1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-(2H3)methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 161004
• Molecular Formular: C10H13N5O4
• Molecular Mass: 267.24132
• Monoisotopic Mass: 267.09675392
• SMILES: [nH]1c(=O)c(cn(c1=O)[C@H]1C[C@@H]([C@H](O1)CO)N=[N+]=[N-])C
• Canonical SMILES: OC[C@H]1O[C@H](C[C@@H]1N=[N+]=[N-])n1cc(C)c(=O)[nH]c1=O
• InChI: InChI=1S/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1
• InChIKey: HBOMLICNUCNMMY-XLPZGREQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-(^2H₃)methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-(^2H₃)methyl-3H-pyrimidine-2,4-dione
• Synonyms: AZT-d3; Zidovudine-d3; Retrovis-d3; Timazid-d3; Retrovir-d3; NSC 602670-d3; 3'-Azido-3'-deoxythymidine, Methyl-d3

Database IDs

• PubChem SID: 162255139
• PubChem CID: 71313574

CALCULATED PROPERTIES

• Acid pKa: 9.960416
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.41276968
• LogD (pH = 7.4): -0.41393453
• Log P: -0.29870915
• Molar Refractivity: 61.7045 cm^3
• Polarizability: 23.694994 Å^3
• Polar Surface Area: 108.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off White Solid
• Melting Point: 118-120°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A825002

A deuterated, potent and selective inhibitor of HIV-1 replication.

REFERENCES

• Mitsuya, H., et al.: Nature, 325, 773 (1987)
• Brehm, J., et al.: Biochem., 47, 14020 (1987)
• Paredes, R., et al.: J. Virol., 83, 2038 (1987)
• Wan, J., et al.: J. Med. Chem., 52, 1144 (1987)
• Mainardes, R., et al.: J. Pharm. Sci., 98, 257 (1987)