2.0 2012-07-30 14:55:10 -0600 2015-12-09 17:01:23 -0700 ECMDB21267 M2MDB001674 PG(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-phosphoglycerol 1,2-Distearoyl-rac-glycero-3-phosphoglycerol GPG(18:0/18:0) GPG(36:0) PG(36:0) Phosphatidylglycerol(18:0/18:0) Phosphatidylglycerol(36:0) C42H83O10P 779.09 778.572385871 [(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)CCCCCCCCCCCCCCCCC InChI=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/s1 FVJZSBGHRPJMMA-XRSDMRJBSA-N Solid Membrane logp 8.60 ALOGPS logs -7.03 ALOGPS solubility 7.31e-05 g/l ALOGPS logp 12.72 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -3 ChemAxon iupac [(2R)-2,3-bis(octadecanoyloxy)propoxy][(2R)-2,3-dihydroxypropoxy]phosphinic acid ChemAxon average_mass 779.09 ChemAxon mono_mass 778.572385871 ChemAxon smiles [H][C@@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC ChemAxon formula C42H83O10P ChemAxon inchi InChI=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/s1 ChemAxon inchikey FVJZSBGHRPJMMA-XRSDMRJBSA-N ChemAxon polar_surface_area 148.82 ChemAxon refractivity 213.71 ChemAxon polarizability 95.75 ChemAxon rotatable_bond_count 44 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis I (18:0, 18:0) PW001001 Metabolic Specdb::CMs 1086939 Specdb::NmrOneD 328252 Specdb::NmrOneD 328253 Specdb::NmrOneD 328254 Specdb::NmrOneD 328255 Specdb::NmrOneD 328256 Specdb::NmrOneD 328257 Specdb::NmrOneD 328258 Specdb::NmrOneD 328259 Specdb::NmrOneD 328260 Specdb::NmrOneD 328261 Specdb::NmrOneD 328262 Specdb::NmrOneD 328263 Specdb::NmrOneD 328264 Specdb::NmrOneD 328265 Specdb::NmrOneD 328266 Specdb::NmrOneD 328267 Specdb::NmrOneD 328268 Specdb::NmrOneD 328269 Specdb::NmrOneD 328270 Specdb::NmrOneD 328271 Specdb::MsMs 1232554 Specdb::MsMs 1232555 Specdb::MsMs 1232556 Specdb::MsMs 1348081 Specdb::MsMs 1348082 Specdb::MsMs 1348083 HMDB10602 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 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 Lysophospholipase L2 P07000 PLDB_ECOLI pldB http://ecmdb.ca/proteins/P07000.xml Phospholipase A1 P0A921 PA1_ECOLI pldA http://ecmdb.ca/proteins/P0A921.xml Phosphatidylglycerophosphatase B P0A924 PGPB_ECOLI pgpB http://ecmdb.ca/proteins/P0A924.xml Phosphatidylglycerophosphatase A P18200 PGPA_ECOLI pgpA http://ecmdb.ca/proteins/P18200.xml Bifunctional protein aas P31119 AAS_ECOLI aas http://ecmdb.ca/proteins/P31119.xml Lipid A export ATP-binding/permease protein msbA P60752 MSBA_ECOLI msbA http://ecmdb.ca/proteins/P60752.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 Lipid A export ATP-binding/permease protein msbA P60752 MSBA_ECOLI msbA http://ecmdb.ca/proteins/P60752.xml Water + PGP(18:0/18:0) > PG(18:0/18:0) + Phosphate 2 PG(18:0/18:0) <> cardiolipin (tetraoctadecanoyl, n-C18:0) + Glycerol Adenosine 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) + Pyrophosphate Water + 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) + Glycerylphosphorylethanolamine 2-Acyl-sn-glycero-3-phosphoglycerol (N-C18:0) + PG(18:0/18:0) > Acyl phosphatidylglycerol (N-C18:0) + Glycerophosphoglycerol PGP(18:0/18:0) + Water > Phosphate + PG(18:0/18:0) + PG(18:0/18:0) PW_R003741 PG(18:0/18:0) + PE(18:0/18:0) + PG(18:0/18:0) > CL(16:0/16:0/16:0/16:1(9Z)) + Ethanolamine PW_R003744 PG(18:0/18:0) + PG(18:0/18:0) > Glycerol + CL(16:0/16:0/16:0/16:1(9Z)) PW_R003743