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 06:50:03 UTC |
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Update Date | 2022-11-30 19:26:27 UTC |
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HMDB ID | HMDB0116050 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | CDP-DG(18:2(9Z,11Z)/a-21:0) |
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Description | CDP-DG(18:2(9Z,11Z)/a-21:0) 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(18:2(9Z,11Z)/a-21:0), in particular, consists of one chain of (9Z,11Z)-octadecadienoic acid at the C-1 position and one chain of anteisoheneicosanoic 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)CCCCCCC\C=C/C=C\CCCCCC)(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)CC InChI=1S/C51H91N3O15P2/c1-4-6-7-8-9-10-11-12-13-17-20-23-26-29-32-35-46(55)64-39-43(67-47(56)36-33-30-27-24-21-18-15-14-16-19-22-25-28-31-34-42(3)5-2)40-65-70(60,61)69-71(62,63)66-41-44-48(57)49(58)50(68-44)54-38-37-45(52)53-51(54)59/h10-13,37-38,42-44,48-50,57-58H,4-9,14-36,39-41H2,1-3H3,(H,60,61)(H,62,63)(H2,52,53,59)/b11-10-,13-12-/t42?,43-,44-,48+,49?,50-/m1/s1 |
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Synonyms | Value | Source |
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1-(9Z,11Z)-octadecadienoyl-2-anteisoheneicosanoyl-sn-glycero-3-CDP | SMPDB, HMDB | 1-(9Z,11Z)-octadecadienoyl-2-anteisoheneicosanoyl-sn-glycero-3-cytidine-5'-diphosphate | SMPDB, HMDB | CDP-DG(18:2/a-21:0) | SMPDB, HMDB | CDP-DG(18:2n7/a-21:0) | SMPDB, HMDB | CDP-DG(18:2w7/a-21:0) | SMPDB, HMDB | CDP-DG(39:2) | SMPDB, HMDB | CDP-diacylglycerol(18:2(9Z,11Z)/a-21:0) | SMPDB, HMDB | CDP-diacylglycerol(18:2/a-21:0) | SMPDB, HMDB | CDP-diacylglycerol(18:2n7/a-21:0) | SMPDB, HMDB | CDP-diacylglycerol(18:2w7/a-21:0) | SMPDB, HMDB | CDP-diacylglycerol(39:2) | SMPDB, HMDB | CDP-DG(18:2(9Z,11Z)/a-21:0) | SMPDB | {[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({hydroxy[(2R)-2-[(18-methylicosanoyl)oxy]-3-[(9Z,11Z)-octadeca-9,11-dienoyloxy]propoxy]phosphoryl}oxy)phosphinate | Generator, HMDB |
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Chemical Formula | C51H91N3O15P2 |
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Average Molecular Weight | 1048.243 |
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Monoisotopic Molecular Weight | 1047.592543238 |
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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-[(18-methylicosanoyl)oxy]-3-[(9Z,11Z)-octadeca-9,11-dienoyloxy]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-[(18-methylicosanoyl)oxy]-3-[(9Z,11Z)-octadeca-9,11-dienoyloxy]propoxy)phosphoryl]oxy)phosphinic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCC\C=C/C=C\CCCCCC)(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)CC |
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InChI Identifier | InChI=1S/C51H91N3O15P2/c1-4-6-7-8-9-10-11-12-13-17-20-23-26-29-32-35-46(55)64-39-43(67-47(56)36-33-30-27-24-21-18-15-14-16-19-22-25-28-31-34-42(3)5-2)40-65-70(60,61)69-71(62,63)66-41-44-48(57)49(58)50(68-44)54-38-37-45(52)53-51(54)59/h10-13,37-38,42-44,48-50,57-58H,4-9,14-36,39-41H2,1-3H3,(H,60,61)(H,62,63)(H2,52,53,59)/b11-10-,13-12-/t42?,43-,44-,48+,49?,50-/m1/s1 |
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InChI Key | NBDKMEJRAARVCN-RGFPJOAESA-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 | Naturally occurring processBiological processBiochemical pathwayDisease pathway- Cardiolipin Biosynthesis CL(a-13:0/18:2(9Z,11Z)/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0043326)
- Cardiolipin Biosynthesis CL(a-13:0/a-13:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0043648)
- Cardiolipin Biosynthesis CL(a-13:0/a-15:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0043971)
- Cardiolipin Biosynthesis CL(a-13:0/a-17:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0044293)
- Cardiolipin Biosynthesis CL(a-13:0/a-21:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0044615)
- Cardiolipin Biosynthesis CL(a-13:0/a-25:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0044938)
- Cardiolipin Biosynthesis CL(a-13:0/i-12:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0045262)
- Cardiolipin Biosynthesis CL(a-13:0/i-13:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0045584)
- Cardiolipin Biosynthesis CL(a-13:0/i-15:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0046226)
- Cardiolipin Biosynthesis CL(a-13:0/i-16:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0046549)
- Cardiolipin Biosynthesis CL(a-13:0/i-17:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0046872)
- Cardiolipin Biosynthesis CL(a-13:0/i-18:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0047195)
- Cardiolipin Biosynthesis CL(a-13:0/i-19:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0047517)
- Cardiolipin Biosynthesis CL(a-13:0/i-20:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0047840)
- Cardiolipin Biosynthesis CL(a-13:0/i-21:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0048159)
- Cardiolipin Biosynthesis CL(a-13:0/i-22:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0048482)
- Cardiolipin Biosynthesis CL(a-13:0/i-24:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0048804)
- Cardiolipin Biosynthesis CL(i-12:0/18:2(9Z,11Z)/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0049127)
- Cardiolipin Biosynthesis CL(i-12:0/a-13:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0049450)
- Cardiolipin Biosynthesis CL(i-12:0/a-15:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0049771)
- Cardiolipin Biosynthesis CL(i-12:0/a-17:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0050095)
