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

• ChemBase ID: 161079
• Molecular Formular: C9H11N5O6
• Molecular Mass: 285.21354
• Monoisotopic Mass: 285.0709331
• SMILES: n1([C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)cc(c(=O)[nH]c1=O)N=[N+]=[N-]
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cc(N=[N+]=[N-])c(=O)[nH]c1=O
• InChI: InChI=1S/C9H11N5O6/c10-13-12-3-1-14(9(19)11-7(3)18)8-6(17)5(16)4(2-15)20-8/h1,4-6,8,15-17H,2H2,(H,11,18,19)/t4-,5-,6-,8-/m1/s1
• InChIKey: VOPROYOABONMOS-UAKXSSHOSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 1355028-82-8
• PubChem SID: 162255214
• PubChem CID: 20832934

CALCULATED PROPERTIES

• Acid pKa: 9.2705
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.4861395
• LogD (pH = 7.4): -2.4918127
• Log P: -2.3720212
• Molar Refractivity: 60.8255 cm^3
• Polarizability: 23.322956 Å^3
• Polar Surface Area: 148.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A926800

Used in a method and kit for labeling nucleic acid in living cells. The labeled nucleic acid can be used for detecting cell proliferation and cell apoptosis, labeling plasmid vector, virus, small interfering RNA and microRNA, and studying early developme