2.02012-10-11 06:39:44 -06002015-12-09 12:15:14 -0700ECMDB23389M2MDB003779CDP-DG(19:1(9Z)/18:0)CDP-DG(19:1(9Z)/18:0) belongs to the family of CDP-diacylglycerols. It is a glycerophospholipid containing a diacylglycerol, with a cytidine diphosphate attached to the oxygen O1 or O2 of the glycerol part. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms. CDP-DG(19:1(9Z)/18:0), in particular, consists of one 9Z-nonadecenoyl chain to C-1 atom, and one octadecanoyl to the C-2 atom. In E. coli glycerophospholipid metabolism, The biosynthesis of CDP-diacylglycerol (CDP-DG) involves condensation of phosphatidic acid (PA) and cytidine triphosphate, with elimination of pyrophosphate, catalysed by the enzyme CDP-diacylglycerol synthase. The resulting CDP-diacylglycerol can be utilized immediately for the synthesis of phosphatidylglycerol (PG), and thence cardiolipin (CL), and of phosphatidylinositol (PI). CDP-DG(19:1(9Z)/18:0) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway.1-(9Z-nonadecenoyl)-2-octadecanoyl-sn-glycero-3-CDP1-(9Z-nonadecenoyl)-2-octadecanoyl-sn-glycero-3-cytidine-5'-diphosphate1-(9Z-Nonadecenoyl)-2-octadecanoyl-sn-glycero-3-cytidine-5'-diphosphoric acid1-9Z-nonadecenoyl-2-stearoyl-sn-glycero-3-cytidine-5'-diphosphate1-9Z-Nonadecenoyl-2-stearoyl-sn-glycero-3-cytidine-5'-diphosphoric acidCDP-DG(19:1/18:0)CDP-DG(37:1)CDP-Diacylglycerol(19:1/18:0)CDP-Diacylglycerol(37:1)C49H89N3O15P21022.2051021.576893174{[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[(2R)-3-[(9Z)-nonadec-9-enoyloxy]-2-(octadecanoyloxy)propoxy]phosphoryl}oxy)phosphinic acid[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([hydroxy((2R)-3-[(9Z)-nonadec-9-enoyloxy]-2-(octadecanoyloxy)propoxy)phosphoryl]oxy)phosphinic acid[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCCCCCCCCCInChI=1S/C49H89N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-44(53)62-38-41(65-45(54)35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2)39-63-68(58,59)67-69(60,61)64-40-42-46(55)47(56)48(66-42)52-37-36-43(50)51-49(52)57/h19,21,36-37,41-42,46-48,55-56H,3-18,20,22-35,38-40H2,1-2H3,(H,58,59)(H,60,61)(H2,50,51,57)/b21-19-/t41-,42-,46+,47?,48-/m1/s1VVPAJMBXQQSQQX-FQCYUAKFSA-NSolidMembranelogp7.11logs-5.67solubility2.18e-03 g/llogp11.42pka_strongest_acidic1.86pka_strongest_basic-0.032iupac{[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[(2R)-3-[(9Z)-nonadec-9-enoyloxy]-2-(octadecanoyloxy)propoxy]phosphoryl}oxy)phosphinic acidaverage_mass1022.205mono_mass1021.576893174smiles[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCCCCCCCCCformulaC49H89N3O15P2inchiInChI=1S/C49H89N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-44(53)62-38-41(65-45(54)35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2)39-63-68(58,59)67-69(60,61)64-40-42-46(55)47(56)48(66-42)52-37-36-43(50)51-49(52)57/h19,21,36-37,41-42,46-48,55-56H,3-18,20,22-35,38-40H2,1-2H3,(H,58,59)(H,60,61)(H2,50,51,57)/b21-19-/t41-,42-,46+,47?,48-/m1/s1inchikeyVVPAJMBXQQSQQX-FQCYUAKFSA-Npolar_surface_area263.27refractivity264.33polarizability113.72rotatable_bond_count46acceptor_count12donor_count5physiological_charge-2formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CDP-DG(19:1(9Z)/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 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.
PW001791Metabolicphospholipid biosynthesis IPHOSLIPSYN-PWYSpecdb::EiMs4018Specdb::NmrOneD295095Specdb::NmrOneD295096Specdb::NmrOneD295097Specdb::NmrOneD295098Specdb::NmrOneD295099Specdb::NmrOneD295100Specdb::NmrOneD295101Specdb::NmrOneD295102Specdb::NmrOneD295103Specdb::NmrOneD295104Specdb::NmrOneD295105Specdb::NmrOneD295106Specdb::NmrOneD295107Specdb::NmrOneD295108Specdb::NmrOneD295109Specdb::NmrOneD295110Specdb::NmrOneD295111Specdb::NmrOneD295112Specdb::NmrOneD295113Specdb::NmrOneD295114Specdb::MsMs1218571Specdb::MsMs1218572Specdb::MsMs1218573Specdb::MsMs1334284Specdb::MsMs1334285Specdb::MsMs1334286Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510Yurtsever 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.xmlProtein crcAP37001CRCA_ECOLIcrcAhttp://ecmdb.ca/proteins/P37001.xmlCDP-diacylglycerol--serine O-phosphatidyltransferaseP23830PSS_ECOLIpssAhttp://ecmdb.ca/proteins/P23830.xmlProbable phospholipid ABC transporter-binding protein mlaBP64602MLAB_ECOLImlaBhttp://ecmdb.ca/proteins/P64602.xmlProbable phospholipid ABC transporter-binding protein mlaDP64604MLAD_ECOLImlaDhttp://ecmdb.ca/proteins/P64604.xmlProbable phospholipid ABC transporter permease protein mlaEP64606MLAE_ECOLImlaEhttp://ecmdb.ca/proteins/P64606.xmlDG(19:1(9Z)/18:0/0:0) + Cytidine triphosphate + Hydrogen ion > CDP-DG(19:1(9Z)/18:0) + PyrophosphatePW_R004762