2.0 2015-09-08 19:54:29 -0600 2015-12-09 12:13:04 -0700 ECMDB24658 M2MDB006775 CDP-DG(12:0/17:0cycw7c) CDP-DG(12:0/17:0cycw7c) 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(12:0/17:0cycw7c), in particular, consists of one dodecanoyl 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(12:0/17:0cycw7c) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. C41H73N3O15P2 909.989 909.451692659 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-3-(dodecanoyloxy)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)phosphinic acid [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-3-(dodecanoyloxy)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy(hydroxy)phosphoryl]oxy)phosphinic acid [H][C@@](COC(=O)CCCCCCCCCCC)(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/C41H73N3O15P2/c1-3-5-7-9-10-11-12-15-19-23-36(45)54-28-33(57-37(46)24-20-16-13-14-18-22-32-27-31(32)21-17-8-6-4-2)29-55-60(50,51)59-61(52,53)56-30-34-38(47)39(48)40(58-34)44-26-25-35(42)43-41(44)49/h25-26,31-34,38-40,47-48H,3-24,27-30H2,1-2H3,(H,50,51)(H,52,53)(H2,42,43,49)/t31?,32?,33-,34-,38+,39?,40-/m1/s1 LITZUTFUCFSGMK-NXJNZTMPSA-N logp 4.91 ALOGPS logs -4.71 ALOGPS solubility 1.79e-02 g/l ALOGPS logp 7.44 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)-3-(dodecanoyloxy)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 909.989 ChemAxon mono_mass 909.451692659 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCCCCC)(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 C41H73N3O15P2 ChemAxon inchi InChI=1S/C41H73N3O15P2/c1-3-5-7-9-10-11-12-15-19-23-36(45)54-28-33(57-37(46)24-20-16-13-14-18-22-32-27-31(32)21-17-8-6-4-2)29-55-60(50,51)59-61(52,53)56-30-34-38(47)39(48)40(58-34)44-26-25-35(42)43-41(44)49/h25-26,31-34,38-40,47-48H,3-24,27-30H2,1-2H3,(H,50,51)(H,52,53)(H2,42,43,49)/t31?,32?,33-,34-,38+,39?,40-/m1/s1 ChemAxon inchikey LITZUTFUCFSGMK-NXJNZTMPSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 224.5 ChemAxon polarizability 98.09 ChemAxon rotatable_bond_count 37 ChemAxon acceptor_count 12 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(12:0/17:0cycw7c/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. PW001932 Metabolic Specdb::NmrOneD 286535 Specdb::NmrOneD 286536 Specdb::NmrOneD 286537 Specdb::NmrOneD 286538 Specdb::NmrOneD 286539 Specdb::NmrOneD 286540 Specdb::NmrOneD 286541 Specdb::NmrOneD 286542 Specdb::NmrOneD 286543 Specdb::NmrOneD 286544 Specdb::NmrOneD 286545 Specdb::NmrOneD 286546 Specdb::NmrOneD 286547 Specdb::NmrOneD 286548 Specdb::NmrOneD 286549 Specdb::NmrOneD 286550 Specdb::NmrOneD 286551 Specdb::NmrOneD 286552 Specdb::NmrOneD 286553 Specdb::NmrOneD 286554 Specdb::MsMs 1314877 Specdb::MsMs 1314878 Specdb::MsMs 1314879 Specdb::MsMs 1429354 Specdb::MsMs 1429355 Specdb::MsMs 1429356 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 CDP-diacylglycerol--serine O-phosphatidyltransferase P23830 PSS_ECOLI pssA http://ecmdb.ca/proteins/P23830.xml DG(12:0/17:0cycw7c/0:0) + Cytidine triphosphate + Hydrogen ion > CDP-DG(12:0/17:0cycw7c) + Pyrophosphate PW_R005417 CDP-DG(12:0/17:0cycw7c) + L-Serine + L-Serine > PS(12:0/17:0cycw7c) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005418