4-amino-1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one

• ChemBase ID: 160924
• Molecular Formular: C8H12N4O4
• Molecular Mass: 228.20528
• Monoisotopic Mass: 228.08585488
• SMILES: [C@H]1(C[C@@H](O[C@@H]1CO)n1c(=O)nc(nc1)N)O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1cnc(nc1=O)N
• InChI: InChI=1S/C8H12N4O4/c9-7-10-3-12(8(15)11-7)6-1-4(14)5(2-13)16-6/h3-6,13-14H,1-2H2,(H2,9,11,15)/t4-,5-,6-/m1/s1
• InChIKey: XAUDJQYHKZQPEU-HSUXUTPPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one
• IUPAC Traditional name: 4-amino-1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
• Synonyms: 4-Amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,3,5-triazin-2(1H)-one; 2-Desoxy-5-azacytidine; 2'-Deoxy-5-azacytidine; DAC; Dacogen; Decitabine; NSC 127716; β-Decitabine; 5-Aza-2'-deoxy Cytidine

Database IDs

• CAS Number: 2353-33-5
• PubChem SID: 162255059
• PubChem CID: 42104882

CALCULATED PROPERTIES

• Acid pKa: 13.894836
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -2.1646957
• LogD (pH = 7.4): -2.164695
• Log P: -2.1646948
• Molar Refractivity: 50.6825 cm^3
• Polarizability: 19.995268 Å^3
• Polar Surface Area: 120.74 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: >200°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A796950

Used as cancer treatment, in particular to inhibit the growth of pancreatic endocrine tumor cell lines.

REFERENCES

• Deng, T., et al.: Life Sci., 84, 311 (2009)
• Horne, H., et al.: Mol. Cancer Res., 7, 199 (2009)
• Zinner, R., et al.: Mol. Cancer Ther., 8, 521 (2009)