Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-09-09 07:51:23 UTC |
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Update Date | 2022-11-30 19:26:34 UTC |
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HMDB ID | HMDB0116326 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | CDP-DG(i-21:0/i-20:0) |
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Description | CDP-DG(i-21:0/i-20:0) is a cytidine diphosphate diacylglycerol or CDP-diacylglycerol (CDP-DG). CDP-diacylglycerol is an important branchpoint intermediate in eukaryotic phospholipid biosynthesis and could be a key regulatory molecule in phospholipid metabolism. It is a glycerophospholipid in which a cytidine diphosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, CDP-diacylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. CDP-DG(i-21:0/i-20:0), in particular, consists of one chain of isoheneicosanoic acid at the C-1 position and one chain of isoeicosanoic acid at the C-2 position. Cytidine diphosphate diacylglycerols are rarely noticed in analyses of lipid compositions of tissues, as they are present is such small amounts (perhaps only 0.05% or so of the total phospholipids). |
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Structure | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCCC(C)C)(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(C)C InChI=1S/C53H99N3O15P2/c1-43(2)34-30-26-22-18-14-10-6-5-7-12-16-20-24-28-32-36-48(57)66-40-45(69-49(58)37-33-29-25-21-17-13-9-8-11-15-19-23-27-31-35-44(3)4)41-67-72(62,63)71-73(64,65)68-42-46-50(59)51(60)52(70-46)56-39-38-47(54)55-53(56)61/h38-39,43-46,50-52,59-60H,5-37,40-42H2,1-4H3,(H,62,63)(H,64,65)(H2,54,55,61)/t45-,46-,50+,51?,52-/m1/s1 |
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Synonyms | Value | Source |
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1-isoheneicosanoyl-2-isoeicosanoyl-sn-glycero-3-CDP | SMPDB, HMDB | 1-isoheneicosanoyl-2-isoeicosanoyl-sn-glycero-3-cytidine-5'-diphosphate | SMPDB, HMDB | CDP-DG(i-21:0/i-20:0) | SMPDB | CDP-DG(41:0) | SMPDB, HMDB | CDP-diacylglycerol(i-21:0/i-20:0) | SMPDB, HMDB | CDP-diacylglycerol(41:0) | SMPDB, HMDB | {[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({hydroxy[(2R)-3-[(19-methylicosanoyl)oxy]-2-[(18-methylnonadecanoyl)oxy]propoxy]phosphoryl}oxy)phosphinate | Generator, HMDB |
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Chemical Formula | C53H99N3O15P2 |
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Average Molecular Weight | 1080.329 |
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Monoisotopic Molecular Weight | 1079.655143496 |
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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-[(19-methylicosanoyl)oxy]-2-[(18-methylnonadecanoyl)oxy]propoxy]phosphoryl}oxy)phosphinic acid |
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Traditional Name | [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([hydroxy((2R)-3-[(19-methylicosanoyl)oxy]-2-[(18-methylnonadecanoyl)oxy]propoxy)phosphoryl]oxy)phosphinic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCCC(C)C)(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(C)C |
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InChI Identifier | InChI=1S/C53H99N3O15P2/c1-43(2)34-30-26-22-18-14-10-6-5-7-12-16-20-24-28-32-36-48(57)66-40-45(69-49(58)37-33-29-25-21-17-13-9-8-11-15-19-23-27-31-35-44(3)4)41-67-72(62,63)71-73(64,65)68-42-46-50(59)51(60)52(70-46)56-39-38-47(54)55-53(56)61/h38-39,43-46,50-52,59-60H,5-37,40-42H2,1-4H3,(H,62,63)(H,64,65)(H2,54,55,61)/t45-,46-,50+,51?,52-/m1/s1 |
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InChI Key | XEPPHQUVFDJGFI-FAWUFZMXSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as cdp-diacylglycerols. These are glycerolipids containing a diacylglycerol, with a cytidine diphosphate attached to the oxygen O1 or O2 of the glycerol part. |
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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 | CDP-glycerols |
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Direct Parent | CDP-diacylglycerols |
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Alternative Parents | |
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Substituents | - Cdp-diacylglycerol
- Pyrimidine ribonucleoside diphosphate
- Diacyl-glycerol-3-pyrophosphate
- Pentose phosphate
- Pentose-5-phosphate
- Glycosyl compound
- N-glycosyl compound
- Monosaccharide phosphate
- Organic pyrophosphate
- Fatty acid ester
- Monoalkyl phosphate
- Hydroxypyrimidine
- Dicarboxylic acid or derivatives
- Fatty acyl
- Alkyl phosphate
- Hydropyrimidine
- Pyrimidine
- Phosphoric acid ester
- Monosaccharide
- Organic phosphoric acid derivative
- Heteroaromatic compound
- Tetrahydrofuran
- Carboxylic acid ester
- 1,2-diol
- Secondary alcohol
- Oxacycle
- Organoheterocyclic compound
- Azacycle
- Carboxylic acid derivative
- Organopnictogen compound
- Organic oxide
- Alcohol
- Organic nitrogen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | Not Available |
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Process | |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesNot Available |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-21:0/i-20:0) 10V, Positive-QTOF | splash10-03di-1911000100-7983939026c374e83e45 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-21:0/i-20:0) 20V, Positive-QTOF | splash10-03di-2910000100-703f0bef3f2664bf09f8 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-21:0/i-20:0) 40V, Positive-QTOF | splash10-03di-3921000000-011c9a275f120bb47770 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-21:0/i-20:0) 10V, Negative-QTOF | splash10-0bvi-3619000200-cc5ad7ebb50dcbb8a263 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-21:0/i-20:0) 20V, Negative-QTOF | splash10-06vi-5519110020-a3d5858785a100293780 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-21:0/i-20:0) 40V, Negative-QTOF | splash10-0bvi-5903000000-a566729a7d3d195baae9 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-21:0/i-20:0) 10V, Negative-QTOF | splash10-004i-9001000100-50447e5adc724c4d7e6f | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-21:0/i-20:0) 20V, Negative-QTOF | splash10-004l-9013400300-b616933928f9edd9934f | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-21:0/i-20:0) 40V, Negative-QTOF | splash10-0006-9237130300-41540ef9eedb3e54894f | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-21:0/i-20:0) 10V, Positive-QTOF | splash10-001i-9000001003-67dbbf3b6f1ea9ec8943 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-21:0/i-20:0) 20V, Positive-QTOF | splash10-0aos-7100000019-009902ecb9917e1ded22 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-21:0/i-20:0) 40V, Positive-QTOF | splash10-0uk9-0014900000-a18371630d7f883443a0 | 2021-09-24 | Wishart Lab | View Spectrum |
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