2.0 2015-09-08 19:02:47 -0600 2015-12-09 14:11:36 -0700 ECMDB24351 M2MDB006468 DG(19:0/16:1(9Z)/0:0) DG(19:0/16:1(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(19:0/16:1(9Z)/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway. C38H72O5 608.989 608.537975418 (2S)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropyl nonadecanoate (2S)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropyl nonadecanoate [H][C@](O)(COC(=O)CCCCCCCCCCCCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCC InChI=1S/C38H72O5/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-31-33-38(41)43-35-36(39)34-42-37(40)32-30-28-26-24-22-20-16-14-12-10-8-6-4-2/h14,16,36,39H,3-13,15,17-35H2,1-2H3/b16-14-/t36-/m1/s1 YFMYUYNLURJGEB-ZYODFBQNSA-N logp 10.26 ALOGPS logs -7.57 ALOGPS solubility 1.63e-05 g/l ALOGPS logp 12.97 ChemAxon pka_strongest_acidic 13.63 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac (2S)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropyl nonadecanoate ChemAxon average_mass 608.989 ChemAxon mono_mass 608.537975418 ChemAxon smiles [H][C@](O)(COC(=O)CCCCCCCCCCCCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCC ChemAxon formula C38H72O5 ChemAxon inchi InChI=1S/C38H72O5/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-31-33-38(41)43-35-36(39)34-42-37(40)32-30-28-26-24-22-20-16-14-12-10-8-6-4-2/h14,16,36,39H,3-13,15,17-35H2,1-2H3/b16-14-/t36-/m1/s1 ChemAxon inchikey YFMYUYNLURJGEB-ZYODFBQNSA-N ChemAxon polar_surface_area 72.83 ChemAxon refractivity 182.62 ChemAxon polarizability 81.14 ChemAxon rotatable_bond_count 36 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(19:0/16:1(9Z)/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. PW001983 Metabolic phospholipid biosynthesis (CL(19:0/16:1(9Z)/16:0/16:0)) 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. PW001984 Metabolic phospholipid biosynthesis (CL(19:0/16:1(9Z)/19:0/16:1(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. PW001985 Metabolic Specdb::CMs 1089968 Specdb::MsMs 27713 Specdb::MsMs 27714 Specdb::MsMs 27715 Specdb::MsMs 34271 Specdb::MsMs 34272 Specdb::MsMs 34273 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(19:0/16:1(9Z)/0:0) + Cytidine triphosphate + Hydrogen ion >2 CDP-DG(19:0/16:1(9Z)) + Pyrophosphate PW_R005590