2.0 2015-09-08 19:30:26 -0600 2015-12-09 12:07:57 -0700 ECMDB24389 M2MDB006506 PG(17:0cycw7c/16:1(9Z)) PG(17:0cycw7c/16:1(9Z)) 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(17:0cycw7c/16:1(9Z)), in particular, consists of one heptadec-9-10-cyclo-anoyl chain to the C-1 atom, and one 9Z-hexadecenoyl 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. C39H73O10P 732.977 732.494135549 [(2S)-2,3-dihydroxypropoxy][(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy]phosphinic acid (2S)-2,3-dihydroxypropoxy((2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy)phosphinic acid [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCC1CC1CCCCCC InChI=1S/C39H73O10P/c1-3-5-7-9-10-11-12-13-14-15-16-19-23-27-38(42)46-32-37(33-48-50(44,45)47-31-36(41)30-40)49-39(43)28-24-20-17-18-22-26-35-29-34(35)25-21-8-6-4-2/h11-12,34-37,40-41H,3-10,13-33H2,1-2H3,(H,44,45)/b12-11-/t34?,35?,36-,37+/m0/s1 HLOQZXBLCJTBOH-GIBPPOJLSA-N logp 7.48 ALOGPS logs -6.70 ALOGPS solubility 1.47e-04 g/l ALOGPS logp 10.24 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -3 ChemAxon iupac [(2S)-2,3-dihydroxypropoxy][(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy]phosphinic acid ChemAxon average_mass 732.977 ChemAxon mono_mass 732.494135549 ChemAxon smiles [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCC1CC1CCCCCC ChemAxon formula C39H73O10P ChemAxon inchi InChI=1S/C39H73O10P/c1-3-5-7-9-10-11-12-13-14-15-16-19-23-27-38(42)46-32-37(33-48-50(44,45)47-31-36(41)30-40)49-39(43)28-24-20-17-18-22-26-35-29-34(35)25-21-8-6-4-2/h11-12,34-37,40-41H,3-10,13-33H2,1-2H3,(H,44,45)/b12-11-/t34?,35?,36-,37+/m0/s1 ChemAxon inchikey HLOQZXBLCJTBOH-GIBPPOJLSA-N ChemAxon polar_surface_area 148.82 ChemAxon refractivity 199.12 ChemAxon polarizability 86.56 ChemAxon rotatable_bond_count 38 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis CL(16:0/16:0/17:0cycw7c/16:1(9Z)) "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." PW001273 Metabolic Specdb::CMs 1085649 Specdb::NmrOneD 307991 Specdb::NmrOneD 307992 Specdb::NmrOneD 307993 Specdb::NmrOneD 307994 Specdb::NmrOneD 307995 Specdb::NmrOneD 307996 Specdb::NmrOneD 307997 Specdb::NmrOneD 307998 Specdb::NmrOneD 307999 Specdb::NmrOneD 308000 Specdb::NmrOneD 308001 Specdb::NmrOneD 308002 Specdb::NmrOneD 308003 Specdb::NmrOneD 308004 Specdb::NmrOneD 308005 Specdb::NmrOneD 308006 Specdb::NmrOneD 308007 Specdb::NmrOneD 308008 Specdb::NmrOneD 308009 Specdb::NmrOneD 308010 Specdb::MsMs 1315234 Specdb::MsMs 1315235 Specdb::MsMs 1315236 Specdb::MsMs 1429708 Specdb::MsMs 1429709 Specdb::MsMs 1429710 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 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 Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. 22102590 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 Phosphatidylglycerophosphatase B P0A924 PGPB_ECOLI pgpB http://ecmdb.ca/proteins/P0A924.xml Phosphatidylglycerophosphatase A P18200 PGPA_ECOLI pgpA http://ecmdb.ca/proteins/P18200.xml 2 PGP(17:0cycw7c/16:1(9Z)) + Water >2 PG(17:0cycw7c/16:1(9Z)) + Phosphate PW_R005788