7H-purine-2-thiol

• ChemBase ID: 104294
• Molecular Formular: C5H4N4S
• Molecular Mass: 152.17706
• Monoisotopic Mass: 152.01566715
• SMILES: Sc1nc2c([nH]cn2)cn1
• Canonical SMILES: Sc1ncc2c(n1)nc[nH]2
• InChI: InChI=1S/C5H4N4S/c10-5-6-1-3-4(9-5)8-2-7-3/h1-2H,(H2,6,7,8,9,10)
• InChIKey: HDBQZGJWHMCXIL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7H-purine-2-thiol; 9H-purine-2-thiol
• IUPAC Traditional name: 7H-purine-2-thiol; 9H-purine-2-thiol
• Synonyms: 2-Thiopurine; 2-MERCAPTOPURINE; 2-MP; 2-Purinethiol; 2-Mercaptopurine

Database IDs

• CAS Number: 28128-19-0
• EC Number: 248-855-0
• MDL Number: MFCD00047145
• PubChem SID: 24897120; 162091030
• PubChem CID: 3015569

CALCULATED PROPERTIES

• Acid pKa: 9.284596
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.47537297
• LogD (pH = 7.4): 0.47005153
• Log P: 0.4754489
• Molar Refractivity: 39.5412 cm^3
• Polarizability: 15.285526 Å^3
• Polar Surface Area: 54.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: yellow crystalline
• Melting Point: > 300°C

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-41
• Safety Statements: 26-39
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: ≥95%

DETAILS

MP Biomedicals - 05204218

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02155356

Yellow crystals.

Sigma Aldrich - M6875

Application
2-Mercaptopurine (2-MP), a thiopurine and analog of the anti-cancer drug 6-mercaptopurine (6-MP), has been used to study the substrate and binding specificity and kinetics of xanthine oxidase-catalyzed hydroxylation and myeloperoxidase (MPO) reactions. 2-Mercaptopurine inhibited lipopolysacharide (LPS)-dependent nitric oxide (NO) production in B cells.