2.0 2012-10-11 06:39:33 -0600 2015-12-09 12:12:42 -0700 ECMDB23327 M2MDB003717 CDP-DG(10:0/16:1(9Z)) CDP-DG(10:0/16:1(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(10:0/16:1(9Z)), in particular, consists of one decanoyl 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(10:0/16:1(9Z)) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. 1-decanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-CDP 1-decanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-cytidine-5'-diphosphate 1-Decanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-cytidine-5'-diphosphoric acid 1-decanoyl-2-palmitoleoyl-sn-glycero-3-cytidine-5'-diphosphate 1-Decanoyl-2-palmitoleoyl-sn-glycero-3-cytidine-5'-diphosphoric acid CDP-DG(10:0/16:1) CDP-DG(26:1) CDP-Diacylglycerol(10:0/16:1) CDP-Diacylglycerol(26:1) C38H67N3O15P2 867.908 867.404742465 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-3-(decanoyloxy)-2-[(9Z)-hexadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-3-(decanoyloxy)-2-[(9Z)-hexadec-9-enoyloxy]propoxy(hydroxy)phosphoryl]oxy)phosphinic acid [H][C@@](COC(=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)CCCCCCC\C=C/CCCCCC InChI=1S/C38H67N3O15P2/c1-3-5-7-9-11-12-13-14-15-16-18-20-22-24-34(43)54-30(27-51-33(42)23-21-19-17-10-8-6-4-2)28-52-57(47,48)56-58(49,50)53-29-31-35(44)36(45)37(55-31)41-26-25-32(39)40-38(41)46/h12-13,25-26,30-31,35-37,44-45H,3-11,14-24,27-29H2,1-2H3,(H,47,48)(H,49,50)(H2,39,40,46)/b13-12-/t30-,31-,35+,36?,37-/m1/s1 XLYUUYSQHZZNIM-SNQDRQLHSA-N Solid Membrane logp 4.45 ALOGPS logs -4.35 ALOGPS solubility 3.87e-02 g/l ALOGPS logp 6.53 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-(decanoyloxy)-2-[(9Z)-hexadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 867.908 ChemAxon mono_mass 867.404742465 ChemAxon smiles [H][C@@](COC(=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)CCCCCCC\C=C/CCCCCC ChemAxon formula C38H67N3O15P2 ChemAxon inchi InChI=1S/C38H67N3O15P2/c1-3-5-7-9-11-12-13-14-15-16-18-20-22-24-34(43)54-30(27-51-33(42)23-21-19-17-10-8-6-4-2)28-52-57(47,48)56-58(49,50)53-29-31-35(44)36(45)37(55-31)41-26-25-32(39)40-38(41)46/h12-13,25-26,30-31,35-37,44-45H,3-11,14-24,27-29H2,1-2H3,(H,47,48)(H,49,50)(H2,39,40,46)/b13-12-/t30-,31-,35+,36?,37-/m1/s1 ChemAxon inchikey XLYUUYSQHZZNIM-SNQDRQLHSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 213.72 ChemAxon polarizability 91.44 ChemAxon rotatable_bond_count 35 ChemAxon acceptor_count 12 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis CDP-DG(10:0/16:1(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 PS (16:1(9z)/18:1(11z))L-1-phosphatidylserine or a L-1-phosphatidy PE(16:1(9z)/18:1(11z)) (phosphatidylethanolamine) through a phosphatidylserine decarboxylase, on the other hand PGP(16:1(9z)/18:1(11z)) L-1-phosphatidylglycerol-phosphate gets transformed into a PG(16:1(9z)/18:1(11z)) 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. PW001752 Metabolic phospholipid biosynthesis CDP-DG(10:0/16:1(9Z)) II 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 PS (16:1(9z)/18:1(11z))L-1-phosphatidylserine or a L-1-phosphatidy PE(16:1(9z)/18:1(11z)) (phosphatidylethanolamine) through a phosphatidylserine decarboxylase, on the other hand PGP(16:1(9z)/18:1(11z)) L-1-phosphatidylglycerol-phosphate gets transformed into a PG(16:1(9z)/18:1(11z)) 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. PW001828 Metabolic phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::EiMs 3623 Specdb::NmrOneD 307951 Specdb::NmrOneD 307952 Specdb::NmrOneD 307953 Specdb::NmrOneD 307954 Specdb::NmrOneD 307955 Specdb::NmrOneD 307956 Specdb::NmrOneD 307957 Specdb::NmrOneD 307958 Specdb::NmrOneD 307959 Specdb::NmrOneD 307960 Specdb::NmrOneD 307961 Specdb::NmrOneD 307962 Specdb::NmrOneD 307963 Specdb::NmrOneD 307964 Specdb::NmrOneD 307965 Specdb::NmrOneD 307966 Specdb::NmrOneD 307967 Specdb::NmrOneD 307968 Specdb::NmrOneD 307969 Specdb::NmrOneD 307970 Specdb::MsMs 1255738 Specdb::MsMs 1255739 Specdb::MsMs 1255740 Specdb::MsMs 1370926 Specdb::MsMs 1370927 Specdb::MsMs 1370928 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 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(10:0/16:1(9Z)/0:0) + Hydrogen ion + Cytidine triphosphate > CDP-DG(10:0/16:1(9Z)) + Pyrophosphate PW_R004700 CDP-DG(10:0/16:1(9Z)) + L-Serine + L-Serine > PS(10:0(3-OH)/16:1(9Z)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R004846