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 07:03:21 UTC |
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Update Date | 2022-11-30 19:26:28 UTC |
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HMDB ID | HMDB0116109 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | CDP-DG(a-17:0/i-18:0) |
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Description | CDP-DG(a-17:0/i-18:0) 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(a-17:0/i-18:0), in particular, consists of one chain of anteisoheptadecanoic acid at the C-1 position and one chain of isooctadecanoic 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)CCCCCCCCCCCCC(C)CC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCCCCCCC(C)C InChI=1S/C47H87N3O15P2/c1-5-38(4)29-25-21-17-13-10-11-14-18-22-26-30-42(51)60-34-39(63-43(52)31-27-23-19-15-9-7-6-8-12-16-20-24-28-37(2)3)35-61-66(56,57)65-67(58,59)62-36-40-44(53)45(54)46(64-40)50-33-32-41(48)49-47(50)55/h32-33,37-40,44-46,53-54H,5-31,34-36H2,1-4H3,(H,56,57)(H,58,59)(H2,48,49,55)/t38?,39-,40-,44+,45?,46-/m1/s1 |
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Synonyms | Value | Source |
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1-anteisoheptadecanoyl-2-isooctadecanoyl-sn-glycero-3-CDP | SMPDB, HMDB | 1-anteisoheptadecanoyl-2-isooctadecanoyl-sn-glycero-3-cytidine-5'-diphosphate | SMPDB, HMDB | CDP-DG(a-17:0/i-18:0) | SMPDB | CDP-DG(35:0) | SMPDB, HMDB | CDP-diacylglycerol(a-17:0/i-18:0) | SMPDB, HMDB | CDP-diacylglycerol(35:0) | SMPDB, HMDB | {[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({hydroxy[(2R)-2-[(16-methylheptadecanoyl)oxy]-3-[(14-methylhexadecanoyl)oxy]propoxy]phosphoryl}oxy)phosphinate | Generator, HMDB |
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Chemical Formula | C47H87N3O15P2 |
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Average Molecular Weight | 996.167 |
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Monoisotopic Molecular Weight | 995.561243109 |
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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)-2-[(16-methylheptadecanoyl)oxy]-3-[(14-methylhexadecanoyl)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)-2-[(16-methylheptadecanoyl)oxy]-3-[(14-methylhexadecanoyl)oxy]propoxy)phosphoryl]oxy)phosphinic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCCCCCCCC(C)CC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCCCCCCC(C)C |
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InChI Identifier | InChI=1S/C47H87N3O15P2/c1-5-38(4)29-25-21-17-13-10-11-14-18-22-26-30-42(51)60-34-39(63-43(52)31-27-23-19-15-9-7-6-8-12-16-20-24-28-37(2)3)35-61-66(56,57)65-67(58,59)62-36-40-44(53)45(54)46(64-40)50-33-32-41(48)49-47(50)55/h32-33,37-40,44-46,53-54H,5-31,34-36H2,1-4H3,(H,56,57)(H,58,59)(H2,48,49,55)/t38?,39-,40-,44+,45?,46-/m1/s1 |
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InChI Key | QTOSHVKRVOYUQG-SVSFWXGDSA-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(a-17:0/i-18:0) 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(a-17:0/i-18:0) 10V, Positive-QTOF | splash10-03di-0920000101-bd31359fdbccd2878faa | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-17:0/i-18:0) 20V, Positive-QTOF | splash10-03di-1920000000-34e225cf55783a3369ba | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-17:0/i-18:0) 40V, Positive-QTOF | splash10-03di-4931000100-f0125fe659937bfb90fa | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-17:0/i-18:0) 10V, Negative-QTOF | splash10-0n30-0690000303-5418dd28d5b6b7ead9f3 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-17:0/i-18:0) 20V, Negative-QTOF | splash10-0i00-4692200301-6718bfab7d391e388edc | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-17:0/i-18:0) 40V, Negative-QTOF | splash10-0bvi-5921000000-81829b85b806bb7b420c | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-17:0/i-18:0) 10V, Positive-QTOF | splash10-0002-4000010029-53b3a6c4a45f22a245b8 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-17:0/i-18:0) 20V, Positive-QTOF | splash10-0ab9-7100000096-12ea0b8d6ed59165772f | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-17:0/i-18:0) 40V, Positive-QTOF | splash10-00di-1033900000-ce621469f107f8523f89 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-17:0/i-18:0) 10V, Negative-QTOF | splash10-0006-0000000109-d541f04e3c0e18cdce0d | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-17:0/i-18:0) 20V, Negative-QTOF | splash10-00ou-9050601201-5afb259a638ef8eeddd7 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-17:0/i-18:0) 40V, Negative-QTOF | splash10-069u-8359503302-1d5a1da5eca0bbc4acfc | 2021-09-24 | Wishart Lab | View Spectrum |
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