2.0 2012-10-24 09:54:52 -0600 2015-12-09 12:06:01 -0700 ECMDB23638 M2MDB004028 PG(10:0(3-OH)/15:0cyclo) PG(10:0(3-OH)/15:0cyclo) 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(10:0(3-OH)/15:0cyclo), in particular, consists of one 3-hydroxydecanoyl chain to the C-1 atom, and one cis-9,10-Methylenetetradecanoic acid 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-hydroxydecanoyl-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phospho-(1'-glycerol) 1-3-hydroxydecanoyl-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phosphoglycerol 1-NULL-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phospho-(1'-glycerol) 1-NULL-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phosphoglycerol GPG(10:0/15:0) GPG(25:0) PG(10:0/15:0) PG(25:0) Phosphatidylglycerol(10:0/15:0) Phosphatidylglycerol(25:0) C31H59O11P 638.776 638.379499718 [(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxydecanoyl)oxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid (2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxydecanoyl)oxy]propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCC)OC(=O)CC(O)CCCCCCC InChI=1S/C31H59O11P/c1-3-5-7-9-13-17-27(33)20-31(36)42-29(24-41-43(37,38)40-22-28(34)21-32)23-39-30(35)18-14-11-8-10-12-16-26-19-25(26)15-6-4-2/h25-29,32-34H,3-24H2,1-2H3,(H,37,38)/t25?,26?,27?,28-,29+/m0/s1 OKIUYVUZRIMBGJ-IFULXZEUSA-N Solid Membrane logp 4.37 ALOGPS logs -5.86 ALOGPS solubility 8.79e-04 g/l ALOGPS logp 5.82 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac [(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxydecanoyl)oxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid ChemAxon average_mass 638.776 ChemAxon mono_mass 638.379499718 ChemAxon smiles [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCC)OC(=O)CC(O)CCCCCCC ChemAxon formula C31H59O11P ChemAxon inchi InChI=1S/C31H59O11P/c1-3-5-7-9-13-17-27(33)20-31(36)42-29(24-41-43(37,38)40-22-28(34)21-32)23-39-30(35)18-14-11-8-10-12-16-26-19-25(26)15-6-4-2/h25-29,32-34H,3-24H2,1-2H3,(H,37,38)/t25?,26?,27?,28-,29+/m0/s1 ChemAxon inchikey OKIUYVUZRIMBGJ-IFULXZEUSA-N ChemAxon polar_surface_area 169.05 ChemAxon refractivity 162.71 ChemAxon polarizability 71.58 ChemAxon rotatable_bond_count 31 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis (CL(10:0(3-OH)/15:0cyclo/10:0(3-OH)/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. PW001902 Metabolic Specdb::CMs 1084116 Specdb::EiMs 5082 Specdb::NmrOneD 271258 Specdb::NmrOneD 271259 Specdb::NmrOneD 271260 Specdb::NmrOneD 271261 Specdb::NmrOneD 271262 Specdb::NmrOneD 271263 Specdb::NmrOneD 271264 Specdb::NmrOneD 271265 Specdb::NmrOneD 271266 Specdb::NmrOneD 271267 Specdb::NmrOneD 271268 Specdb::NmrOneD 271269 Specdb::NmrOneD 271270 Specdb::NmrOneD 271271 Specdb::NmrOneD 271272 Specdb::NmrOneD 271273 Specdb::NmrOneD 271274 Specdb::NmrOneD 271275 Specdb::NmrOneD 271276 Specdb::NmrOneD 271277 Specdb::MsMs 1233280 Specdb::MsMs 1233281 Specdb::MsMs 1233282 Specdb::MsMs 1348792 Specdb::MsMs 1348793 Specdb::MsMs 1348794 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 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(10:0(3-OH)/15:0cyclo) + Water >2 PG(10:0(3-OH)/15:0cyclo) + Phosphate PW_R005295 2 PG(10:0(3-OH)/15:0cyclo) > CL(10:0(3-OH)/15:0cyclo/10:0(3-OH)/15:0cyclo) + Glycerol PW_R005297