2.02012-05-31 14:19:09 -06002015-12-09 12:08:06 -0700ECMDB10615M2MDB000797PG(18:1(11Z)/16:0)PG(18:1(11Z)/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(18:1(11Z)/16:0), in particular, consists of one 11Z-octadecenoyl 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.1-(11Z-Octadecenoyl)-2-hexadecanoyl-sn-glycero-3-phospho-(1'-glycerol)1-(11Z-octadecenoyl)-2-hexadecanoyl-sn-glycero-3-phosphoglycerol1-phosphatidylglycerol1-Vaccenoyl-2-palmitoyl-sn-glycero-3-phosphoglycerol3(3-phosphatidyl-)glycerol3-(3-<i>sn</i>-phosphatidyl)glycerol3-(3-sn-Phosphatidyl)glycerolGPG(18:1/16:0)GPG(18:1n7/16:0)GPG(18:1w7/16:0)GPG(34:1)PG(18:1/16:0)PG(18:1n7/16:0)PG(18:1w7/16:0)PG(34:1)PhosphatidylglycerolPhosphatidylglycerol(18:1/16:0)Phosphatidylglycerol(18:1n7/16:0)Phosphatidylglycerol(18:1w7/16:0)Phosphatidylglycerol(34:1)C40H77O10P749.0071748.525435196[(2S)-2,3-dihydroxypropoxy][(2R)-3-(hexadecanoyloxy)-2-[(11Z)-octadec-11-enoyloxy]propoxy]phosphinic acid(2S)-2,3-dihydroxypropoxy(2R)-3-(hexadecanoyloxy)-2-[(11Z)-octadec-11-enoyloxy]propoxyphosphinic acid[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCCInChI=1S/C40H77O10P/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/h13,15,37-38,41-42H,3-12,14,16-36H2,1-2H3,(H,45,46)/b15-13-/t37-,38+/m0/s1ADYWCMPUNIVOEA-GPJPVTGXSA-NSolidInner membraneMembraneOuter membranelogp8.16logs-6.86solubility1.03e-04 g/llogp11.46pka_strongest_acidic1.89pka_strongest_basic-3iupac[(2S)-2,3-dihydroxypropoxy][(2R)-3-(hexadecanoyloxy)-2-[(11Z)-octadec-11-enoyloxy]propoxy]phosphinic acidaverage_mass749.0071mono_mass748.525435196smiles[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCCformulaC40H77O10PinchiInChI=1S/C40H77O10P/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/h13,15,37-38,41-42H,3-12,14,16-36H2,1-2H3,(H,45,46)/b15-13-/t37-,38+/m0/s1inchikeyADYWCMPUNIVOEA-GPJPVTGXSA-Npolar_surface_area148.82refractivity205.63polarizability90.5rotatable_bond_count41acceptor_count6donor_count3physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis IPHOSLIPSYN-PWYSpecdb::CMs777415Specdb::CMs777416Specdb::CMs777417Specdb::CMs777418Specdb::CMs777419Specdb::CMs777420Specdb::CMs777421Specdb::CMs777422Specdb::CMs777423Specdb::NmrOneD337748Specdb::NmrOneD337749Specdb::NmrOneD337750Specdb::NmrOneD337751Specdb::NmrOneD337752Specdb::NmrOneD337753Specdb::NmrOneD337754Specdb::NmrOneD337755Specdb::NmrOneD337756Specdb::NmrOneD337757Specdb::NmrOneD337758Specdb::NmrOneD337759Specdb::NmrOneD337760Specdb::NmrOneD337761Specdb::NmrOneD337762Specdb::NmrOneD337763Specdb::NmrOneD337764Specdb::NmrOneD337765Specdb::NmrOneD337766Specdb::NmrOneD337767Specdb::MsMs24698Specdb::MsMs24699Specdb::MsMs24700Specdb::MsMs31256Specdb::MsMs31257Specdb::MsMs31258Specdb::MsMs2279956Specdb::MsMs2279957Specdb::MsMs2279958HMDB1061524768114C00344L-1-PHOSPHATIDYL-GLYCEROLKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75.22102590Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.APhosphatidylglycerophosphatase BP0A924PGPB_ECOLIpgpBhttp://ecmdb.ca/proteins/P0A924.xmlPhosphatidylglycerophosphatase AP18200PGPA_ECOLIpgpAhttp://ecmdb.ca/proteins/P18200.xmlProtein crcAP37001CRCA_ECOLIcrcAhttp://ecmdb.ca/proteins/P37001.xmlCardiolipin synthaseP0A6H8CLS_ECOLIclshttp://ecmdb.ca/proteins/P0A6H8.xmlPutative cardiolipin synthase ybhOP0AA84YBHO_ECOLIybhOhttp://ecmdb.ca/proteins/P0AA84.xmlProbable phospholipid ABC transporter-binding protein mlaBP64602MLAB_ECOLImlaBhttp://ecmdb.ca/proteins/P64602.xmlProbable phospholipid ABC transporter-binding protein mlaDP64604MLAD_ECOLImlaDhttp://ecmdb.ca/proteins/P64604.xmlProbable phospholipid ABC transporter permease protein mlaEP64606MLAE_ECOLImlaEhttp://ecmdb.ca/proteins/P64606.xmlPGP(18:1(11Z)/16:0) + Water > PG(18:1(11Z)/16:0) + PhosphatePW_R003649