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 06:52:15 UTC |
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Update Date | 2022-11-30 19:26:27 UTC |
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HMDB ID | HMDB0116062 |
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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)/i-22:0) |
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Description | CDP-DG(18:2(9Z,11Z)/i-22:0) 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)/i-22:0), in particular, consists of one chain of (9Z,11Z)-octadecadienoic acid at the C-1 position and one chain of isodocosanoic 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)CCCCCCCCCCCCCCCCCCC(C)C InChI=1S/C52H93N3O15P2/c1-4-5-6-7-8-9-10-11-14-18-21-24-27-30-33-36-47(56)65-40-44(68-48(57)37-34-31-28-25-22-19-16-13-12-15-17-20-23-26-29-32-35-43(2)3)41-66-71(61,62)70-72(63,64)67-42-45-49(58)50(59)51(69-45)55-39-38-46(53)54-52(55)60/h9-11,14,38-39,43-45,49-51,58-59H,4-8,12-13,15-37,40-42H2,1-3H3,(H,61,62)(H,63,64)(H2,53,54,60)/b10-9-,14-11-/t44-,45-,49+,50?,51-/m1/s1 |
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Synonyms | Value | Source |
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1-(9Z,11Z)-octadecadienoyl-2-isodocosanoyl-sn-glycero-3-CDP | SMPDB, HMDB | 1-(9Z,11Z)-octadecadienoyl-2-isodocosanoyl-sn-glycero-3-cytidine-5'-diphosphate | SMPDB, HMDB | CDP-DG(18:2/i-22:0) | SMPDB, HMDB | CDP-DG(18:2n7/i-22:0) | SMPDB, HMDB | CDP-DG(18:2w7/i-22:0) | SMPDB, HMDB | CDP-DG(40:2) | SMPDB, HMDB | CDP-diacylglycerol(18:2(9Z,11Z)/i-22:0) | SMPDB, HMDB | CDP-diacylglycerol(18:2/i-22:0) | SMPDB, HMDB | CDP-diacylglycerol(18:2n7/i-22:0) | SMPDB, HMDB | CDP-diacylglycerol(18:2w7/i-22:0) | SMPDB, HMDB | CDP-diacylglycerol(40:2) | SMPDB, HMDB | CDP-DG(18:2(9Z,11Z)/i-22:0) | SMPDB | {[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({hydroxy[(2R)-2-[(20-methylhenicosanoyl)oxy]-3-[(9Z,11Z)-octadeca-9,11-dienoyloxy]propoxy]phosphoryl}oxy)phosphinate | Generator, HMDB |
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Chemical Formula | C52H93N3O15P2 |
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Average Molecular Weight | 1062.27 |
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Monoisotopic Molecular Weight | 1061.608193303 |
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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-[(20-methylhenicosanoyl)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-[(20-methylhenicosanoyl)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)CCCCCCCCCCCCCCCCCCC(C)C |
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InChI Identifier | InChI=1S/C52H93N3O15P2/c1-4-5-6-7-8-9-10-11-14-18-21-24-27-30-33-36-47(56)65-40-44(68-48(57)37-34-31-28-25-22-19-16-13-12-15-17-20-23-26-29-32-35-43(2)3)41-66-71(61,62)70-72(63,64)67-42-45-49(58)50(59)51(69-45)55-39-38-46(53)54-52(55)60/h9-11,14,38-39,43-45,49-51,58-59H,4-8,12-13,15-37,40-42H2,1-3H3,(H,61,62)(H,63,64)(H2,53,54,60)/b10-9-,14-11-/t44-,45-,49+,50?,51-/m1/s1 |
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InChI Key | CVRBALUKJXIKCJ-APYFJBOSSA-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)/i-22:0) (PathBank: SMP0043338)
- Cardiolipin Biosynthesis CL(a-13:0/a-13:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0043660)
- Cardiolipin Biosynthesis CL(a-13:0/a-15:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0043983)
- Cardiolipin Biosynthesis CL(a-13:0/a-17:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0044305)
- Cardiolipin Biosynthesis CL(a-13:0/a-21:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0044627)
- Cardiolipin Biosynthesis CL(a-13:0/a-25:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0044950)
- Cardiolipin Biosynthesis CL(a-13:0/i-12:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0045274)
- Cardiolipin Biosynthesis CL(a-13:0/i-13:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0045595)
- Cardiolipin Biosynthesis CL(a-13:0/i-14:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0045914)
- Cardiolipin Biosynthesis CL(a-13:0/i-15:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0046238)
- Cardiolipin Biosynthesis CL(a-13:0/i-16:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0046561)
- Cardiolipin Biosynthesis CL(a-13:0/i-17:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0046884)
- Cardiolipin Biosynthesis CL(a-13:0/i-18:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0047207)
- Cardiolipin Biosynthesis CL(a-13:0/i-19:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0047529)
- Cardiolipin Biosynthesis CL(a-13:0/i-20:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0047852)
- Cardiolipin Biosynthesis CL(a-13:0/i-21:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0048171)
- Cardiolipin Biosynthesis CL(a-13:0/i-22:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0048494)
- Cardiolipin Biosynthesis CL(a-13:0/i-24:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0048816)
- Cardiolipin Biosynthesis CL(i-12:0/18:2(9Z,11Z)/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0049139)
- Cardiolipin Biosynthesis CL(i-12:0/a-13:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0049462)
- Cardiolipin Biosynthesis CL(i-12:0/a-15:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0049783)
- Cardiolipin Biosynthesis CL(i-12:0/a-17:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0050107)
- Cardiolipin Biosynthesis CL(i-12:0/a-21:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0050430)
- Cardiolipin Biosynthesis CL(i-12:0/a-25:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0050753)
