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

• ChemBase ID: 166034
• Molecular Formular: C9H12N2O5
• Molecular Mass: 228.20198
• Monoisotopic Mass: 228.07462149
• SMILES: [nH]1c(=O)n(ccc1=O)[C@H]1C(C[C@H](O1)CO)O
• Canonical SMILES: OC1C[C@H](O[C@H]1n1ccc(=O)[nH]c1=O)CO
• InChI: InChI=1S/C9H12N2O5/c12-4-5-3-6(13)8(16-5)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6?,8+/m0/s1
• InChIKey: QOXJRLADYHZRGC-OHEWIBQUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,5S)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,5S)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-pyrimidine-2,4-dione
• Synonyms: 3'-Deoxyuridine; 3'-Deoxy Uridine

Database IDs

• CAS Number: 7057-27-4
• PubChem SID: 162260167
• PubChem CID: 44374620

CALCULATED PROPERTIES

• Acid pKa: 9.701471
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.7249745
• LogD (pH = 7.4): -1.7270865
• Log P: -1.7249475
• Molar Refractivity: 51.4685 cm^3
• Polarizability: 20.191685 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMSO; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 176-177°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D288000

A potential anti-cancer and anti-viral agents.

REFERENCES

• Lin, T-S., et al.: J. Med. Chem., 34, 693 (1991)