2.0 2012-10-10 13:28:18 -0600 2015-12-09 14:09:57 -0700 ECMDB23305 M2MDB003695 DG(18:1(9Z)/12:0/0:0) DG(18:1(9Z)/12:0/0:0) 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(18:1(9Z)/12:0/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway. 1-(9Z-octadecenoyl)-2-dodecanoyl-sn-glycerol 1-oleoyl-2-dodecanoyl-sn-glycerol DAG(18:1/12:0) DAG(30:1) DG(18:1/12:0) DG(30:1) Diacylglycerol Diacylglycerol(18:1/12:0) Diacylglycerol(30:1) Diglyceride C33H62O5 538.854 538.459725096 (2R)-3-(dodecanoyloxy)-2-hydroxypropyl (9Z)-octadec-9-enoate (2R)-3-(dodecanoyloxy)-2-hydroxypropyl (9Z)-octadec-9-enoate [H][C@@](O)(COC(=O)CCCCCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC InChI=1S/C33H62O5/c1-3-5-7-9-11-13-14-15-16-17-18-20-22-24-26-28-33(36)38-30-31(34)29-37-32(35)27-25-23-21-19-12-10-8-6-4-2/h15-16,31,34H,3-14,17-30H2,1-2H3/b16-15-/t31-/m1/s1 PQTQNYZOCAKARX-AHVPQQLLSA-N Membrane logp 9.49 ALOGPS logs -7.37 ALOGPS solubility 2.31e-05 g/l ALOGPS logp 10.75 ChemAxon pka_strongest_acidic 13.63 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac (2R)-3-(dodecanoyloxy)-2-hydroxypropyl (9Z)-octadec-9-enoate ChemAxon average_mass 538.854 ChemAxon mono_mass 538.459725096 ChemAxon smiles [H][C@@](O)(COC(=O)CCCCCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC ChemAxon formula C33H62O5 ChemAxon inchi InChI=1S/C33H62O5/c1-3-5-7-9-11-13-14-15-16-17-18-20-22-24-26-28-33(36)38-30-31(34)29-37-32(35)27-25-23-21-19-12-10-8-6-4-2/h15-16,31,34H,3-14,17-30H2,1-2H3/b16-15-/t31-/m1/s1 ChemAxon inchikey PQTQNYZOCAKARX-AHVPQQLLSA-N ChemAxon polar_surface_area 72.83 ChemAxon refractivity 159.61 ChemAxon polarizability 70.18 ChemAxon rotatable_bond_count 31 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (PE(18:1(9Z)/12:0(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. PW001780 Metabolic Specdb::CMs 1088435 Specdb::NmrOneD 282499 Specdb::NmrOneD 282500 Specdb::NmrOneD 282501 Specdb::NmrOneD 282502 Specdb::NmrOneD 282503 Specdb::NmrOneD 282504 Specdb::NmrOneD 282505 Specdb::NmrOneD 282506 Specdb::NmrOneD 282507 Specdb::NmrOneD 282508 Specdb::NmrOneD 282509 Specdb::NmrOneD 282510 Specdb::NmrOneD 282511 Specdb::NmrOneD 282512 Specdb::NmrOneD 282513 Specdb::NmrOneD 282514 Specdb::NmrOneD 282515 Specdb::NmrOneD 282516 Specdb::NmrOneD 282517 Specdb::NmrOneD 282518 Specdb::MsMs 1272856 Specdb::MsMs 1272857 Specdb::MsMs 1272858 Specdb::MsMs 1387849 Specdb::MsMs 1387850 Specdb::MsMs 1387851 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(18:1(9Z)/12:0/0:0) + Cytidine triphosphate + Hydrogen ion > CDP-DG(18:1(9Z)/12:0) + Pyrophosphate PW_R004744