- Cardiolipin Biosynthesis CL(i-12:0/i-12:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0051078)
- Cardiolipin Biosynthesis CL(i-12:0/i-13:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0051402)
- Cardiolipin Biosynthesis CL(i-12:0/i-14:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0051726)
- Cardiolipin Biosynthesis CL(i-12:0/i-15:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0052048)
- Cardiolipin Biosynthesis CL(i-12:0/i-16:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0052371)
- Cardiolipin Biosynthesis CL(i-12:0/i-17:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0052694)
- Cardiolipin Biosynthesis CL(i-12:0/i-18:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0053017)
- Cardiolipin Biosynthesis CL(i-12:0/i-19:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0053340)
- Cardiolipin Biosynthesis CL(i-12:0/i-20:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0053663)
- Cardiolipin Biosynthesis CL(i-12:0/i-21:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0053987)
- Cardiolipin Biosynthesis CL(i-12:0/i-22:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0054310)
- Cardiolipin Biosynthesis CL(i-12:0/i-24:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0054632)
- Cardiolipin Biosynthesis CL(i-13:0/18:2(9Z,11Z)/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0054954)
- Cardiolipin Biosynthesis CL(i-13:0/a-13:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0055278)
- Cardiolipin Biosynthesis CL(i-13:0/a-15:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0055602)
- Cardiolipin Biosynthesis CL(i-13:0/a-17:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0055924)
- Cardiolipin Biosynthesis CL(i-13:0/a-21:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0056250)
- Cardiolipin Biosynthesis CL(i-13:0/a-25:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0056576)
- Cardiolipin Biosynthesis CL(i-13:0/i-12:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0056901)
- Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0057222)
- Cardiolipin Biosynthesis CL(i-13:0/i-14:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0057545)
- Cardiolipin Biosynthesis CL(i-13:0/i-15:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0057878)
- Cardiolipin Biosynthesis CL(i-13:0/i-16:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0058203)
- Cardiolipin Biosynthesis CL(i-13:0/i-17:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0058523)
- Cardiolipin Biosynthesis CL(i-13:0/i-18:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0058853)
- Cardiolipin Biosynthesis CL(i-13:0/i-19:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0059194)
- Cardiolipin Biosynthesis CL(i-13:0/i-20:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0059518)
- Cardiolipin Biosynthesis CL(i-13:0/i-21:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0059853)
- Cardiolipin Biosynthesis CL(i-13:0/i-22:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0060188)
- Cardiolipin Biosynthesis CL(i-13:0/i-24:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0060518)
- Cardiolipin Biosynthesis CL(i-14:0/a-13:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0060846)
- Cardiolipin Biosynthesis CL(i-14:0/a-15:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0061170)
- Cardiolipin Biosynthesis CL(i-14:0/i-12:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0061663)
- Cardiolipin Biosynthesis CL(i-14:0/i-13:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0061985)
- Cardiolipin Biosynthesis CL(i-14:0/i-14:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0062308)
- Cardiolipin Biosynthesis CL(i-14:0/i-15:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0062636)
- Cardiolipin Biosynthesis CL(i-14:0/i-16:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0062971)
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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(18:2(9Z,11Z)/i-22:0) 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(18:2(9Z,11Z)/i-22:0) 10V, Positive-QTOF | splash10-03di-1911000100-6546f3ee81648f6ae24f | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/i-22:0) 20V, Positive-QTOF | splash10-03di-2911000100-01e4b1512a85c30f0a4f | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/i-22:0) 40V, Positive-QTOF | splash10-03di-3922000000-8a41cb053bf00837240d | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/i-22:0) 10V, Negative-QTOF | splash10-08fr-4893000300-bed500590bbe04879e02 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/i-22:0) 20V, Negative-QTOF | splash10-03fr-7793210020-2fafd2e8679bba7bfe95 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/i-22:0) 40V, Negative-QTOF | splash10-0bvi-5911000000-6669f9ecdfb554d3ce62 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/i-22:0) 10V, Positive-QTOF | splash10-08fu-9001000004-d0502fa52e9cc5b75c3d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/i-22:0) 20V, Positive-QTOF | splash10-0a4u-7000000009-5d403c96e879df07f227 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/i-22:0) 40V, Positive-QTOF | splash10-004i-0124900000-fd289af7fe9ce0e877cd | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/i-22:0) 10V, Negative-QTOF | splash10-03di-9000000000-0175f831589b80440549 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/i-22:0) 20V, Negative-QTOF | splash10-00bc-9023600310-dba6023fd70e6622bfe2 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(18:2(9Z,11Z)/i-22:0) 40V, Negative-QTOF | splash10-0aw9-5309100300-80506385d4908eb9fe04 | 2021-09-22 | Wishart Lab | View Spectrum |
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