| Record Information |
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| Version | 1.0 |
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| Created at | 2020-04-17 19:19:16 UTC |
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| Updated at | 2020-11-18 16:39:30 UTC |
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| CannabisDB ID | CDB005199 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | CDP-Choline |
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| Description | Citicoline, also known as CDP-colina or nicholin, belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety. Citicoline has also been shown to be able to inhibit mechanisms of apoptosis associated to cerebral ischemia and in certain neurodegeneration models, and to potentiate neuroplasticity mechanisms. Citicoline is a drug. Citicoline is an extremely weak basic (essentially neutral) compound (based on its pKa). Citicoline is an essential intermediate in the biosynthetic pathway of structural phospholipids in cell membranes, particularly phosphatidylcholine. Citicoline exists in all eukaryotes, ranging from yeast to humans. In humans, citicoline is involved in phospholipid biosynthesis. Outside of the human body, Citicoline has been detected, but not quantified in, several different foods, such as mountain yams, oil-seed camellia, rowals, mango, and pineappple sages. This could make citicoline a potential biomarker for the consumption of these foods. Citicoline is a safe drug, as shown by the toxicological tests conducted, that has no significant systemic cholinergic effects and is a well tolerated product. Thus, citicoline has been experimentally shown to increase norepinephrine and dopamine levels in the CNS. Citicoline activates biosynthesis of structural phospholipids of neuronal membranes, increases brain metabolism, and acts upon the levels of different neurotransmitters. Once absorbed, citicoline is widely distributed throughout the body, crosses the blood-brain barrier and reaches the central nervous system (CNS), where it is incorporated into the membrane and microsomal phospholipid fraction. In addition, citicoline has been shown to restore the activity of mitochondrial ATPase and membrane Na+/K+ATPase, to inhibit activation of certain phospholipases, and to accelerate reabsorption of cerebral edema in various experimental models. Owing to these pharmacological mechanisms, citicoline has a neuroprotective effect in hypoxic and ischemic conditions, decreasing the volume of ischemic lesion, and also improves learning and memory performance in animal models of brain aging. CDP-Choline is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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| Structure | |
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| Synonyms | | Value | Source |
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| [2-CYTIDYLATE-o'-phosphonyloxyl]-ethyl-trimethyl-ammonium | ChEBI | | CDP-Colina | ChEBI | | Citicolina | ChEBI | | Citicolinum | ChEBI | | Citidin difosfato de colina | ChEBI | | Cyticholine | ChEBI | | Cytidindiphosphocholin | ChEBI | | Cytidine 5'-(choline diphosphate) | ChEBI | | Cytidine 5'-(cholinyl pyrophosphate) | ChEBI | | Cytidine 5'-diphosphocholine | ChEBI | | Cytidine 5'-diphosphoric choline | ChEBI | | Nicholin | Kegg | | [2-CYTIDYLic acid-o'-phosphonyloxyl]-ethyl-trimethyl-ammonium | Generator | | Cytidine 5'-(choline diphosphoric acid) | Generator | | Cytidine 5'-(cholinyl pyrophosphoric acid) | Generator | | Audes | HMDB | | CDP-Choline | HMDB | | Cereb | HMDB | | Choline 5'-cytidine diphosphate | HMDB | | Choline cytidine diphosphate | HMDB | | Citicholine | HMDB | | Citidoline | HMDB | | Citifar | HMDB | | Colite | HMDB | | Corenalin | HMDB | | Cyscholin | HMDB | | Cytidine 5'-diphosphate choline | HMDB | | Cytidine 5-diphosphate-trihydrogen | HMDB | | Cytidine choline diphosphate | HMDB | | Cytidine diphosphate choline | HMDB | | Cytidine diphosphate choline ester | HMDB | | Cytidine diphosphocholine | HMDB | | Cytidine diphosphorylcholine | HMDB | | Cytidine-5' diphosphocholine | HMDB | | Cytidine-5'-pyrophosphate-hydroxycholine | HMDB | | Cytidoline | HMDB | | Difosfocin | HMDB | | Emicholine F | HMDB | | Ensign | HMDB | | Haocolin | HMDB | | Hornbest | HMDB | | Neucolis | HMDB | | Nicolin | HMDB | | Niticolin | HMDB | | p-Hydroxide[2-(trimethylammonio)ethyl] ester | HMDB | | Reagin | HMDB | | Recofnan | HMDB | | Recognan | HMDB | | Rexort | HMDB | | Sintoclar | HMDB | | Somazina | HMDB | | Somazine | HMDB | | Suncholin | HMDB | | Cidifos | HMDB | | Diphosphate choline, cytidine | HMDB | | Choline, CDP | HMDB | | CDP Choline | HMDB | | 5'-Diphosphocholine, cytidine | HMDB | | Cytidine 5' diphosphocholine | HMDB | | Choline, cytidine diphosphate | HMDB |
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| Chemical Formula | C14H26N4O11P2 |
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| Average Molecular Weight | 488.32 |
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| Monoisotopic Molecular Weight | 488.1073 |
