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

• ChemBase ID: 102593
• Molecular Formular: C10H12N4O4S
• Molecular Mass: 284.29168
• Monoisotopic Mass: 284.05792588
• SMILES: Sc1ncnc2c1ncn2[C@@H]1O[C@@H]([C@@H](O)[C@H]1O)CO
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2S
• InChI: InChI=1S/C10H12N4O4S/c15-1-4-6(16)7(17)10(18-4)14-3-13-5-8(14)11-2-12-9(5)19/h2-4,6-7,10,15-17H,1H2,(H,11,12,19)/t4-,6-,7-,10-/m1/s1
• InChIKey: NKGPJODWTZCHGF-KQYNXXCUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-sulfanyl-9H-purin-9-yl)oxolane-3,4-diol
• IUPAC Traditional name: thioinosine
• Synonyms: 9-[β-D-Ribofuranosyl]-6-thiopurine; 6-Mercaptopurine riboside; 6-Purinethiol riboside; 6-Thioinosine; 6-MERCAPTOPURINE RIBONUCLEOSIDE; 6-Mercaptopurine-9-β-D-ribofuranoside; 6-嘌呤硫醇核苷; 6-巯基嘌呤核苷; 6-硫肌苷; 6-巯基嘌呤-9-β-D-核苷

Database IDs

• CAS Number: 574-25-4
• EC Number: 209-371-5
• MDL Number: MFCD00005743
• Beilstein Number: 40536
• PubChem SID: 24888331; 162089987; 24882925
• PubChem CID: 676166

CALCULATED PROPERTIES

• Acid pKa: 7.437681
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.1736318
• LogD (pH = 7.4): -1.4367582
• Log P: -1.1688308
• Molar Refractivity: 66.505 cm^3
• Polarizability: 26.447287 Å^3
• Polar Surface Area: 113.52 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: > 200°C (dec.); 220-223 °C; 220-223 °C(lit.)
• Optical Rotation: [α]/D -74±4°, c = 1% in 0.1 M NaOH; [α]20/D -74±3°, c = 1% in 0.1 M NaOH

Safety Information

• Storage Condition: 0°C
• RTECS: UP0710000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; R:22
• Safety Statements: 22-24/25; S:36/37/39
• 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

Product Information

• Purity: ~99%; ≥95.0% (HPLC); 95%
• Grade: purum
• Compostion: carbon, 40.1-44.4%; nitrogen, 18.7-20.7%
• Impurities: ≤5% water
• Empirical Formula (Hill Notation): C10H12N4O4S

DETAILS

MP Biomedicals - 02102264

Crystalline
Purity: ~99%

Sigma Aldrich - 852686

Packaging
1 g in glass bottle

Sigma Aldrich - 63830

Other Notes
Nucleoside analogue; building block used for the synthesis of N6-alkylated adenosines by reaction with an amine1