2.02012-07-30 14:54:38 -06002015-06-03 17:20:38 -0600ECMDB21104M2MDB0015131,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1)1,2-diacyl-sn-glycerol (dihexadec-9-enoyl, n-c16:1) belongs to the class of Diacylglycerols. These are glycerides consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. (inferred from compound structure)(2S)-2-(Z)-hexadec-9-enoyloxy-3-hydroxypropyl (Z)-hexadec-9-enoate(2S)-2-(Z)-Hexadec-9-enoyloxy-3-hydroxypropyl (Z)-hexadec-9-enoic acidC35H64O5564.8797564.475375158(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (9Z)-hexadec-9-enoatediacylglycerol[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCInChI=1S/C35H64O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(37)39-32-33(31-36)40-35(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,33,36H,3-12,17-32H2,1-2H3/b15-13-,16-14-/t33-/m0/s1HSQHRRHRYJNSOC-DWCRPSDDSA-NMembranelogp9.63logs-7.57solubility1.51e-05 g/llogp11.28pka_strongest_acidic14.58pka_strongest_basic-3iupac(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (9Z)-hexadec-9-enoateaverage_mass564.8797mono_mass564.475375158smiles[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCformulaC35H64O5inchiInChI=1S/C35H64O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(37)39-32-33(31-36)40-35(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,33,36H,3-12,17-32H2,1-2H3/b15-13-,16-14-/t33-/m0/s1inchikeyHSQHRRHRYJNSOC-DWCRPSDDSA-Npolar_surface_area72.83refractivity169.93polarizability72.16rotatable_bond_count32acceptor_count3donor_count1physiological_charge0formal_charge0phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))"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."PW001549MetabolicSpecdb::CMs39250Specdb::CMs282098Specdb::CMs358990Specdb::NmrOneD289935Specdb::NmrOneD289936Specdb::NmrOneD289937Specdb::NmrOneD289938Specdb::NmrOneD289939Specdb::NmrOneD289940Specdb::NmrOneD289941Specdb::NmrOneD289942Specdb::NmrOneD289943Specdb::NmrOneD289944Specdb::NmrOneD289945Specdb::NmrOneD289946Specdb::NmrOneD289947Specdb::NmrOneD289948Specdb::NmrOneD289949Specdb::NmrOneD289950Specdb::NmrOneD289951Specdb::NmrOneD289952Specdb::NmrOneD289953Specdb::NmrOneD289954Specdb::MsMs640405Specdb::MsMs640406Specdb::MsMs640407Specdb::MsMs2421702Specdb::MsMs2421703Specdb::MsMs2421704Specdb::MsMs2513342Specdb::MsMs2513343Specdb::MsMs2513344Specdb::MsMs2889355Specdb::MsMs2889356Specdb::MsMs2889357Specdb::MsMs3033926Specdb::MsMs3033927Specdb::MsMs30339289543679Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.APhosphatidylglycerophosphatase BP0A924PGPB_ECOLIpgpBhttp://ecmdb.ca/proteins/P0A924.xmlPhosphatidate cytidylyltransferaseP0ABG1CDSA_ECOLIcdsAhttp://ecmdb.ca/proteins/P0ABG1.xmlDiacylglycerol kinaseP0ABN1KDGL_ECOLIdgkAhttp://ecmdb.ca/proteins/P0ABN1.xmlPhosphoethanolamine transferase eptBP37661EPTB_ECOLIeptBhttp://ecmdb.ca/proteins/P37661.xmlWater + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + PhosphateKDO2-Lipid A + PE(14:0/14:0) > 1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Phosphoethanolamine KDO(2)-lipid (A)1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0)2 1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Cytidine triphosphate + Hydrogen ion >2 CDP-1,2-dihexadec-9-enoylglycerol + PyrophosphatePW_R005696