2.0 2015-09-08 18:59:45 -0600 2015-12-09 12:08:03 -0700 ECMDB24271 M2MDB006388 PG(18:0/16:0) PG(18:0/16:0) 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(18:0/16:0), in particular, consists of one octadecanoyl chain to the C-1 atom, and one hexadecanoyl 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. C40H79O10P 751.023 750.54108526 [(2S)-2,3-dihydroxypropoxy][(2R)-3-(hexadecanoyloxy)-2-(octadecanoyloxy)propoxy]phosphinic acid (2S)-2,3-dihydroxypropoxy((2R)-3-(hexadecanoyloxy)-2-(octadecanoyloxy)propoxy)phosphinic acid [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC InChI=1S/C40H79O10P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-40(44)50-38(36-49-51(45,46)48-34-37(42)33-41)35-47-39(43)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h37-38,41-42H,3-36H2,1-2H3,(H,45,46)/t37-,38+/m0/s1 KBPVYRBBONZJHF-QPPIDDCLSA-N logp 8.27 ALOGPS logs -6.84 ALOGPS solubility 1.09e-04 g/l ALOGPS logp 11.83 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -3 ChemAxon iupac [(2S)-2,3-dihydroxypropoxy][(2R)-3-(hexadecanoyloxy)-2-(octadecanoyloxy)propoxy]phosphinic acid ChemAxon average_mass 751.023 ChemAxon mono_mass 750.54108526 ChemAxon smiles [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC ChemAxon formula C40H79O10P ChemAxon inchi InChI=1S/C40H79O10P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-40(44)50-38(36-49-51(45,46)48-34-37(42)33-41)35-47-39(43)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h37-38,41-42H,3-36H2,1-2H3,(H,45,46)/t37-,38+/m0/s1 ChemAxon inchikey KBPVYRBBONZJHF-QPPIDDCLSA-N ChemAxon polar_surface_area 148.82 ChemAxon refractivity 204.51 ChemAxon polarizability 92.31 ChemAxon rotatable_bond_count 42 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 777641 Specdb::CMs 777642 Specdb::CMs 777643 Specdb::CMs 777644 Specdb::CMs 777645 Specdb::CMs 777646 Specdb::CMs 777647 Specdb::CMs 777648 Specdb::CMs 777649 Specdb::NmrOneD 260248 Specdb::NmrOneD 260249 Specdb::NmrOneD 260250 Specdb::NmrOneD 260251 Specdb::NmrOneD 260252 Specdb::NmrOneD 260253 Specdb::NmrOneD 260254 Specdb::NmrOneD 260255 Specdb::NmrOneD 260256 Specdb::NmrOneD 260257 Specdb::NmrOneD 260258 Specdb::NmrOneD 260259 Specdb::NmrOneD 260260 Specdb::NmrOneD 260261 Specdb::NmrOneD 260262 Specdb::NmrOneD 260263 Specdb::NmrOneD 260264 Specdb::NmrOneD 260265 Specdb::NmrOneD 260266 Specdb::NmrOneD 260267 Specdb::MsMs 23363 Specdb::MsMs 23364 Specdb::MsMs 23365 Specdb::MsMs 30161 Specdb::MsMs 30162 Specdb::MsMs 30163 Specdb::MsMs 2744718 Specdb::MsMs 2744719 Specdb::MsMs 2744720 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