2-amino-9-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purine-6-thione

• ChemBase ID: 166018
• Molecular Formular: C10H13N5O3S
• Molecular Mass: 283.30692
• Monoisotopic Mass: 283.0739103
• SMILES: c12c(c(=S)nc([nH]1)N)ncn2[C@H]1C[C@H]([C@H](O1)CO)O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1cnc2c1[nH]c(N)nc2=S
• InChI: InChI=1S/C10H13N5O3S/c11-10-13-8-7(9(19)14-10)12-3-15(8)6-1-4(17)5(2-16)18-6/h3-6,16-17H,1-2H2,(H3,11,13,14,19)/t4-,5-,6-/m1/s1
• InChIKey: SCVJRXQHFJXZFZ-HSUXUTPPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purine-6-thione
• IUPAC Traditional name: 2-amino-9-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-6-thione
• Synonyms: 2-Amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-9H-purine-6(1H)-thione; 2-Amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercaptopurine; 2'-Deoxythioguanosine; 2'-Desoxy-6-thioguanosine; NSC 71261; TGdR; Thioguanine Deoxyriboside; β-Thioguanine Deoxyriboside; 2'-Deoxy-6-thio Guanosine

Database IDs

• CAS Number: 789-61-7
• PubChem SID: 162260151
• PubChem CID: 12852974

CALCULATED PROPERTIES

• Acid pKa: 9.132695
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.0530834
• LogD (pH = 7.4): -1.0573891
• Log P: -1.0480998
• Molar Refractivity: 70.6679 cm^3
• Polarizability: 27.054274 Å^3
• Polar Surface Area: 117.92 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D281650

Guanosine (G837900) derivative with cancer chemotherapeutic properties. It is involved in the inhibition of human RNase H-mediated RNA cleavage from DNA-RNA duplexes via incorporation into DNA.

REFERENCES

• Momparler, R.L. et al.: Cancer Treat. Rep., 62, 135 (1978)
• Krynetskaia, N.F. et al.: Mol. Pharmacol., 56, 841 (1978)