2.0 2012-05-31 14:12:07 -0600 2015-09-17 15:41:26 -0600 ECMDB06996 M2MDB000736 CDP-DG(18:1(9Z)/18:0) CDP-DG(18:1(9Z)/18:0) 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(9Z)/18:0), in particular, consists of one 9Z-octadecenoyl chain to C-1 atom, and one octadecanoyl 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)/18:0) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. 1-(9Z-Octadecenoyl)-2-octadecanoyl-sn-glycero-3-CDP 1-(9Z-octadecenoyl)-2-octadecanoyl-sn-glycero-3-cytidine-5'-diphosphate 1-(9Z-Octadecenoyl)-2-octadecanoyl-sn-glycero-3-cytidine-5'-diphosphoric acid 1-Oleoyl-2-stearoyl-sn-glycero-3-cytidine-5'-diphosphate 1-Oleoyl-2-stearoyl-sn-glycero-3-cytidine-5'-diphosphoric acid CDP-DG(18:1/18:0) CDP-DG(18:1n9/18:0) CDP-DG(18:1w9/18:0) CDP-DG(36:1) CDP-Diacylglycerol(18:1/18:0) CDP-Diacylglycerol(18:1n9/18:0) CDP-Diacylglycerol(18:1w9/18:0) 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)-3-[(9Z)-octadec-9-enoyloxy]-2-(octadecanoyloxy)propoxy]phosphoryl}oxy)phosphinic acid [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([hydroxy((2R)-3-[(9Z)-octadec-9-enoyloxy]-2-(octadecanoyloxy)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)CCCCCCCCCCCCCCCCC 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/h17,19,35-36,40-41,45-47,54-55H,3-16,18,20-34,37-39H2,1-2H3,(H,57,58)(H,59,60)(H2,49,50,56)/b19-17-/t40-,41-,45+,46?,47-/m1/s1 MLSXVHUEBZQJSW-INSNHAQQSA-N Solid Inner membrane Membrane Outer membrane logp 6.91 ALOGPS logs -5.58 ALOGPS solubility 2.68e-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)-3-[(9Z)-octadec-9-enoyloxy]-2-(octadecanoyloxy)propoxy]phosphoryl}oxy)phosphinic acid ChemAxon average_mass 1008.163 ChemAxon mono_mass 1007.561242153 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)CCCCCCCCCCCCCCCCC 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/h17,19,35-36,40-41,45-47,54-55H,3-16,18,20-34,37-39H2,1-2H3,(H,57,58)(H,59,60)(H2,49,50,56)/b19-17-/t40-,41-,45+,46?,47-/m1/s1 ChemAxon inchikey MLSXVHUEBZQJSW-INSNHAQQSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 259.73 ChemAxon polarizability 111.87 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 (CL(18:1/18:1/18:1/18:1)) "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." PW001027 Metabolic phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::EiMs 2149 Specdb::NmrOneD 303391 Specdb::NmrOneD 303392 Specdb::NmrOneD 303393 Specdb::NmrOneD 303394 Specdb::NmrOneD 303395 Specdb::NmrOneD 303396 Specdb::NmrOneD 303397 Specdb::NmrOneD 303398 Specdb::NmrOneD 303399 Specdb::NmrOneD 303400 Specdb::NmrOneD 303401 Specdb::NmrOneD 303402 Specdb::NmrOneD 303403 Specdb::NmrOneD 303404 Specdb::NmrOneD 303405 Specdb::NmrOneD 303406 Specdb::NmrOneD 303407 Specdb::NmrOneD 303408 Specdb::NmrOneD 303409 Specdb::NmrOneD 303410 Specdb::MsMs 315712 Specdb::MsMs 315713 Specdb::MsMs 315714 Specdb::MsMs 361786 Specdb::MsMs 361787 Specdb::MsMs 361788 Specdb::MsMs 2334376 Specdb::MsMs 2334377 Specdb::MsMs 2334378 Specdb::MsMs 2627879 Specdb::MsMs 2627880 Specdb::MsMs 2627881 HMDB06996 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 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 DG(18:1(9Z)/18:1(9Z)/0:0) + Hydrogen ion + Cytidine triphosphate + DG(18:1(9Z)/18:1(9Z)/0:0) > Pyrophosphate + CDP-DG(18:1(9Z)/18:0) + CDP-DG(18:1(9Z)/18:0) PW_R003828 CDP-DG(18:1(9Z)/18:0) + L-Serine + CDP-DG(18:1(9Z)/18:0) + L-Serine > Hydrogen ion + Cytidine monophosphate + PS(18:1(9Z)/18:0) + Cytidine monophosphate PW_R003830 CDP-DG(18:1(9Z)/18:0) + Glycerol 3-phosphate + CDP-DG(18:1(9Z)/18:0) > Hydrogen ion + Cytidine monophosphate + PGP(18:1(9Z)/18:1(9Z)) + Cytidine monophosphate PW_R003829