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

• ChemBase ID: 160917
• Molecular Formular: C8H12N4O5
• Molecular Mass: 244.20468
• Monoisotopic Mass: 244.0807695
• SMILES: [C@H]1(C([C@@H](O[C@@H]1CO)n1c(=O)nc(nc1)N)O)O
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1cnc(nc1=O)N
• InChI: InChI=1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4+,5?,6-/m1/s1
• InChIKey: NMUSYJAQQFHJEW-WGDKFINWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one
• IUPAC Traditional name: 4-amino-1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
• Synonyms: Azacitidine; 4-Amino-1-β-D-ribofuranosyl-1,3,5-triazin-2(1H)-one; 5-AC; 5-AZC; 5-AZCR; 5-AzaC; Antibiotic U 18496; Azacytidine; Ladakamycin; Ledakamycin; Mylosar; NSC 102816; NSC 103-627; U 18496; Vidaza; WR 183027; 5-Azacytidine

Database IDs

• CAS Number: 320-67-2
• PubChem SID: 162255052
• PubChem CID: 57416895

CALCULATED PROPERTIES

• Acid pKa: 12.55147
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -3.0653336
• LogD (pH = 7.4): -3.065336
• Log P: -3.065333
• Molar Refractivity: 52.1932 cm^3
• Polarizability: 20.70783 Å^3
• Polar Surface Area: 140.97 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol
• Apperance: White-to-Off-White Solid
• Melting Point: 235-237°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere

DETAILS

Toronto Research Chemicals - A796000

A potent growth inhibitor and cytotoxic agent. It acts as a demethylating agent by inhibiting DNA methyltransferase.

REFERENCES

• Kusaba, H., et al.: Eur. J. Biochem., 262, 924 (1999)
• Broday, L., et al.: Mol. Cell Biol., 19, 3198 (1999)
• Qian, X., et al.: Am. J. Pathol., 153, 1475 (1999)
• Canova, C., et al.: Mech. Ageing Dev., 101, 153 (1998)