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

• ChemBase ID: 134026
• Molecular Formular: C8H11N3O6
• Molecular Mass: 245.18944
• Monoisotopic Mass: 245.06478509
• SMILES: c1c(=O)[nH]c(=O)n(n1)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1ncc(=O)[nH]c1=O
• InChI: InChI=1S/C8H11N3O6/c12-2-3-5(14)6(15)7(17-3)11-8(16)10-4(13)1-9-11/h1,3,5-7,12,14-15H,2H2,(H,10,13,16)/t3-,5-,6-,7-/m1/s1
• InChIKey: WYXSYVWAUAUWLD-SHUUEZRQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,3,4,5-tetrahydro-1,2,4-triazine-3,5-dione
• IUPAC Traditional name: AzUR
• Synonyms: 2-β-D-Ribofuranosyl-1,2,4-triazine-3,5(2H,4H)-dione; 6-Azauracil riboside; 6-Azauridine

Database IDs

• CAS Number: 54-25-1
• EC Number: 200-199-6
• MDL Number: MFCD00006472
• PubChem SID: 162228303; 24890597
• PubChem CID: 5901

CALCULATED PROPERTIES

• Acid pKa: 7.7811575
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.3942468
• LogD (pH = 7.4): -2.5409417
• Log P: -2.3920054
• Molar Refractivity: 50.6182 cm^3
• Polarizability: 20.132685 Å^3
• Polar Surface Area: 131.69 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 157-159 °C(lit.)

Safety Information

• RTECS: XY8575000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-40
• Safety Statements: 22-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332-H351
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - A1882

Application
6-Azauridine (AzUrd) blocks the conversion of orotic acid into UMP and it is used in antiviral studies.