2.0 2012-10-10 13:28:09 -0600 2015-12-09 14:07:18 -0700 ECMDB23263 M2MDB003653 DG(14:0/16:0/0:0) DG(14:0/16:0/0:0) 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(14:0/16:0/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway. 1-myristoyl-2-palmitoyl-sn-glycerol 1-tetradecanoyl-2-hexadecanoyl-sn-glycerol DAG(14:0/16:0) DAG(30:0) DG(14:0/16:0) DG(30:0) Diacylglycerol Diacylglycerol(14:0/16:0) Diacylglycerol(30:0) Diglyceride C33H64O5 540.87 540.475375161 (2S)-2-hydroxy-3-(tetradecanoyloxy)propyl hexadecanoate (2S)-2-hydroxy-3-(tetradecanoyloxy)propyl hexadecanoate [H][C@](O)(COC(=O)CCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC InChI=1S/C33H64O5/c1-3-5-7-9-11-13-15-16-18-20-22-24-26-28-33(36)38-30-31(34)29-37-32(35)27-25-23-21-19-17-14-12-10-8-6-4-2/h31,34H,3-30H2,1-2H3/t31-/m0/s1 MDJXLANKTSDJQI-HKBQPEDESA-N Membrane logp 9.61 ALOGPS logs -7.39 ALOGPS solubility 2.21e-05 g/l ALOGPS logp 11.11 ChemAxon pka_strongest_acidic 13.63 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac (2S)-2-hydroxy-3-(tetradecanoyloxy)propyl hexadecanoate ChemAxon average_mass 540.87 ChemAxon mono_mass 540.475375161 ChemAxon smiles [H][C@](O)(COC(=O)CCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC ChemAxon formula C33H64O5 ChemAxon inchi InChI=1S/C33H64O5/c1-3-5-7-9-11-13-15-16-18-20-22-24-26-28-33(36)38-30-31(34)29-37-32(35)27-25-23-21-19-17-14-12-10-8-6-4-2/h31,34H,3-30H2,1-2H3/t31-/m0/s1 ChemAxon inchikey MDJXLANKTSDJQI-HKBQPEDESA-N ChemAxon polar_surface_area 72.83 ChemAxon refractivity 158.5 ChemAxon polarizability 71.68 ChemAxon rotatable_bond_count 32 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(19:0cycv8c/16:0/14:0/16:0)) 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. PW001321 Metabolic phospholipid biosynthesis (CL(19:0cycv8c/19:0cycv8c/14:0/16:0)) 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. PW001434 Metabolic Specdb::CMs 49784 Specdb::CMs 265336 Specdb::CMs 281402 Specdb::MsMs 2846945 Specdb::MsMs 2846946 Specdb::MsMs 2846947 Specdb::MsMs 2862828 Specdb::MsMs 2862829 Specdb::MsMs 2862830 HMDB07011 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 Phosphatidylglycerophosphatase B P0A924 PGPB_ECOLI pgpB http://ecmdb.ca/proteins/P0A924.xml Phosphatidate cytidylyltransferase P0ABG1 CDSA_ECOLI cdsA http://ecmdb.ca/proteins/P0ABG1.xml Diacylglycerol kinase P0ABN1 KDGL_ECOLI dgkA http://ecmdb.ca/proteins/P0ABN1.xml DG(14:0/16:0/0:0) + Cytidine triphosphate + Hydrogen ion + DG(14:0/16:0/0:0) > CDP-DG(14:0/16:0) + Pyrophosphate PW_R005234 2 DG(14:0/16:0/0:0) + Cytidine triphosphate + Hydrogen ion + 2 DG(14:0/16:0/0:0) >2 CDP-DG(14:0/16:0) + Pyrophosphate PW_R005271