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 07:36:41 UTC |
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Update Date | 2022-11-30 19:26:32 UTC |
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HMDB ID | HMDB0116259 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | CDP-DG(i-18:0/18:2(9Z,11Z)) |
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Description | CDP-DG(i-18:0/18:2(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-18:0/18:2(9Z,11Z)), in particular, consists of one chain of isooctadecanoic 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)CCCCCCCCCCCCCCC(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/C48H85N3O15P2/c1-4-5-6-7-8-9-10-11-12-13-18-21-24-27-30-33-44(53)64-40(36-61-43(52)32-29-26-23-20-17-15-14-16-19-22-25-28-31-39(2)3)37-62-67(57,58)66-68(59,60)63-38-41-45(54)46(55)47(65-41)51-35-34-42(49)50-48(51)56/h9-12,34-35,39-41,45-47,54-55H,4-8,13-33,36-38H2,1-3H3,(H,57,58)(H,59,60)(H2,49,50,56)/b10-9-,12-11-/t40-,41-,45+,46?,47-/m1/s1 |
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Synonyms | Value | Source |
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1-isooctadecanoyl-2-(9Z,11Z)-octadecadienoyl-sn-glycero-3-CDP | SMPDB, HMDB | 1-isooctadecanoyl-2-(9Z,11Z)-octadecadienoyl-sn-glycero-3-cytidine-5'-diphosphate | SMPDB, HMDB | CDP-DG(i-18:0/18:2) | SMPDB, HMDB | CDP-DG(i-18:0/18:2n7) | SMPDB, HMDB | CDP-DG(i-18:0/18:2w7) | SMPDB, HMDB | CDP-DG(36:2) | SMPDB, HMDB | CDP-diacylglycerol(i-18:0/18:2(9Z,11Z)) | SMPDB, HMDB | CDP-diacylglycerol(i-18:0/18:2) | SMPDB, HMDB | CDP-diacylglycerol(i-18:0/18:2n7) | SMPDB, HMDB | CDP-diacylglycerol(i-18:0/18:2w7) | SMPDB, HMDB | CDP-diacylglycerol(36:2) | SMPDB, HMDB | CDP-DG(i-18:0/18:2(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-[(16-methylheptadecanoyl)oxy]-2-[(9Z,11Z)-octadeca-9,11-dienoyloxy]propoxy]phosphoryl}oxy)phosphinate | Generator, HMDB |
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Chemical Formula | C48H85N3O15P2 |
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Average Molecular Weight | 1006.162 |
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Monoisotopic Molecular Weight | 1005.545593045 |
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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-[(16-methylheptadecanoyl)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-[(16-methylheptadecanoyl)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)CCCCCCCCCCCCCCC(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/C48H85N3O15P2/c1-4-5-6-7-8-9-10-11-12-13-18-21-24-27-30-33-44(53)64-40(36-61-43(52)32-29-26-23-20-17-15-14-16-19-22-25-28-31-39(2)3)37-62-67(57,58)66-68(59,60)63-38-41-45(54)46(55)47(65-41)51-35-34-42(49)50-48(51)56/h9-12,34-35,39-41,45-47,54-55H,4-8,13-33,36-38H2,1-3H3,(H,57,58)(H,59,60)(H2,49,50,56)/b10-9-,12-11-/t40-,41-,45+,46?,47-/m1/s1 |
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InChI Key | IDDGUAZFGGZQPH-VKDWSAOJSA-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-18:0/18:2(9Z,11Z)) (PathBank: SMP0043537)
- Cardiolipin Biosynthesis CL(a-13:0/a-13:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0043859)
- Cardiolipin Biosynthesis CL(a-13:0/a-15:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0044182)
- Cardiolipin Biosynthesis CL(a-13:0/a-17:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0044503)
- Cardiolipin Biosynthesis CL(a-13:0/a-21:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0044827)
- Cardiolipin Biosynthesis CL(a-13:0/a-25:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0045150)
- Cardiolipin Biosynthesis CL(a-13:0/i-12:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0045472)
- Cardiolipin Biosynthesis CL(a-13:0/i-13:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0045791)
- Cardiolipin Biosynthesis CL(a-13:0/i-14:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0046114)
- Cardiolipin Biosynthesis CL(a-13:0/i-15:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0046438)
- Cardiolipin Biosynthesis CL(a-13:0/i-16:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0046760)
- Cardiolipin Biosynthesis CL(a-13:0/i-17:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0047084)
- Cardiolipin Biosynthesis CL(a-13:0/i-18:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0047405)
- Cardiolipin Biosynthesis CL(a-13:0/i-19:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0047728)
- Cardiolipin Biosynthesis CL(a-13:0/i-20:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0048049)
- Cardiolipin Biosynthesis CL(a-13:0/i-21:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0048369)
- Cardiolipin Biosynthesis CL(a-13:0/i-22:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0048693)
- Cardiolipin Biosynthesis CL(a-13:0/i-24:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0049015)
- Cardiolipin Biosynthesis CL(i-12:0/18:2(9Z,11Z)/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0049338)
- Cardiolipin Biosynthesis CL(i-12:0/a-13:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0049660)
- Cardiolipin Biosynthesis CL(i-12:0/a-15:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0049983)
- Cardiolipin Biosynthesis CL(i-12:0/a-17:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0050307)
- Cardiolipin Biosynthesis CL(i-12:0/a-21:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0050629)
- Cardiolipin Biosynthesis CL(i-12:0/a-25:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0050953)
- Cardiolipin Biosynthesis CL(i-12:0/i-12:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0051278)
