2.02015-09-08 17:49:17 -06002015-12-09 15:40:01 -0700ECMDB24098M2MDB006215DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/0:0)DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/0:0) belongs to the family of Diacylglycerols. These are glycerolipids lipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway.C43H70O5667.028666.522325354(2R)-2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate(2R)-2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate[H][C@@](O)(COC(=O)CCCCCCCCC\C=C/CCCCCC)COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCInChI=1S/C43H70O5/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-43(46)48-40-41(44)39-47-42(45)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11,13-14,16-17,19,21-22,26,28,32,34,41,44H,3-4,6,8-10,12,15,18,20,23-25,27,29-31,33,35-40H2,1-2H3/b7-5-,13-11-,16-14-,19-17-,22-21-,28-26-,34-32-/t41-/m1/s1IPJYPLOTNXCEAB-VYXKUJIYSA-Nlogp9.19logs-7.70solubility1.34e-05 g/llogp13.03pka_strongest_acidic13.63pka_strongest_basic-3.4iupac(2R)-2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoateaverage_mass667.028mono_mass666.522325354smiles[H][C@@](O)(COC(=O)CCCCCCCCC\C=C/CCCCCC)COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCformulaC43H70O5inchiInChI=1S/C43H70O5/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-43(46)48-40-41(44)39-47-42(45)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11,13-14,16-17,19,21-22,26,28,32,34,41,44H,3-4,6,8-10,12,15,18,20,23-25,27,29-31,33,35-40H2,1-2H3/b7-5-,13-11-,16-14-,19-17-,22-21-,28-26-,34-32-/t41-/m1/s1inchikeyIPJYPLOTNXCEAB-VYXKUJIYSA-Npolar_surface_area72.83refractivity212.32polarizability82.44rotatable_bond_count35acceptor_count3donor_count1physiological_charge0formal_charge0phospholipid biosynthesis I (CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) )"Phospholipids are membrane components in E. coli.
The major phospholipids of E. coli are phosphatidylethanolamine, phosphatidylglycerol and cardiolipin. All phospholipids contain sn-glycerol-3-phosphate esterified with fatty acids at the sn-1 and sn-2 positions.
The reaction starts from a glycerone phosphate (dihydroxyacetone phosphate) produced in glycolysis. The glycerone phosphate is transformed to a sn-glycerol 3-phosphate (glycerol 3 phosphate) by NADPH driven glycerol-3-phosphate dehydrogenase.
Sn-glycerol 3-phosphate is transformed to a 1-acyl-sn-glycerol 3-phosphate(1-oleyl-2-lyso-phosphatidate , 1-palmitoylglycerol 3-phosphate , 1-stearoyl-sn-glycerol 3-phosphate). This can be achieve by a sn-glycerol-3-phosphate 1-0-acyltransferase that interacts either with a long-chain acyl-CoA or with an acyl-[acp]. The 1-acyl-sn-glycerol 3-phosphate is transformed into a 1,2-diacyl-sn-glycerol 3-phosphate through a 1-acylglycerol-3-phosphate O-acyltransferase.
This compound is then converted into a CPD-diacylglycerol through a CTP (phosphatidate cytididyltransferase. CPD-diacylglycerol can be transformed either to a L-1-phosphatidylserine or a L-1-phosphatidylglycerol-phosphate through a phosphatidylserine synthase or a phosphatidylglycerophosphate synthase respectively. The L-1-phosphatidylserine transforms into L-1-phosphatidylethanolamine through a phosphatidylserine decarboxylase, o the other hand L-1-phosphatidylglycerol-phosphate gets transformed into a L-1-phosphatidyl-glycerol through a phosphatidylglycerophosphatase. These 2 products combines produce a cardiolipin and a ethanolamine.
The L-1 phosphatidyl-glycerol can also interact with cardiolipin synthase resulting in a glycerol and a cardiolipin."
PW001025MetabolicSpecdb::CMs700218Specdb::CMs700219Specdb::MsMs2702958Specdb::MsMs2702959Specdb::MsMs2702960Specdb::MsMs3002359Specdb::MsMs3002360Specdb::MsMs3002361Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.APhosphatidate cytidylyltransferaseP0ABG1CDSA_ECOLIcdsAhttp://ecmdb.ca/proteins/P0ABG1.xml1-acyl-sn-glycerol-3-phosphate acyltransferaseP26647PLSC_ECOLIplsChttp://ecmdb.ca/proteins/P26647.xmlLPA(18:1(9Z)/0:0) + acyl-[acp] > DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/0:0) + a holo-[acyl-carrier protein] PW_R003813LPA(18:1(9Z)/0:0) + Octadecenoyl-CoA (N-C18:1CoA) > DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/0:0) + Coenzyme APW_R003814DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/0:0) + Cytidine triphosphate + Hydrogen ion > CDP-DG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + Pyrophosphate + CDP-DG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))PW_R003812