2.02015-09-08 20:08:50 -06002015-12-09 14:07:14 -0700ECMDB24775M2MDB006892DG(14:0/14:0(3-OH)/0:0)DG(14:0/14:0(3-OH)/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(14:0/14:0(3-OH)/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway.C31H60O6528.815528.438989652(2S)-2-hydroxy-3-(tetradecanoyloxy)propyl 3-hydroxytetradecanoate(2S)-2-hydroxy-3-(tetradecanoyloxy)propyl 3-hydroxytetradecanoate[H][C@](O)(COC(=O)CCCCCCCCCCCCC)COC(=O)CC(O)CCCCCCCCCCCInChI=1S/C31H60O6/c1-3-5-7-9-11-13-14-16-18-20-22-24-30(34)36-26-29(33)27-37-31(35)25-28(32)23-21-19-17-15-12-10-8-6-4-2/h28-29,32-33H,3-27H2,1-2H3/t28?,29-/m0/s1WQTIZQDRYDLJAR-XIJSCUBXSA-Nlogp8.29logs-6.61solubility1.29e-04 g/llogp8.99pka_strongest_acidic13.61pka_strongest_basic-2.8iupac(2S)-2-hydroxy-3-(tetradecanoyloxy)propyl 3-hydroxytetradecanoateaverage_mass528.815mono_mass528.438989652smiles[H][C@](O)(COC(=O)CCCCCCCCCCCCC)COC(=O)CC(O)CCCCCCCCCCCformulaC31H60O6inchiInChI=1S/C31H60O6/c1-3-5-7-9-11-13-14-16-18-20-22-24-30(34)36-26-29(33)27-37-31(35)25-28(32)23-21-19-17-15-12-10-8-6-4-2/h28-29,32-33H,3-27H2,1-2H3/t28?,29-/m0/s1inchikeyWQTIZQDRYDLJAR-XIJSCUBXSA-Npolar_surface_area93.06refractivity150.81polarizability68.53rotatable_bond_count30acceptor_count4donor_count2physiological_charge0formal_charge0phospholipid biosynthesis (CL(14:0/14:0(3-OH)/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.
PW001944MetabolicSpecdb::CMs1087424Specdb::NmrOneD325712Specdb::NmrOneD325713Specdb::NmrOneD325714Specdb::NmrOneD325715Specdb::NmrOneD325716Specdb::NmrOneD325717Specdb::NmrOneD325718Specdb::NmrOneD325719Specdb::NmrOneD325720Specdb::NmrOneD325721Specdb::NmrOneD325722Specdb::NmrOneD325723Specdb::NmrOneD325724Specdb::NmrOneD325725Specdb::NmrOneD325726Specdb::NmrOneD325727Specdb::NmrOneD325728Specdb::NmrOneD325729Specdb::NmrOneD325730Specdb::NmrOneD325731Specdb::MsMs1258768Specdb::MsMs1258769Specdb::MsMs1258770Specdb::MsMs1373908Specdb::MsMs1373909Specdb::MsMs1373910Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.APhosphatidate cytidylyltransferaseP0ABG1CDSA_ECOLIcdsAhttp://ecmdb.ca/proteins/P0ABG1.xmlDG(14:0/14:0(3-OH)/0:0) + Cytidine triphosphate + Hydrogen ion > CDP-DG(14:0/14:0(3-OH)) + PyrophosphatePW_R005463