- Cardiolipin Biosynthesis CL(i-12:0/i-13:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0051602)
- Cardiolipin Biosynthesis CL(i-12:0/i-14:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0051925)
- Cardiolipin Biosynthesis CL(i-12:0/i-15:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0052248)
- Cardiolipin Biosynthesis CL(i-12:0/i-16:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0052569)
- Cardiolipin Biosynthesis CL(i-12:0/i-17:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0052893)
- Cardiolipin Biosynthesis CL(i-12:0/i-18:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0053217)
- Cardiolipin Biosynthesis CL(i-12:0/i-19:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0053540)
- Cardiolipin Biosynthesis CL(i-12:0/i-20:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0053862)
- Cardiolipin Biosynthesis CL(i-12:0/i-21:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0054187)
- Cardiolipin Biosynthesis CL(i-12:0/i-22:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0054509)
- Cardiolipin Biosynthesis CL(i-12:0/i-24:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0054830)
- Cardiolipin Biosynthesis CL(i-13:0/18:2(9Z,11Z)/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0055154)
- Cardiolipin Biosynthesis CL(i-13:0/a-13:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0055479)
- Cardiolipin Biosynthesis CL(i-13:0/a-15:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0055802)
- Cardiolipin Biosynthesis CL(i-13:0/a-17:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0056126)
- Cardiolipin Biosynthesis CL(i-13:0/a-21:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0056450)
- Cardiolipin Biosynthesis CL(i-13:0/a-25:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0056776)
- Cardiolipin Biosynthesis CL(i-13:0/i-12:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0057099)
- Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0057422)
- Cardiolipin Biosynthesis CL(i-13:0/i-14:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0057755)
- Cardiolipin Biosynthesis CL(i-13:0/i-15:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0058079)
- Cardiolipin Biosynthesis CL(i-13:0/i-16:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0058401)
- Cardiolipin Biosynthesis CL(i-13:0/i-17:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0058722)
- Cardiolipin Biosynthesis CL(i-13:0/i-18:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0059068)
- Cardiolipin Biosynthesis CL(i-13:0/i-19:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0059395)
- Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0059727)
- Cardiolipin Biosynthesis CL(i-13:0/i-21:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0060055)
- Cardiolipin Biosynthesis CL(i-13:0/i-22:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0060394)
- Cardiolipin Biosynthesis CL(i-13:0/i-24:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0060717)
- Cardiolipin Biosynthesis CL(i-14:0/a-13:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0061045)
- Cardiolipin Biosynthesis CL(i-14:0/a-15:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0061371)
- Cardiolipin Biosynthesis CL(i-14:0/i-12:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0061862)
- Cardiolipin Biosynthesis CL(i-14:0/i-13:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0062185)
- Cardiolipin Biosynthesis CL(i-14:0/i-14:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0062507)
- Cardiolipin Biosynthesis CL(i-14:0/i-15:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0062837)
- Cardiolipin Biosynthesis CL(i-14:0/i-16:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0063171)
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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-18:0/18:2(9Z,11Z)) 10V, Positive-QTOF | splash10-03di-0920000101-a63af1de82e5e2efc1ca | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-18:0/18:2(9Z,11Z)) 20V, Positive-QTOF | splash10-03di-1920001000-968f0d3f007160bdf435 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-18:0/18:2(9Z,11Z)) 40V, Positive-QTOF | splash10-03di-3931000100-e4bf9e8527493dd6e09d | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-18:0/18:2(9Z,11Z)) 10V, Negative-QTOF | splash10-0ce9-1690000201-4c5467a43c85e91d5c08 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-18:0/18:2(9Z,11Z)) 20V, Negative-QTOF | splash10-03yi-4692200201-75666f8526b630ec6a1a | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-18:0/18:2(9Z,11Z)) 40V, Negative-QTOF | splash10-0bvi-5921000000-169bea21ee3b59e441ba | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-18:0/18:2(9Z,11Z)) 10V, Negative-QTOF | splash10-0udi-9000000201-399043c928a08b40833f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-18:0/18:2(9Z,11Z)) 20V, Negative-QTOF | splash10-005c-9060700500-d11bf4d80ac982f556f6 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-18:0/18:2(9Z,11Z)) 40V, Negative-QTOF | splash10-0api-9348400201-a149b1d8774fc3d4c5fb | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-18:0/18:2(9Z,11Z)) 10V, Positive-QTOF | splash10-0a4i-9100000013-c5980ddd95349c52b85f | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-18:0/18:2(9Z,11Z)) 20V, Positive-QTOF | splash10-0aor-6100000059-3d73a121e297e9aac6de | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-18:0/18:2(9Z,11Z)) 40V, Positive-QTOF | splash10-0gi0-0014910000-4b5adae68186c48dd7ee | 2021-09-23 | Wishart Lab | View Spectrum |
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