2.0 2012-10-10 13:28:06 -0600 2015-12-09 14:06:50 -0700 ECMDB23252 M2MDB003642 DG(12:0/14:0/0:0) DG(12:0/14:0/0:0) 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(12:0/14:0/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway. 1-dodecanoyl-2-myristoyl-sn-glycerol 1-dodecanoyl-2-tetradecanoyl-sn-glycerol DAG(12:0/14:0) DAG(26:0) DG(12:0/14:0) DG(26:0) Diacylglycerol Diacylglycerol(12:0/14:0) Diacylglycerol(26:0) Diglyceride C29H56O5 484.762 484.412774903 (2S)-3-(dodecanoyloxy)-2-hydroxypropyl tetradecanoate (2S)-3-(dodecanoyloxy)-2-hydroxypropyl tetradecanoate [H][C@](O)(COC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCCCC InChI=1S/C29H56O5/c1-3-5-7-9-11-13-14-16-18-20-22-24-29(32)34-26-27(30)25-33-28(31)23-21-19-17-15-12-10-8-6-4-2/h27,30H,3-26H2,1-2H3/t27-/m0/s1 UODDDZYTHJZBML-MHZLTWQESA-N Membrane logp 8.76 ALOGPS logs -7.06 ALOGPS solubility 4.24e-05 g/l ALOGPS logp 9.34 ChemAxon pka_strongest_acidic 13.63 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac (2S)-3-(dodecanoyloxy)-2-hydroxypropyl tetradecanoate ChemAxon average_mass 484.762 ChemAxon mono_mass 484.412774903 ChemAxon smiles [H][C@](O)(COC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCCCC ChemAxon formula C29H56O5 ChemAxon inchi InChI=1S/C29H56O5/c1-3-5-7-9-11-13-14-16-18-20-22-24-29(32)34-26-27(30)25-33-28(31)23-21-19-17-15-12-10-8-6-4-2/h27,30H,3-26H2,1-2H3/t27-/m0/s1 ChemAxon inchikey UODDDZYTHJZBML-MHZLTWQESA-N ChemAxon polar_surface_area 72.83 ChemAxon refractivity 140.09 ChemAxon polarizability 63.2 ChemAxon rotatable_bond_count 28 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis CDP-DG(12:0/14:0) 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. PW001768 Metabolic phospholipid biosynthesis CDP-DG(12:0/14:0) 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. PW001836 Metabolic phospholipid biosynthesis CDP-DG(12:0/14:0) III 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. PW001837 Metabolic phospholipid biosynthesis CDP-DG(12:0/14:0) IV 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. PW001840 Metabolic Specdb::CMs 49518 Specdb::CMs 154001 Specdb::NmrOneD 293415 Specdb::NmrOneD 293416 Specdb::NmrOneD 293417 Specdb::NmrOneD 293418 Specdb::NmrOneD 293419 Specdb::NmrOneD 293420 Specdb::NmrOneD 293421 Specdb::NmrOneD 293422 Specdb::NmrOneD 293423 Specdb::NmrOneD 293424 Specdb::NmrOneD 293425 Specdb::NmrOneD 293426 Specdb::NmrOneD 293427 Specdb::NmrOneD 293428 Specdb::NmrOneD 293429 Specdb::NmrOneD 293430 Specdb::NmrOneD 293431 Specdb::NmrOneD 293432 Specdb::NmrOneD 293433 Specdb::NmrOneD 293434 Specdb::MsMs 2698641 Specdb::MsMs 2698642 Specdb::MsMs 2698643 Specdb::MsMs 2983259 Specdb::MsMs 2983260 Specdb::MsMs 2983261 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(12:0/14:0/0:0) + Cytidine triphosphate + Hydrogen ion > CDP-DG(12:0/14:0) + Pyrophosphate PW_R004725