2.02012-10-24 09:55:06 -06002015-09-16 17:34:55 -0600ECMDB23718M2MDB004108PG(19:iso/14:0(3-OH))PG(19:iso/14:0(3-OH)) 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(19:iso/14:0(3-OH)), in particular, consists of one 17-methylocatdecanoyl chain to the C-1 atom, and one 3-hydroxytetradecanoyl 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.1-17-methylocatdecanoyl-2-3-hydroxytetradecanoyl-sn-glycero-3-phospho-(1'-glycerol)1-17-methylocatdecanoyl-2-3-hydroxytetradecanoyl-sn-glycero-3-phosphoglycerol1-17-methylocatdecanoyl-2-3-hydroxytetradecanoyl-sn-glycero-3-phosphoglycerolGPG(19:0/14:0)GPG(33:0)PG(19:0/14:0)PG(33:0)Phosphatidylglycerol(19:0/14:0)Phosphatidylglycerol(33:0)C39H77O11P752.9958752.520349818(2,3-dihydroxypropoxy)({2-[(3-hydroxytetradecanoyl)oxy]-3-[(17-methyloctadecanoyl)oxy]propoxy})phosphinic acid2,3-dihydroxypropoxy(2-[(3-hydroxytetradecanoyl)oxy]-3-[(17-methyloctadecanoyl)oxy]propoxy)phosphinic acidCCCCCCCCCCCC(O)CC(=O)OC(COC(=O)CCCCCCCCCCCCCCCC(C)C)COP(O)(=O)OCC(O)COInChI=1S/C39H77O11P/c1-4-5-6-7-8-14-18-21-24-27-35(41)29-39(44)50-37(33-49-51(45,46)48-31-36(42)30-40)32-47-38(43)28-25-22-19-16-13-11-9-10-12-15-17-20-23-26-34(2)3/h34-37,40-42H,4-33H2,1-3H3,(H,45,46)YWSQPWCEOLJTJR-UHFFFAOYSA-NSolidMembranelogp6.89logs-6.53solubility2.22e-04 g/llogp9.99pka_strongest_acidic1.89pka_strongest_basic-2.8iupac(2,3-dihydroxypropoxy)({2-[(3-hydroxytetradecanoyl)oxy]-3-[(17-methyloctadecanoyl)oxy]propoxy})phosphinic acidaverage_mass752.9958mono_mass752.520349818smilesCCCCCCCCCCCC(O)CC(=O)OC(COC(=O)CCCCCCCCCCCCCCCC(C)C)COP(O)(=O)OCC(O)COformulaC39H77O11PinchiInChI=1S/C39H77O11P/c1-4-5-6-7-8-14-18-21-24-27-35(41)29-39(44)50-37(33-49-51(45,46)48-31-36(42)30-40)32-47-38(43)28-25-22-19-16-13-11-9-10-12-15-17-20-23-26-34(2)3/h34-37,40-42H,4-33H2,1-3H3,(H,45,46)inchikeyYWSQPWCEOLJTJR-UHFFFAOYSA-Npolar_surface_area169.05refractivity201.37polarizability91.08rotatable_bond_count40acceptor_count7donor_count4physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564Specdb::CMs1085537Specdb::NmrOneD260948Specdb::NmrOneD260949Specdb::NmrOneD260950Specdb::NmrOneD260951Specdb::NmrOneD260952Specdb::NmrOneD260953Specdb::NmrOneD260954Specdb::NmrOneD260955Specdb::NmrOneD260956Specdb::NmrOneD260957Specdb::NmrOneD260958Specdb::NmrOneD260959Specdb::NmrOneD260960Specdb::NmrOneD260961Specdb::NmrOneD260962Specdb::NmrOneD260963Specdb::NmrOneD260964Specdb::NmrOneD260965Specdb::NmrOneD260966Specdb::NmrOneD260967Specdb::MsMs28025Specdb::MsMs28026Specdb::MsMs28027Specdb::MsMs34583Specdb::MsMs34584Specdb::MsMs34585Kanehisa, 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-D114.22080510Yuan Y, Leeds JA, Meredith TC (2012). "Pseudomonas aeruginosa Directly Shunts β-Oxidation Degradation Intermediates into De Novo Fatty Acid Biosynthesis." J Bacteriol. 194(19):5185-9622753057Casadei MA, Mañas P, Niven G, Needs E, Mackey BM. (2002) "Role of membrane fluidity in pressure resistance of Escherichia coli NCTC 8164." Appl Environ Microbiol. 68(12):5965-72.12450817Yurtsever 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.xmlPhosphatidylglycerophosphatase BP0A924PGPB_ECOLIpgpBhttp://ecmdb.ca/proteins/P0A924.xmlPhosphatidylglycerophosphatase AP18200PGPA_ECOLIpgpAhttp://ecmdb.ca/proteins/P18200.xmlLipid A export ATP-binding/permease protein msbAP60752MSBA_ECOLImsbAhttp://ecmdb.ca/proteins/P60752.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.xmlLipid A export ATP-binding/permease protein msbAP60752MSBA_ECOLImsbAhttp://ecmdb.ca/proteins/P60752.xmlProbable phospholipid ABC transporter-binding protein mlaDP64604MLAD_ECOLImlaDhttp://ecmdb.ca/proteins/P64604.xmlProbable phospholipid ABC transporter permease protein mlaEP64606MLAE_ECOLImlaEhttp://ecmdb.ca/proteins/P64606.xml