Citicoline (CHEM035209)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:34:41 UTC
Update Date2016-11-09 01:21:16 UTC
Accession NumberCHEM035209
Identification
Common NameCiticoline
ClassSmall Molecule
DescriptionA member of the class of phosphocholines that is the chloine ester of CDP. It is an intermediate obtained in the biosynthetic pathway of structural phospholipids in cell membranes.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
[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
Chemical FormulaC14H26N4O11P2
Average Molecular Mass488.324 g/mol
Monoisotopic Mass488.107 g/mol
CAS Registry Number987-78-0
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
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
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
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fr-7649200000-859d046834f1fbd3d535Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00yi-7947012000-9f83d07fb5a59a93e770Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-0001900000-a9f38ff6b185b45f04b3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03e9-0590000000-b021677d064d65810ee0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-0900000000-7570bbb10dd9fa288442Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-0000900000-8b411373962b073b4d22Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-000i-0001900000-6e7cc437ad79eb13c032Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-01qi-1932200000-9c3803cefdd9c6285a7cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004i-6505900000-3d534aab6e40915c3642Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004i-6505900000-fc13e5ad403e7faf8218Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-6505900000-3d534aab6e40915c3642Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-6505900000-fc13e5ad403e7faf8218Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0000900000-8b411373962b073b4d22Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0001900000-6e7cc437ad79eb13c032Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01qi-1932200000-4a7ae92c6e127d2ce453Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2900100000-0ce672506aae2d1e5eefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3900000000-c05f3e5b6782e32eeebbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-8900000000-17466c845e643c77969bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01p9-0501900000-be567596c9f980cea8c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3904100000-4c2e6535887540a12444Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fu-9600000000-e42f82159eabb4ec781aSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04290
HMDB IDHMDB0001413
FooDB IDFDB022608
Phenol Explorer IDNot Available
KNApSAcK IDC00007231
BiGG ID1485298
BioCyc IDNot Available
METLIN ID6229
PDB IDNot Available
Wikipedia LinkCiticoline
Chemspider ID13207
ChEBI ID16436
PubChem Compound ID13804
Kegg Compound IDC00307
YMDB IDYMDB00090
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10701532
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10796523
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=8709678
4. Fujio, Tatsuro. New production method of useful substances using ATP regeneration system. Kiraru Tekunoroji no Shintenkai (2001), 187-198.
5. Porciatti V, Schiavi C, Benedetti P, Baldi A, Campos EC: Cytidine-5'-diphosphocholine improves visual acuity, contrast sensitivity and visually-evoked potentials of amblyopic subjects. Curr Eye Res. 1998 Feb;17(2):141-8.
6. Babb SM, Wald LL, Cohen BM, Villafuerte RA, Gruber SA, Yurgelun-Todd DA, Renshaw PF: Chronic citicoline increases phosphodiesters in the brains of healthy older subjects: an in vivo phosphorus magnetic resonance spectroscopy study. Psychopharmacology (Berl). 2002 May;161(3):248-54. Epub 2002 Mar 22.
7. Alvarez XA, Mouzo R, Pichel V, Perez P, Laredo M, Fernandez-Novoa L, Corzo L, Zas R, Alcaraz M, Secades JJ, Lozano R, Cacabelos R: Double-blind placebo-controlled study with citicoline in APOE genotyped Alzheimer's disease patients. Effects on cognitive performance, brain bioelectrical activity and cerebral perfusion. Methods Find Exp Clin Pharmacol. 1999 Nov;21(9):633-44.
8. Laurence AD, Layton M, Duley JA, Simmonds HA: Elevated erythrocyte CDP-choline levels associated with beta-thalassaemia in patients with transfusion independent anaemia. Nucleosides Nucleotides Nucleic Acids. 2004 Oct;23(8-9):1265-7.
9. Friedman D, Cycowicz YM, Bersick M: The late negative episodic memory effect: the effect of recapitulating study details at test. Brain Res Cogn Brain Res. 2005 May;23(2-3):185-98. Epub 2004 Nov 21.
10. Alvarez XA, Laredo M, Corzo D, Fernandez-Novoa L, Mouzo R, Perea JE, Daniele D, Cacabelos R: Citicoline improves memory performance in elderly subjects. Methods Find Exp Clin Pharmacol. 1997 Apr;19(3):201-10.
11. Paglia DE, Valentine WN, Nakatani M, Rauth BJ: Selective accumulation of cytosol CDP-choline as an isolated erythrocyte defect in chronic hemolysis. Proc Natl Acad Sci U S A. 1983 May;80(10):3081-5.
12. Hayashida K: [Usefulness of SPECT images in helping radiologists understand brain diseases]. Nihon Igaku Hoshasen Gakkai Zasshi. 2001 Apr;61(5):208-14.
13. Renshaw PF, Daniels S, Lundahl LH, Rogers V, Lukas SE: Short-term treatment with citicoline (CDP-choline) attenuates some measures of craving in cocaine-dependent subjects: a preliminary report. Psychopharmacology (Berl). 1999 Feb;142(2):132-8.
14. Weiss GB: Metabolism and actions of CDP-choline as an endogenous compound and administered exogenously as citicoline. Life Sci. 1995;56(9):637-60.
15. Petersen A, Borregaard N: A family with chronic haemolysis and selective accumulation of erythrocyte CDP-choline. Leukemia. 1997 Aug;11(8):1373-6.
16. de la Morena E: Efficacy of CDP-choline in the treatment of senile alterations in memory. Ann N Y Acad Sci. 1991;640:233-6.
17. Secades JJ, Lorenzo JL: Citicoline: pharmacological and clinical review, 2006 update. Methods Find Exp Clin Pharmacol. 2006 Sep;28 Suppl B:1-56.