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 07:48:49 UTC |
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Update Date | 2022-11-30 19:26:33 UTC |
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HMDB ID | HMDB0116308 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | CDP-DG(i-20:0/i-20:0) |
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Description | CDP-DG(i-20:0/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-20:0/i-20:0), in particular, consists of one chain of isoeicosanoic 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)CCCCCCCCCCCCCCCCC(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/C52H97N3O15P2/c1-42(2)33-29-25-21-17-13-9-5-7-11-15-19-23-27-31-35-47(56)65-39-44(68-48(57)36-32-28-24-20-16-12-8-6-10-14-18-22-26-30-34-43(3)4)40-66-71(61,62)70-72(63,64)67-41-45-49(58)50(59)51(69-45)55-38-37-46(53)54-52(55)60/h37-38,42-45,49-51,58-59H,5-36,39-41H2,1-4H3,(H,61,62)(H,63,64)(H2,53,54,60)/t44-,45-,49+,50?,51-/m1/s1 |
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Synonyms | Value | Source |
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1-isoeicosanoyl-2-isoeicosanoyl-sn-glycero-3-CDP | SMPDB, HMDB | 1-isoeicosanoyl-2-isoeicosanoyl-sn-glycero-3-cytidine-5'-diphosphate | SMPDB, HMDB | CDP-DG(i-20:0/i-20:0) | SMPDB | CDP-DG(40:0) | SMPDB, HMDB | CDP-diacylglycerol(i-20:0/i-20:0) | SMPDB, HMDB | CDP-diacylglycerol(40:0) | SMPDB, HMDB | ({[(2R)-2,3-bis[(18-methylnonadecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)({[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinate | Generator, HMDB |
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Chemical Formula | C52H97N3O15P2 |
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Average Molecular Weight | 1066.302 |
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Monoisotopic Molecular Weight | 1065.639493431 |
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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}({[(2R)-2,3-bis[(18-methylnonadecanoyl)oxy]propoxy](hydroxy)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([(2R)-2,3-bis[(18-methylnonadecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy)phosphinic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC(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/C52H97N3O15P2/c1-42(2)33-29-25-21-17-13-9-5-7-11-15-19-23-27-31-35-47(56)65-39-44(68-48(57)36-32-28-24-20-16-12-8-6-10-14-18-22-26-30-34-43(3)4)40-66-71(61,62)70-72(63,64)67-41-45-49(58)50(59)51(69-45)55-38-37-46(53)54-52(55)60/h37-38,42-45,49-51,58-59H,5-36,39-41H2,1-4H3,(H,61,62)(H,63,64)(H2,53,54,60)/t44-,45-,49+,50?,51-/m1/s1 |
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InChI Key | SAFCGMHMWFGFKG-QFBGIDFLSA-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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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - CDP-DG(i-20:0/i-20:0) GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-13 | Wishart Lab | View Spectrum |
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-20:0/i-20:0) 10V, Positive-QTOF | splash10-03di-2910000100-6ed1c6bb088557a71bf7 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-20:0/i-20:0) 20V, Positive-QTOF | splash10-03di-2910000100-fdc5823605b3f1c4b0c0 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-20:0/i-20:0) 40V, Positive-QTOF | splash10-03di-3911001010-ac85567b1cc1e88f57a9 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-20:0/i-20:0) 10V, Negative-QTOF | splash10-03di-5945000310-68eb487c17b36665b8e6 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-20:0/i-20:0) 20V, Negative-QTOF | splash10-03di-8849120130-e507ec081fa65b77ec30 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-20:0/i-20:0) 40V, Negative-QTOF | splash10-08i0-4902000000-c5e369a224ec98ac513f | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-20:0/i-20:0) 10V, Negative-QTOF | splash10-03di-9001000100-91e16d33888d18f8c6ce | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-20:0/i-20:0) 20V, Negative-QTOF | splash10-01r6-9022400300-55d6604563efc4acd28f | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-20:0/i-20:0) 40V, Negative-QTOF | splash10-0ziu-9438140600-b6e4de988f61db016443 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-20:0/i-20:0) 10V, Positive-QTOF | splash10-014i-9000001003-5bf0a3020d9d58d820de | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-20:0/i-20:0) 20V, Positive-QTOF | splash10-0aos-7100000019-5b570fa3973803a5f887 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-20:0/i-20:0) 40V, Positive-QTOF | splash10-0udj-1014900000-58688092ac034d84bd4c | 2021-09-24 | Wishart Lab | View Spectrum |
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