2.0 2012-10-10 13:28:07 -0600 2015-12-09 14:06:59 -0700 ECMDB23256 M2MDB003646 DG(12:0/18:0/0:0) DG(12:0/18:0/0:0) 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(12:0/18:0/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway. 1-dodecanoyl-2-octadecanoyl-sn-glycerol 1-dodecanoyl-2-stearoyl-sn-glycerol DAG(12:0/18:0) DAG(30:0) DG(12:0/18:0) DG(30:0) Diacylglycerol Diacylglycerol(12:0/18:0) Diacylglycerol(30:0) Diglyceride C33H64O5 540.87 540.475375161 (2S)-3-(dodecanoyloxy)-2-hydroxypropyl octadecanoate (2S)-3-(dodecanoyloxy)-2-hydroxypropyl octadecanoate [H][C@](O)(COC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC InChI=1S/C33H64O5/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/h31,34H,3-30H2,1-2H3/t31-/m0/s1 SLGMWTYQQRQEKQ-HKBQPEDESA-N Membrane logp 9.62 ALOGPS logs -7.38 ALOGPS solubility 2.24e-05 g/l ALOGPS logp 11.11 ChemAxon pka_strongest_acidic 13.63 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac (2S)-3-(dodecanoyloxy)-2-hydroxypropyl octadecanoate ChemAxon average_mass 540.87 ChemAxon mono_mass 540.475375161 ChemAxon smiles [H][C@](O)(COC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC ChemAxon formula C33H64O5 ChemAxon inchi InChI=1S/C33H64O5/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/h31,34H,3-30H2,1-2H3/t31-/m0/s1 ChemAxon inchikey SLGMWTYQQRQEKQ-HKBQPEDESA-N ChemAxon polar_surface_area 72.83 ChemAxon refractivity 158.5 ChemAxon polarizability 71.73 ChemAxon rotatable_bond_count 32 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis CDP-DG(12:0/18:0) 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 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. PW001775 Metabolic Specdb::CMs 49973 Specdb::CMs 265362 Specdb::CMs 281428 Specdb::NmrOneD 271558 Specdb::NmrOneD 271559 Specdb::NmrOneD 271560 Specdb::NmrOneD 271561 Specdb::NmrOneD 271562 Specdb::NmrOneD 271563 Specdb::NmrOneD 271564 Specdb::NmrOneD 271565 Specdb::NmrOneD 271566 Specdb::NmrOneD 271567 Specdb::NmrOneD 271568 Specdb::NmrOneD 271569 Specdb::NmrOneD 271570 Specdb::NmrOneD 271571 Specdb::NmrOneD 271572 Specdb::NmrOneD 271573 Specdb::NmrOneD 271574 Specdb::NmrOneD 271575 Specdb::NmrOneD 271576 Specdb::NmrOneD 271577 Specdb::MsMs 2262847 Specdb::MsMs 2262848 Specdb::MsMs 2262849 Specdb::MsMs 3078774 Specdb::MsMs 3078775 Specdb::MsMs 3078776 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(12:0/18:0/0:0) + Cytidine triphosphate + Hydrogen ion CDP-DG(12:0/18:0) + Pyrophosphate PW_R004738