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Identification
YMDB IDYMDB00090
NameCiticoline
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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 an extremely weak basic (essentially neutral) compound (based on its pKa). Citicoline exists in all eukaryotes, ranging from yeast to humans.
Structure
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Synonyms
  • Audes
  • CDP-choline
  • Cereb
  • Choline 5'-cytidine diphosphate
  • Choline cytidine diphosphate
  • Citicholine
  • Citicoline
  • Citidoline
  • Citifar
  • Colite
  • Corenalin
  • Cyscholin
  • Cytidine 5-diphosphate-trihydrogen
  • Cytidine 5'-(choline diphosphate)
  • Cytidine 5'-(cholinyl pyrophosphate)
  • Cytidine 5'-diphosphate choline
  • Cytidine 5'-diphosphocholine
  • Cytidine choline diphosphate
  • Cytidine diphosphate choline
  • Cytidine diphosphate choline ester
  • Cytidine diphosphocholine
  • Cytidine diphosphorylcholine
  • cytidine-5' diphosphocholine
  • cytidine-5'-pyrophosphate-hydroxycholine
  • Cytidoline
  • Difosfocin
  • Emicholine F
  • Ensign
  • Haocolin
  • Hornbest
  • Neucolis
  • Nicholin
  • Nicolin
  • Niticolin
  • P-hydroxide[2-(trimethylammonio)ethyl] ester
  • Reagin
  • Recofnan
  • Recognan
  • Rexort
  • Sintoclar
  • Somazina
  • Somazine
  • Suncholin
  • [2-CYTIDYLATE-o'-phosphonyloxyl]-ethyl-trimethyl-ammonium
  • CDP-Colina
  • Citicolina
  • Citicolinum
  • Citidin difosfato de colina
  • Cyticholine
  • Cytidindiphosphocholin
  • Cytidine 5'-diphosphoric choline
  • [2-CYTIDYLic acid-o'-phosphonyloxyl]-ethyl-trimethyl-ammonium
  • Cytidine 5'-(choline diphosphoric acid)
  • Cytidine 5'-(cholinyl pyrophosphoric acid)
  • Cidifos
  • Diphosphate choline, cytidine
  • Choline, CDP
  • CDP Choline
  • 5'-Diphosphocholine, cytidine
  • Cytidine 5' diphosphocholine
  • Choline, cytidine diphosphate
CAS number987-78-0
WeightAverage: 488.324
Monoisotopic: 488.107330718
InChI KeyRZZPDXZPRHQOCG-OJAKKHQRSA-N
InChIInChI=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
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 IUPAC 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
Chemical FormulaC14H26N4O11P2
SMILES[H]O[C@@]1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP(=O)(O[H])OP([O-])(=O)OC([H])([H])C([H])([H])[N+](C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])[C@@]1([H])O[H])N1C([H])=C([H])C(=NC1=O)N([H])[H]
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • endoplasmic reticulum
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Choline metabolismPW002494 ThumbThumb?image type=greyscaleThumb?image type=simple
Ether lipid metabolismPW002492 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ERPW002532 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ER PC(10:0/10:0)PW002780 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Ether lipid metabolismec00565 Map00565
Glycerophospholipid metabolismec00564 Map00564
SMPDB Reactions
Citicoline + 1-O-Hexadecyl-2-O-acetyl-sn-glycerolCytidine monophosphate + 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine
1-O-Hexadecyl-2-palmitoyl-sn-glycerol + Citicoline1-O-Palmityl-2-palmitoyl-rac-glycero-3-phosphocholine + Cytidine monophosphate
Citicoline + DG(16:0/16:0/0:0)PC(16:0/16:0) + Cytidine monophosphate + hydron
Citicoline + DG(14:0/14:0/0:0)Cytidine monophosphate + hydron + PC(14:0/14:0)
Citicoline + DG(10:0/10:0/0:0) → Cytidine monophosphate + hydron + PC(10:0/10:0)
KEGG Reactions
Phosphorylcholine + hydron + Cytidine triphosphatePyrophosphate + Citicoline
Citicoline + 1,2-dioleoylglycerolPC(18:1(9Z)/18:1(9Z)) + Cytidine monophosphate
Citicoline + DG(16:0/16:0/0:0) → phosphatidylcholine + Cytidine monophosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Friesen, J. A., Park, Y. S., Kent, C. (2001). "Purification and kinetic characterization of CTP:phosphocholine cytidylyltransferase from Saccharomyces cerevisiae." Protein Expr Purif 21:141-148.11162399
  • Percy, A. K., Carson, M. A., Moore, J. F., Waechter, C. J. (1984). "Control of phosphatidylethanolamine metabolism in yeast: diacylglycerol ethanolaminephosphotransferase and diacylglycerol cholinephosphotransferase are separate enzymes." Arch Biochem Biophys 230:69-81.6324684
  • McMaster, C. R., Bell, R. M. (1994). "Phosphatidylcholine biosynthesis in Saccharomyces cerevisiae. Regulatory insights from studies employing null and chimeric sn-1,2-diacylglycerol choline- and ethanolaminephosphotransferases." J Biol Chem 269:28010-28016.7961735
  • Hjelmstad, R. H., Bell, R. M. (1987). "Mutants of Saccharomyces cerevisiae defective in sn-1,2-diacylglycerol cholinephosphotransferase. Isolation, characterization, and cloning of the CPT1 gene." J Biol Chem 262:3909-3917.3029130
Synthesis Reference:Fujio, Tatsuro. New production method of useful substances using ATP regeneration system. Kiraru Tekunoroji no Shintenkai (2001), 187-198.
External Links:
ResourceLink
CHEBI ID16436
HMDB IDHMDB01413
Pubchem Compound ID291
Kegg IDC00307
ChemSpider ID13207
FOODB IDFDB022608
WikipediaCiticoline
BioCyc IDCDP-CHOLINE

Enzymes

General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Involved in protein-dependent process of phospholipid transport to distribute phosphatidyl choline to the lumenal surface. The multiple transmembrane domains and lumenal hydrophilic domains of the cholinephosphotransferase might participate in the transport process
Gene Name:
CPT1
Uniprot ID:
P17898
Molecular weight:
44829.0
Reactions
CDP-choline + 1,2-diacylglycerol → CMP + a phosphatidylcholine.
General function:
Involved in catalytic activity
Specific function:
CTP + choline phosphate = diphosphate + CDP- choline
Gene Name:
PCT1
Uniprot ID:
P13259
Molecular weight:
49405.80078
Reactions
CTP + choline phosphate → diphosphate + CDP-choline.
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Involved in protein-dependent process of phospholipid transport to distribute phosphatidyl ethanolamine to the lumenal surface. The multiple transmembrane domains and lumenal hydrophilic domains of the ethanolaminephosphotransferase might participate in the transport process. EPT1 catalyzes both choline- and ethanolamine-phosphotransferase reactions
Gene Name:
EPT1
Uniprot ID:
P22140
Molecular weight:
44559.30078
Reactions
CDP-ethanolamine + 1,2-diacylglycerol → CMP + a phosphatidylethanolamine.
CDP-choline + 1,2-diacylglycerol → CMP + a phosphatidylcholine.