2.02012-10-10 13:28:18 -06002015-12-09 14:09:57 -0700ECMDB23305M2MDB003695DG(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-glycerol1-oleoyl-2-dodecanoyl-sn-glycerolDAG(18:1/12:0)DAG(30:1)DG(18:1/12:0)DG(30:1)DiacylglycerolDiacylglycerol(18:1/12:0)Diacylglycerol(30:1)DiglycerideC33H62O5538.854538.459725096(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/CCCCCCCCInChI=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/s1PQTQNYZOCAKARX-AHVPQQLLSA-NMembranelogp9.49logs-7.37solubility2.31e-05 g/llogp10.75pka_strongest_acidic13.63pka_strongest_basic-3.4iupac(2R)-3-(dodecanoyloxy)-2-hydroxypropyl (9Z)-octadec-9-enoateaverage_mass538.854mono_mass538.459725096smiles[H][C@@](O)(COC(=O)CCCCCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCCformulaC33H62O5inchiInChI=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/s1inchikeyPQTQNYZOCAKARX-AHVPQQLLSA-Npolar_surface_area72.83refractivity159.61polarizability70.18rotatable_bond_count31acceptor_count3donor_count1physiological_charge0formal_charge0phospholipid 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.PW001780MetabolicSpecdb::CMs1088435Specdb::NmrOneD282499Specdb::NmrOneD282500Specdb::NmrOneD282501Specdb::NmrOneD282502Specdb::NmrOneD282503Specdb::NmrOneD282504Specdb::NmrOneD282505Specdb::NmrOneD282506Specdb::NmrOneD282507Specdb::NmrOneD282508Specdb::NmrOneD282509Specdb::NmrOneD282510Specdb::NmrOneD282511Specdb::NmrOneD282512Specdb::NmrOneD282513Specdb::NmrOneD282514Specdb::NmrOneD282515Specdb::NmrOneD282516Specdb::NmrOneD282517Specdb::NmrOneD282518Specdb::MsMs1272856Specdb::MsMs1272857Specdb::MsMs1272858Specdb::MsMs1387849Specdb::MsMs1387850Specdb::MsMs1387851Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.APhosphatidylglycerophosphatase BP0A924PGPB_ECOLIpgpBhttp://ecmdb.ca/proteins/P0A924.xmlPhosphatidate cytidylyltransferaseP0ABG1CDSA_ECOLIcdsAhttp://ecmdb.ca/proteins/P0ABG1.xmlDiacylglycerol kinaseP0ABN1KDGL_ECOLIdgkAhttp://ecmdb.ca/proteins/P0ABN1.xmlDG(18:1(9Z)/12:0/0:0) + Cytidine triphosphate + Hydrogen ion > CDP-DG(18:1(9Z)/12:0) + PyrophosphatePW_R004744