2.0 2012-08-09 09:16:18 -0600 2015-12-09 12:07:30 -0700 ECMDB21453 M2MDB001848 PG(16:0/18:0) PG(16:0/18:0) 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(16:0/18:0), in particular, consists of one hexadecanoyl 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. (2R)-1-(2S)-2,3-dihydroxypropoxy-hydroxyphosphoryloxy-3-hexadecanoyloxypropan-2-yl octadecanoate (2R)-1-(2S)-2,3-Dihydroxypropoxy-hydroxyphosphoryloxy-3-hexadecanoyloxypropan-2-yl octadecanoic acid 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phospho-(1'-glycerol) 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphoglycerol 1-palmitoyl-2-stearoyl-sn-glycero-3-phosphoglycerol GPG(16:0/18:0) GPG(34:0) PG(34:0) Phosphatidylglycerol(16:0/18:0) Phosphatidylglycerol(34:0) C40H79O10P 751.023 750.54108526 [(2S)-2,3-dihydroxypropoxy][(2R)-2-(hexadecanoyloxy)-3-(octadecanoyloxy)propoxy]phosphinic acid (2S)-2,3-dihydroxypropoxy((2R)-2-(hexadecanoyloxy)-3-(octadecanoyloxy)propoxy)phosphinic acid [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC InChI=1S/C40H79O10P/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-39(43)47-35-38(36-49-51(45,46)48-34-37(42)33-41)50-40(44)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2/h37-38,41-42H,3-36H2,1-2H3,(H,45,46)/t37-,38+/m0/s1 WYVBOKLMHDFYQD-QPPIDDCLSA-N Solid Membrane 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)-2-(hexadecanoyloxy)-3-(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)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC ChemAxon formula C40H79O10P ChemAxon inchi InChI=1S/C40H79O10P/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-39(43)47-35-38(36-49-51(45,46)48-34-37(42)33-41)50-40(44)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2/h37-38,41-42H,3-36H2,1-2H3,(H,45,46)/t37-,38+/m0/s1 ChemAxon inchikey WYVBOKLMHDFYQD-QPPIDDCLSA-N ChemAxon polar_surface_area 148.82 ChemAxon refractivity 204.51 ChemAxon polarizability 91.74 ChemAxon rotatable_bond_count 42 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::CMs 777650 Specdb::CMs 777651 Specdb::CMs 777652 Specdb::CMs 777653 Specdb::CMs 777654 Specdb::CMs 777655 Specdb::CMs 777656 Specdb::CMs 777657 Specdb::CMs 777658 Specdb::NmrOneD 255128 Specdb::NmrOneD 255129 Specdb::NmrOneD 255130 Specdb::NmrOneD 255131 Specdb::NmrOneD 255132 Specdb::NmrOneD 255133 Specdb::NmrOneD 255134 Specdb::NmrOneD 255135 Specdb::NmrOneD 255136 Specdb::NmrOneD 255137 Specdb::NmrOneD 255138 Specdb::NmrOneD 255139 Specdb::NmrOneD 255140 Specdb::NmrOneD 255141 Specdb::NmrOneD 255142 Specdb::NmrOneD 255143 Specdb::NmrOneD 255144 Specdb::NmrOneD 255145 Specdb::NmrOneD 255146 Specdb::NmrOneD 255147 Specdb::MsMs 29687 Specdb::MsMs 29688 Specdb::MsMs 29689 Specdb::MsMs 36245 Specdb::MsMs 36246 Specdb::MsMs 36247 Specdb::MsMs 2915576 Specdb::MsMs 2915577 Specdb::MsMs 2915578 HMDB10572 395645 NULL 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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 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 Protein crcA P37001 CRCA_ECOLI crcA http://ecmdb.ca/proteins/P37001.xml Cardiolipin synthase P0A6H8 CLS_ECOLI cls http://ecmdb.ca/proteins/P0A6H8.xml Putative cardiolipin synthase ybhO P0AA84 YBHO_ECOLI ybhO http://ecmdb.ca/proteins/P0AA84.xml Cardiolipin synthase C P75919 CLSC_ECOLI clsC http://ecmdb.ca/proteins/P75919.xml Probable phospholipid ABC transporter-binding protein mlaB P64602 MLAB_ECOLI mlaB http://ecmdb.ca/proteins/P64602.xml Probable phospholipid ABC transporter-binding protein mlaD P64604 MLAD_ECOLI mlaD http://ecmdb.ca/proteins/P64604.xml Probable phospholipid ABC transporter permease protein mlaE P64606 MLAE_ECOLI mlaE http://ecmdb.ca/proteins/P64606.xml PGP(16:0/18:0) + Water > PG(16:0/18:0) + Phosphate PW_R004100 PE(14:0/20:0) + PG(16:0/18:0) > Ethanolamine + CL(19:0cycv8c/16:0/19:0cycv8c/18:1(9Z)) PW_R004285