Record Information |
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Version | 2.0 |
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Creation Date | 2012-10-11 06:39:42 -0600 |
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Update Date | 2015-12-09 12:14:47 -0700 |
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Secondary Accession Numbers | |
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Identification |
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Name: | CDP-DG(18:1(9Z)/14:0) |
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Description | CDP-DG(18:1(9Z)/14:0) 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)/14:0), in particular, consists of one 9Z-octadecenoyl chain to C-1 atom, and one tetradecanoyl 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)/14:0) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. |
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Structure | |
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Synonyms: | - 1-(9Z-octadecenoyl)-2-tetradecanoyl-sn-glycero-3-CDP
- 1-(9Z-octadecenoyl)-2-tetradecanoyl-sn-glycero-3-cytidine-5'-diphosphate
- 1-(9Z-Octadecenoyl)-2-tetradecanoyl-sn-glycero-3-cytidine-5'-diphosphoric acid
- 1-oleoyl-2-myristoyl-sn-glycero-3-cytidine-5'-diphosphate
- 1-Oleoyl-2-myristoyl-sn-glycero-3-cytidine-5'-diphosphoric acid
- CDP-DG(18:1/14:0)
- CDP-DG(32:1)
- CDP-Diacylglycerol(18:1/14:0)
- CDP-Diacylglycerol(32:1)
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Chemical Formula: | C44H79N3O15P2 |
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Weight: | Average: 952.07 Monoisotopic: 951.498642852 |
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InChI Key: | CZZBGGRLYQHCSC-RZVQUUPPSA-N |
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InChI: | InChI=1S/C44H79N3O15P2/c1-3-5-7-9-11-13-15-16-17-18-20-21-23-25-27-29-39(48)57-33-36(60-40(49)30-28-26-24-22-19-14-12-10-8-6-4-2)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/h16-17,31-32,36-37,41-43,50-51H,3-15,18-30,33-35H2,1-2H3,(H,53,54)(H,55,56)(H2,45,46,52)/b17-16-/t36-,37-,41+,42?,43-/m1/s1 |
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CAS number: | Not Available |
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IUPAC Name: | {[(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-(tetradecanoyloxy)propoxy]phosphoryl}oxy)phosphinic acid |
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Traditional IUPAC Name: | [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([hydroxy((2R)-3-[(9Z)-octadec-9-enoyloxy]-2-(tetradecanoyloxy)propoxy)phosphoryl]oxy)phosphinic acid |
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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)CCCCCCCCCCCCC |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as phosphatidylserines. These are glycerophosphoserines in which two fatty acids are bonded to the glycerol moiety through ester linkages. 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 positions. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Glycerophospholipids |
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Sub Class | Glycerophosphoserines |
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Direct Parent | Phosphatidylserines |
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Alternative Parents | |
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Substituents | - Diacyl-glycerol-3-phosphoserine
- Alpha-amino acid or derivatives
- Alpha-amino acid
- Tricarboxylic acid or derivatives
- Phosphoethanolamine
- Dialkyl phosphate
- Fatty acid ester
- Fatty acyl
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Amino acid
- Carboxylic acid ester
- Amino acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Carbonyl group
- Amine
- Organic anion
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State: | Solid |
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Charge: | -2 |
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Melting point: | Not Available |
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Experimental Properties: | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Membrane |
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Reactions: | |
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SMPDB Pathways: | phospholipid biosynthesis (CL(18:1(9Z)/14:0/19:0cycv8c/19:0cycv8c) 2) | PW001781 | |
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KEGG Pathways: | - Glycerophospholipid metabolism ec00564
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EcoCyc Pathways: | |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | |
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References |
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References: | - 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. Pubmed: 22080510
- 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. Pubmed: 21097882
- 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
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Synthesis Reference: | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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Links |
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External Links: | Resource | Link |
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CHEBI ID | Not Available | HMDB ID | Not Available | Pubchem Compound ID | Not Available | Kegg ID | Not Available | ChemSpider ID | Not Available | Wikipedia ID | Not Available | BioCyc ID | Not Available |
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