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

• ChemBase ID: 2607
• Molecular Formular: C11H14N4O4S
• Molecular Mass: 298.31826
• Monoisotopic Mass: 298.07357595
• SMILES: CSc1ncnc2c1ncn2[C@@H]1O[C@@H](CO)[C@H](O)[C@H]1O
• Canonical SMILES: OC[C@@H]1O[C@H]([C@@H]([C@H]1O)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/t5-,7-,8+,11+/m0/s1
• InChIKey: ZDRFDHHANOYUTE-WOIOKPISSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4R,5R)-2-(hydroxymethyl)-5-[6-(methylsulfanyl)-9H-purin-9-yl]oxolane-3,4-diol
• IUPAC Traditional name: methylthioinosine
• Synonyms: 6-Methylthioinosine; MMPR; Me6MPR; 6-Methylmercaptopurine; 6-Methyl MP riboside; 6-Methyl MP-riboside; 6-MMPR; 6-Methylthiopurine riboside; Methylmercaptopurine riboside; 6-Methylmercaptopurine riboside; beta-D-Ribosyl-6-methylthiopurine; 6-(Methylthio)purine ribonucleoside; 6-Methylmercaptopurine ribonucleoside; 6-Methyl-9-ribofuranosylpurine-6-thiol; 6-methyl-9-ribofuranosyl-purine-6-thiol; 6-(methylthio)-9-beta-d-ribofuranosyl-9H-purine; Methylthioinosine

Database IDs

• CAS Number: 342-69-8
• PubChem SID: 46505005; 160966056
• PubChem CID: 46936521

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.454004
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.6790425
• LogD (pH = 7.4): -0.63442546
• 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

ALOGPS 2.1

• Log P: -0.4
• LOG S: -1.56
• Solubility (Water): 8.21e+00 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 0.09 [SANGSTER (1994)]

DETAILS

DrugBank - DB02896

• Drug Groups: experimental
• Description: An analog of inosine with a methylthio group replacing the hydroxyl group in the 6-position. [PubChem]
• Toxicity: IPR-RAT LD₅₀: 65 mg/kg