9-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purine-6-thione

• ChemBase ID: 132330
• Molecular Formular: C10H12N4O3S
• Molecular Mass: 268.29228
• Monoisotopic Mass: 268.06301126
• SMILES: c1[nH]c2c(c(=S)n1)ncn2C1CC(C(O1)CO)O
• Canonical SMILES: OCC1OC(CC1O)n1cnc2c1[nH]cnc2=S
• InChI: InChI=1S/C10H12N4O3S/c15-2-6-5(16)1-7(17-6)14-4-13-8-9(14)11-3-12-10(8)18/h3-7,15-16H,1-2H2,(H,11,12,18)
• InChIKey: WACLJMMBCDNRJE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purine-6-thione
• IUPAC Traditional name: 9-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-6-thione
• Synonyms: 2′-Deoxy-6-thioinosine; dI6S; 6-Mercaptopurine-2′-deoxyriboside

Database IDs

• CAS Number: 2239-64-7
• MDL Number: MFCD00056001
• PubChem SID: 162226607; 24897025
• PubChem CID: 4262396

CALCULATED PROPERTIES

• Acid pKa: 7.973156
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.82735646
• LogD (pH = 7.4): -0.9189376
• Log P: -0.8204196
• Molar Refractivity: 67.3786 cm^3
• Polarizability: 25.894453 Å^3
• Polar Surface Area: 91.9 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: UP0762000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - M5628

Biochem/physiol Actions
6-Mercaptopurine-2′-deoxyriboside (2′-deoxy-6-thioinosine; dI6S) is a thiolated inosine deoxynucleoside that may possess antitumor activity.