6-[(2H3)methylsulfanyl]-7H-purin-2-amine

• ChemBase ID: 174356
• Molecular Formular: C6H7N5S
• Molecular Mass: 181.21828
• Monoisotopic Mass: 181.04221625
• SMILES: n1c(nc2c(c1SC)[nH]cn2)N
• Canonical SMILES: CSc1nc(N)nc2c1[nH]cn2
• InChI: InChI=1S/C6H7N5S/c1-12-5-3-4(9-2-8-3)10-6(7)11-5/h2H,1H3,(H3,7,8,9,10,11)
• InChIKey: YEGKYFQLKYGHAR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-[(^2H₃)methylsulfanyl]-7H-purin-2-amine
• IUPAC Traditional name: 6-[(^2H₃)methylsulfanyl]-7H-purin-2-amine
• Synonyms: 6-[(Methyl-d3)thio]-1H-purin-2-amine; 2-Amino-6-(methyl-d3)mercaptopurine; NSC 29420-d3; 2-Amino-6-(methyl-d3)thiopurine; S-(Methyl-d3)-6-thioguanine; S6-(Methyl-d3)-6-thioguanine; 6-Methylthioguanine-d3

Database IDs

• PubChem SID: 164230266
• PubChem CID: 71750616

CALCULATED PROPERTIES

• Acid pKa: 10.575983
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.7333762
• LogD (pH = 7.4): 0.733271
• Log P: 0.7335329
• Molar Refractivity: 50.9244 cm^3
• Polarizability: 18.261282 Å^3
• Polar Surface Area: 80.48 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M330722

A labelled metabolite of 2’-Deoxy-6-thio Guanosine (D281650) and 6-Thioguanine. An effective immunosuppressant and anticancer agent, however chronic exposure can be mutagenic in human cells as long-term use of thiopurines was found to be associated with a

REFERENCES

• Loo, T.L. et al.: Cancer Chemother. Pharmacol., 6, 131 (1981)
• Yuan, B. et al.: ACS Chem. Biol., 5, 1021 (1981)
• Kroplin, T. et al.: Adv. Exp. Med. Biol., 431, 741 (1981)