2.0 2015-09-08 19:30:51 -0600 2015-12-09 12:08:30 -0700 ECMDB24399 M2MDB006516 PG(19:0cycv8c/15:0cyclo) PG(19:0cycv8c/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(19:0cycv8c/15:0cyclo), in particular, consists of one heptadec-11-12-cyclo-anoyl 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. C40H75O10P 747.004 746.509785613 [(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid (2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCC)OC(=O)CCCCCCCCCC1CC1CCCCCC InChI=1S/C40H75O10P/c1-3-5-7-16-22-35-28-36(35)24-17-12-9-8-10-14-20-26-40(44)50-38(32-49-51(45,46)48-30-37(42)29-41)31-47-39(43)25-19-15-11-13-18-23-34-27-33(34)21-6-4-2/h33-38,41-42H,3-32H2,1-2H3,(H,45,46)/t33?,34?,35?,36?,37-,38+/m0/s1 SWDBJXLRNBSNHF-GWHWHECRSA-N logp 7.50 ALOGPS logs -6.79 ALOGPS solubility 1.20e-04 g/l ALOGPS logp 10.27 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -3 ChemAxon iupac [(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid ChemAxon average_mass 747.004 ChemAxon mono_mass 746.509785613 ChemAxon smiles [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCC)OC(=O)CCCCCCCCCC1CC1CCCCCC ChemAxon formula C40H75O10P ChemAxon inchi InChI=1S/C40H75O10P/c1-3-5-7-16-22-35-28-36(35)24-17-12-9-8-10-14-20-26-40(44)50-38(32-49-51(45,46)48-30-37(42)29-41)31-47-39(43)25-19-15-11-13-18-23-34-27-33(34)21-6-4-2/h33-38,41-42H,3-32H2,1-2H3,(H,45,46)/t33?,34?,35?,36?,37-,38+/m0/s1 ChemAxon inchikey SWDBJXLRNBSNHF-GWHWHECRSA-N ChemAxon polar_surface_area 148.82 ChemAxon refractivity 200.7 ChemAxon polarizability 88.98 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(19:0cycv8c/15:0cyclo/17:0cycw7c/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. PW001302 Metabolic phospholipid biosynthesis (CL(19:0cycv8c/15:0cyclo/19:0cycv8c/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. PW001309 Metabolic phospholipid biosynthesis (CL(19:0cycv8c/15:0cyclo/19:0cycv8c/16:0)) 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. PW001316 Metabolic Specdb::CMs 1084975 Specdb::EiMs 3991 Specdb::NmrOneD 307591 Specdb::NmrOneD 307592 Specdb::NmrOneD 307593 Specdb::NmrOneD 307594 Specdb::NmrOneD 307595 Specdb::NmrOneD 307596 Specdb::NmrOneD 307597 Specdb::NmrOneD 307598 Specdb::NmrOneD 307599 Specdb::NmrOneD 307600 Specdb::NmrOneD 307601 Specdb::NmrOneD 307602 Specdb::NmrOneD 307603 Specdb::NmrOneD 307604 Specdb::NmrOneD 307605 Specdb::NmrOneD 307606 Specdb::NmrOneD 307607 Specdb::NmrOneD 307608 Specdb::NmrOneD 307609 Specdb::NmrOneD 307610 Specdb::MsMs 1255576 Specdb::MsMs 1255577 Specdb::MsMs 1255578 Specdb::MsMs 1370764 Specdb::MsMs 1370765 Specdb::MsMs 1370766 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 Cardiolipin synthase C P75919 CLSC_ECOLI clsC http://ecmdb.ca/proteins/P75919.xml PGP(19:0cycv8c/15:0cyclo) + Water PG(19:0cycv8c/15:0cyclo) + Phosphate PW_R005218 PGP(19:0cycv8c/15:0cyclo) + Water > PG(19:0cycv8c/15:0cyclo) + Phosphate PW_R005222 PG(19:0cycv8c/15:0cyclo) + PE(19:0cycv8c/14:0) > CL(19:0cycv8c/15:0cyclo/19:0cycv8c/14:0) + Ethanolamine PW_R005056 PE(17:0cycw7c/17:0cycw7c) + PG(19:0cycv8c/15:0cyclo) > CL(19:0cycv8c/15:0cyclo/17:0cycw7c/17:0cycw7c) + Ethanolamine PW_R005058 PG(19:0cycv8c/15:0cyclo) + PE(19:0cycv8c/16:0) > CL(19:0cycv8c/15:0cyclo/19:0cycv8c/16:0) + Ethanolamine PW_R005120