2.0 2015-09-08 19:30:46 -0600 2015-12-09 12:08:20 -0700 ECMDB24397 M2MDB006514 PG(18:1(9Z)/19:1(9Z)) PG(18:1(9Z)/19:1(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(18:1(9Z)/19:1(9Z)), in particular, consists of one 9Z-octadecenoyl chain to the C-1 atom, and one 9Z-nonadecenoyl 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. C43H81O10P 789.085 788.556735806 [(2S)-2,3-dihydroxypropoxy][(2R)-3-[(9Z)-nonadec-9-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid (2S)-2,3-dihydroxypropoxy((2R)-3-[(9Z)-nonadec-9-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy)phosphinic acid [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC InChI=1S/C43H81O10P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-42(46)50-38-41(39-52-54(48,49)51-37-40(45)36-44)53-43(47)35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h18-21,40-41,44-45H,3-17,22-39H2,1-2H3,(H,48,49)/b20-18-,21-19-/t40-,41+/m0/s1 QRSHKROOJVNJFH-XABOAZGISA-N logp 8.64 ALOGPS logs -7.01 ALOGPS solubility 7.63e-05 g/l ALOGPS logp 12.44 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -3 ChemAxon iupac [(2S)-2,3-dihydroxypropoxy][(2R)-3-[(9Z)-nonadec-9-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid ChemAxon average_mass 789.085 ChemAxon mono_mass 788.556735806 ChemAxon smiles [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC ChemAxon formula C43H81O10P ChemAxon inchi InChI=1S/C43H81O10P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-42(46)50-38-41(39-52-54(48,49)51-37-40(45)36-44)53-43(47)35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h18-21,40-41,44-45H,3-17,22-39H2,1-2H3,(H,48,49)/b20-18-,21-19-/t40-,41+/m0/s1 ChemAxon inchikey QRSHKROOJVNJFH-XABOAZGISA-N ChemAxon polar_surface_area 148.82 ChemAxon refractivity 220.55 ChemAxon polarizability 95.28 ChemAxon rotatable_bond_count 43 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 1084649 Specdb::NmrOneD 293435 Specdb::NmrOneD 293436 Specdb::NmrOneD 293437 Specdb::NmrOneD 293438 Specdb::NmrOneD 293439 Specdb::NmrOneD 293440 Specdb::NmrOneD 293441 Specdb::NmrOneD 293442 Specdb::NmrOneD 293443 Specdb::NmrOneD 293444 Specdb::NmrOneD 293445 Specdb::NmrOneD 293446 Specdb::NmrOneD 293447 Specdb::NmrOneD 293448 Specdb::NmrOneD 293449 Specdb::NmrOneD 293450 Specdb::NmrOneD 293451 Specdb::NmrOneD 293452 Specdb::NmrOneD 293453 Specdb::NmrOneD 293454 Specdb::MsMs 1324402 Specdb::MsMs 1324403 Specdb::MsMs 1324404 Specdb::MsMs 1438768 Specdb::MsMs 1438769 Specdb::MsMs 1438770 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