1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 133624
• Molecular Formular: C9H11N5O4
• Molecular Mass: 253.21474
• Monoisotopic Mass: 253.08110386
• SMILES: c1cn(c(=O)[nH]c1=O)[C@H]1C[C@H]([C@H](O1)CO)N=[N+]=[N-]
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1N=[N+]=[N-])n1ccc(=O)[nH]c1=O
• InChI: InChI=1S/C9H11N5O4/c10-13-12-5-3-8(18-6(5)4-15)14-2-1-7(16)11-9(14)17/h1-2,5-6,8,15H,3-4H2,(H,11,16,17)/t5-,6-,8-/m1/s1
• InChIKey: ZSNNBSPEFVIUDS-ATRFCDNQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-3H-pyrimidine-2,4-dione
• Synonyms: 3′-Azido-2′,3′-dideoxyuridine

Database IDs

• CAS Number: 84472-85-5
• MDL Number: MFCD00132947
• PubChem SID: 24890913; 162227901
• PubChem CID: 452029

CALCULATED PROPERTIES

• Acid pKa: 9.705851
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.808332
• LogD (pH = 7.4): -0.810423
• Log P: -0.69425964
• Molar Refractivity: 57.3474 cm^3
• Polarizability: 21.888466 Å^3
• Polar Surface Area: 108.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (TLC)

DETAILS

Sigma Aldrich - A4810

Biochem/physiol Actions
Inhibitor of HIV replication.
Application
3′-Azido-2′,3′-dideoxyuridine has shown potent anti-HIV activity in vitro.