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 07:54:36 UTC |
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Update Date | 2022-11-30 19:26:34 UTC |
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HMDB ID | HMDB0116348 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | CDP-DG(i-24:0/18:2(9Z,11Z)) |
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Description | CDP-DG(i-24:0/18:2(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-24:0/18:2(9Z,11Z)), in particular, consists of one chain of isotetracosanoic 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)CCCCCCCCCCCCCCCCCCCCC(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/C54H97N3O15P2/c1-4-5-6-7-8-9-10-11-16-21-24-27-30-33-36-39-50(59)70-46(42-67-49(58)38-35-32-29-26-23-20-18-15-13-12-14-17-19-22-25-28-31-34-37-45(2)3)43-68-73(63,64)72-74(65,66)69-44-47-51(60)52(61)53(71-47)57-41-40-48(55)56-54(57)62/h9-11,16,40-41,45-47,51-53,60-61H,4-8,12-15,17-39,42-44H2,1-3H3,(H,63,64)(H,65,66)(H2,55,56,62)/b10-9-,16-11-/t46-,47-,51+,52?,53-/m1/s1 |
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Synonyms | Value | Source |
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1-isotetracosanoyl-2-(9Z,11Z)-octadecadienoyl-sn-glycero-3-CDP | SMPDB, HMDB | 1-isotetracosanoyl-2-(9Z,11Z)-octadecadienoyl-sn-glycero-3-cytidine-5'-diphosphate | SMPDB, HMDB | CDP-DG(i-24:0/18:2) | SMPDB, HMDB | CDP-DG(i-24:0/18:2n7) | SMPDB, HMDB | CDP-DG(i-24:0/18:2w7) | SMPDB, HMDB | CDP-DG(42:2) | SMPDB, HMDB | CDP-diacylglycerol(i-24:0/18:2(9Z,11Z)) | SMPDB, HMDB | CDP-diacylglycerol(i-24:0/18:2) | SMPDB, HMDB | CDP-diacylglycerol(i-24:0/18:2n7) | SMPDB, HMDB | CDP-diacylglycerol(i-24:0/18:2w7) | SMPDB, HMDB | CDP-diacylglycerol(42:2) | SMPDB, HMDB | CDP-DG(i-24:0/18:2(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-[(22-methyltricosanoyl)oxy]-2-[(9Z,11Z)-octadeca-9,11-dienoyloxy]propoxy]phosphoryl}oxy)phosphinate | Generator, HMDB |
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Chemical Formula | C54H97N3O15P2 |
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Average Molecular Weight | 1090.324 |
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Monoisotopic Molecular Weight | 1089.639493431 |
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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-[(22-methyltricosanoyl)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-[(22-methyltricosanoyl)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)CCCCCCCCCCCCCCCCCCCCC(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/C54H97N3O15P2/c1-4-5-6-7-8-9-10-11-16-21-24-27-30-33-36-39-50(59)70-46(42-67-49(58)38-35-32-29-26-23-20-18-15-13-12-14-17-19-22-25-28-31-34-37-45(2)3)43-68-73(63,64)72-74(65,66)69-44-47-51(60)52(61)53(71-47)57-41-40-48(55)56-54(57)62/h9-11,16,40-41,45-47,51-53,60-61H,4-8,12-15,17-39,42-44H2,1-3H3,(H,63,64)(H,65,66)(H2,55,56,62)/b10-9-,16-11-/t46-,47-,51+,52?,53-/m1/s1 |
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InChI Key | OLPGTNKMZPJFAS-AWBPJITLSA-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-24:0/18:2(9Z,11Z)) (PathBank: SMP0043626)
- Cardiolipin Biosynthesis CL(a-13:0/a-13:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0043949)
- Cardiolipin Biosynthesis CL(a-13:0/a-15:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0044271)
- Cardiolipin Biosynthesis CL(a-13:0/a-17:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0044593)
- Cardiolipin Biosynthesis CL(a-13:0/a-21:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0044916)
- Cardiolipin Biosynthesis CL(a-13:0/a-25:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0045240)
- Cardiolipin Biosynthesis CL(a-13:0/i-12:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0045562)
- Cardiolipin Biosynthesis CL(a-13:0/i-13:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0045881)
- Cardiolipin Biosynthesis CL(a-13:0/i-14:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0046204)
- Cardiolipin Biosynthesis CL(a-13:0/i-15:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0046527)
- Cardiolipin Biosynthesis CL(a-13:0/i-16:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0046850)
- Cardiolipin Biosynthesis CL(a-13:0/i-17:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0047174)
- Cardiolipin Biosynthesis CL(a-13:0/i-18:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0047495)
- Cardiolipin Biosynthesis CL(a-13:0/i-19:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0047818)
- Cardiolipin Biosynthesis CL(a-13:0/i-20:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0048138)
- Cardiolipin Biosynthesis CL(a-13:0/i-21:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0048459)
- Cardiolipin Biosynthesis CL(a-13:0/i-22:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0048782)
- Cardiolipin Biosynthesis CL(a-13:0/i-24:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0049105)
- Cardiolipin Biosynthesis CL(i-12:0/18:2(9Z,11Z)/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0049428)
- Cardiolipin Biosynthesis CL(i-12:0/a-13:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0049749)
- Cardiolipin Biosynthesis CL(i-12:0/a-15:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0050074)
- Cardiolipin Biosynthesis CL(i-12:0/a-17:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0050396)
- Cardiolipin Biosynthesis CL(i-12:0/a-21:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0050719)
- Cardiolipin Biosynthesis CL(i-12:0/a-25:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0051044)
- Cardiolipin Biosynthesis CL(i-12:0/i-12:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0051368)
