4-amino-1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidine-2-thione

• ChemBase ID: 178557
• Molecular Formular: C9H13N3O3S
• Molecular Mass: 243.28282
• Monoisotopic Mass: 243.06776229
• SMILES: [C@H]1(C[C@@H](O[C@@H]1CO)n1c(=S)nc(cc1)N)O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1ccc(nc1=S)N
• InChI: InChI=1S/C9H13N3O3S/c10-7-1-2-12(9(16)11-7)8-3-5(14)6(4-13)15-8/h1-2,5-6,8,13-14H,3-4H2,(H2,10,11,16)/t5-,6-,8-/m1/s1
• InChIKey: WMLHZFBXLAULRZ-ATRFCDNQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidine-2-thione
• IUPAC Traditional name: 4-amino-1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2-thione
• Synonyms: 2-Thio-2’-deoxycytidine; 2'-Deoxy-2-thiocytidine; 2-Thio-2'-deoxy Cytidine

Database IDs

• CAS Number: 169557-13-5
• PubChem SID: 164234467
• PubChem CID: 71752528

CALCULATED PROPERTIES

• Acid pKa: 13.895004
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.0070804
• LogD (pH = 7.4): -1.0070107
• Log P: -1.0070096
• Molar Refractivity: 61.025 cm^3
• Polarizability: 24.048525 Å^3
• Polar Surface Area: 91.31 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T350050

2-Thio-2’-deoxy Cytidine is a 2-thiopyrimidine nucleoside with ant-viral activity.

REFERENCES

• Shigeta, S. et al.: Antiviral Chem. Chemother., 10, 195 (1999)
• Bretner, M. et al.: Nucelos. Nuclet., 14, 657 (1999)