2.0 2012-10-10 13:28:06 -0600 2015-12-09 14:06:48 -0700 ECMDB23251 M2MDB003641 DG(12:0/12:0/0:0) DG(12:0/12:0/0:0) 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(12:0/12:0/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway. (2-dodecanoyloxy-3-hydroxypropyl) dodecanoate (2-Dodecanoyloxy-3-hydroxypropyl) dodecanoic acid 1,2-didodecanoyl-rac-glycerol 1,2-didodecanoyl-rac-glycerol DAG(12:0/12:0) DAG(24:0) DG(12:0/12:0) DG(24:0) Diacylglycerol Diacylglycerol(12:0/12:0) Diacylglycerol(24:0) Diglyceride C27H52O5 456.708 456.381474774 3-(dodecanoyloxy)-2-hydroxypropyl dodecanoate 3-(dodecanoyloxy)-2-hydroxypropyl dodecanoate [H]C(O)(COC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC InChI=1S/C27H52O5/c1-3-5-7-9-11-13-15-17-19-21-26(29)31-23-25(28)24-32-27(30)22-20-18-16-14-12-10-8-6-4-2/h25,28H,3-24H2,1-2H3 KUVAEMGNHJQSMH-UHFFFAOYSA-N Membrane logp 8.19 ALOGPS logs -6.84 ALOGPS solubility 6.65e-05 g/l ALOGPS logp 8.45 ChemAxon pka_strongest_acidic 13.63 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac 3-(dodecanoyloxy)-2-hydroxypropyl dodecanoate ChemAxon average_mass 456.708 ChemAxon mono_mass 456.381474774 ChemAxon smiles [H]C(O)(COC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC ChemAxon formula C27H52O5 ChemAxon inchi InChI=1S/C27H52O5/c1-3-5-7-9-11-13-15-17-19-21-26(29)31-23-25(28)24-32-27(30)22-20-18-16-14-12-10-8-6-4-2/h25,28H,3-24H2,1-2H3 ChemAxon inchikey KUVAEMGNHJQSMH-UHFFFAOYSA-N ChemAxon polar_surface_area 72.83 ChemAxon refractivity 130.89 ChemAxon polarizability 58.9 ChemAxon rotatable_bond_count 26 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(12:0(3-OH)/12:0(3-OH)/12:0/12:0)) 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. PW001915 Metabolic phospholipid biosynthesis (CL(12:0/12:0/12:0/12:0)) 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. PW001930 Metabolic Specdb::CMs 49236 Specdb::CMs 163044 Specdb::NmrOneD 300425 Specdb::NmrOneD 300426 Specdb::NmrOneD 300427 Specdb::NmrOneD 300428 Specdb::NmrOneD 300429 Specdb::NmrOneD 300430 Specdb::NmrOneD 300431 Specdb::NmrOneD 300432 Specdb::NmrOneD 300433 Specdb::NmrOneD 300434 Specdb::NmrOneD 300435 Specdb::NmrOneD 300436 Specdb::NmrOneD 300437 Specdb::NmrOneD 300438 Specdb::NmrOneD 300439 Specdb::NmrOneD 300440 Specdb::NmrOneD 300441 Specdb::NmrOneD 300442 Specdb::NmrOneD 300443 Specdb::NmrOneD 300444 Specdb::MsMs 2383934 Specdb::MsMs 2383935 Specdb::MsMs 2383936 Specdb::MsMs 2581623 Specdb::MsMs 2581624 Specdb::MsMs 2581625 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 2 DG(12:0/12:0/0:0) + Cytidine triphosphate + Hydrogen ion >2 CDP-1,2-didodecanoylglycerol + Pyrophosphate PW_R005350