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 07:52:00 UTC |
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Update Date | 2022-11-30 19:26:34 UTC |
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HMDB ID | HMDB0116330 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | CDP-DG(i-22:0/18:2(9Z,11Z)) |
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Description | CDP-DG(i-22:0/18:2(9Z,11Z)) 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-22:0/18:2(9Z,11Z)), in particular, consists of one chain of isodocosanoic acid at the C-1 position and one chain of (9Z,11Z)-octadecadienoic 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)CCCCCCCCCCCCCCCCCCC(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)CCCCCCC\C=C/C=C\CCCCCC InChI=1S/C52H93N3O15P2/c1-4-5-6-7-8-9-10-11-14-19-22-25-28-31-34-37-48(57)68-44(40-65-47(56)36-33-30-27-24-21-18-16-13-12-15-17-20-23-26-29-32-35-43(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-isodocosanoyl-2-(9Z,11Z)-octadecadienoyl-sn-glycero-3-CDP | SMPDB, HMDB | 1-isodocosanoyl-2-(9Z,11Z)-octadecadienoyl-sn-glycero-3-cytidine-5'-diphosphate | SMPDB, HMDB | CDP-DG(i-22:0/18:2) | SMPDB, HMDB | CDP-DG(i-22:0/18:2n7) | SMPDB, HMDB | CDP-DG(i-22:0/18:2w7) | SMPDB, HMDB | CDP-DG(40:2) | SMPDB, HMDB | CDP-diacylglycerol(i-22:0/18:2(9Z,11Z)) | SMPDB, HMDB | CDP-diacylglycerol(i-22:0/18:2) | SMPDB, HMDB | CDP-diacylglycerol(i-22:0/18:2n7) | SMPDB, HMDB | CDP-diacylglycerol(i-22:0/18:2w7) | SMPDB, HMDB | CDP-diacylglycerol(40:2) | SMPDB, HMDB | CDP-DG(i-22:0/18:2(9Z,11Z)) | SMPDB | {[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({hydroxy[(2R)-3-[(20-methylhenicosanoyl)oxy]-2-[(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)-3-[(20-methylhenicosanoyl)oxy]-2-[(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)-3-[(20-methylhenicosanoyl)oxy]-2-[(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)CCCCCCCCCCCCCCCCCCC(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)CCCCCCC\C=C/C=C\CCCCCC |
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InChI Identifier | InChI=1S/C52H93N3O15P2/c1-4-5-6-7-8-9-10-11-14-19-22-25-28-31-34-37-48(57)68-44(40-65-47(56)36-33-30-27-24-21-18-16-13-12-15-17-20-23-26-29-32-35-43(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 | ANWDVNPCXLXVRX-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)/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0043608)
- Cardiolipin Biosynthesis CL(a-13:0/a-13:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0043931)
- Cardiolipin Biosynthesis CL(a-13:0/a-15:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0044253)
- Cardiolipin Biosynthesis CL(a-13:0/a-17:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0044575)
- Cardiolipin Biosynthesis CL(a-13:0/a-21:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0044899)
- Cardiolipin Biosynthesis CL(a-13:0/a-25:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0045222)
- Cardiolipin Biosynthesis CL(a-13:0/i-12:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0045544)
- Cardiolipin Biosynthesis CL(a-13:0/i-13:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0045863)
- Cardiolipin Biosynthesis CL(a-13:0/i-14:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0046186)
- Cardiolipin Biosynthesis CL(a-13:0/i-15:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0046509)
- Cardiolipin Biosynthesis CL(a-13:0/i-16:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0046832)
- Cardiolipin Biosynthesis CL(a-13:0/i-17:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0047156)
- Cardiolipin Biosynthesis CL(a-13:0/i-18:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0047477)
- Cardiolipin Biosynthesis CL(a-13:0/i-19:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0047800)
- Cardiolipin Biosynthesis CL(a-13:0/i-20:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0048120)
- Cardiolipin Biosynthesis CL(a-13:0/i-21:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0048441)
- Cardiolipin Biosynthesis CL(a-13:0/i-22:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0048764)
- Cardiolipin Biosynthesis CL(a-13:0/i-24:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0049087)
- Cardiolipin Biosynthesis CL(i-12:0/18:2(9Z,11Z)/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0049410)
- Cardiolipin Biosynthesis CL(i-12:0/a-13:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0049731)
- Cardiolipin Biosynthesis CL(i-12:0/a-15:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0050056)
- Cardiolipin Biosynthesis CL(i-12:0/a-17:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0050378)
- Cardiolipin Biosynthesis CL(i-12:0/a-21:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0050701)
- Cardiolipin Biosynthesis CL(i-12:0/a-25:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0051025)
- Cardiolipin Biosynthesis CL(i-12:0/i-12:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0051350)
- Cardiolipin Biosynthesis CL(i-12:0/i-13:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0051674)
- Cardiolipin Biosynthesis CL(i-12:0/i-14:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0051997)
- Cardiolipin Biosynthesis CL(i-12:0/i-15:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0052319)
