2.0 2012-10-24 09:55:07 -0600 2015-09-16 17:34:55 -0600 ECMDB23721 M2MDB004111 PG(19:iso/16:0) PG(19:iso/16:0) 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(19:iso/16:0), in particular, consists of one 17-methylocatdecanoyl chain to the C-1 atom, and one hexadecanoyl 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-hexadecanoyl-sn-glycero-3-phospho-(1'-glycerol) 1-17-methylocatdecanoyl-2-hexadecanoyl-sn-glycero-3-phosphoglycerol 1-17-methylocatdecanoyl-2-palmitoyl-sn-glycero-3-phosphoglycerol GPG(19:0/16:0) GPG(35:0) PG(19:0/16:0) PG(35:0) Phosphatidylglycerol(19:0/16:0) Phosphatidylglycerol(35:0) C41H81O10P 765.0496 764.556735324 (2,3-dihydroxypropoxy)[2-(hexadecanoyloxy)-3-[(17-methyloctadecanoyl)oxy]propoxy]phosphinic acid 2,3-dihydroxypropoxy(2-(hexadecanoyloxy)-3-[(17-methyloctadecanoyl)oxy]propoxy)phosphinic acid CCCCCCCCCCCCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCCC(C)C)COP(O)(=O)OCC(O)CO InChI=1S/C41H81O10P/c1-4-5-6-7-8-9-10-12-17-20-23-26-29-32-41(45)51-39(36-50-52(46,47)49-34-38(43)33-42)35-48-40(44)31-28-25-22-19-16-14-11-13-15-18-21-24-27-30-37(2)3/h37-39,42-43H,4-36H2,1-3H3,(H,46,47) VCZTWEXHMLNZIF-UHFFFAOYSA-N Solid Membrane logp 8.19 ALOGPS logs -6.88 ALOGPS solubility 1.01e-04 g/l ALOGPS logp 12.11 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2,3-dihydroxypropoxy)[2-(hexadecanoyloxy)-3-[(17-methyloctadecanoyl)oxy]propoxy]phosphinic acid ChemAxon average_mass 765.0496 ChemAxon mono_mass 764.556735324 ChemAxon smiles CCCCCCCCCCCCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCCC(C)C)COP(O)(=O)OCC(O)CO ChemAxon formula C41H81O10P ChemAxon inchi InChI=1S/C41H81O10P/c1-4-5-6-7-8-9-10-12-17-20-23-26-29-32-41(45)51-39(36-50-52(46,47)49-34-38(43)33-42)35-48-40(44)31-28-25-22-19-16-14-11-13-15-18-21-24-27-30-37(2)3/h37-39,42-43H,4-36H2,1-3H3,(H,46,47) ChemAxon inchikey VCZTWEXHMLNZIF-UHFFFAOYSA-N ChemAxon polar_surface_area 148.82 ChemAxon refractivity 209.06 ChemAxon polarizability 94.53 ChemAxon rotatable_bond_count 42 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 Specdb::CMs 1087069 Specdb::NmrOneD 248268 Specdb::NmrOneD 248269 Specdb::NmrOneD 248270 Specdb::NmrOneD 248271 Specdb::NmrOneD 248272 Specdb::NmrOneD 248273 Specdb::NmrOneD 248274 Specdb::NmrOneD 248275 Specdb::NmrOneD 248276 Specdb::NmrOneD 248277 Specdb::NmrOneD 248278 Specdb::NmrOneD 248279 Specdb::NmrOneD 248280 Specdb::NmrOneD 248281 Specdb::NmrOneD 248282 Specdb::NmrOneD 248283 Specdb::NmrOneD 248284 Specdb::NmrOneD 248285 Specdb::NmrOneD 248286 Specdb::NmrOneD 248287 Specdb::MsMs 25628 Specdb::MsMs 25629 Specdb::MsMs 25630 Specdb::MsMs 32186 Specdb::MsMs 32187 Specdb::MsMs 32188 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 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