{[(2R,3R,5R)-5-[4-amino-2-oxo-1,2-dihydro(1,3,5-15N3)-1,3,5-triazin-1-yl]-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 160927
• Molecular Formular: C8H13N4O7P
• Molecular Mass: 312.15881659
• Monoisotopic Mass: 312.04032498
• SMILES: [C@H]1(C[C@@H](O[C@@H]1COP(=O)(O)O)[15n]1c(=O)[15n]c([15n]c1)[15NH2])O
• Canonical SMILES: O[C@@H]1C[C@@H](O[C@@H]1COP(=O)(O)O)[15n]1c[15n]c([15n]c1=O)[15NH2]
• InChI: InChI=1S/C8H13N4O7P/c9-7-10-3-12(8(14)11-7)6-1-4(13)5(19-6)2-18-20(15,16)17/h3-6,13H,1-2H2,(H2,9,11,14)(H2,15,16,17)/t4-,5-,6-/m1/s1/i9+1,10+1,11+1,12+1
• InChIKey: JQHZISUSXMJEPR-LTMNYYGGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3R,5R)-5-[4-amino-2-oxo-1,2-dihydro(1,3,5-^1^5N₃)-1,3,5-triazin-1-yl]-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: [(2R,3R,5R)-5-[4-amino-2-oxo(1,3,5-^1^5N₃)-1,3,5-triazin-1-yl]-3-hydroxyoxolan-2-yl]methoxyphosphonic acid
• Synonyms: 4-Amino-1-(2-deoxy-5-O-phosphono-β-D-erythro-pentofuranosyl)-1,3,5-triazin-2(1H)-one-15N4; 5-Aza-2'-deoxy Cytidine-15N4 5'-Monophosphate

Database IDs

• PubChem SID: 162255062
• PubChem CID: 71313543

CALCULATED PROPERTIES

• Acid pKa: 1.2450982
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -4.72846
• LogD (pH = 7.4): -5.8117256
• Log P: -2.4727328
• Molar Refractivity: 61.5554 cm^3
• Polarizability: 24.589376 Å^3
• Polar Surface Area: 167.27 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A796962

A labelled metabolite of Azadeoxycytidine (A796950), as neoplasm inhibitor.

REFERENCES

• Cihak, A., et al.: Eur. J. Cancer, 14, 117 (1978)