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

• ChemBase ID: 160776
• Molecular Formular: C9H12N2O6
• Molecular Mass: 244.20138
• Monoisotopic Mass: 244.06953611
• SMILES: C1(O)[C@@H](CO)O[C@H]([C@H]1O)n1ccc(=O)[nH]c1=O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1ccc(=O)[nH]c1=O
• InChI: InChI=1S/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6?,7-,8-/m1/s1
• InChIKey: DRTQHJPVMGBUCF-RNMRRNDGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-pyrimidine-2,4-dione
• Synonyms: 1-β-D-Arabinofuranosyl-2,4(1H,3H)-pyrimidinedione; Ara-U; Arabinosyluracil; Arauridine; NSC 68928; Spongouridin; Spongouridine; Uracil β-D-Arabinofuranoside; Uracil Arabinoside; 1-β-D-Arabinofuranosyluracil

Database IDs

• CAS Number: 3083-77-0
• PubChem SID: 162254911
• PubChem CID: 46780471

CALCULATED PROPERTIES

• Acid pKa: 9.700741
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.4152691
• LogD (pH = 7.4): -2.4173849
• Log P: -2.4152422
• Molar Refractivity: 52.5656 cm^3
• Polarizability: 20.901344 Å^3
• Polar Surface Area: 119.33 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: 220-222°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A764000

Antiviral agent. Used for the treatment of severe acute respiratory syndrome (SARS).

REFERENCES

• Weber, G., et al.: Cancer Res., 43, 3466 (1983)
• Broet, P., et al.: J. Clin. Oncol., 19, 2778 (1983)
• Galmarini, C., et al.: Leukemia, 15, 875 (1983)
• Barth, R., et al.: Cancer Res., 64, 6287 (1983)
• Song, M., et al.: Bioorg. Med. Chem., 12, 489 (1983)