40H,3-30H2,1-2H3,(H,43,44)/t31?,32?,33?,34-,35+/m0/s1 NCFDTLKDDWOMGW-BISNVOBLSA-N Solid Membrane logp 6.27 ALOGPS logs -6.33 ALOGPS solubility 3.41e-04 g/l ALOGPS logp 8.48 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac [(2S)-2,3-dihydroxypropoxy][(2R)-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxytetradecanoyl)oxy]propoxy]phosphinic acid ChemAxon average_mass 722.938 ChemAxon mono_mass 722.473400104 ChemAxon smiles [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCCCC)OC(=O)CC(O)CCCCCCCCCCC ChemAxon formula C37H71O11P ChemAxon inchi InChI=1S/C37H71O11P/c1-3-5-7-9-10-11-12-15-19-23-33(39)26-37(42)48-35(30-47-49(43,44)46-28-34(40)27-38)29-45-36(41)24-20-16-13-14-18-22-32-25-31(32)21-17-8-6-4-2/h31-35,38-40H,3-30H2,1-2H3,(H,43,44)/t31?,32?,33?,34-,35+/m0/s1 ChemAxon inchikey NCFDTLKDDWOMGW-BISNVOBLSA-N ChemAxon polar_surface_area 169.05 ChemAxon refractivity 190.32 ChemAxon polarizability 84.71 ChemAxon rotatable_bond_count 37 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis (CL(14:0(3-OH)/17:0cycw7c/14:0(3-OH)/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. PW001941 Metabolic phospholipid biosynthesis (CL(14:0(3-OH)/17:0cycw7c/14:0/14:0)) 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. PW001942 Metabolic Specdb::CMs 1086852 Specdb::NmrOneD 263228 Specdb::NmrOneD 263229 Specdb::NmrOneD 263230 Specdb::NmrOneD 263231 Specdb::NmrOneD 263232 Specdb::NmrOneD 263233 Specdb::NmrOneD 263234 Specdb::NmrOneD 263235 Specdb::NmrOneD 263236 Specdb::NmrOneD 263237 Specdb::NmrOneD 263238 Specdb::NmrOneD 263239 Specdb::NmrOneD 263240 Specdb::NmrOneD 263241 Specdb::NmrOneD 263242 Specdb::NmrOneD 263243 Specdb::NmrOneD 263244 Specdb::NmrOneD 263245 Specdb::NmrOneD 263246 Specdb::NmrOneD 263247 Specdb::MsMs 1235323 Specdb::MsMs 1235324 Specdb::MsMs 1235325 Specdb::MsMs 1350799 Specdb::MsMs 1350800 Specdb::MsMs 1350801 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 Yuan Y, Leeds JA, Meredith TC (2012). "Pseudomonas aeruginosa Directly Shunts β-Oxidation Degradation Intermediates into De Novo Fatty Acid Biosynthesis." J Bacteriol. 194(19):5185-96 22753057 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(14:0(3-OH)/17:0cycw7c) + Water >2 PG(14:0(3-OH)/17:0cycw7c) + Phosphate PW_R005456 PG(14:0(3-OH)/17:0cycw7c) + PE(14:0/14:0) > Ethanolamine + CL(14:0(3-OH)/17:0cycw7c/14:0/14:0) PW_R005458 2 PG(14:0(3-OH)/17:0cycw7c) > Glycerol + CL(14:0(3-OH)/17:0cycw7c/14:0(3-OH)/17:0cycw7c) PW_R005457