2.0 2012-05-31 14:12:00 -0600 2015-09-18 13:41:01 -0600 ECMDB06994 M2MDB000734 CDP-DG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) CDP-DG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 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(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one 11Z-octadecenoyl chain to C-1 atom, and one 4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl 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(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. 1-(11Z-Octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-CDP 1-(11Z-octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-cytidine-5'-diphosphate 1-(11Z-Octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-cytidine-5'-diphosphoric acid 1-Vaccenoyl-2-docosahexaenoyl-sn-glycero-3-cytidine-5'-diphosphate 1-Vaccenoyl-2-docosahexaenoyl-sn-glycero-3-cytidine-5'-diphosphoric acid CDP-DG(18:1/22:6) CDP-DG(18:1n7/22:6n3) CDP-DG(18:1w7/22:6w3) CDP-DG(40:7) CDP-Diacylglycerol(18:1/22:6) CDP-Diacylglycerol(18:1n7/22:6n3) CDP-Diacylglycerol(18:1w7/22:6w3) CDP-Diacylglycerol(40:7) C52H83N3O15P2 1052.174 1051.529942025 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propoxy(hydroxy)phosphoryl]oxy)phosphinic acid [H][C@@](COC(=O)CCCCCCCCC\C=C/CCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C52H83N3O15P2/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-48(57)68-44(41-65-47(56)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2)42-66-71(61,62)70-72(63,64)67-43-45-49(58)50(59)51(69-45)55-40-39-46(53)54-52(55)60/h5,7,11,13-14,16-17,19,21-22,26,28,32,34,39-40,44-45,49-51,58-59H,3-4,6,8-10,12,15,18,20,23-25,27,29-31,33,35-38,41-43H2,1-2H3,(H,61,62)(H,63,64)(H2,53,54,60)/b7-5-,13-11-,16-14-,19-17-,22-21-,28-26-,34-32-/t44-,45-,49+,50?,51-/m1/s1 DLHOGIVUAZAHPZ-ZDAJIRAHSA-N Solid Inner membrane Membrane Outer membrane logp 7.20 ALOGPS logs -5.94 ALOGPS solubility 1.20e-03 g/l ALOGPS logp 10.58 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -0.032 ChemAxon iupac {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 1052.174 ChemAxon mono_mass 1051.529942025 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCCC\C=C/CCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC ChemAxon formula C52H83N3O15P2 ChemAxon inchi InChI=1S/C52H83N3O15P2/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-48(57)68-44(41-65-47(56)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2)42-66-71(61,62)70-72(63,64)67-43-45-49(58)50(59)51(69-45)55-40-39-46(53)54-52(55)60/h5,7,11,13-14,16-17,19,21-22,26,28,32,34,39-40,44-45,49-51,58-59H,3-4,6,8-10,12,15,18,20,23-25,27,29-31,33,35-38,41-43H2,1-2H3,(H,61,62)(H,63,64)(H2,53,54,60)/b7-5-,13-11-,16-14-,19-17-,22-21-,28-26-,34-32-/t44-,45-,49+,50?,51-/m1/s1 ChemAxon inchikey DLHOGIVUAZAHPZ-ZDAJIRAHSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 284.83 ChemAxon polarizability 113.5 ChemAxon rotatable_bond_count 43 ChemAxon acceptor_count 12 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis I (CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) ) "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." PW001025 Metabolic phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::NmrOneD 269398 Specdb::NmrOneD 269399 Specdb::NmrOneD 269400 Specdb::NmrOneD 269401 Specdb::NmrOneD 269402 Specdb::NmrOneD 269403 Specdb::NmrOneD 269404 Specdb::NmrOneD 269405 Specdb::NmrOneD 269406 Specdb::NmrOneD 269407 Specdb::NmrOneD 269408 Specdb::NmrOneD 269409 Specdb::NmrOneD 269410 Specdb::NmrOneD 269411 Specdb::NmrOneD 269412 Specdb::NmrOneD 269413 Specdb::NmrOneD 269414 Specdb::NmrOneD 269415 Specdb::NmrOneD 269416 Specdb::NmrOneD 269417 Specdb::MsMs 311857 Specdb::MsMs 311858 Specdb::MsMs 311859 Specdb::MsMs 356956 Specdb::MsMs 356957 Specdb::MsMs 356958 Specdb::MsMs 2386913 Specdb::MsMs 2386914 Specdb::MsMs 2386915 Specdb::MsMs 2579562 Specdb::MsMs 2579563 Specdb::MsMs 2579564 HMDB06994 Keseler, 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. 21097882 Kanehisa, 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. 22080510 Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. 22102590 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--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 Protein crcA P37001 CRCA_ECOLI crcA http://ecmdb.ca/proteins/P37001.xml CDP-diacylglycerol--serine O-phosphatidyltransferase P23830 PSS_ECOLI pssA http://ecmdb.ca/proteins/P23830.xml Probable phospholipid ABC transporter-binding protein mlaB P64602 MLAB_ECOLI mlaB http://ecmdb.ca/proteins/P64602.xml Probable phospholipid ABC transporter-binding protein mlaD P64604 MLAD_ECOLI mlaD http://ecmdb.ca/proteins/P64604.xml Probable phospholipid ABC transporter permease protein mlaE P64606 MLAE_ECOLI mlaE http://ecmdb.ca/proteins/P64606.xml DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/0:0) + Cytidine triphosphate + Hydrogen ion > CDP-DG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + Pyrophosphate + CDP-DG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) PW_R003812 L-Serine + CDP-DG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + L-Serine + CDP-DG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) > Hydrogen ion + Cytidine monophosphate + PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)) + Cytidine monophosphate PW_R003811 CDP-DG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + Glycerol 3-phosphate + CDP-DG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) > PGP(18:2(9Z,12Z)/18:2(9Z,12Z)) + Hydrogen ion + Cytidine monophosphate + Cytidine monophosphate PW_R003809