2.02012-05-31 14:19:05 -06002015-12-09 12:07:45 -0700ECMDB10588M2MDB000796PG(16:1(9Z)/18:1(11Z))PG(16:1(9Z)/18:1(11Z)) 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(16:1(9Z)/18:1(11Z)), in particular, consists of one 9Z-hexadecenoyl chain to the C-1 atom, and one 11Z-octadecenoyl 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-(9Z-Hexadecenoyl)-2-(11Z-octadecenoyl)-sn-glycero-3-phospho-(1'-glycerol)1-(9Z-hexadecenoyl)-2-(11Z-octadecenoyl)-sn-glycero-3-phosphoglycerol1-Palmitoleoyl-2-vaccenoyl-sn-glycero-3-phosphoglycerol1-phosphatidylglycerol3(3-phosphatidyl-)glycerol3-(3-<i>sn</i>-phosphatidyl)glycerol3-(3-sn-Phosphatidyl)glycerolGPG(16:1/18:1)GPG(16:1n7/18:1n7)GPG(16:1w7/18:1w7)GPG(34:2)PG(16:1/18:1)PG(16:1n7/18:1n7)PG(16:1w7/18:1w7)PG(34:2)PhosphatidylglycerolPhosphatidylglycerol(16:1/18:1)Phosphatidylglycerol(16:1n7/18:1n7)Phosphatidylglycerol(16:1w7/18:1w7)Phosphatidylglycerol(34:2)C40H75O10P746.9913746.509785132[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propoxy]phosphinic acid(2S)-2,3-dihydroxypropoxy(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propoxyphosphinic acid[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCInChI=1S/C40H75O10P/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/h13-16,37-38,41-42H,3-12,17-36H2,1-2H3,(H,45,46)/b15-13-,16-14-/t37-,38+/m0/s1ICYKSOZJGJBBNU-GFJSAGKOSA-NSolidInner membraneMembraneOuter membranelogp8.01logs-6.85solubility1.06e-04 g/llogp11.1pka_strongest_acidic1.89pka_strongest_basic-3iupac[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propoxy]phosphinic acidaverage_mass746.9913mono_mass746.509785132smiles[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCformulaC40H75O10PinchiInChI=1S/C40H75O10P/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/h13-16,37-38,41-42H,3-12,17-36H2,1-2H3,(H,45,46)/b15-13-,16-14-/t37-,38+/m0/s1inchikeyICYKSOZJGJBBNU-GFJSAGKOSA-Npolar_surface_area148.82refractivity206.74polarizability88.49rotatable_bond_count40acceptor_count6donor_count3physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis IPHOSLIPSYN-PWYSpecdb::CMs773800Specdb::CMs773801Specdb::CMs773802Specdb::CMs773803Specdb::CMs773804Specdb::CMs773805Specdb::CMs773806Specdb::CMs773807Specdb::CMs773808Specdb::NmrOneD336618Specdb::NmrOneD336619Specdb::NmrOneD336620Specdb::NmrOneD336621Specdb::NmrOneD336622Specdb::NmrOneD336623Specdb::NmrOneD336624Specdb::NmrOneD336625Specdb::NmrOneD336626Specdb::NmrOneD336627Specdb::NmrOneD336628Specdb::NmrOneD336629Specdb::NmrOneD336630Specdb::NmrOneD336631Specdb::NmrOneD336632Specdb::NmrOneD336633Specdb::NmrOneD336634Specdb::NmrOneD336635Specdb::NmrOneD336636Specdb::NmrOneD336637Specdb::MsMs28991Specdb::MsMs28992Specdb::MsMs28993Specdb::MsMs35549Specdb::MsMs35550Specdb::MsMs35551Specdb::MsMs2815102Specdb::MsMs2815103Specdb::MsMs2815104HMDB1058824768087C00344L-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.xmlWater + PGP(16:1(9Z)/18:1(11Z)) > Phosphate + PG(16:1(9Z)/18:1(11Z))PW_R003630