2.0 2012-05-31 14:11:38 -0600 2015-12-09 12:14:42 -0700 ECMDB06988 M2MDB000728 CDP-DG(18:1(11Z)/18:1(11Z)) CDP-DG(18:1(11Z)/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 positions. CDP-DG(18:1(11Z)/18:1(11Z)), in particular, consists of two 11Z-octadecenoyl chain at positions C-1 and C2. 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)/18:1(11Z)) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. 1,2-Di(11Z-octadecenoyl)-rac-glycero-3-CDP 1,2-di(11Z-octadecenoyl)-rac-glycero-3-cytidine-5'-diphosphate 1,2-Di(11Z-octadecenoyl)-rac-glycero-3-cytidine-5'-diphosphoric acid 1,2-Divaccenoyl-rac-glycero-3-cytidine-5'-diphosphate 1,2-Divaccenoyl-rac-glycero-3-cytidine-5'-diphosphoric acid CDP-DG(18:1/18:1) CDP-DG(18:1n7/18:1n7) CDP-DG(18:1w7/18:1w7) CDP-DG(36:2) CDP-Diacylglycerol(18:1/18:1) CDP-Diacylglycerol(18:1n7/18:1n7) CDP-Diacylglycerol(18:1w7/18:1w7) 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}({[(2R)-2,3-bis[(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)-2,3-bis[(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)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/h13-16,35-36,40-41,45-47,54-55H,3-12,17-34,37-39H2,1-2H3,(H,57,58)(H,59,60)(H2,49,50,56)/b15-13-,16-14-/t40-,41-,45+,46?,47-/m1/s1 KISJWPWNABZPGN-PYYNXHAWSA-N Solid Inner membrane Membrane Outer membrane logp 6.88 ALOGPS logs -5.54 ALOGPS solubility 2.92e-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}({[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 1006.1471 ChemAxon mono_mass 1005.545592089 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)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/h13-16,35-36,40-41,45-47,54-55H,3-12,17-34,37-39H2,1-2H3,(H,57,58)(H,59,60)(H2,49,50,56)/b15-13-,16-14-/t40-,41-,45+,46?,47-/m1/s1 ChemAxon inchikey KISJWPWNABZPGN-PYYNXHAWSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 260.85 ChemAxon polarizability 109.59 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::NmrOneD 312541 Specdb::NmrOneD 312542 Specdb::NmrOneD 312543 Specdb::NmrOneD 312544 Specdb::NmrOneD 312545 Specdb::NmrOneD 312546 Specdb::NmrOneD 312547 Specdb::NmrOneD 312548 Specdb::NmrOneD 312549 Specdb::NmrOneD 312550 Specdb::NmrOneD 312551 Specdb::NmrOneD 312552 Specdb::NmrOneD 312553 Specdb::NmrOneD 312554 Specdb::NmrOneD 312555 Specdb::NmrOneD 312556 Specdb::NmrOneD 312557 Specdb::NmrOneD 312558 Specdb::NmrOneD 312559 Specdb::NmrOneD 312560 Specdb::MsMs 301612 Specdb::MsMs 301613 Specdb::MsMs 301614 Specdb::MsMs 344152 Specdb::MsMs 344153 Specdb::MsMs 344154 Specdb::MsMs 2408312 Specdb::MsMs 2408313 Specdb::MsMs 2408314 Specdb::MsMs 2554105 Specdb::MsMs 2554106 Specdb::MsMs 2554107 HMDB06988 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