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 06:56:02 UTC |
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Update Date | 2022-11-30 19:26:28 UTC |
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HMDB ID | HMDB0116080 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | CDP-DG(a-15:0/18:2(9Z,11Z)) |
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Description | CDP-DG(a-15:0/18:2(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(a-15:0/18:2(9Z,11Z)), in particular, consists of one chain of anteisopentadecanoic 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)CCCCCCCCCCC(C)CC)(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/C45H79N3O15P2/c1-4-6-7-8-9-10-11-12-13-14-15-16-21-24-27-30-41(50)61-37(33-58-40(49)29-26-23-20-18-17-19-22-25-28-36(3)5-2)34-59-64(54,55)63-65(56,57)60-35-38-42(51)43(52)44(62-38)48-32-31-39(46)47-45(48)53/h10-13,31-32,36-38,42-44,51-52H,4-9,14-30,33-35H2,1-3H3,(H,54,55)(H,56,57)(H2,46,47,53)/b11-10-,13-12-/t36?,37-,38-,42+,43?,44-/m1/s1 |
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Synonyms | Value | Source |
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1-anteisopentadecanoyl-2-(9Z,11Z)-octadecadienoyl-sn-glycero-3-CDP | SMPDB, HMDB | 1-anteisopentadecanoyl-2-(9Z,11Z)-octadecadienoyl-sn-glycero-3-cytidine-5'-diphosphate | SMPDB, HMDB | CDP-DG(a-15:0/18:2) | SMPDB, HMDB | CDP-DG(a-15:0/18:2n7) | SMPDB, HMDB | CDP-DG(a-15:0/18:2w7) | SMPDB, HMDB | CDP-DG(33:2) | SMPDB, HMDB | CDP-diacylglycerol(a-15:0/18:2(9Z,11Z)) | SMPDB, HMDB | CDP-diacylglycerol(a-15:0/18:2) | SMPDB, HMDB | CDP-diacylglycerol(a-15:0/18:2n7) | SMPDB, HMDB | CDP-diacylglycerol(a-15:0/18:2w7) | SMPDB, HMDB | CDP-diacylglycerol(33:2) | SMPDB, HMDB | CDP-DG(a-15:0/18:2(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-[(12-methyltetradecanoyl)oxy]-2-[(9Z,11Z)-octadeca-9,11-dienoyloxy]propoxy]phosphoryl}oxy)phosphinate | Generator, HMDB |
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Chemical Formula | C45H79N3O15P2 |
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Average Molecular Weight | 964.081 |
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Monoisotopic Molecular Weight | 963.498642852 |
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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-[(12-methyltetradecanoyl)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-[(12-methyltetradecanoyl)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)CCCCCCCCCCC(C)CC)(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/C45H79N3O15P2/c1-4-6-7-8-9-10-11-12-13-14-15-16-21-24-27-30-41(50)61-37(33-58-40(49)29-26-23-20-18-17-19-22-25-28-36(3)5-2)34-59-64(54,55)63-65(56,57)60-35-38-42(51)43(52)44(62-38)48-32-31-39(46)47-45(48)53/h10-13,31-32,36-38,42-44,51-52H,4-9,14-30,33-35H2,1-3H3,(H,54,55)(H,56,57)(H2,46,47,53)/b11-10-,13-12-/t36?,37-,38-,42+,43?,44-/m1/s1 |
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InChI Key | WLZIUCHXTXVQIE-LAVVVQILSA-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)/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0043358)
- Cardiolipin Biosynthesis CL(a-13:0/a-13:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0043680)
- Cardiolipin Biosynthesis CL(a-13:0/a-15:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0044003)
- Cardiolipin Biosynthesis CL(a-13:0/a-17:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0044325)
- Cardiolipin Biosynthesis CL(a-13:0/a-21:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0044647)
- Cardiolipin Biosynthesis CL(a-13:0/a-25:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0044970)
- Cardiolipin Biosynthesis CL(a-13:0/i-12:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0045293)
- Cardiolipin Biosynthesis CL(a-13:0/i-13:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0045614)
- Cardiolipin Biosynthesis CL(a-13:0/i-14:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0045934)
- Cardiolipin Biosynthesis CL(a-13:0/i-15:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0046258)
- Cardiolipin Biosynthesis CL(a-13:0/i-16:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0046581)
- Cardiolipin Biosynthesis CL(a-13:0/i-17:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0046904)
- Cardiolipin Biosynthesis CL(a-13:0/i-18:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0047227)
- Cardiolipin Biosynthesis CL(a-13:0/i-19:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0047549)
- Cardiolipin Biosynthesis CL(a-13:0/i-20:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0047872)
- Cardiolipin Biosynthesis CL(a-13:0/i-21:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0048191)
- Cardiolipin Biosynthesis CL(a-13:0/i-22:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0048514)
- Cardiolipin Biosynthesis CL(a-13:0/i-24:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0048836)
- Cardiolipin Biosynthesis CL(i-12:0/18:2(9Z,11Z)/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0049159)
- Cardiolipin Biosynthesis CL(i-12:0/a-13:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0049482)
- Cardiolipin Biosynthesis CL(i-12:0/a-15:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0049803)
- Cardiolipin Biosynthesis CL(i-12:0/a-17:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0050127)
- Cardiolipin Biosynthesis CL(i-12:0/a-21:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0050450)
- Cardiolipin Biosynthesis CL(i-12:0/a-25:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0050773)
- Cardiolipin Biosynthesis CL(i-12:0/i-12:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0051098)
- Cardiolipin Biosynthesis CL(i-12:0/i-13:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0051422)