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| IUPAC Name | {2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphono)oxy]ethyl}trimethylazanium |
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| Traditional Name | [2-({[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl phosphono}oxy)ethyl]trimethylazanium |
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| CAS Registry Number | 987-78-0 |
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| SMILES | C[N+](C)(C)CCOP([O-])(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O |
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| InChI Identifier | InChI=1S/C14H26N4O11P2/c1-18(2,3)6-7-26-30(22,23)29-31(24,25)27-8-9-11(19)12(20)13(28-9)17-5-4-10(15)16-14(17)21/h4-5,9,11-13,19-20H,6-8H2,1-3H3,(H3-,15,16,21,22,23,24,25)/t9-,11-,12-,13-/m1/s1 |
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| InChI Key | RZZPDXZPRHQOCG-OJAKKHQRSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Nucleosides, nucleotides, and analogues |
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| Class | Pyrimidine nucleotides |
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| Sub Class | Pyrimidine ribonucleotides |
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| Direct Parent | Pyrimidine ribonucleoside diphosphates |
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| Alternative Parents | |
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| Substituents | - Pyrimidine ribonucleoside diphosphate
- Pentose phosphate
- Pentose-5-phosphate
- Glycosyl compound
- N-glycosyl compound
- Phosphocholine
- Monosaccharide phosphate
- Organic pyrophosphate
- Pentose monosaccharide
- Aminopyrimidine
- Pyrimidone
- Monoalkyl phosphate
- Hydropyrimidine
- Monosaccharide
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Pyrimidine
- Imidolactam
- Alkyl phosphate
- Tetrahydrofuran
- Quaternary ammonium salt
- Tetraalkylammonium salt
- Heteroaromatic compound
- Secondary alcohol
- 1,2-diol
- Organoheterocyclic compound
- Oxacycle
- Azacycle
- Organic nitrogen compound
- Organonitrogen compound
- Organopnictogen compound
- Amine
- Alcohol
- Organic oxide
- Organooxygen compound
- Organic oxygen compound
- Organic salt
- Hydrocarbon derivative
- Organic zwitterion
- Primary amine
- Aromatic heteromonocyclic compound
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| Molecular Framework | Aromatic heteromonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Disposition | Route of exposure: Source: Biological location: |
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| Role | Industrial application: |
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| Physical Properties |
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| State | Solid |
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| Experimental 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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| Predicted Properties | [] |
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| MS/MS | | Type | Description | Splash Key | View |
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| MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0006-0001900000-a9f38ff6b185b45f04b3 | 2012-07-24 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-03e9-0590000000-b021677d064d65810ee0 | 2012-07-24 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-001i-0900000000-7570bbb10dd9fa288442 | 2012-07-24 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-000i-0000900000-8b411373962b073b4d22 | 2012-08-31 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-000i-0001900000-6e7cc437ad79eb13c032 | 2012-08-31 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-01qi-1932200000-9c3803cefdd9c6285a7c | 2012-08-31 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-004i-6505900000-3d534aab6e40915c3642 | 2012-08-31 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-004i-6505900000-fc13e5ad403e7faf8218 | 2012-08-31 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-004i-6505900000-3d534aab6e40915c3642 | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-004i-6505900000-fc13e5ad403e7faf8218 | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-000i-0000900000-8b411373962b073b4d22 | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-000i-0001900000-6e7cc437ad79eb13c032 | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-01qi-1932200000-4a7ae92c6e127d2ce453 | 2017-09-14 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-2900100000-0ce672506aae2d1e5eef | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-3900000000-c05f3e5b6782e32eeebb | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-8900000000-17466c845e643c77969b | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-01p9-0501900000-be567596c9f980cea8c2 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-3904100000-4c2e6535887540a12444 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03fu-9600000000-e42f82159eabb4ec781a | 2017-09-01 | View Spectrum |
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