2.0 2012-07-30 14:54:48 -0600 2015-06-03 17:20:50 -0600 ECMDB21188 M2MDB001597 CDP-1,2-dihexadec-9-enoylglycerol Cdp-1,2-dihexadec-9-enoylglycerol belongs to the class of CDP-Diacylglycerols. These are glycerolipids containing a diacylglycerol, with a cytidine diphosphate attached to the oxygen O1 or O2 of the glycerol part. (inferred from compound structure) C44H77N3O15P2 950.0408 949.482991833 [({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy]phosphinic acid {[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxyphosphinic acid CCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCC\C=C/CCCCCC InChI=1S/C44H77N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-39(48)57-33-36(60-40(49)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)34-58-63(53,54)62-64(55,56)59-35-37-41(50)42(51)43(61-37)47-32-31-38(45)46-44(47)52/h13-16,31-32,36-37,41-43,50-51H,3-12,17-30,33-35H2,1-2H3,(H,53,54)(H,55,56)(H2,45,46,52)/b15-13-,16-14-/t36-,37-,41-,42-,43-/m1/s1 LBKBJHVQQNUXGQ-ATKZGQRLSA-N Membrane logp 6.03 ALOGPS logs -5.10 ALOGPS solubility 7.60e-03 g/l ALOGPS logp 8.56 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -0.52 ChemAxon iupac [({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy]phosphinic acid ChemAxon average_mass 950.0408 ChemAxon mono_mass 949.482991833 ChemAxon smiles CCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCC\C=C/CCCCCC ChemAxon formula C44H77N3O15P2 ChemAxon inchi InChI=1S/C44H77N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-39(48)57-33-36(60-40(49)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)34-58-63(53,54)62-64(55,56)59-35-37-41(50)42(51)43(61-37)47-32-31-38(45)46-44(47)52/h13-16,31-32,36-37,41-43,50-51H,3-12,17-30,33-35H2,1-2H3,(H,53,54)(H,55,56)(H2,45,46,52)/b15-13-,16-14-/t36-,37-,41-,42-,43-/m1/s1 ChemAxon inchikey LBKBJHVQQNUXGQ-ATKZGQRLSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 242.44 ChemAxon polarizability 100.27 ChemAxon rotatable_bond_count 40 ChemAxon acceptor_count 12 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(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 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." PW001549 Metabolic Specdb::EiMs 3935 Specdb::NmrOneD 302925 Specdb::NmrOneD 302926 Specdb::NmrOneD 302927 Specdb::NmrOneD 302928 Specdb::NmrOneD 302929 Specdb::NmrOneD 302930 Specdb::NmrOneD 302931 Specdb::NmrOneD 302932 Specdb::NmrOneD 302933 Specdb::NmrOneD 302934 Specdb::NmrOneD 302935 Specdb::NmrOneD 302936 Specdb::NmrOneD 302937 Specdb::NmrOneD 302938 Specdb::NmrOneD 302939 Specdb::NmrOneD 302940 Specdb::NmrOneD 302941 Specdb::NmrOneD 302942 Specdb::NmrOneD 302943 Specdb::NmrOneD 302944 Specdb::MsMs 37553 Specdb::MsMs 37554 Specdb::MsMs 37555 Specdb::MsMs 40001 Specdb::MsMs 40002 Specdb::MsMs 40003 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 CDP-diacylglycerol pyrophosphatase P06282 CDH_ECOLI cdh http://ecmdb.ca/proteins/P06282.xml CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase P0ABF8 PGSA_ECOLI pgsA http://ecmdb.ca/proteins/P0ABF8.xml Phosphatidate cytidylyltransferase P0ABG1 CDSA_ECOLI cdsA http://ecmdb.ca/proteins/P0ABG1.xml CDP-diacylglycerol--serine O-phosphatidyltransferase P23830 PSS_ECOLI pssA http://ecmdb.ca/proteins/P23830.xml Cytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-dihexadec-9-enoylglycerol + Pyrophosphate CDP-1,2-dihexadec-9-enoylglycerol + Glycerol 3-phosphate > Cytidine monophosphate + Hydrogen ion + PGP(16:1(9Z)/16:1(9Z)) CDP-1,2-dihexadec-9-enoylglycerol + L-Serine > Cytidine monophosphate + Hydrogen ion + PS(16:0/16:0) CDP-1,2-dihexadec-9-enoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0) 2 1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Cytidine triphosphate + Hydrogen ion >2 CDP-1,2-dihexadec-9-enoylglycerol + Pyrophosphate PW_R005696