- Cardiolipin Biosynthesis CL(i-12:0/i-14:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0051745)
- Cardiolipin Biosynthesis CL(i-12:0/i-15:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0052068)
- Cardiolipin Biosynthesis CL(i-12:0/i-16:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0052391)
- Cardiolipin Biosynthesis CL(i-12:0/i-17:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0052714)
- Cardiolipin Biosynthesis CL(i-12:0/i-18:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0053037)
- Cardiolipin Biosynthesis CL(i-12:0/i-19:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0053360)
- Cardiolipin Biosynthesis CL(i-12:0/i-20:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0053683)
- Cardiolipin Biosynthesis CL(i-12:0/i-21:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0054007)
- Cardiolipin Biosynthesis CL(i-12:0/i-22:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0054330)
- Cardiolipin Biosynthesis CL(i-12:0/i-24:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0054652)
- Cardiolipin Biosynthesis CL(i-13:0/18:2(9Z,11Z)/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0054974)
- Cardiolipin Biosynthesis CL(i-13:0/a-13:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0055298)
- Cardiolipin Biosynthesis CL(i-13:0/a-15:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0055622)
- Cardiolipin Biosynthesis CL(i-13:0/a-17:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0055944)
- Cardiolipin Biosynthesis CL(i-13:0/a-21:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0056270)
- Cardiolipin Biosynthesis CL(i-13:0/a-25:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0056596)
- Cardiolipin Biosynthesis CL(i-13:0/i-12:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0056921)
- Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0057242)
- Cardiolipin Biosynthesis CL(i-13:0/i-14:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0057565)
- Cardiolipin Biosynthesis CL(i-13:0/i-15:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0057898)
- Cardiolipin Biosynthesis CL(i-13:0/i-16:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0058223)
- Cardiolipin Biosynthesis CL(i-13:0/i-17:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0058543)
- Cardiolipin Biosynthesis CL(i-13:0/i-18:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0058873)
- Cardiolipin Biosynthesis CL(i-13:0/i-19:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0059215)
- Cardiolipin Biosynthesis CL(i-13:0/i-20:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0059538)
- Cardiolipin Biosynthesis CL(i-13:0/i-21:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0059876)
- Cardiolipin Biosynthesis CL(i-13:0/i-22:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0060212)
- Cardiolipin Biosynthesis CL(i-13:0/i-24:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0060538)
- Cardiolipin Biosynthesis CL(i-14:0/a-13:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0060866)
- Cardiolipin Biosynthesis CL(i-14:0/a-15:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0061193)
- Cardiolipin Biosynthesis CL(i-14:0/a-17:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0061500)
- Cardiolipin Biosynthesis CL(i-14:0/i-12:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0061683)
- Cardiolipin Biosynthesis CL(i-14:0/i-13:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0062005)
- Cardiolipin Biosynthesis CL(i-14:0/i-14:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0062328)
- Cardiolipin Biosynthesis CL(i-14:0/i-15:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0062656)
- Cardiolipin Biosynthesis CL(i-14:0/i-16:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0062991)
- Cardiolipin Biosynthesis CL(i-14:0/i-17:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0063300)
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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(a-15:0/18:2(9Z,11Z)) 10V, Positive-QTOF | splash10-03di-0920000101-8aece11ef5c130a35074 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-15:0/18:2(9Z,11Z)) 20V, Positive-QTOF | splash10-03di-1920001000-5c3129cdfaa87e309434 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-15:0/18:2(9Z,11Z)) 40V, Positive-QTOF | splash10-03di-3930000000-7734b7c0938467dbec85 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-15:0/18:2(9Z,11Z)) 10V, Negative-QTOF | splash10-08ml-0690001203-03d79a993a39e5be974d | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-15:0/18:2(9Z,11Z)) 20V, Negative-QTOF | splash10-044l-5792200201-bc441ca851c37ca2c143 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-15:0/18:2(9Z,11Z)) 40V, Negative-QTOF | splash10-0bvl-5921000000-ecc607bcaebecf3b92d3 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-15:0/18:2(9Z,11Z)) 10V, Positive-QTOF | splash10-03e9-7100000059-495bb4a00327de9c9181 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-15:0/18:2(9Z,11Z)) 20V, Positive-QTOF | splash10-0aor-5000000095-6f00bcdb5c7106abdcc1 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-15:0/18:2(9Z,11Z)) 40V, Positive-QTOF | splash10-01b9-0118900000-1e24f77449162e03f65d | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-15:0/18:2(9Z,11Z)) 10V, Negative-QTOF | splash10-03di-0000001009-f912465ea39f8b2baff9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-15:0/18:2(9Z,11Z)) 20V, Negative-QTOF | splash10-01r6-9071805001-77a47930452c87c62c9a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CDP-DG(a-15:0/18:2(9Z,11Z)) 40V, Negative-QTOF | splash10-0a4i-9448402002-2d680bad695352c69c9a | 2021-09-24 | Wishart Lab | View Spectrum |
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