2.0 2015-09-08 20:10:07 -0600 2015-12-09 14:08:21 -0700 ECMDB24797 M2MDB006914 DG(16:1(9Z)/14:0(3-OH)/0:0) DG(16:1(9Z)/14:0(3-OH)/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(16:1(9Z)/14:0(3-OH)/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway. C33H62O6 554.853 554.454639716 (2S)-2-hydroxy-3-[(3-hydroxytetradecanoyl)oxy]propyl (9Z)-hexadec-9-enoate (2S)-2-hydroxy-3-[(3-hydroxytetradecanoyl)oxy]propyl (9Z)-hexadec-9-enoate [H][C@](O)(COC(=O)CCCCCCC\C=C/CCCCCC)COC(=O)CC(O)CCCCCCCCCCC InChI=1S/C33H62O6/c1-3-5-7-9-11-13-14-15-16-18-20-22-24-26-32(36)38-28-31(35)29-39-33(37)27-30(34)25-23-21-19-17-12-10-8-6-4-2/h13-14,30-31,34-35H,3-12,15-29H2,1-2H3/b14-13-/t30?,31-/m0/s1 PZQLSZIGHYFCLW-BLMZFMLHSA-N logp 8.57 ALOGPS logs -6.88 ALOGPS solubility 7.37e-05 g/l ALOGPS logp 9.52 ChemAxon pka_strongest_acidic 13.61 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac (2S)-2-hydroxy-3-[(3-hydroxytetradecanoyl)oxy]propyl (9Z)-hexadec-9-enoate ChemAxon average_mass 554.853 ChemAxon mono_mass 554.454639716 ChemAxon smiles [H][C@](O)(COC(=O)CCCCCCC\C=C/CCCCCC)COC(=O)CC(O)CCCCCCCCCCC ChemAxon formula C33H62O6 ChemAxon inchi InChI=1S/C33H62O6/c1-3-5-7-9-11-13-14-15-16-18-20-22-24-26-32(36)38-28-31(35)29-39-33(37)27-30(34)25-23-21-19-17-12-10-8-6-4-2/h13-14,30-31,34-35H,3-12,15-29H2,1-2H3/b14-13-/t30?,31-/m0/s1 ChemAxon inchikey PZQLSZIGHYFCLW-BLMZFMLHSA-N ChemAxon polar_surface_area 93.06 ChemAxon refractivity 161.13 ChemAxon polarizability 71.3 ChemAxon rotatable_bond_count 31 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(16:1(9Z)/14:0(3-OH)/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. PW001957 Metabolic phospholipid biosynthesis (CL(16:1(9Z)/14:0(3-OH)/16:1(9Z)/14:0(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. PW001958 Metabolic Specdb::CMs 1086375 Specdb::MsMs 1265437 Specdb::MsMs 1265438 Specdb::MsMs 1265439 Specdb::MsMs 1380508 Specdb::MsMs 1380509 Specdb::MsMs 1380510 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(16:1(9Z)/14:0(3-OH)/0:0) + Cytidine triphosphate + Hydrogen ion >2 CDP-DG(16:1(9Z)/14:0(3-OH)) + Pyrophosphate PW_R005498