2.0 2012-07-30 14:54:38 -0600 2015-06-03 17:20:39 -0600 ECMDB21109 M2MDB001518 1,2-Diacyl-sn-glycerol (ditetradecanoyl, n-C14:0) 1,2-diacyl-sn-glycerol (ditetradecanoyl, n-c14:0) belongs to the class of Diacylglycerols. These are glycerides consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. (inferred from compound structure) (2S)-3-Hydroxy-1,2-propanediyl ditetradecanoate (2S)-3-Hydroxy-1,2-propanediyl ditetradecanoic acid (2S)-3-hydroxy-2-tetradecanoyloxypropyl tetradecanoate (2S)-3-Hydroxy-2-tetradecanoyloxypropyl tetradecanoic acid 1,2-dimyristoyl-rac-glycerol 1,2-Ditetradecanoyl-sn-glycerol DAG(14:0/14:0) DAG(28:0) DG(14:0/14:0) DG(28:0) Diacylglycerol Diacylglycerol(14:0/14:0) Diacylglycerol(28:0) Diglyceride C31H60O5 512.8051 512.44407503 (2S)-1-hydroxy-3-(tetradecanoyloxy)propan-2-yl tetradecanoate diacylglycerol [H][C@](CO)(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC InChI=1S/C31H60O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-30(33)35-28-29(27-32)36-31(34)26-24-22-20-18-16-14-12-10-8-6-4-2/h29,32H,3-28H2,1-2H3/t29-/m0/s1 JFBCSFJKETUREV-LJAQVGFWSA-N Membrane logp 9.19 ALOGPS logs -7.26 ALOGPS solubility 2.80e-05 g/l ALOGPS logp 10.22 ChemAxon pka_strongest_acidic 14.58 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2S)-1-hydroxy-3-(tetradecanoyloxy)propan-2-yl tetradecanoate ChemAxon average_mass 512.8051 ChemAxon mono_mass 512.44407503 ChemAxon smiles [H][C@](CO)(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC ChemAxon formula C31H60O5 ChemAxon inchi InChI=1S/C31H60O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-30(33)35-28-29(27-32)36-31(34)26-24-22-20-18-16-14-12-10-8-6-4-2/h29,32H,3-28H2,1-2H3/t29-/m0/s1 ChemAxon inchikey JFBCSFJKETUREV-LJAQVGFWSA-N ChemAxon polar_surface_area 72.83 ChemAxon refractivity 149.29 ChemAxon polarizability 66.14 ChemAxon rotatable_bond_count 30 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(10:0(3-OH)/17:0cycw7c/14:0/14:0)) 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 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. PW001907 Metabolic phospholipid biosynthesis (CL(10:0/17:0cycw7c/14:0/14:0)) 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 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. PW001912 Metabolic phospholipid biosynthesis (CL(14:0(3-OH)/17:0cycw7c/14:0/14:0)) 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 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. PW001942 Metabolic Specdb::CMs 39151 Specdb::NmrOneD 265888 Specdb::NmrOneD 265889 Specdb::NmrOneD 265890 Specdb::NmrOneD 265891 Specdb::NmrOneD 265892 Specdb::NmrOneD 265893 Specdb::NmrOneD 265894 Specdb::NmrOneD 265895 Specdb::NmrOneD 265896 Specdb::NmrOneD 265897 Specdb::NmrOneD 265898 Specdb::NmrOneD 265899 Specdb::NmrOneD 265900 Specdb::NmrOneD 265901 Specdb::NmrOneD 265902 Specdb::NmrOneD 265903 Specdb::NmrOneD 265904 Specdb::NmrOneD 265905 Specdb::NmrOneD 265906 Specdb::NmrOneD 265907 Specdb::MsMs 619777 Specdb::MsMs 619778 Specdb::MsMs 619779 Specdb::MsMs 2401460 Specdb::MsMs 2401461 Specdb::MsMs 2401462 Specdb::MsMs 2760620 Specdb::MsMs 2760621 Specdb::MsMs 2760622 Specdb::MsMs 2944554 Specdb::MsMs 2944555 Specdb::MsMs 2944556 Specdb::MsMs 3055349 Specdb::MsMs 3055350 Specdb::MsMs 3055351 HMDB07008 C16667 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 Water + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (ditetradecanoyl, n-C14:0) + Phosphate 1,2-Diacyl-sn-glycerol (ditetradecanoyl, n-C14:0) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0) 1,2-Diacyl-sn-glycerol (ditetradecanoyl, n-C14:0) + Cytidine triphosphate + Hydrogen ion > CDP-1,2-ditetradecanoylglycerol + Pyrophosphate PW_R005311 2 1,2-Diacyl-sn-glycerol (ditetradecanoyl, n-C14:0) + Cytidine triphosphate + Hydrogen ion >2 CDP-1,2-ditetradecanoylglycerol + Pyrophosphate PW_R005334