2.0 2012-05-31 14:12:10 -0600 2015-12-09 12:14:51 -0700 ECMDB06997 M2MDB000737 CDP-DG(18:1(9Z)/18:1(11Z)) CDP-DG(18:1(9Z)/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(18:1(9Z)/18:1(11Z)), in particular, consists of one 9Z-octadecenoyl 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(18:1(9Z)/18:1(11Z)) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. 1-(9Z-Octadecenoyl)-2-(11Z-octadecenoyl)-sn-glycero-3-CDP 1-(9Z-octadecenoyl)-2-(11Z-octadecenoyl)-sn-glycero-3-cytidine-5'-diphosphate 1-(9Z-Octadecenoyl)-2-(11Z-octadecenoyl)-sn-glycero-3-cytidine-5'-diphosphoric acid 1-Oleoyl-2-vaccenoyl-sn-glycero-3-cytidine-5'-diphosphate 1-Oleoyl-2-vaccenoyl-sn-glycero-3-cytidine-5'-diphosphoric acid CDP-DG(18:1/18:1) CDP-DG(18:1n9/18:1n7) CDP-DG(18:1w9/18:1w7) CDP-DG(36:2) CDP-Diacylglycerol(18:1/18:1) CDP-Diacylglycerol(18:1n9/18:1n7) CDP-Diacylglycerol(18:1w9/18:1w7) CDP-Diacylglycerol(36:2) C48H85N3O15P2 1006.1471 1005.545592089 {[(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-[(9Z)-octadec-9-enoyloxy]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-[(9Z)-octadec-9-enoyloxy]propoxy)phosphoryl]oxy)phosphinic acid [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(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/C48H85N3O15P2/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/h14,16-17,19,35-36,40-41,45-47,54-55H,3-13,15,18,20-34,37-39H2,1-2H3,(H,57,58)(H,59,60)(H2,49,50,56)/b16-14-,19-17-/t40-,41-,45+,46?,47-/m1/s1 OAHLYURAXDZWKU-HKGKMMGUSA-N Solid Inner membrane Membrane Outer membrane logp 6.89 ALOGPS logs -5.54 ALOGPS solubility 2.91e-03 g/l ALOGPS logp 10.61 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-[(9Z)-octadec-9-enoyloxy]propoxy]phosphoryl}oxy)phosphinic acid ChemAxon average_mass 1006.1471 ChemAxon mono_mass 1005.545592089 ChemAxon smiles [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(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 C48H85N3O15P2 ChemAxon inchi InChI=1S/C48H85N3O15P2/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/h14,16-17,19,35-36,40-41,45-47,54-55H,3-13,15,18,20-34,37-39H2,1-2H3,(H,57,58)(H,59,60)(H2,49,50,56)/b16-14-,19-17-/t40-,41-,45+,46?,47-/m1/s1 ChemAxon inchikey OAHLYURAXDZWKU-HKGKMMGUSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 260.85 ChemAxon polarizability 109.52 ChemAxon rotatable_bond_count 44 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::EiMs 4676 Specdb::NmrOneD 296435 Specdb::NmrOneD 296436 Specdb::NmrOneD 296437 Specdb::NmrOneD 296438 Specdb::NmrOneD 296439 Specdb::NmrOneD 296440 Specdb::NmrOneD 296441 Specdb::NmrOneD 296442 Specdb::NmrOneD 296443 Specdb::NmrOneD 296444 Specdb::NmrOneD 296445 Specdb::NmrOneD 296446 Specdb::NmrOneD 296447 Specdb::NmrOneD 296448 Specdb::NmrOneD 296449 Specdb::NmrOneD 296450 Specdb::NmrOneD 296451 Specdb::NmrOneD 296452 Specdb::NmrOneD 296453 Specdb::NmrOneD 296454 Specdb::MsMs 324463 Specdb::MsMs 324464 Specdb::MsMs 324465 Specdb::MsMs 372874 Specdb::MsMs 372875 Specdb::MsMs 372876 Specdb::MsMs 2801302 Specdb::MsMs 2801303 Specdb::MsMs 2801304 Specdb::MsMs 2877728 Specdb::MsMs 2877729 Specdb::MsMs 2877730 HMDB06997 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