2.0 2012-05-31 14:11:02 -0600 2015-12-09 12:14:36 -0700 ECMDB06979 M2MDB000719 CDP-DG(18:0/18:1(11Z)) CDP-DG(18:0/18:1(11Z)) 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(18:0/18:1(11Z)), in particular, consists of one octadecanoyl chain to C-1 atom, and one 11Z-octadecenoyl 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(18:0/18:1(11Z)) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. 1-Octadecanoyl-2-(11Z-octadecenoyl)-sn-glycero-3-CDP 1-octadecanoyl-2-(11Z-octadecenoyl)-sn-glycero-3-cytidine-5'-diphosphate 1-Octadecanoyl-2-(11Z-octadecenoyl)-sn-glycero-3-cytidine-5'-diphosphoric acid 1-Stearoyl-2-vaccenoyl-sn-glycero-3-cytidine-5'-diphosphate 1-Stearoyl-2-vaccenoyl-sn-glycero-3-cytidine-5'-diphosphoric acid CDP-DG(18:0/18:1) CDP-DG(18:0/18:1n7) CDP-DG(18:0/18:1w7) CDP-DG(36:1) CDP-Diacylglycerol(18:0/18:1) CDP-Diacylglycerol(18:0/18:1n7) CDP-Diacylglycerol(18:0/18:1w7) CDP-Diacylglycerol(36:1) C48H87N3O15P2 1008.163 1007.561242153 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[(2R)-2-[(11Z)-octadec-11-enoyloxy]-3-(octadecanoyloxy)propoxy]phosphoryl}oxy)phosphinic acid [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([hydroxy((2R)-2-[(11Z)-octadec-11-enoyloxy]-3-(octadecanoyloxy)propoxy)phosphoryl]oxy)phosphinic acid [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCC\C=C/CCCCCC InChI=1S/C48H87N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-43(52)61-37-40(64-44(53)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)38-62-67(57,58)66-68(59,60)63-39-41-45(54)46(55)47(65-41)51-36-35-42(49)50-48(51)56/h14,16,35-36,40-41,45-47,54-55H,3-13,15,17-34,37-39H2,1-2H3,(H,57,58)(H,59,60)(H2,49,50,56)/b16-14-/t40-,41-,45+,46?,47-/m1/s1 FBSLHTWQFOZAGL-DNLPIHBOSA-N Solid Inner membrane Membrane Outer membrane logp 6.90 ALOGPS logs -5.57 ALOGPS solubility 2.69e-03 g/l ALOGPS logp 10.97 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}({hydroxy[(2R)-2-[(11Z)-octadec-11-enoyloxy]-3-(octadecanoyloxy)propoxy]phosphoryl}oxy)phosphinic acid ChemAxon average_mass 1008.163 ChemAxon mono_mass 1007.561242153 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCC\C=C/CCCCCC ChemAxon formula C48H87N3O15P2 ChemAxon inchi InChI=1S/C48H87N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-43(52)61-37-40(64-44(53)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)38-62-67(57,58)66-68(59,60)63-39-41-45(54)46(55)47(65-41)51-36-35-42(49)50-48(51)56/h14,16,35-36,40-41,45-47,54-55H,3-13,15,17-34,37-39H2,1-2H3,(H,57,58)(H,59,60)(H2,49,50,56)/b16-14-/t40-,41-,45+,46?,47-/m1/s1 ChemAxon inchikey FBSLHTWQFOZAGL-DNLPIHBOSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 259.73 ChemAxon polarizability 111.69 ChemAxon rotatable_bond_count 45 ChemAxon acceptor_count 12 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::NmrOneD 341868 Specdb::NmrOneD 341869 Specdb::NmrOneD 341870 Specdb::NmrOneD 341871 Specdb::NmrOneD 341872 Specdb::NmrOneD 341873 Specdb::NmrOneD 341874 Specdb::NmrOneD 341875 Specdb::NmrOneD 341876 Specdb::NmrOneD 341877 Specdb::NmrOneD 341878 Specdb::NmrOneD 341879 Specdb::NmrOneD 341880 Specdb::NmrOneD 341881 Specdb::NmrOneD 341882 Specdb::NmrOneD 341883 Specdb::NmrOneD 341884 Specdb::NmrOneD 341885 Specdb::NmrOneD 341886 Specdb::NmrOneD 341887 Specdb::MsMs 288592 Specdb::MsMs 288593 Specdb::MsMs 288594 Specdb::MsMs 327769 Specdb::MsMs 327770 Specdb::MsMs 327771 Specdb::MsMs 2774180 Specdb::MsMs 2774181 Specdb::MsMs 2774182 Specdb::MsMs 2904297 Specdb::MsMs 2904298 Specdb::MsMs 2904299 HMDB06979 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 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