2.0 2012-10-10 13:28:09 -0600 2015-12-09 14:07:24 -0700 ECMDB23266 M2MDB003656 DG(14:0/18:1(9Z)/0:0) DG(14:0/18:1(9Z)/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(14:0/18:1(9Z)/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway. 1-myristoyl-2-oleoyl-sn-glycerol 1-tetradecanoyl-2-(9Z-octadecenoyl)-sn-glycerol DAG(14:0/18:1) DAG(14:0/18:1n9) DAG(14:0/18:1w9) DAG(32:1) DG(14:0/18:1) DG(14:0/18:1n9) DG(14:0/18:1w9) DG(32:1) Diacylglycerol Diacylglycerol(14:0/18:1) Diacylglycerol(14:0/18:1n9) Diacylglycerol(14:0/18:1w9) Diacylglycerol(32:1) Diglyceride C35H66O5 566.908 566.491025225 (2S)-2-hydroxy-3-(tetradecanoyloxy)propyl (9Z)-octadec-9-enoate (2S)-2-hydroxy-3-(tetradecanoyloxy)propyl (9Z)-octadec-9-enoate [H][C@](O)(COC(=O)CCCCCCCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC InChI=1S/C35H66O5/c1-3-5-7-9-11-13-15-16-17-18-20-22-24-26-28-30-35(38)40-32-33(36)31-39-34(37)29-27-25-23-21-19-14-12-10-8-6-4-2/h16-17,33,36H,3-15,18-32H2,1-2H3/b17-16-/t33-/m0/s1 DPKKTCYRXHCYKZ-ASUORMEESA-N Membrane logp 9.84 ALOGPS logs -7.46 ALOGPS solubility 1.98e-05 g/l ALOGPS logp 11.64 ChemAxon pka_strongest_acidic 13.63 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac (2S)-2-hydroxy-3-(tetradecanoyloxy)propyl (9Z)-octadec-9-enoate ChemAxon average_mass 566.908 ChemAxon mono_mass 566.491025225 ChemAxon smiles [H][C@](O)(COC(=O)CCCCCCCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC ChemAxon formula C35H66O5 ChemAxon inchi InChI=1S/C35H66O5/c1-3-5-7-9-11-13-15-16-17-18-20-22-24-26-28-30-35(38)40-32-33(36)31-39-34(37)29-27-25-23-21-19-14-12-10-8-6-4-2/h16-17,33,36H,3-15,18-32H2,1-2H3/b17-16-/t33-/m0/s1 ChemAxon inchikey DPKKTCYRXHCYKZ-ASUORMEESA-N ChemAxon polar_surface_area 72.83 ChemAxon refractivity 168.82 ChemAxon polarizability 74.27 ChemAxon rotatable_bond_count 33 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(18:1(9Z)/19:0cycv8c/14:0/18:1(9Z))) 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. PW001233 Metabolic phospholipid biosynthesis (CL(19:0cycv8c/18:1(9Z)/14:0/18:1(9Z))) 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. PW001415 Metabolic phospholipid biosynthesis CDP-DG(14:0/18:1(9Z)) 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. PW001803 Metabolic Specdb::CMs 1088056 Specdb::NmrOneD 329382 Specdb::NmrOneD 329383 Specdb::NmrOneD 329384 Specdb::NmrOneD 329385 Specdb::NmrOneD 329386 Specdb::NmrOneD 329387 Specdb::NmrOneD 329388 Specdb::NmrOneD 329389 Specdb::NmrOneD 329390 Specdb::NmrOneD 329391 Specdb::NmrOneD 329392 Specdb::NmrOneD 329393 Specdb::NmrOneD 329394 Specdb::NmrOneD 329395 Specdb::NmrOneD 329396 Specdb::NmrOneD 329397 Specdb::NmrOneD 329398 Specdb::NmrOneD 329399 Specdb::NmrOneD 329400 Specdb::NmrOneD 329401 Specdb::MsMs 1306123 Specdb::MsMs 1306124 Specdb::MsMs 1306125 Specdb::MsMs 1420636 Specdb::MsMs 1420637 Specdb::MsMs 1420638 HMDB07015 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(14:0/18:1(9Z)/0:0) + Hydrogen ion + Cytidine triphosphate + DG(14:0/18:1(9Z)/0:0) > CDP-DG(14:0/18:1(9Z)) + Pyrophosphate PW_R004789