2.0 2012-10-10 13:28:05 -0600 2015-12-09 12:15:35 -0700 ECMDB23246 M2MDB003636 DG(10:0/16:1(9Z)/0:0) DG(10:0/16:1(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(10:0/16:1(9Z)/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway. 1-decanoyl-2-(9Z-hexadecenoyl)-sn-glycerol 1-decanoyl-2-palmitoleoyl-sn-glycerol DAG(10:0/16:1) DAG(26:1) DG(10:0/16:1) DG(26:1) Diacylglycerol Diacylglycerol(10:0/16:1) Diacylglycerol(26:1) Diglyceride C29H54O5 482.746 482.397124839 (2S)-3-(decanoyloxy)-2-hydroxypropyl (9Z)-hexadec-9-enoate (2S)-3-(decanoyloxy)-2-hydroxypropyl (9Z)-hexadec-9-enoate [H][C@](O)(COC(=O)CCCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCC InChI=1S/C29H54O5/c1-3-5-7-9-11-12-13-14-15-16-18-20-22-24-29(32)34-26-27(30)25-33-28(31)23-21-19-17-10-8-6-4-2/h12-13,27,30H,3-11,14-26H2,1-2H3/b13-12-/t27-/m0/s1 RRCKOPRDFJZIHY-OFQPSRFPSA-N Membrane logp 8.49 ALOGPS logs -7.04 ALOGPS solubility 4.43e-05 g/l ALOGPS logp 8.97 ChemAxon pka_strongest_acidic 13.63 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac (2S)-3-(decanoyloxy)-2-hydroxypropyl (9Z)-hexadec-9-enoate ChemAxon average_mass 482.746 ChemAxon mono_mass 482.397124839 ChemAxon smiles [H][C@](O)(COC(=O)CCCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCC ChemAxon formula C29H54O5 ChemAxon inchi InChI=1S/C29H54O5/c1-3-5-7-9-11-12-13-14-15-16-18-20-22-24-29(32)34-26-27(30)25-33-28(31)23-21-19-17-10-8-6-4-2/h12-13,27,30H,3-11,14-26H2,1-2H3/b13-12-/t27-/m0/s1 ChemAxon inchikey RRCKOPRDFJZIHY-OFQPSRFPSA-N ChemAxon polar_surface_area 72.83 ChemAxon refractivity 141.21 ChemAxon polarizability 61.53 ChemAxon rotatable_bond_count 27 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis CDP-DG(10:0/16:1(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 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. PW001752 Metabolic phospholipid biosynthesis CDP-DG(10:0/16:1(9Z)) 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. PW001828 Metabolic Specdb::CMs 1087395 Specdb::NmrOneD 293615 Specdb::NmrOneD 293616 Specdb::NmrOneD 293617 Specdb::NmrOneD 293618 Specdb::NmrOneD 293619 Specdb::NmrOneD 293620 Specdb::NmrOneD 293621 Specdb::NmrOneD 293622 Specdb::NmrOneD 293623 Specdb::NmrOneD 293624 Specdb::NmrOneD 293625 Specdb::NmrOneD 293626 Specdb::NmrOneD 293627 Specdb::NmrOneD 293628 Specdb::NmrOneD 293629 Specdb::NmrOneD 293630 Specdb::NmrOneD 293631 Specdb::NmrOneD 293632 Specdb::NmrOneD 293633 Specdb::NmrOneD 293634 Specdb::MsMs 3622740 Specdb::MsMs 3622741 Specdb::MsMs 3622742 Specdb::MsMs 3622743 Specdb::MsMs 3622744 Specdb::MsMs 3622745 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(10:0/16:1(9Z)/0:0) + Hydrogen ion + Cytidine triphosphate > CDP-DG(10:0/16:1(9Z)) + Pyrophosphate PW_R004700