2.02012-07-30 14:55:10 -06002015-12-09 17:01:23 -0700ECMDB21267M2MDB001674PG(18:0/18:0)PG(18:0/18:0) 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(18:0/18:0), in particular, consists of two octadecanoyl chains at positions C-1 and C-2. 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.1,2-Dioctadecanoyl-rac-glycero-3-phospho-(1'-glycerol)1,2-dioctadecanoyl-rac-glycero-3-phosphoglycerol1,2-Distearoyl-rac-glycero-3-phosphoglycerolGPG(18:0/18:0)GPG(36:0)PG(36:0)Phosphatidylglycerol(18:0/18:0)Phosphatidylglycerol(36:0)C42H83O10P779.09778.572385871[(2R)-2,3-bis(octadecanoyloxy)propoxy][(2R)-2,3-dihydroxypropoxy]phosphinic acid(2R)-2,3-bis(octadecanoyloxy)propoxy((2R)-2,3-dihydroxypropoxy)phosphinic acid[H][C@@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCInChI=1S/C42H83O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(45)49-37-40(38-51-53(47,48)50-36-39(44)35-43)52-42(46)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h39-40,43-44H,3-38H2,1-2H3,(H,47,48)/t39-,40-/m1/s1FVJZSBGHRPJMMA-XRSDMRJBSA-NSolidMembranelogp8.60logs-7.03solubility7.31e-05 g/llogp12.72pka_strongest_acidic1.89pka_strongest_basic-3iupac[(2R)-2,3-bis(octadecanoyloxy)propoxy][(2R)-2,3-dihydroxypropoxy]phosphinic acidaverage_mass779.09mono_mass778.572385871smiles[H][C@@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCformulaC42H83O10PinchiInChI=1S/C42H83O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(45)49-37-40(38-51-53(47,48)50-36-39(44)35-43)52-42(46)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h39-40,43-44H,3-38H2,1-2H3,(H,47,48)/t39-,40-/m1/s1inchikeyFVJZSBGHRPJMMA-XRSDMRJBSA-Npolar_surface_area148.82refractivity213.71polarizability95.75rotatable_bond_count44acceptor_count6donor_count3physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis I (18:0, 18:0)PW001001MetabolicSpecdb::CMs1086939Specdb::NmrOneD328252Specdb::NmrOneD328253Specdb::NmrOneD328254Specdb::NmrOneD328255Specdb::NmrOneD328256Specdb::NmrOneD328257Specdb::NmrOneD328258Specdb::NmrOneD328259Specdb::NmrOneD328260Specdb::NmrOneD328261Specdb::NmrOneD328262Specdb::NmrOneD328263Specdb::NmrOneD328264Specdb::NmrOneD328265Specdb::NmrOneD328266Specdb::NmrOneD328267Specdb::NmrOneD328268Specdb::NmrOneD328269Specdb::NmrOneD328270Specdb::NmrOneD328271Specdb::MsMs1232554Specdb::MsMs1232555Specdb::MsMs1232556Specdb::MsMs1348081Specdb::MsMs1348082Specdb::MsMs1348083HMDB10602Kanehisa, 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-D114.22080510Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.ALysophospholipase L2P07000PLDB_ECOLIpldBhttp://ecmdb.ca/proteins/P07000.xmlPhospholipase A1P0A921PA1_ECOLIpldAhttp://ecmdb.ca/proteins/P0A921.xmlPhosphatidylglycerophosphatase BP0A924PGPB_ECOLIpgpBhttp://ecmdb.ca/proteins/P0A924.xmlPhosphatidylglycerophosphatase AP18200PGPA_ECOLIpgpAhttp://ecmdb.ca/proteins/P18200.xmlBifunctional protein aasP31119AAS_ECOLIaashttp://ecmdb.ca/proteins/P31119.xmlLipid A export ATP-binding/permease protein msbAP60752MSBA_ECOLImsbAhttp://ecmdb.ca/proteins/P60752.xmlCardiolipin synthaseP0A6H8CLS_ECOLIclshttp://ecmdb.ca/proteins/P0A6H8.xmlPutative cardiolipin synthase ybhOP0AA84YBHO_ECOLIybhOhttp://ecmdb.ca/proteins/P0AA84.xmlCardiolipin synthase CP75919CLSC_ECOLIclsChttp://ecmdb.ca/proteins/P75919.xmlLipid A export ATP-binding/permease protein msbAP60752MSBA_ECOLImsbAhttp://ecmdb.ca/proteins/P60752.xmlWater + PGP(18:0/18:0) > PG(18:0/18:0) + Phosphate2 PG(18:0/18:0) <> cardiolipin (tetraoctadecanoyl, n-C18:0) + GlycerolAdenosine triphosphate + Water + PG(18:0/18:0) > ADP + Hydrogen ion + Phosphate + PG(18:0/18:0)Adenosine triphosphate + Water + PG(18:0/18:0) > ADP + Hydrogen ion + Phosphate + PG(18:0/18:0)2-Acyl-sn-glycero-3-phosphoglycerol (N-C18:0) + Adenosine triphosphate + Octadecanoate (N-C18:0) > Adenosine monophosphate + PG(18:0/18:0) + PyrophosphateWater + PG(18:0/18:0) > 1-Acyl-sn-glycero-3-phosphoglycerol (N-C18:0) + Hydrogen ion + Octadecanoate (N-C18:0)Water + PG(18:0/18:0) > 2-Acyl-sn-glycero-3-phosphoglycerol (N-C18:0) + Hydrogen ion + Octadecanoate (N-C18:0)2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:0) + PG(18:0/18:0) > Acyl phosphatidylglycerol (N-C18:0) + Glycerylphosphorylethanolamine2-Acyl-sn-glycero-3-phosphoglycerol (N-C18:0) + PG(18:0/18:0) > Acyl phosphatidylglycerol (N-C18:0) + GlycerophosphoglycerolPGP(18:0/18:0) + Water > Phosphate + PG(18:0/18:0) + PG(18:0/18:0)PW_R003741PG(18:0/18:0) + PE(18:0/18:0) + PG(18:0/18:0) > CL(16:0/16:0/16:0/16:1(9Z)) + EthanolaminePW_R003744PG(18:0/18:0) + PG(18:0/18:0) > Glycerol + CL(16:0/16:0/16:0/16:1(9Z))PW_R003743