2.0 2015-09-08 19:53:38 -0600 2015-12-09 12:12:54 -0700 ECMDB24650 M2MDB006767 CDP-DG(12:0(3-OH)/17:0cycw7c) CDP-DG(12:0(3-OH)/17:0cycw7c) 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(12:0(3-OH)/17:0cycw7c), in particular, consists of one 3-hydroxydodecanoyl chain to C-1 atom, and one heptadec-9-10-cyclo-anoyl 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(12:0(3-OH)/17:0cycw7c) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. C41H73N3O16P2 925.988 925.446607279 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-[(3-hydroxydodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-[(3-hydroxydodecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy)phosphinic acid [H][C@@](COC(=O)CC(O)CCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCC1CC1CCCCCC InChI=1S/C41H73N3O16P2/c1-3-5-7-9-10-13-17-21-32(45)26-37(47)55-27-33(58-36(46)22-18-14-11-12-16-20-31-25-30(31)19-15-8-6-4-2)28-56-61(51,52)60-62(53,54)57-29-34-38(48)39(49)40(59-34)44-24-23-35(42)43-41(44)50/h23-24,30-34,38-40,45,48-49H,3-22,25-29H2,1-2H3,(H,51,52)(H,53,54)(H2,42,43,50)/t30?,31?,32?,33-,34-,38+,39?,40-/m1/s1 YMTLUJUNCLHCBP-VGXUDMJPSA-N logp 4.18 ALOGPS logs -4.40 ALOGPS solubility 3.69e-02 g/l ALOGPS logp 6.21 ChemAxon pka_strongest_acidic -0.032 ChemAxon pka_strongest_basic 3.27 ChemAxon iupac {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-[(3-hydroxydodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 925.988 ChemAxon mono_mass 925.446607279 ChemAxon smiles [H][C@@](COC(=O)CC(O)CCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCC1CC1CCCCCC ChemAxon formula C41H73N3O16P2 ChemAxon inchi InChI=1S/C41H73N3O16P2/c1-3-5-7-9-10-13-17-21-32(45)26-37(47)55-27-33(58-36(46)22-18-14-11-12-16-20-31-25-30(31)19-15-8-6-4-2)28-56-61(51,52)60-62(53,54)57-29-34-38(48)39(49)40(59-34)44-24-23-35(42)43-41(44)50/h23-24,30-34,38-40,45,48-49H,3-22,25-29H2,1-2H3,(H,51,52)(H,53,54)(H2,42,43,50)/t30?,31?,32?,33-,34-,38+,39?,40-/m1/s1 ChemAxon inchikey YMTLUJUNCLHCBP-VGXUDMJPSA-N ChemAxon polar_surface_area 283.5 ChemAxon refractivity 226.02 ChemAxon polarizability 99.07 ChemAxon rotatable_bond_count 37 ChemAxon acceptor_count 13 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(12:0(3-OH)/17:0cycw7c/12:0(3-OH)/17:0cycw7c)) 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. PW001922 Metabolic phospholipid biosynthesis (CL(12:0(3-OH)/17:0cycw7c/12:0/12:0)) 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. PW001923 Metabolic Specdb::NmrOneD 265268 Specdb::NmrOneD 265269 Specdb::NmrOneD 265270 Specdb::NmrOneD 265271 Specdb::NmrOneD 265272 Specdb::NmrOneD 265273 Specdb::NmrOneD 265274 Specdb::NmrOneD 265275 Specdb::NmrOneD 265276 Specdb::NmrOneD 265277 Specdb::NmrOneD 265278 Specdb::NmrOneD 265279 Specdb::NmrOneD 265280 Specdb::NmrOneD 265281 Specdb::NmrOneD 265282 Specdb::NmrOneD 265283 Specdb::NmrOneD 265284 Specdb::NmrOneD 265285 Specdb::NmrOneD 265286 Specdb::NmrOneD 265287 Specdb::MsMs 1287976 Specdb::MsMs 1287977 Specdb::MsMs 1287978 Specdb::MsMs 1402750 Specdb::MsMs 1402751 Specdb::MsMs 1402752 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 CDP-diacylglycerol--serine O-phosphatidyltransferase P23830 PSS_ECOLI pssA http://ecmdb.ca/proteins/P23830.xml 2 DG(12:0(3-OH)/17:0cycw7c/0:0) + Cytidine triphosphate + Hydrogen ion >2 CDP-DG(12:0(3-OH)/17:0cycw7c) + Pyrophosphate PW_R005378 DG(12:0(3-OH)/17:0cycw7c/0:0) + Cytidine triphosphate + Hydrogen ion > CDP-DG(12:0(3-OH)/17:0cycw7c) + Pyrophosphate PW_R005383 CDP-DG(12:0(3-OH)/17:0cycw7c) + L-Serine + L-Serine > PS(12:0(3-OH)/17:0cycw7c) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005384 2 CDP-DG(12:0(3-OH)/17:0cycw7c) + Glycerol 3-phosphate >2 PGP(12:0(3-OH)/17:0cycw7c) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005380