2.0 2015-09-08 18:59:45 -0600 2015-12-09 12:08:07 -0700 ECMDB24274 M2MDB006391 PG(18:1(11Z)/18:0) PG(18:1(11Z)/18:0) 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(18:1(11Z)/18:0), in particular, consists of one 11Z-octadecenoyl chain to the C-1 atom, and one octadecanoyl 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. C42H81O10P 777.0603 776.556735324 [(2S)-2,3-dihydroxypropoxy][(2R)-2-[(11Z)-octadec-11-enoyloxy]-3-(octadecanoyloxy)propoxy]phosphinic acid (2S)-2,3-dihydroxypropoxy(2R)-2-[(11Z)-octadec-11-enoyloxy]-3-(octadecanoyloxy)propoxyphosphinic acid [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC InChI=1S/C42H81O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(45)49-37-40(38-51-53(47,48)50-36-39(44)35-43)52-42(46)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h14,16,39-40,43-44H,3-13,15,17-38H2,1-2H3,(H,47,48)/b16-14-/t39-,40+/m0/s1 DLNHWYPDKXOVLH-KBTQSRGQSA-N logp 8.57 ALOGPS logs -6.96 ALOGPS solubility 8.44e-05 g/l ALOGPS logp 12.35 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -3 ChemAxon iupac [(2S)-2,3-dihydroxypropoxy][(2R)-2-[(11Z)-octadec-11-enoyloxy]-3-(octadecanoyloxy)propoxy]phosphinic acid ChemAxon average_mass 777.0603 ChemAxon mono_mass 776.556735324 ChemAxon smiles [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC ChemAxon formula C42H81O10P ChemAxon inchi InChI=1S/C42H81O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(45)49-37-40(38-51-53(47,48)50-36-39(44)35-43)52-42(46)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h14,16,39-40,43-44H,3-13,15,17-38H2,1-2H3,(H,47,48)/b16-14-/t39-,40+/m0/s1 ChemAxon inchikey DLNHWYPDKXOVLH-KBTQSRGQSA-N ChemAxon polar_surface_area 148.82 ChemAxon refractivity 214.83 ChemAxon polarizability 94.18 ChemAxon rotatable_bond_count 43 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 784627 Specdb::CMs 784628 Specdb::CMs 784629 Specdb::CMs 784630 Specdb::CMs 784631 Specdb::CMs 784632 Specdb::NmrOneD 264048 Specdb::NmrOneD 264049 Specdb::NmrOneD 264050 Specdb::NmrOneD 264051 Specdb::NmrOneD 264052 Specdb::NmrOneD 264053 Specdb::NmrOneD 264054 Specdb::NmrOneD 264055 Specdb::NmrOneD 264056 Specdb::NmrOneD 264057 Specdb::NmrOneD 264058 Specdb::NmrOneD 264059 Specdb::NmrOneD 264060 Specdb::NmrOneD 264061 Specdb::NmrOneD 264062 Specdb::NmrOneD 264063 Specdb::NmrOneD 264064 Specdb::NmrOneD 264065 Specdb::NmrOneD 264066 Specdb::NmrOneD 264067 Specdb::MsMs 25691 Specdb::MsMs 25692 Specdb::MsMs 25693 Specdb::MsMs 32249 Specdb::MsMs 32250 Specdb::MsMs 32251 Specdb::MsMs 2451493 Specdb::MsMs 2451494 Specdb::MsMs 2451495 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