6-(methylsulfanyl)-9H-purine

• ChemBase ID: 101604
• Molecular Formular: C6H6N4S
• Molecular Mass: 166.20364
• Monoisotopic Mass: 166.03131721
• SMILES: c12c([nH]cn1)ncnc2SC
• Canonical SMILES: CSc1ncnc2c1nc[nH]2
• InChI: InChI=1S/C6H6N4S/c1-11-6-4-5(8-2-7-4)9-3-10-6/h2-3H,1H3,(H,7,8,9,10)
• InChIKey: UIJIQXGRFSPYQW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(methylsulfanyl)-9H-purine; 6-(methylsulfanyl)-7H-purine
• IUPAC Traditional name: 6-methylthiopurine; 6-(methylthio)purine
• Synonyms: 6-(methylsulfanyl)-9H-purine; 6-(Methylthio)purine; 6-METHYLMERCAPTOPURINE; 6-Methylmercaptopurine; 6-(Methylthio)-9H-purine; NSC 20105; S-Methyl-6-mercaptopurine; SQ 8343; 6-(Methylmercapto)purine; 6-(Methylthio)purine; 6-(Methylthio)purine; 6-(甲硫基)嘌呤; 6-甲巯基嘌呤; 6-(甲硫基)嘌呤

Database IDs

• CAS Number: 50-66-8
• EC Number: 200-057-3
• MDL Number: MFCD00005576; MFCD00225354
• Beilstein Number: 7695
• PubChem SID: 162087168
• PubChem CID: 5778

CALCULATED PROPERTIES

• Acid pKa: 8.977497
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.8029285
• LogD (pH = 7.4): 0.87238497
• Log P: 0.88367283
• Molar Refractivity: 46.278 cm^3
• Polarizability: 17.11955 Å^3
• Polar Surface Area: 54.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 213-215°C; 220-223°C; 221-222 °C(lit.); 221-222°C

Safety Information

• Storage Condition: 0°C; Refrigerator
• RTECS: UO8976000
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C6H6N4S

DETAILS

MP Biomedicals - 02102332

Crystalline

MP Biomedicals - 05203517

MP Biomedicals Rare Chemical collection

Toronto Research Chemicals - M320270

Metabolite of 6-Mercaptopurine, an immunosuppressive drug used to treat leukemia.

REFERENCES

• Chou, C., et al.: Biochem. Pharmacol., 75, 1601 (2008)
• Conejo-Garcia, A., et al.: Eur. J. Med. Chem., 43, 1742 (2008)
• Hawwa, A., et al.: Brit. J. Clin. Pharmacol., 66, 826 (2008)
• Askanase, A., et al.: J. Rheumatol., 36, 89 (2008)