2.0 2015-09-08 20:07:33 -0600 2015-12-09 12:15:41 -0700 ECMDB24751 M2MDB006868 DG(12:0(3-OH)/10:0/0:0) DG(12:0(3-OH)/10:0/0:0) 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(3-OH)/10:0/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway. C25H48O6 444.653 444.345089266 (2R)-3-(decanoyloxy)-2-hydroxypropyl 3-hydroxydodecanoate (2R)-3-(decanoyloxy)-2-hydroxypropyl 3-hydroxydodecanoate [H][C@@](O)(COC(=O)CCCCCCCCC)COC(=O)CC(O)CCCCCCCCC InChI=1S/C25H48O6/c1-3-5-7-9-11-13-15-17-22(26)19-25(29)31-21-23(27)20-30-24(28)18-16-14-12-10-8-6-4-2/h22-23,26-27H,3-21H2,1-2H3/t22?,23-/m1/s1 ZDRBWAVREGYZMF-OZAIVSQSSA-N logp 6.14 ALOGPS logs -5.34 ALOGPS solubility 2.01e-03 g/l ALOGPS logp 6.33 ChemAxon pka_strongest_acidic 13.61 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac (2R)-3-(decanoyloxy)-2-hydroxypropyl 3-hydroxydodecanoate ChemAxon average_mass 444.653 ChemAxon mono_mass 444.345089266 ChemAxon smiles [H][C@@](O)(COC(=O)CCCCCCCCC)COC(=O)CC(O)CCCCCCCCC ChemAxon formula C25H48O6 ChemAxon inchi InChI=1S/C25H48O6/c1-3-5-7-9-11-13-15-17-22(26)19-25(29)31-21-23(27)20-30-24(28)18-16-14-12-10-8-6-4-2/h22-23,26-27H,3-21H2,1-2H3/t22?,23-/m1/s1 ChemAxon inchikey ZDRBWAVREGYZMF-OZAIVSQSSA-N ChemAxon polar_surface_area 93.06 ChemAxon refractivity 123.2 ChemAxon polarizability 55.67 ChemAxon rotatable_bond_count 24 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(12:0(3-OH)/10:0(3-OH)/12:0(3-OH)/10:0(3-OH))) 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. PW001913 Metabolic phospholipid biosynthesis (CL(12:0(3-OH)/10:0/12:0(3-OH)/10:0)) 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. PW001914 Metabolic Specdb::CMs 1088163 Specdb::MsMs 3637140 Specdb::MsMs 3637141 Specdb::MsMs 3637142 Specdb::MsMs 3637143 Specdb::MsMs 3637144 Specdb::MsMs 3637145 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 Phosphatidate cytidylyltransferase P0ABG1 CDSA_ECOLI cdsA http://ecmdb.ca/proteins/P0ABG1.xml 2 DG(12:0(3-OH)/10:0/0:0) + Cytidine triphosphate + Hydrogen ion >2 CDP-DG(12:0(3-OH)/10:0(3-OH)) + Pyrophosphate PW_R005338 2 DG(12:0(3-OH)/10:0/0:0) + Cytidine triphosphate + Hydrogen ion >2 CDP-DG(12:0(3-OH)/10:0) + Pyrophosphate PW_R005343