- Cardiolipin Biosynthesis CL(i-12:0/a-21:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0050418)
- Cardiolipin Biosynthesis CL(i-12:0/a-25:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0050741)
- Cardiolipin Biosynthesis CL(i-12:0/i-12:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0051066)
- Cardiolipin Biosynthesis CL(i-12:0/i-13:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0051390)
- Cardiolipin Biosynthesis CL(i-12:0/i-14:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0051714)
- Cardiolipin Biosynthesis CL(i-12:0/i-15:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0052036)
- Cardiolipin Biosynthesis CL(i-12:0/i-16:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0052359)
- Cardiolipin Biosynthesis CL(i-12:0/i-17:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0052682)
- Cardiolipin Biosynthesis CL(i-12:0/i-18:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0053005)
- Cardiolipin Biosynthesis CL(i-12:0/i-19:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0053328)
- Cardiolipin Biosynthesis CL(i-12:0/i-20:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0053651)
- Cardiolipin Biosynthesis CL(i-12:0/i-21:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0053975)
- Cardiolipin Biosynthesis CL(i-12:0/i-22:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0054298)
- Cardiolipin Biosynthesis CL(i-12:0/i-24:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0054620)
- Cardiolipin Biosynthesis CL(i-13:0/18:2(9Z,11Z)/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0054942)
- Cardiolipin Biosynthesis CL(i-13:0/a-13:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0055266)
- Cardiolipin Biosynthesis CL(i-13:0/a-15:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0055590)
- Cardiolipin Biosynthesis CL(i-13:0/a-17:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0055912)
- Cardiolipin Biosynthesis CL(i-13:0/a-21:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0056238)
- Cardiolipin Biosynthesis CL(i-13:0/a-25:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0056564)
- Cardiolipin Biosynthesis CL(i-13:0/i-12:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0056889)
- Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0057211)
- Cardiolipin Biosynthesis CL(i-13:0/i-14:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0057534)
- Cardiolipin Biosynthesis CL(i-13:0/i-15:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0057866)
- Cardiolipin Biosynthesis CL(i-13:0/i-16:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0058191)
- Cardiolipin Biosynthesis CL(i-13:0/i-17:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0058512)
- Cardiolipin Biosynthesis CL(i-13:0/i-18:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0058841)
- Cardiolipin Biosynthesis CL(i-13:0/i-19:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0059182)
- Cardiolipin Biosynthesis CL(i-13:0/i-20:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0059506)
- Cardiolipin Biosynthesis CL(i-13:0/i-21:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0059841)
- Cardiolipin Biosynthesis CL(i-13:0/i-22:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0060176)
- Cardiolipin Biosynthesis CL(i-13:0/i-24:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0060506)
- Cardiolipin Biosynthesis CL(i-14:0/a-13:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0060834)
- Cardiolipin Biosynthesis CL(i-14:0/a-15:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0061158)
- Cardiolipin Biosynthesis CL(i-14:0/i-12:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0061651)
- Cardiolipin Biosynthesis CL(i-14:0/i-13:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0061973)
- Cardiolipin Biosynthesis CL(i-14:0/i-14:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0062296)
- Cardiolipin Biosynthesis CL(i-14:0/i-15:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0062619)
- Cardiolipin Biosynthesis CL(i-14:0/i-16:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0062959)
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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(18:2(9Z,11Z)/a-21:0) 10V, Negative-QTOF | splash10-08i0-4893000300-3029464c4f26373f5384 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/a-21:0) 20V, Negative-QTOF | splash10-03fr-7793210020-c2a186200efba91903b0 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/a-21:0) 40V, Negative-QTOF | splash10-0bvi-5911000000-a2f12c29b1ba1a5b02b7 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/a-21:0) 10V, Negative-QTOF | splash10-0002-9000000100-be8342e16107f48ad222 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/a-21:0) 20V, Negative-QTOF | splash10-004l-9023600310-28ff319d1d77e1e2c1b3 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/a-21:0) 40V, Negative-QTOF | splash10-0a4i-5309100200-ee727f073903168730e5 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/a-21:0) 10V, Positive-QTOF | splash10-03di-1911000100-ea18033f840cfa2ad171 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/a-21:0) 20V, Positive-QTOF | splash10-03di-2910000100-da523be983603d3cb6e4 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/a-21:0) 40V, Positive-QTOF | splash10-03di-3922000000-8fe9eaa07ee0253b2f25 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/a-21:0) 10V, Positive-QTOF | splash10-0002-9001000005-363e183847cf2cb9da1a | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/a-21:0) 20V, Positive-QTOF | splash10-0ab9-6000000009-ef65aab97da04037d706 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/a-21:0) 40V, Positive-QTOF | splash10-014i-0124900000-d1dff8740f189ce13ad8 | 2021-09-21 | Wishart Lab | View Spectrum |
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