You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Bovine Metabolome Database.
Record Information
Version1.0
Creation Date2016-09-30 22:45:35 UTC
Update Date2020-05-21 16:27:01 UTC
BMDB IDBMDB0001413
Secondary Accession Numbers
  • BMDB01413
Metabolite Identification
Common 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 is a drug. Citicoline is an extremely weak basic (essentially neutral) compound (based on its pKa). Citicoline exists in all eukaryotes, ranging from yeast to humans. In cattle, citicoline is involved in the metabolic pathway called phospholipid biosynthesis pathway.
Structure
Thumb
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 Weight488.324
Monoisotopic Molecular Weight488.107330718
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
CAS Registry Number987-78-0
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
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
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
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fr-7649200000-859d046834f1fbd3d535View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00yi-7947012000-9f83d07fb5a59a93e770View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-0001900000-a9f38ff6b185b45f04b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03e9-0590000000-b021677d064d65810ee0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-0900000000-7570bbb10dd9fa288442View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-0000900000-8b411373962b073b4d22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-000i-0001900000-6e7cc437ad79eb13c032View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-01qi-1932200000-9c3803cefdd9c6285a7cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004i-6505900000-3d534aab6e40915c3642View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004i-6505900000-fc13e5ad403e7faf8218View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-6505900000-3d534aab6e40915c3642View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-6505900000-fc13e5ad403e7faf8218View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0000900000-8b411373962b073b4d22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0001900000-6e7cc437ad79eb13c032View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01qi-1932200000-4a7ae92c6e127d2ce453View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2900100000-0ce672506aae2d1e5eefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3900000000-c05f3e5b6782e32eeebbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-8900000000-17466c845e643c77969bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01p9-0501900000-be567596c9f980cea8c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3904100000-4c2e6535887540a12444View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fu-9600000000-e42f82159eabb4ec781aView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Brain
  • Erythrocyte
  • Intestine
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
ErythrocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001413
DrugBank IDDB04290
Phenol Explorer Compound IDNot Available
FooDB IDFDB022608
KNApSAcK IDC00007231
Chemspider ID13207
KEGG Compound IDC00307
BioCyc IDNot Available
BiGG ID1485298
Wikipedia LinkCiticoline
METLIN ID6229
PubChem Compound13804
PDB IDNot Available
ChEBI ID16436
References
Synthesis ReferenceFujio, Tatsuro. New production method of useful substances using ATP regeneration system. Kiraru Tekunoroji no Shintenkai (2001), 187-198.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in ADP-ribose diphosphatase activity
Specific function:
Hydrolyzes ADP-ribose, IDP-ribose, CDP-glycerol, CDP-choline and CDP-ethanolamine, but not other non-reducing ADP-sugars or CDP-glucose. May be involved in immune cell signaling as suggested by the second-messenger role of ADP-ribose, which activates TRPM2 as a mediator of oxidative/nitrosative stress (By similarity).
Gene Name:
ADPRM
Uniprot ID:
A7YY53
Molecular weight:
39235.0
General function:
Lipid transport and metabolism
Specific function:
Catalyzes phosphatidylcholine biosynthesis from CDP-choline. It thereby plays a central role in the formation and maintenance of vesicular membranes (By similarity).
Gene Name:
CHPT1
Uniprot ID:
Q1LZE6
Molecular weight:
45249.0
Reactions
Citicoline → PC(16:0/16:0) + DG(16:0/16:0/0:0)details
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Plays an important role in the biosynthesis of the phospholipid phosphatidylethanolamine. Catalyzes the formation of CDP-ethanolamine (By similarity).
Gene Name:
PCYT2
Uniprot ID:
Q5EA75
Molecular weight:
44158.0
Reactions
Cytidine triphosphate + Phosphorylcholine → Pyrophosphate + Citicolinedetails
Phosphorylcholine → Citicolinedetails
General function:
Energy production and conversion
Specific function:
Has glycerophosphoinositol phosphodiesterase activity. Hydrolyzes lysoglycerophospholipids to produce lysophosphatidic acid (LPA) and the corresponding amines. Has little or no activity towards glycerophosphocholine. GDE1 activity can be modulated by G-protein signaling pathways (By similarity).
Gene Name:
GDE1
Uniprot ID:
Q3T0T0
Molecular weight:
37653.0
Reactions
Citicoline → Glycerol 3-phosphate + Cholinedetails
General function:
Involved in hydrolase activity
Specific function:
Acts as a acyl-protein thioesterase hydrolyzing fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS (By similarity). Has depalmitoylating activity toward KCNMA1 (By similarity). Acts as a lysophospholipase hydrolyzing various lysophospholipids including lysophosphatidylcholine (lyso-PC), lysophosphatidylethanolamine (lyso-PE), lysophosphatidylinositol (lyso-PI) and lysophosphatidylserine (lyso-PS) (By similarity). Has much higher thioesterase activity than lysophospholipase activity (By similarity). Contributes to the production of lysophosphatidic acid (LPA) during blood coagulation by recognizing and cleaving plasma phospholipids to generate lysophospholipids which in turn act as substrates for ENPP2 to produce LPA (By similarity).
Gene Name:
LYPLA1
Uniprot ID:
Q3MHR0
Molecular weight:
24596.0
Reactions
LysoPC(16:0/0:0) → Citicolinedetails