2.0 2012-10-11 06:39:39 -0600 2015-12-09 12:13:57 -0700 ECMDB23360 M2MDB003750 CDP-DG(16:0/16:1(9Z)) CDP-DG(16:0/16:1(9Z)) 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(16:0/16:1(9Z)), in particular, consists of one hexadecanoyl chain to C-1 atom, and one 9Z-hexadecenoyl 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(16:0/16:1(9Z)) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. 1-hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-CDP 1-hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-cytidine-5'-diphosphate 1-Hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-cytidine-5'-diphosphoric acid 1-palmitoyl-2-palmitoleoyl-sn-glycero-3-cytidine-5'-diphosphate 1-Palmitoyl-2-palmitoleoyl-sn-glycero-3-cytidine-5'-diphosphoric acid CDP-DG(16:0/16:1) CDP-DG(32:1) CDP-Diacylglycerol(16:0/16:1) CDP-Diacylglycerol(32:1) C44H79N3O15P2 952.07 951.498642852 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)phosphinic acid [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy)phosphinic acid [H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCC\C=C/CCCCCC InChI=1S/C44H79N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-39(48)57-33-36(60-40(49)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)34-58-63(53,54)62-64(55,56)59-35-37-41(50)42(51)43(61-37)47-32-31-38(45)46-44(47)52/h14,16,31-32,36-37,41-43,50-51H,3-13,15,17-30,33-35H2,1-2H3,(H,53,54)(H,55,56)(H2,45,46,52)/b16-14-/t36-,37-,41+,42?,43-/m1/s1 PQSHMALAWALIIC-RGZJOJOVSA-N Solid Membrane logp 6.06 ALOGPS logs -5.14 ALOGPS solubility 6.84e-03 g/l ALOGPS logp 9.19 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-[(9Z)-hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 952.07 ChemAxon mono_mass 951.498642852 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCC\C=C/CCCCCC ChemAxon formula C44H79N3O15P2 ChemAxon inchi InChI=1S/C44H79N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-39(48)57-33-36(60-40(49)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)34-58-63(53,54)62-64(55,56)59-35-37-41(50)42(51)43(61-37)47-32-31-38(45)46-44(47)52/h14,16,31-32,36-37,41-43,50-51H,3-13,15,17-30,33-35H2,1-2H3,(H,53,54)(H,55,56)(H2,45,46,52)/b16-14-/t36-,37-,41+,42?,43-/m1/s1 ChemAxon inchikey PQSHMALAWALIIC-RGZJOJOVSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 241.33 ChemAxon polarizability 102.92 ChemAxon rotatable_bond_count 41 ChemAxon acceptor_count 12 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis CL(16:0/16:1(9Z)/16:0/16:1(9Z)) "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." PW001297 Metabolic phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::NmrOneD 291095 Specdb::NmrOneD 291096 Specdb::NmrOneD 291097 Specdb::NmrOneD 291098 Specdb::NmrOneD 291099 Specdb::NmrOneD 291100 Specdb::NmrOneD 291101 Specdb::NmrOneD 291102 Specdb::NmrOneD 291103 Specdb::NmrOneD 291104 Specdb::NmrOneD 291105 Specdb::NmrOneD 291106 Specdb::NmrOneD 291107 Specdb::NmrOneD 291108 Specdb::NmrOneD 291109 Specdb::NmrOneD 291110 Specdb::NmrOneD 291111 Specdb::NmrOneD 291112 Specdb::NmrOneD 291113 Specdb::NmrOneD 291114 Specdb::MsMs 1278088 Specdb::MsMs 1278089 Specdb::MsMs 1278090 Specdb::MsMs 1392997 Specdb::MsMs 1392998 Specdb::MsMs 1392999 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 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 L-Serine + CDP-DG(16:0/16:1(9Z)) + L-Serine > Cytidine monophosphate + Hydrogen ion + PS(16:0/16:1(9Z)) + Cytidine monophosphate PW_R003180 Glycerol 3-phosphate + CDP-DG(16:0/16:1(9Z)) > Hydrogen ion + PGP(16:0/16:1(9Z)) + Cytidine monophosphate + Cytidine monophosphate PW_R003604 2 DG(16:0/16:1(9Z)/0:0) + Cytidine triphosphate + Hydrogen ion + 2 DG(16:0/16:1(9Z)/0:0) >2 CDP-DG(16:0/16:1(9Z)) + Pyrophosphate PW_R005688