2.0 2015-09-08 19:30:09 -0600 2015-12-09 12:07:22 -0700 ECMDB24382 M2MDB006499 PG(15:0cyclo/17:0cycw7c) PG(15:0cyclo/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(15:0cyclo/17:0cycw7c), in particular, consists of one cis-9,10-Methylenetetradecanoic acid 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. C38H71O10P 718.95 718.478485484 [(2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid (2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCCC1CC1CCCC InChI=1S/C38H71O10P/c1-3-5-7-14-20-33-26-34(33)22-16-10-8-12-17-23-37(41)45-29-36(30-47-49(43,44)46-28-35(40)27-39)48-38(42)24-18-13-9-11-15-21-32-25-31(32)19-6-4-2/h31-36,39-40H,3-30H2,1-2H3,(H,43,44)/t31?,32?,33?,34?,35-,36+/m0/s1 KMFKTOIJVNSQTK-CWMDRTTDSA-N logp 7.07 ALOGPS logs -6.60 ALOGPS solubility 1.81e-04 g/l ALOGPS logp 9.38 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -3 ChemAxon iupac [(2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid ChemAxon average_mass 718.95 ChemAxon mono_mass 718.478485484 ChemAxon smiles [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCCC1CC1CCCC ChemAxon formula C38H71O10P ChemAxon inchi InChI=1S/C38H71O10P/c1-3-5-7-14-20-33-26-34(33)22-16-10-8-12-17-23-37(41)45-29-36(30-47-49(43,44)46-28-35(40)27-39)48-38(42)24-18-13-9-11-15-21-32-25-31(32)19-6-4-2/h31-36,39-40H,3-30H2,1-2H3,(H,43,44)/t31?,32?,33?,34?,35-,36+/m0/s1 ChemAxon inchikey KMFKTOIJVNSQTK-CWMDRTTDSA-N ChemAxon polar_surface_area 148.82 ChemAxon refractivity 191.49 ChemAxon polarizability 84.5 ChemAxon rotatable_bond_count 36 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/17:0cycw7c/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." PW001193 Metabolic Specdb::CMs 1085332 Specdb::EiMs 3551 Specdb::NmrOneD 300645 Specdb::NmrOneD 300646 Specdb::NmrOneD 300647 Specdb::NmrOneD 300648 Specdb::NmrOneD 300649 Specdb::NmrOneD 300650 Specdb::NmrOneD 300651 Specdb::NmrOneD 300652 Specdb::NmrOneD 300653 Specdb::NmrOneD 300654 Specdb::NmrOneD 300655 Specdb::NmrOneD 300656 Specdb::NmrOneD 300657 Specdb::NmrOneD 300658 Specdb::NmrOneD 300659 Specdb::NmrOneD 300660 Specdb::NmrOneD 300661 Specdb::NmrOneD 300662 Specdb::NmrOneD 300663 Specdb::NmrOneD 300664 Specdb::MsMs 1242664 Specdb::MsMs 1242665 Specdb::MsMs 1242666 Specdb::MsMs 1358050 Specdb::MsMs 1358051 Specdb::MsMs 1358052 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(15:0cyclo/17:0cycw7c) + Water >2 PG(15:0cyclo/17:0cycw7c) + Phosphate PW_R005778