sodium 2-(trimethylazaniumyl)ethyl ({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphonate

• ChemBase ID: 164810
• Molecular Formular: C14H25N4NaO11P2
• Molecular Mass: 510.305792
• Monoisotopic Mass: 510.08927518
• SMILES: [C@@H]1([C@H]([C@@H](O[C@@H]1COP(=O)(OP(=O)(OCC[N+](C)(C)C)[O-])[O-])n1ccc(nc1=O)N)O)O.[Na+]
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(OCC[N+](C)(C)C)[O-])[O-])O[C@H]([C@@H]1O)n1ccc(nc1=O)N.[Na+]
• InChI: InChI=1S/C14H26N4O11P2.Na/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);/q;+1/p-1/t9-,11-,12-,13-;/m1./s1
• InChIKey: YWAFNFGRBBBSPD-OCMLZEEQSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 2-(trimethylazaniumyl)ethyl ({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphonate
• IUPAC Traditional name: sodium cdp-choline(1-)
• Synonyms: Cytidine 5'-(Trihydrogen Diphosphate) P'-[2-(Trimethylammonio)ethyl] Ester Inner Salt Sodium Salt; Acticolin; Brassel; Cebroton; Cidifos; Citicoline Sodium; Flussorex; Gerolin; IP 302 Sodium; Logan; Neurotron; Sinkron; Citicoline Sodium Salt; Cytidine 5'-(Trihydrogen Diphosphate) P'-[2-(Trimethylammonio-d9)ethyl] Ester Inner Salt Sodium Salt; Acticolin-d9; Brassel-d9; Cebroton-d9; Cidifos-d9; Citicoline-d9 Sodium; Flussorex-d9; Gerolin-d9; IP 302-d9 Sodium; Logan-d9; Neurotron-d9; Sinkron-d9; Citicoline-d9 Sodium Salt

Database IDs

• CAS Number: 33818-15-4
• PubChem SID: 162258944
• PubChem CID: 36605

CALCULATED PROPERTIES

• Acid pKa: 1.8501823
• H Acceptors: 10
• H Donor: 3
• LogD (pH = 5.5): -7.0900073
• LogD (pH = 7.4): -7.454044
• Log P: -7.108613
• Molar Refractivity: 112.4622 cm^3
• Polarizability: 41.268536 Å^3
• Polar Surface Area: 216.33 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 259-268°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C508052

Labelled Citicoline (C508050). Naturally occurring nucleotide; intermediate in the major pathway of lecitin biosynthesis. Neuroprotective. It is used in the treatment of ischemic stroke and head trauma.

Toronto Research Chemicals - C508050

Naturally occurring nucleotide; intermediate in the major pathway of lecitin biosynthesis. Neuroprotective. It is used in the treatment of ischemic stroke and head trauma.

REFERENCES

• Kennedy, E.P., et al.: J. Biol. Chem., 222, 185 (1956)
• Rao, A., et al.: J. Neurosci. Res., 58, 697 (1956)
• Wurtman, R., et al.: Biochem. Pharmacol., 60, 989 (1956)
• Kennedy, E.P., et al.: J. Biol. Chem., 222, 185 (1956)
• Rao, A., et al.: J. Neurosci. Res., 58, 697 (1956)
• Wurtman, R., et al.: Biochem. Pharmacol., 60, 989 (1956)