2-(hydroxymethyl)-5-[6-(methylsulfanyl)-9H-purin-9-yl]oxolane-3,4-diol

• ChemBase ID: 133438
• Molecular Formular: C11H14N4O4S
• Molecular Mass: 298.31826
• Monoisotopic Mass: 298.07357595
• SMILES: CSc1c2c(ncn1)n(cn2)C1C(C(C(O1)CO)O)O
• Canonical SMILES: OCC1OC(C(C1O)O)n1cnc2c1ncnc2SC
• InChI: InChI=1S/C11H14N4O4S/c1-20-10-6-9(12-3-13-10)15(4-14-6)11-8(18)7(17)5(2-16)19-11/h3-5,7-8,11,16-18H,2H2,1H3
• InChIKey: ZDRFDHHANOYUTE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(hydroxymethyl)-5-[6-(methylsulfanyl)-9H-purin-9-yl]oxolane-3,4-diol
• IUPAC Traditional name: 6-methyl mp riboside
• Synonyms: 6MMPr; 6-Methylmercaptopurine riboside; 6-(Methylthio)-9-β-D-ribofuranosyl-9H-purine

Database IDs

• CAS Number: 342-69-8
• EC Number: 206-442-2
• MDL Number: MFCD00022826
• PubChem SID: 162227715; 24896894
• PubChem CID: 237358

CALCULATED PROPERTIES

• Acid pKa: 12.454004
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.67504233
• LogD (pH = 7.4): -0.6343692
• Log P: -0.6338208
• Molar Refractivity: 71.2541 cm^3
• Polarizability: 28.271502 Å^3
• Polar Surface Area: 113.52 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: UO8985000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥99% (HPLC)

DETAILS

Sigma Aldrich - M4002

Application
6-Methylmercaptopurine riboside (6MMPr) is used in studies on thiopurine metabolism by enzymes such as inosine-5′-monophosphate dehydrogenase and thiopurine methyltransferase. 6MMPr may also be used to study mechanisms of bovine viral diarrhea virus (BVDV) inhibition.