2.0 2012-10-24 09:54:51 -0600 2015-12-09 12:05:51 -0700 ECMDB23632 M2MDB004022 PG(10:0(3-OH)/10:0(3-OH)) PG(10:0(3-OH)/10:0(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(10:0(3-OH)/10:0(3-OH)), in particular, consists of two 3-hydroxydecanoyl chains at positions C-1 and C-2. 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. 1,2-di3-hydroxydecanoyl-rac-glycero-3-phospho-(1'-glycerol) 1,2-di3-hydroxydecanoyl-rac-glycero-3-phosphoglycerol 1,2-diNULL-rac-glycero-3-phospho-(1'-glycerol) 1,2-diNULL-rac-glycero-3-phosphoglycerol GPG(10:0/10:0) GPG(20:0) PG(10:0/10:0) PG(20:0) Phosphatidylglycerol(10:0/10:0) Phosphatidylglycerol(20:0) C26H51O12P 586.656 586.31181408 [(2R)-2,3-bis[(3-hydroxydecanoyl)oxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid (2R)-2,3-bis[(3-hydroxydecanoyl)oxy]propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCC)OC(=O)CC(O)CCCCCCC InChI=1S/C26H51O12P/c1-3-5-7-9-11-13-21(28)15-25(31)35-19-24(20-37-39(33,34)36-18-23(30)17-27)38-26(32)16-22(29)14-12-10-8-6-4-2/h21-24,27-30H,3-20H2,1-2H3,(H,33,34)/t21?,22?,23-,24+/m0/s1 RNMLJIBTZIFLAP-STTLMXHVSA-N Solid Membrane logp 2.06 ALOGPS logs -4.22 ALOGPS solubility 3.56e-02 g/l ALOGPS logp 3.14 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac [(2R)-2,3-bis[(3-hydroxydecanoyl)oxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid ChemAxon average_mass 586.656 ChemAxon mono_mass 586.31181408 ChemAxon smiles [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCC)OC(=O)CC(O)CCCCCCC ChemAxon formula C26H51O12P ChemAxon inchi InChI=1S/C26H51O12P/c1-3-5-7-9-11-13-21(28)15-25(31)35-19-24(20-37-39(33,34)36-18-23(30)17-27)38-26(32)16-22(29)14-12-10-8-6-4-2/h21-24,27-30H,3-20H2,1-2H3,(H,33,34)/t21?,22?,23-,24+/m0/s1 ChemAxon inchikey RNMLJIBTZIFLAP-STTLMXHVSA-N ChemAxon polar_surface_area 189.28 ChemAxon refractivity 143.13 ChemAxon polarizability 64.08 ChemAxon rotatable_bond_count 28 ChemAxon acceptor_count 8 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis (CL(18:0/10:0/10:0/10:0)) 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. PW001974 Metabolic Specdb::CMs 1084489 Specdb::NmrOneD 271238 Specdb::NmrOneD 271239 Specdb::NmrOneD 271240 Specdb::NmrOneD 271241 Specdb::NmrOneD 271242 Specdb::NmrOneD 271243 Specdb::NmrOneD 271244 Specdb::NmrOneD 271245 Specdb::NmrOneD 271246 Specdb::NmrOneD 271247 Specdb::NmrOneD 271248 Specdb::NmrOneD 271249 Specdb::NmrOneD 271250 Specdb::NmrOneD 271251 Specdb::NmrOneD 271252 Specdb::NmrOneD 271253 Specdb::NmrOneD 271254 Specdb::NmrOneD 271255 Specdb::NmrOneD 271256 Specdb::NmrOneD 271257 Specdb::MsMs 1264870 Specdb::MsMs 1264871 Specdb::MsMs 1264872 Specdb::MsMs 1379944 Specdb::MsMs 1379945 Specdb::MsMs 1379946 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)/10:0(3-OH)) + Water >2 PG(10:0(3-OH)/10:0(3-OH)) + Phosphate PW_R005713