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

• ChemBase ID: 159990
• Molecular Formular: C10H15N3O4
• Molecular Mass: 241.2438
• Monoisotopic Mass: 241.10625598
• SMILES: C1C([C@H](O[C@H]1n1c(=O)[nH]c(=O)c(c1)C)CO)N
• Canonical SMILES: OC[C@H]1O[C@H](CC1N)n1cc(C)c(=O)[nH]c1=O
• InChI: InChI=1S/C10H15N3O4/c1-5-3-13(10(16)12-9(5)15)8-2-6(11)7(4-14)17-8/h3,6-8,14H,2,4,11H2,1H3,(H,12,15,16)/t6?,7-,8-/m1/s1
• InChIKey: ADVCGXWUUOVPPB-SPDVFEMOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,5S)-4-amino-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,5S)-4-amino-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-3H-pyrimidine-2,4-dione
• Synonyms: 3’-Amino-3’-deoxy-thymidine; 3’-Deoxy-3’-aminothymidine; AMT; 3'-Amino-3'-deoxythymidine

Database IDs

• CAS Number: 52450-18-7
• PubChem SID: 162254125
• PubChem CID: 21118337

CALCULATED PROPERTIES

• Acid pKa: 9.995324
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -4.098751
• LogD (pH = 7.4): -2.7118218
• Log P: -1.5163128
• Molar Refractivity: 57.0695 cm^3
• Polarizability: 22.836971 Å^3
• Polar Surface Area: 104.89 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Etanol; Methanol
• Apperance: Off-White Solid
• Melting Point: 161-162°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A604250

A metabolite of Zidovudine (3'-Azido-3'-deoxythymidine; AZT).

REFERENCES

• Von Tungeln, L., et al.: Carcinogenesis, 23, 1427 (1994)
• Qian, M., et al.: Biochem. Pharmacol., 48, 383 (1994)
• Diwan, B., et al.: Toxicol. Appl. Pharmacol., 161, 82 (1994)
• Lim, S., et al.: J. Biol. Chem., 276, 23616 (1994)