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

• ChemBase ID: 132476
• Molecular Formular: C14H25N4NaO11P2
• Molecular Mass: 510.305792
• Monoisotopic Mass: 510.08927518
• SMILES: C[N+](C)(C)CCOP(=O)([O-])OP(=O)([O-])OCC1[C@H]([C@H](C(O1)n1ccc(nc1=O)N)O)O.[Na+]
• Canonical SMILES: O[C@@H]1C(COP(=O)(OP(=O)(OCC[N+](C)(C)C)[O-])[O-])OC([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-MBWJOHGMSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 2-(trimethylazaniumyl)ethyl ({[(3S,4R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphonate
• IUPAC Traditional name: sodium 2-(trimethylammonio)ethyl {[(3S,4R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxyphosphonate
• Synonyms: CDP-choline-Na; CDP-coline; Citicoline sodium; P′-[2-(Trimethylammonio)-ethyl]-ester cytidine 5′-(tri-hydro-gen di-phos-phate) inner salt monosodium; Cytidine 5′-diphosphocholine sodium salt dihydrate; Cytidine 5′-diphosphocholine sodium salt hydrate

Database IDs

• CAS Number: 33818-15-4; 33818-15-4(anhydrous)
• MDL Number: MFCD00150508
• Beilstein Number: 4110040
• PubChem SID: 24858280; 162226753; 24278064
• PubChem CID: 16211925

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: H2O: soluble100 mg/mL
• Apperance: white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ~98%; ≥99.0% (HPLC)
• Impurities: ≤8% water
• Biological Source: from yeast
• Empirical Formula (Hill Notation): C14H25N4NaO11P2 · xH2O

DETAILS

Sigma Aldrich - C0256

Biochem/physiol Actions
Neuroprotective in situations of hypoxia and ischemia; biosynthetic intermediate of membrane phospholipids; cerebral vasodilator; inhibits PLA2 activation.
Caution
Hygroscopic

Sigma Aldrich - 30290

Application
Cytidine 5′-diphosphocholine (CDP-choline) is generated by choline-phosphate cytidylyltransferase EC 2.7.7.15 in support of the synthesis of phosphatidylcholine. CDP-choline is being used in studies of its affects on neurorecovery.