2.0 2012-10-10 13:28:07 -0600 2015-12-09 14:06:54 -0700 ECMDB23254 M2MDB003644 DG(12:0/16:0/0:0) DG(12:0/16:0/0:0) 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(12:0/16:0/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway. 1-dodecanoyl-2-hexadecanoyl-sn-glycerol 1-dodecanoyl-2-palmitoyl-sn-glycerol DAG(12:0/16:0) DAG(28:0) DG(12:0/16:0) DG(28:0) Diacylglycerol Diacylglycerol(12:0/16:0) Diacylglycerol(28:0) Diglyceride C31H60O5 512.816 512.444075032 (2S)-3-(dodecanoyloxy)-2-hydroxypropyl hexadecanoate (2S)-3-(dodecanoyloxy)-2-hydroxypropyl hexadecanoate [H][C@](O)(COC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC InChI=1S/C31H60O5/c1-3-5-7-9-11-13-14-15-16-18-20-22-24-26-31(34)36-28-29(32)27-35-30(33)25-23-21-19-17-12-10-8-6-4-2/h29,32H,3-28H2,1-2H3/t29-/m0/s1 LANMFMOMCREFAD-LJAQVGFWSA-N Membrane logp 9.22 ALOGPS logs -7.27 ALOGPS solubility 2.73e-05 g/l ALOGPS logp 10.22 ChemAxon pka_strongest_acidic 13.63 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac (2S)-3-(dodecanoyloxy)-2-hydroxypropyl hexadecanoate ChemAxon average_mass 512.816 ChemAxon mono_mass 512.444075032 ChemAxon smiles [H][C@](O)(COC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC ChemAxon formula C31H60O5 ChemAxon inchi InChI=1S/C31H60O5/c1-3-5-7-9-11-13-14-15-16-18-20-22-24-26-31(34)36-28-29(32)27-35-30(33)25-23-21-19-17-12-10-8-6-4-2/h29,32H,3-28H2,1-2H3/t29-/m0/s1 ChemAxon inchikey LANMFMOMCREFAD-LJAQVGFWSA-N ChemAxon polar_surface_area 72.83 ChemAxon refractivity 149.29 ChemAxon polarizability 67.45 ChemAxon rotatable_bond_count 30 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis CDP-DG(12:0/16:0) 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 PS (16:1(9z)/18:1(11z))L-1-phosphatidylserine or a L-1-phosphatidy PE(16:1(9z)/18:1(11z)) (phosphatidylethanolamine) through a phosphatidylserine decarboxylase, on the other hand PGP(16:1(9z)/18:1(11z)) L-1-phosphatidylglycerol-phosphate gets transformed into a PG(16:1(9z)/18:1(11z)) 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. PW001771 Metabolic phospholipid biosynthesis CDP-DG(12:0/16:0) II 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 PS (16:1(9z)/18:1(11z))L-1-phosphatidylserine or a L-1-phosphatidy PE(16:1(9z)/18:1(11z)) (phosphatidylethanolamine) through a phosphatidylserine decarboxylase, on the other hand PGP(16:1(9z)/18:1(11z)) L-1-phosphatidylglycerol-phosphate gets transformed into a PG(16:1(9z)/18:1(11z)) 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. PW001841 Metabolic Specdb::CMs 49765 Specdb::NmrOneD 308851 Specdb::NmrOneD 308852 Specdb::NmrOneD 308853 Specdb::NmrOneD 308854 Specdb::NmrOneD 308855 Specdb::NmrOneD 308856 Specdb::NmrOneD 308857 Specdb::NmrOneD 308858 Specdb::NmrOneD 308859 Specdb::NmrOneD 308860 Specdb::NmrOneD 308861 Specdb::NmrOneD 308862 Specdb::NmrOneD 308863 Specdb::NmrOneD 308864 Specdb::NmrOneD 308865 Specdb::NmrOneD 308866 Specdb::NmrOneD 308867 Specdb::NmrOneD 308868 Specdb::NmrOneD 308869 Specdb::NmrOneD 308870 Specdb::MsMs 2762188 Specdb::MsMs 2762189 Specdb::MsMs 2762190 Specdb::MsMs 2947518 Specdb::MsMs 2947519 Specdb::MsMs 2947520 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(12:0/16:0/0:0) + Hydrogen ion + Cytidine triphosphate > CDP-DG(12:0/16:0) + Pyrophosphate PW_R004733