2.0 2015-09-08 18:59:30 -0600 2015-12-09 12:07:37 -0700 ECMDB24265 M2MDB006382 PG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)) PG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)) 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(16:0/22:5(7Z,10Z,13Z,16Z,19Z)), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 7Z,10Z,13Z,16Z,19Z-docosapentaenoyl 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. C44H77O10P 797.064 796.525435677 [(2S)-2,3-dihydroxypropoxy][(2R)-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-2-(hexadecanoyloxy)propoxy]phosphinic acid (2S)-2,3-dihydroxypropoxy((2R)-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-2-(hexadecanoyloxy)propoxy)phosphinic acid [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCCCCCCCCCC InChI=1S/C44H77O10P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-25-27-29-31-33-35-43(47)51-39-42(40-53-55(49,50)52-38-41(46)37-45)54-44(48)36-34-32-30-28-26-23-16-14-12-10-8-6-4-2/h5,7,11,13,17-18,20-21,24-25,41-42,45-46H,3-4,6,8-10,12,14-16,19,22-23,26-40H2,1-2H3,(H,49,50)/b7-5-,13-11-,18-17-,21-20-,25-24-/t41-,42+/m0/s1 IUTIUWYTMFXMMO-RUVFBLPJSA-N logp 8.21 ALOGPS logs -7.00 ALOGPS solubility 7.90e-05 g/l ALOGPS logp 11.79 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -3 ChemAxon iupac [(2S)-2,3-dihydroxypropoxy][(2R)-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-2-(hexadecanoyloxy)propoxy]phosphinic acid ChemAxon average_mass 797.064 ChemAxon mono_mass 796.525435677 ChemAxon smiles [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCCCCCCCCCC ChemAxon formula C44H77O10P ChemAxon inchi InChI=1S/C44H77O10P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-25-27-29-31-33-35-43(47)51-39-42(40-53-55(49,50)52-38-41(46)37-45)54-44(48)36-34-32-30-28-26-23-16-14-12-10-8-6-4-2/h5,7,11,13,17-18,20-21,24-25,41-42,45-46H,3-4,6,8-10,12,14-16,19,22-23,26-40H2,1-2H3,(H,49,50)/b7-5-,13-11-,18-17-,21-20-,25-24-/t41-,42+/m0/s1 ChemAxon inchikey IUTIUWYTMFXMMO-RUVFBLPJSA-N ChemAxon polar_surface_area 148.82 ChemAxon refractivity 228.5 ChemAxon polarizability 93.77 ChemAxon rotatable_bond_count 41 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 787610 Specdb::CMs 787611 Specdb::CMs 787612 Specdb::NmrOneD 260228 Specdb::NmrOneD 260229 Specdb::NmrOneD 260230 Specdb::NmrOneD 260231 Specdb::NmrOneD 260232 Specdb::NmrOneD 260233 Specdb::NmrOneD 260234 Specdb::NmrOneD 260235 Specdb::NmrOneD 260236 Specdb::NmrOneD 260237 Specdb::NmrOneD 260238 Specdb::NmrOneD 260239 Specdb::NmrOneD 260240 Specdb::NmrOneD 260241 Specdb::NmrOneD 260242 Specdb::NmrOneD 260243 Specdb::NmrOneD 260244 Specdb::NmrOneD 260245 Specdb::NmrOneD 260246 Specdb::NmrOneD 260247 Specdb::MsMs 1224466 Specdb::MsMs 1224467 Specdb::MsMs 1224468 Specdb::MsMs 1340077 Specdb::MsMs 1340078 Specdb::MsMs 1340079 Specdb::MsMs 2274630 Specdb::MsMs 2274631 Specdb::MsMs 2274632 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