{[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 165894
• Molecular Formular: C9H14N3O7P
• Molecular Mass: 307.197121
• Monoisotopic Mass: 307.05693643
• SMILES: n1([C@H]2C[C@H]([C@H](O2)COP(=O)(O)O)O)ccc(nc1=O)N
• Canonical SMILES: O[C@@H]1C[C@@H](O[C@@H]1COP(=O)(O)O)n1ccc(nc1=O)N
• InChI: InChI=1S/C9H14N3O7P/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(19-8)4-18-20(15,16)17/h1-2,5-6,8,13H,3-4H2,(H2,10,11,14)(H2,15,16,17)/t5-,6-,8-/m1/s1
• InChIKey: NCMVOABPESMRCP-ATRFCDNQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxyphosphonic acid
• Synonyms: 2'-Deoxy-5'-cytidylic Acid Hydrate; 2'-Deoxycytidine 5'-(Dihydrogen Phosphate) Hydrate; 2'-Deoxycytidine 5'-Monophosphate Hydrate

Database IDs

• PubChem SID: 162260027
• PubChem CID: 12133245

CALCULATED PROPERTIES

• Acid pKa: 1.2800924
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -4.4607296
• LogD (pH = 7.4): -5.543908
• Log P: -2.284406
• Molar Refractivity: 63.907 cm^3
• Polarizability: 25.347824 Å^3
• Polar Surface Area: 154.91 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D232675

A phosphorylated metabolite of the deoxyribonucleoside 2’-Deoxycytidine. A constituent of Deoxyribonucleic acid. Studies show that it increases influenza virus antigen-induced immune cell proliferation.

REFERENCES

• Holen, E. et al.: Nutrition, 21, 1003 (2005)
• Alexandre, J.A. et al.: Nucleosides Nucleotides Nucelic Acids, 26, 1375 (2005)