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Showing Compound Citicoline (FDB022608)

Record Information
Version1.0
Creation date2011-09-21 00:16:49 UTC
Update date2020-09-17 15:41:05 UTC
Primary IDFDB022608
Secondary Accession Numbers
  • FDB030718
Chemical Information
FooDB NameCiticoline
DescriptionCiticoline, 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.
CAS Number987-78-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
[2-CYTIDYLATE-o'-phosphonyloxyl]-ethyl-trimethyl-ammoniumChEBI
CDP-ColinaChEBI
CiticolinaChEBI
CiticolinumChEBI
Citidin difosfato de colinaChEBI
CyticholineChEBI
CytidindiphosphocholinChEBI
Cytidine 5'-(choline diphosphate)ChEBI
Cytidine 5'-(cholinyl pyrophosphate)ChEBI
Cytidine 5'-diphosphocholineChEBI
Cytidine 5'-diphosphoric cholineChEBI
NicholinKegg
[2-CYTIDYLic acid-o'-phosphonyloxyl]-ethyl-trimethyl-ammoniumGenerator
Cytidine 5'-(choline diphosphoric acid)Generator
Cytidine 5'-(cholinyl pyrophosphoric acid)Generator
AudesHMDB
CDP-CholineHMDB
CerebHMDB
Choline 5'-cytidine diphosphateHMDB
Choline cytidine diphosphateHMDB
CiticholineHMDB
CitidolineHMDB
CitifarHMDB
ColiteHMDB
CorenalinHMDB
CyscholinHMDB
Cytidine 5'-diphosphate cholineHMDB
Cytidine 5-diphosphate-trihydrogenHMDB
Cytidine choline diphosphateHMDB
Cytidine diphosphate cholineHMDB
Cytidine diphosphate choline esterHMDB
Cytidine diphosphocholineHMDB
Cytidine diphosphorylcholineHMDB
Cytidine-5' diphosphocholineHMDB
Cytidine-5'-pyrophosphate-hydroxycholineHMDB
CytidolineHMDB
DifosfocinHMDB
Emicholine FHMDB
EnsignHMDB
HaocolinHMDB
HornbestHMDB
NeucolisHMDB
NicolinHMDB
NiticolinHMDB
p-Hydroxide[2-(trimethylammonio)ethyl] esterHMDB
ReaginHMDB
RecofnanHMDB
RecognanHMDB
RexortHMDB
SintoclarHMDB
SomazinaHMDB
SomazineHMDB
SuncholinHMDB
CidifosHMDB
Diphosphate choline, cytidineHMDB
Choline, CDPHMDB
CDP CholineHMDB
5'-Diphosphocholine, cytidineHMDB
Cytidine 5' diphosphocholineHMDB
Choline, cytidine diphosphateHMDB
[2-CYTIDYLATE-o'-onyloxyl]-ethyl-trimethyl-ammoniumChEBI
[2-CYTIDYLic acid-o'-onyloxyl]-ethyl-trimethyl-ammoniumGenerator
CDP-cholinehmdb
Choline 5'-cytidine diateHMDB
Choline cytidine diateHMDB
Citicolinehmdb
CytidindiocholinChEBI
Cytidine 5-diate-trihydrogenHMDB
Cytidine 5'-(choline diate)ChEBI
Cytidine 5'-(choline diic acid)Generator
Cytidine 5'-(cholinyl pyroate)ChEBI
Cytidine 5'-(cholinyl pyroic acid)Generator
Cytidine 5'-diate cholineHMDB
Cytidine 5'-diocholineChEBI
Cytidine 5'-dioric cholineChEBI
Cytidine choline diateHMDB
Cytidine diate cholineHMDB
Cytidine diate choline esterHMDB
Cytidine diocholineHMDB
Cytidine diorylcholineHMDB
Cytidine-5' diocholineHMDB
cytidine-5' diphosphocholinehmdb
Cytidine-5'-pyroate-hydroxycholineHMDB
cytidine-5'-pyrophosphate-hydroxycholinehmdb
P-hydroxide[2-(trimethylammonio)ethyl] esterhmdb
Predicted Properties
PropertyValueSource
Water Solubility7.99 g/LALOGPS
logP-1.4ALOGPS
logP-7.1ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.85ChemAxon
pKa (Strongest Basic)-0.032ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area213.5 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity113.58 m³·mol⁻¹ChemAxon
Polarizability42.54 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC14H26N4O11P2
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
InChI IdentifierInChI=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
InChI KeyRZZPDXZPRHQOCG-OJAKKHQRSA-N
Isomeric SMILESC[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
Average Molecular Weight488.324
Monoisotopic Molecular Weight488.107330718
Classification
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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine ribonucleotides
Direct ParentPyrimidine ribonucleoside diphosphates
Alternative Parents
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
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCiticoline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fr-7649200000-859d046834f1fbd3d535Spectrum
Predicted GC-MSCiticoline, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00yi-7947012000-9f83d07fb5a59a93e770Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-0001900000-a9f38ff6b185b45f04b32012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03e9-0590000000-b021677d064d65810ee02012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-0900000000-7570bbb10dd9fa2884422012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-0000900000-8b411373962b073b4d222012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-000i-0001900000-6e7cc437ad79eb13c0322012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-01qi-1932200000-9c3803cefdd9c6285a7c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004i-6505900000-3d534aab6e40915c36422012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004i-6505900000-fc13e5ad403e7faf82182012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-6505900000-3d534aab6e40915c36422017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-6505900000-fc13e5ad403e7faf82182017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0000900000-8b411373962b073b4d222017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0001900000-6e7cc437ad79eb13c0322017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01qi-1932200000-4a7ae92c6e127d2ce4532017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2900100000-0ce672506aae2d1e5eef2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3900000000-c05f3e5b6782e32eeebb2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-8900000000-17466c845e643c77969b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01p9-0501900000-be567596c9f980cea8c22017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3904100000-4c2e6535887540a124442017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fu-9600000000-e42f82159eabb4ec781a2017-09-01View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID13207
ChEMBL IDCHEMBL1231700
KEGG Compound IDC00307
Pubchem Compound ID13804
Pubchem Substance IDNot Available
ChEBI ID16436
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01413
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID1485298
KNApSAcK IDNot Available
HET IDCDC
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCiticoline
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Choline-phosphate cytidylyltransferase BPCYT1BQ9Y5K3
Choline-phosphate cytidylyltransferase APCYT1AP49585
Phosphatidylcholine:ceramide cholinephosphotransferase 2SGMS2Q8NHU3
Phosphatidylcholine:ceramide cholinephosphotransferase 1SGMS1Q86VZ5
Pathways
NameSMPDB LinkKEGG Link
Phospholipid BiosynthesisSMP00025 map00564
Plasmalogen SynthesisSMP00479 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference