2.0 2012-10-24 09:55:06 -0600 2015-09-16 17:34:55 -0600 ECMDB23718 M2MDB004108 PG(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-phosphoglycerol 1-17-methylocatdecanoyl-2-3-hydroxytetradecanoyl-sn-glycero-3-phosphoglycerol GPG(19:0/14:0) GPG(33:0) PG(19:0/14:0) PG(33:0) Phosphatidylglycerol(19:0/14:0) Phosphatidylglycerol(33:0) C39H77O11P 752.9958 752.520349818 (2,3-dihydroxypropoxy)({2-[(3-hydroxytetradecanoyl)oxy]-3-[(17-methyloctadecanoyl)oxy]propoxy})phosphinic acid 2,3-dihydroxypropoxy(2-[(3-hydroxytetradecanoyl)oxy]-3-[(17-methyloctadecanoyl)oxy]propoxy)phosphinic acid CCCCCCCCCCCC(O)CC(=O)OC(COC(=O)CCCCCCCCCCCCCCCC(C)C)COP(O)(=O)OCC(O)CO InChI=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-N Solid Membrane logp 6.89 ALOGPS logs -6.53 ALOGPS solubility 2.22e-04 g/l ALOGPS logp 9.99 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac (2,3-dihydroxypropoxy)({2-[(3-hydroxytetradecanoyl)oxy]-3-[(17-methyloctadecanoyl)oxy]propoxy})phosphinic acid ChemAxon average_mass 752.9958 ChemAxon mono_mass 752.520349818 ChemAxon smiles CCCCCCCCCCCC(O)CC(=O)OC(COC(=O)CCCCCCCCCCCCCCCC(C)C)COP(O)(=O)OCC(O)CO ChemAxon formula C39H77O11P ChemAxon inchi InChI=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) ChemAxon inchikey YWSQPWCEOLJTJR-UHFFFAOYSA-N ChemAxon polar_surface_area 169.05 ChemAxon refractivity 201.37 ChemAxon polarizability 91.08 ChemAxon rotatable_bond_count 40 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 Specdb::CMs 1085537 Specdb::NmrOneD 260948 Specdb::NmrOneD 260949 Specdb::NmrOneD 260950 Specdb::NmrOneD 260951 Specdb::NmrOneD 260952 Specdb::NmrOneD 260953 Specdb::NmrOneD 260954 Specdb::NmrOneD 260955 Specdb::NmrOneD 260956 Specdb::NmrOneD 260957 Specdb::NmrOneD 260958 Specdb::NmrOneD 260959 Specdb::NmrOneD 260960 Specdb::NmrOneD 260961 Specdb::NmrOneD 260962 Specdb::NmrOneD 260963 Specdb::NmrOneD 260964 Specdb::NmrOneD 260965 Specdb::NmrOneD 260966 Specdb::NmrOneD 260967 Specdb::MsMs 28025 Specdb::MsMs 28026 Specdb::MsMs 28027 Specdb::MsMs 34583 Specdb::MsMs 34584 Specdb::MsMs 34585 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 Yuan Y, Leeds JA, Meredith TC (2012). "Pseudomonas aeruginosa Directly Shunts β-Oxidation Degradation Intermediates into De Novo Fatty Acid Biosynthesis." J Bacteriol. 194(19):5185-96 22753057 Casadei 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. 12450817 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 Phosphatidylglycerophosphatase B P0A924 PGPB_ECOLI pgpB http://ecmdb.ca/proteins/P0A924.xml Phosphatidylglycerophosphatase A P18200 PGPA_ECOLI pgpA http://ecmdb.ca/proteins/P18200.xml Lipid A export ATP-binding/permease protein msbA P60752 MSBA_ECOLI msbA http://ecmdb.ca/proteins/P60752.xml Protein crcA P37001 CRCA_ECOLI crcA http://ecmdb.ca/proteins/P37001.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 Probable phospholipid ABC transporter-binding protein mlaB P64602 MLAB_ECOLI mlaB http://ecmdb.ca/proteins/P64602.xml Lipid A export ATP-binding/permease protein msbA P60752 MSBA_ECOLI msbA http://ecmdb.ca/proteins/P60752.xml Probable phospholipid ABC transporter-binding protein mlaD P64604 MLAD_ECOLI mlaD http://ecmdb.ca/proteins/P64604.xml Probable phospholipid ABC transporter permease protein mlaE P64606 MLAE_ECOLI mlaE http://ecmdb.ca/proteins/P64606.xml