- Cardiolipin Biosynthesis CL(i-12:0/i-16:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0052642)
- Cardiolipin Biosynthesis CL(i-12:0/i-17:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0052965)
- Cardiolipin Biosynthesis CL(i-12:0/i-18:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0053288)
- Cardiolipin Biosynthesis CL(i-12:0/i-19:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0053611)
- Cardiolipin Biosynthesis CL(i-12:0/i-20:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0053935)
- Cardiolipin Biosynthesis CL(i-12:0/i-21:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0054258)
- Cardiolipin Biosynthesis CL(i-12:0/i-22:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0054580)
- Cardiolipin Biosynthesis CL(i-12:0/i-24:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0054902)
- Cardiolipin Biosynthesis CL(i-13:0/18:2(9Z,11Z)/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0055226)
- Cardiolipin Biosynthesis CL(i-13:0/a-13:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0055550)
- Cardiolipin Biosynthesis CL(i-13:0/a-15:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0055874)
- Cardiolipin Biosynthesis CL(i-13:0/a-17:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0056198)
- Cardiolipin Biosynthesis CL(i-13:0/a-21:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0056524)
- Cardiolipin Biosynthesis CL(i-13:0/a-25:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0056849)
- Cardiolipin Biosynthesis CL(i-13:0/i-12:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0057171)
- Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0057494)
- Cardiolipin Biosynthesis CL(i-13:0/i-14:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0057826)
- Cardiolipin Biosynthesis CL(i-13:0/i-15:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0058151)
- Cardiolipin Biosynthesis CL(i-13:0/i-16:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0058472)
- Cardiolipin Biosynthesis CL(i-13:0/i-17:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0058798)
- Cardiolipin Biosynthesis CL(i-13:0/i-18:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0059142)
- Cardiolipin Biosynthesis CL(i-13:0/i-19:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0059466)
- Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0059801)
- Cardiolipin Biosynthesis CL(i-13:0/i-21:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0060130)
- Cardiolipin Biosynthesis CL(i-13:0/i-22:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0060466)
- Cardiolipin Biosynthesis CL(i-13:0/i-24:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0060794)
- Cardiolipin Biosynthesis CL(i-14:0/a-13:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0061119)
- Cardiolipin Biosynthesis CL(i-14:0/a-15:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0061443)
- Cardiolipin Biosynthesis CL(i-14:0/i-12:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0061934)
- Cardiolipin Biosynthesis CL(i-14:0/i-13:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0062256)
- Cardiolipin Biosynthesis CL(i-14:0/i-14:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0062579)
- Cardiolipin Biosynthesis CL(i-14:0/i-15:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0062919)
- Cardiolipin Biosynthesis CL(i-14:0/i-16:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0063243)
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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-22:0/18:2(9Z,11Z)) 10V, Positive-QTOF | splash10-03di-1911000100-2915de3ffbcbf7751858 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-22:0/18:2(9Z,11Z)) 20V, Positive-QTOF | splash10-03di-2911000100-581f2e39f0968daa5603 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-22:0/18:2(9Z,11Z)) 40V, Positive-QTOF | splash10-03di-3921000000-8618c5cec40d7296967e | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-22:0/18:2(9Z,11Z)) 10V, Negative-QTOF | splash10-08mr-4948000300-254ae04e33f1d97a13e8 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-22:0/18:2(9Z,11Z)) 20V, Negative-QTOF | splash10-044r-6629200020-c57659bb6b3533dcd8b6 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-22:0/18:2(9Z,11Z)) 40V, Negative-QTOF | splash10-0bvi-5902000000-d0ef4efd6c3831e876ef | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-22:0/18:2(9Z,11Z)) 10V, Negative-QTOF | splash10-03di-9000000100-8184cf05e27e5f432514 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-22:0/18:2(9Z,11Z)) 20V, Negative-QTOF | splash10-01tl-9033600400-4af82ed3d7cca54586e1 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-22:0/18:2(9Z,11Z)) 40V, Negative-QTOF | splash10-0a4i-9328120000-a99c6cbe5be9f1bf84f9 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-22:0/18:2(9Z,11Z)) 10V, Positive-QTOF | splash10-08fu-9100000003-112999efebb55beebefb | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-22:0/18:2(9Z,11Z)) 20V, Positive-QTOF | splash10-0aor-9100000038-12a999c56cbc17a84d95 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-22:0/18:2(9Z,11Z)) 40V, Positive-QTOF | splash10-0gi0-0014900000-8d5deccceffa81b0f468 | 2021-09-25 | Wishart Lab | View Spectrum |
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