2.0 2012-05-31 14:11:29 -0600 2015-12-09 12:14:40 -0700 ECMDB06986 M2MDB000726 CDP-DG(18:1(11Z)/16:0) CDP-DG(18:1(11Z)/16:0) 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(18:1(11Z)/16:0), in particular, consists of one 11Z-octadecenoyl chain to C-1 atom, and one hexadecanoyl 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)/16:0) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. 1-(11Z-Octadecenoyl)-2-hexadecanoyl-sn-glycero-3-CDP 1-(11Z-octadecenoyl)-2-hexadecanoyl-sn-glycero-3-cytidine-5'-diphosphate 1-(11Z-Octadecenoyl)-2-hexadecanoyl-sn-glycero-3-cytidine-5'-diphosphoric acid 1-Vaccenoyl-2-palmitoyl-sn-glycero-3-cytidine-5'-diphosphate 1-Vaccenoyl-2-palmitoyl-sn-glycero-3-cytidine-5'-diphosphoric acid CDP-DG(18:1/16:0) CDP-DG(18:1n7/16:0) CDP-DG(18:1w7/16:0) CDP-DG(34:1) CDP-Diacylglycerol(18:1/16:0) CDP-Diacylglycerol(18:1n7/16:0) CDP-Diacylglycerol(18:1w7/16:0) CDP-Diacylglycerol(34:1) C46H83N3O15P2 980.1098 979.529942025 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2-(hexadecanoyloxy)-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-(hexadecanoyloxy)-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)CCCCCCCCCCCCCCC InChI=1S/C46H83N3O15P2/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-41(50)59-35-38(62-42(51)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2)36-60-65(55,56)64-66(57,58)61-37-39-43(52)44(53)45(63-39)49-34-33-40(47)48-46(49)54/h13,15,33-34,38-39,43-45,52-53H,3-12,14,16-32,35-37H2,1-2H3,(H,55,56)(H,57,58)(H2,47,48,54)/b15-13-/t38-,39-,43+,44?,45-/m1/s1 JYZDWTGASQILGK-PAKZJQHWSA-N Solid Inner membrane Membrane Outer membrane logp 6.50 ALOGPS logs -5.35 ALOGPS solubility 4.36e-03 g/l ALOGPS logp 10.08 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-(hexadecanoyloxy)-3-[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 980.1098 ChemAxon mono_mass 979.529942025 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)CCCCCCCCCCCCCCC ChemAxon formula C46H83N3O15P2 ChemAxon inchi InChI=1S/C46H83N3O15P2/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-41(50)59-35-38(62-42(51)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2)36-60-65(55,56)64-66(57,58)61-37-39-43(52)44(53)45(63-39)49-34-33-40(47)48-46(49)54/h13,15,33-34,38-39,43-45,52-53H,3-12,14,16-32,35-37H2,1-2H3,(H,55,56)(H,57,58)(H2,47,48,54)/b15-13-/t38-,39-,43+,44?,45-/m1/s1 ChemAxon inchikey JYZDWTGASQILGK-PAKZJQHWSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 250.53 ChemAxon polarizability 107.4 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 PHOSLIPSYN-PWY Specdb::EiMs 3471 Specdb::NmrOneD 303151 Specdb::NmrOneD 303152 Specdb::NmrOneD 303153 Specdb::NmrOneD 303154 Specdb::NmrOneD 303155 Specdb::NmrOneD 303156 Specdb::NmrOneD 303157 Specdb::NmrOneD 303158 Specdb::NmrOneD 303159 Specdb::NmrOneD 303160 Specdb::NmrOneD 303161 Specdb::NmrOneD 303162 Specdb::NmrOneD 303163 Specdb::NmrOneD 303164 Specdb::NmrOneD 303165 Specdb::NmrOneD 303166 Specdb::NmrOneD 303167 Specdb::NmrOneD 303168 Specdb::NmrOneD 303169 Specdb::NmrOneD 303170 Specdb::MsMs 294514 Specdb::MsMs 294515 Specdb::MsMs 294516 Specdb::MsMs 335257 Specdb::MsMs 335258 Specdb::MsMs 335259 Specdb::MsMs 2785807 Specdb::MsMs 2785808 Specdb::MsMs 2785809 Specdb::MsMs 2922655 Specdb::MsMs 2922656 Specdb::MsMs 2922657 HMDB06986 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