- Cardiolipin Biosynthesis CL(i-12:0/i-13:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0051692)
- Cardiolipin Biosynthesis CL(i-12:0/i-14:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0052014)
- Cardiolipin Biosynthesis CL(i-12:0/i-15:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0052337)
- Cardiolipin Biosynthesis CL(i-12:0/i-16:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0052660)
- Cardiolipin Biosynthesis CL(i-12:0/i-17:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0052983)
- Cardiolipin Biosynthesis CL(i-12:0/i-18:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0053306)
- Cardiolipin Biosynthesis CL(i-12:0/i-19:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0053629)
- Cardiolipin Biosynthesis CL(i-12:0/i-20:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0053953)
- Cardiolipin Biosynthesis CL(i-12:0/i-21:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0054276)
- Cardiolipin Biosynthesis CL(i-12:0/i-22:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0054598)
- Cardiolipin Biosynthesis CL(i-12:0/i-24:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0054920)
- Cardiolipin Biosynthesis CL(i-13:0/18:2(9Z,11Z)/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0055244)
- Cardiolipin Biosynthesis CL(i-13:0/a-13:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0055568)
- Cardiolipin Biosynthesis CL(i-13:0/a-15:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0055890)
- Cardiolipin Biosynthesis CL(i-13:0/a-17:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0056216)
- Cardiolipin Biosynthesis CL(i-13:0/a-21:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0056542)
- Cardiolipin Biosynthesis CL(i-13:0/a-25:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0056867)
- Cardiolipin Biosynthesis CL(i-13:0/i-12:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0057189)
- Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0057512)
- Cardiolipin Biosynthesis CL(i-13:0/i-14:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0057844)
- Cardiolipin Biosynthesis CL(i-13:0/i-15:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0058169)
- Cardiolipin Biosynthesis CL(i-13:0/i-16:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0058490)
- Cardiolipin Biosynthesis CL(i-13:0/i-17:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0058819)
- Cardiolipin Biosynthesis CL(i-13:0/i-18:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0059160)
- Cardiolipin Biosynthesis CL(i-13:0/i-19:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0059484)
- Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0059819)
- Cardiolipin Biosynthesis CL(i-13:0/i-21:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0060148)
- Cardiolipin Biosynthesis CL(i-13:0/i-22:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0060484)
- Cardiolipin Biosynthesis CL(i-13:0/i-24:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0060812)
- Cardiolipin Biosynthesis CL(i-14:0/a-13:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0061137)
- Cardiolipin Biosynthesis CL(i-14:0/a-15:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0061461)
- Cardiolipin Biosynthesis CL(i-14:0/i-12:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0061951)
- Cardiolipin Biosynthesis CL(i-14:0/i-13:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0062274)
- Cardiolipin Biosynthesis CL(i-14:0/i-14:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0062597)
- Cardiolipin Biosynthesis CL(i-14:0/i-15:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0062937)
- Cardiolipin Biosynthesis CL(i-14:0/i-16:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0063261)
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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(i-24:0/18:2(9Z,11Z)) 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(i-24:0/18:2(9Z,11Z)) 10V, Positive-QTOF | splash10-03di-1911000010-8e8b5b12a43eebfe35e3 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-24:0/18:2(9Z,11Z)) 20V, Positive-QTOF | splash10-03di-2911000000-f285e0e0656ba9b55b12 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-24:0/18:2(9Z,11Z)) 40V, Positive-QTOF | splash10-03di-3921100000-824f0adb7a707199ff57 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-24:0/18:2(9Z,11Z)) 10V, Negative-QTOF | splash10-0cfs-4839000130-5811f53293dc55630e1f | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-24:0/18:2(9Z,11Z)) 20V, Negative-QTOF | splash10-02ta-5519200020-381b6f1b3002cbced35b | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-24:0/18:2(9Z,11Z)) 40V, Negative-QTOF | splash10-0bvi-5902000000-c27b86faf8904914b5ed | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-24:0/18:2(9Z,11Z)) 10V, Negative-QTOF | splash10-000i-9000000010-878e0aaed6fbf7e7b293 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-24:0/18:2(9Z,11Z)) 20V, Negative-QTOF | splash10-02dl-9033510040-f9fac4fb9974fdcd5204 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-24:0/18:2(9Z,11Z)) 40V, Negative-QTOF | splash10-0a59-9328120010-8671cbdde705a7ea09e9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-24:0/18:2(9Z,11Z)) 10V, Positive-QTOF | splash10-0006-9000000003-8ce859e15220d29d48cd | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-24:0/18:2(9Z,11Z)) 20V, Positive-QTOF | splash10-0a4i-9000000016-f88b12a40b3e05c33dba | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(i-24:0/18:2(9Z,11Z)) 40V, Positive-QTOF | splash10-0g4i-1015920000-2ab0ba7d6b0bf9ba6b89 | 2021-09-22 | Wishart Lab | View Spectrum |
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