2.0 2015-09-08 19:36:34 -0600 2015-12-09 17:21:23 -0700 ECMDB24513 M2MDB006630 PGP(18:1(9Z)/19:1(9Z)) PGP(18:1(9Z)/19:1(9Z)) belongs to the class of glycerophosphoglycerophosphates, also called phosphatidylglycerophosphates (PGPs). These lipids contain a common glycerophosphate skeleton linked to at least one fatty acyl chain and a glycero-3-phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerophosphates can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PGP(18:1(9Z)/19:1(9Z)), in particular, consists of one 9Z-octadecenoyl chain to the C-1 atom, and one 9Z-nonadecenoyl to the C-2 atom. In E. coli, PGPs can be found in the cytoplasmic membrane. The are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to Phosphatidylglycerols (PGs) by the enzyme Phosphatidylglycerophosphatase. C43H82O13P2 869.064 868.523066696 [(2R)-2-hydroxy-3-({hydroxy[(2R)-2-[(9Z)-nonadec-9-enoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid (2R)-2-hydroxy-3-{[hydroxy((2R)-2-[(9Z)-nonadec-9-enoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy)phosphoryl]oxy}propoxyphosphonic acid [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCCC InChI=1S/C43H82O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-43(46)56-41(39-55-58(50,51)54-37-40(44)36-53-57(47,48)49)38-52-42(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h18-21,40-41,44H,3-17,22-39H2,1-2H3,(H,50,51)(H2,47,48,49)/b20-18-,21-19-/t40-,41-/m1/s1 GPEXXDGSKBETNR-OJZYNHBYSA-N logp 7.66 ALOGPS logs -6.23 ALOGPS solubility 5.10e-04 g/l ALOGPS logp 12.31 ChemAxon pka_strongest_acidic 1.35 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [(2R)-2-hydroxy-3-({hydroxy[(2R)-2-[(9Z)-nonadec-9-enoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid ChemAxon average_mass 869.064 ChemAxon mono_mass 868.523066696 ChemAxon smiles [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCCC ChemAxon formula C43H82O13P2 ChemAxon inchi InChI=1S/C43H82O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-43(46)56-41(39-55-58(50,51)54-37-40(44)36-53-57(47,48)49)38-52-42(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h18-21,40-41,44H,3-17,22-39H2,1-2H3,(H,50,51)(H2,47,48,49)/b20-18-,21-19-/t40-,41-/m1/s1 ChemAxon inchikey GPEXXDGSKBETNR-OJZYNHBYSA-N ChemAxon polar_surface_area 195.35 ChemAxon refractivity 231.42 ChemAxon polarizability 100.56 ChemAxon rotatable_bond_count 45 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 248628 Specdb::NmrOneD 248629 Specdb::NmrOneD 248630 Specdb::NmrOneD 248631 Specdb::NmrOneD 248632 Specdb::NmrOneD 248633 Specdb::NmrOneD 248634 Specdb::NmrOneD 248635 Specdb::NmrOneD 248636 Specdb::NmrOneD 248637 Specdb::NmrOneD 248638 Specdb::NmrOneD 248639 Specdb::NmrOneD 248640 Specdb::NmrOneD 248641 Specdb::NmrOneD 248642 Specdb::NmrOneD 248643 Specdb::NmrOneD 248644 Specdb::NmrOneD 248645 Specdb::NmrOneD 248646 Specdb::NmrOneD 248647 Specdb::MsMs 1228012 Specdb::MsMs 1228013 Specdb::MsMs 1228014 Specdb::MsMs 1343590 Specdb::MsMs 1343591 Specdb::MsMs 1343592 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