2-sulfanyl-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one

• ChemBase ID: 78066
• Molecular Formular: C6H5N3OS
• Molecular Mass: 167.1884
• Monoisotopic Mass: 167.0153328
• SMILES: [nH]1ccc2c1nc([nH]c2=O)S
• Canonical SMILES: Sc1[nH]c(=O)c2c(n1)[nH]cc2
• InChI: InChI=1S/C6H5N3OS/c10-5-3-1-2-7-4(3)8-6(11)9-5/h1-2H,(H3,7,8,9,10,11)
• InChIKey: QCZHCRBHXAFBDJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-sulfanyl-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one
• IUPAC Traditional name: 2-sulfanyl-3H,7H-pyrrolo[2,3-d]pyrimidin-4-one
• Synonyms: 7-Deaza-6-hydroxy-2-mercaptopurine; 2-Thioxo-7-deazahypoxanthine; NSC 25976; 1,2,3,7-Tetrahydro-2-thioxo-4H-pyrrolo[2,3-d]pyrimidin-4-one; 7-Deaza-2-mercapto-hypoxanthine; 3,7-Dihydro-2-sulphanyl-4H-pyrrolo[2,3-d]pyrimidin-4-one; 3,7-Dihydro-2-mercapto-4H-pyrrolo[2,3-d]pyrimidin-4-one; 3,7-Dihydro-2-thio-4H-pyrrolo[2,3-d]pyrimidin-4-one

Database IDs

• CAS Number: 67831-84-9
• MDL Number: MFCD12196502
• PubChem SID: 162042898
• PubChem CID: 4091939

CALCULATED PROPERTIES

• Acid pKa: 6.366825
• H Acceptors: 2
• H Donor: 3
• LogD (pH = 5.5): 0.9012046
• LogD (pH = 7.4): 0.12279387
• Log P: 0.92952704
• Molar Refractivity: 44.6703 cm^3
• Polarizability: 15.834865 Å^3
• Polar Surface Area: 57.25 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Aqueous Alkali; DMF
• Apperance: Colourless Crystalline Solid
• Melting Point: 335-345°C dec.

Safety Information

• Storage Warning: Harmful/Irritant/Keep Cold

DETAILS

Toronto Research Chemicals - D201700

Activator of Xanthine oxidase

REFERENCES

• Reigan, P., et al.: Bioorg. Med. Chem. Lett., 14, 5247 (2004)
• Reigan, P., et al.: Eur. J. Med. Chem., 43, 1248 (2004)