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

• ChemBase ID: 102248
• Molecular Formular: C8H12N4O5
• Molecular Mass: 244.20468
• Monoisotopic Mass: 244.0807695
• SMILES: Nc1nc(=O)n(cn1)C1OC(CO)C(O)C1O
• Canonical SMILES: OCC1OC(C(C1O)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)
• InChIKey: NMUSYJAQQFHJEW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one
• IUPAC Traditional name: @azacitidine
• Synonyms: 4-Amino-1-beta-D-Ribofuranosyl-D-Triazin-2-(1H)-one; Ladakamycin; 5-AZACYTIDINE

Database IDs

• CAS Number: 320-67-2
• EC Number: 206-280-2
• PubChem SID: 162089559
• PubChem CID: 1805

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

• Melting Point: 228°C

Safety Information

• Storage Condition: 0°C
• RTECS: XZ3017500
• European Hazard Symbols: Toxic (T)
• Risk Statements: R:45
• Safety Statements: S:28-36/37/39-45-53

DETAILS

MP Biomedicals - 02100821

A powerful mutagen. The molecule is incorporated to form nonsense RNA, but in addition, slowly degrades with time.
SUSPECTED CANCER AGENT!