2.0 2012-07-30 14:55:10 -0600 2015-12-09 12:07:07 -0700 ECMDB21266 M2MDB001673 PG(14:1(7Z)/14:1(7Z)) PG(14:1(7Z)/14:1(7Z)) 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(14:1(7Z)/14:1(7Z)), in particular, consists of two 7Z,tetradecenoyl 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-di(7Z-tetradecenoyl)-rac-glycero-3-phospho-(1'-glycerol) 1,2-di(7Z-tetradecenoyl)-rac-glycero-3-phosphoglycerol 1,2-di7Z-tetradecenoyl-rac-glycero-3-phosphoglycerol GPG(14:1/14:1) GPG(28:2) PG(14:1/14:1) PG(28:2) Phosphatidylglycerol(14:1/14:1) Phosphatidylglycerol(28:2) C34H63O10P 662.842 662.415885227 [(2R)-2,3-bis[(7Z)-tetradec-7-enoyloxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid (2R)-2,3-bis[(7Z)-tetradec-7-enoyloxy]propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCC\C=C/CCCCCC)OC(=O)CCCCC\C=C/CCCCCC InChI=1S/C34H63O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-33(37)41-29-32(30-43-45(39,40)42-28-31(36)27-35)44-34(38)26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,31-32,35-36H,3-12,17-30H2,1-2H3,(H,39,40)/b15-13-,16-14-/t31-,32+/m0/s1 CBUSDRUVJCLICO-OZGVVRQRSA-N Solid Membrane logp 6.58 ALOGPS logs -6.28 ALOGPS solubility 3.44e-04 g/l ALOGPS logp 8.43 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -3 ChemAxon iupac [(2R)-2,3-bis[(7Z)-tetradec-7-enoyloxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid ChemAxon average_mass 662.842 ChemAxon mono_mass 662.415885227 ChemAxon smiles [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCC\C=C/CCCCCC)OC(=O)CCCCC\C=C/CCCCCC ChemAxon formula C34H63O10P ChemAxon inchi InChI=1S/C34H63O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-33(37)41-29-32(30-43-45(39,40)42-28-31(36)27-35)44-34(38)26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,31-32,35-36H,3-12,17-30H2,1-2H3,(H,39,40)/b15-13-,16-14-/t31-,32+/m0/s1 ChemAxon inchikey CBUSDRUVJCLICO-OZGVVRQRSA-N ChemAxon polar_surface_area 148.82 ChemAxon refractivity 179.14 ChemAxon polarizability 75.82 ChemAxon rotatable_bond_count 34 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 Specdb::CMs 1086343 Specdb::NmrOneD 318771 Specdb::NmrOneD 318772 Specdb::NmrOneD 318773 Specdb::NmrOneD 318774 Specdb::NmrOneD 318775 Specdb::NmrOneD 318776 Specdb::NmrOneD 318777 Specdb::NmrOneD 318778 Specdb::NmrOneD 318779 Specdb::NmrOneD 318780 Specdb::NmrOneD 318781 Specdb::NmrOneD 318782 Specdb::NmrOneD 318783 Specdb::NmrOneD 318784 Specdb::NmrOneD 318785 Specdb::NmrOneD 318786 Specdb::NmrOneD 318787 Specdb::NmrOneD 318788 Specdb::NmrOneD 318789 Specdb::NmrOneD 318790 Specdb::MsMs 1267630 Specdb::MsMs 1267631 Specdb::MsMs 1267632 Specdb::MsMs 1382668 Specdb::MsMs 1382669 Specdb::MsMs 1382670 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 Lipid A export ATP-binding/permease protein msbA P60752 MSBA_ECOLI msbA http://ecmdb.ca/proteins/P60752.xml Water + PGP(14:1(7Z)/14:1(7Z)) > PG(14:1(7Z)/14:1(7Z)) + Phosphate 2 PG(14:1(7Z)/14:1(7Z)) <> cardiolipin (tetratetradec-7-enoyl, n-C14:1) + Glycerol Adenosine triphosphate + Water + PG(14:1(7Z)/14:1(7Z)) > ADP + Hydrogen ion + Phosphate + PG(14:1(7Z)/14:1(7Z)) Adenosine triphosphate + Water + PG(14:1(7Z)/14:1(7Z)) > ADP + Hydrogen ion + Phosphate + PG(14:1(7Z)/14:1(7Z)) 2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:1) + Adenosine triphosphate + Tetradecenoate (N-C14:1) > Adenosine monophosphate + PG(14:1(7Z)/14:1(7Z)) + Pyrophosphate Water + PG(14:1(7Z)/14:1(7Z)) > 1-Acyl-sn-glycero-3-phosphoglycerol (N-C14:1) + Hydrogen ion + Tetradecenoate (N-C14:1) Water + PG(14:1(7Z)/14:1(7Z)) > 2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:1) + Hydrogen ion + Tetradecenoate (N-C14:1) 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:1) + PG(14:1(7Z)/14:1(7Z)) > Acyl phosphatidylglycerol (N-C14:1) + Glycerylphosphorylethanolamine 2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:1) + PG(14:1(7Z)/14:1(7Z)) > Acyl phosphatidylglycerol (N-C14:1) + Glycerophosphoglycerol