9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 137413
• Molecular Formular: C10H12N4O4
• Molecular Mass: 252.22668
• Monoisotopic Mass: 252.08585488
• SMILES: c1[nH]c(=O)c2c(n1)n(cn2)[C@H]1C[C@@H]([C@H](O1)CO)O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@@H]1O)n1cnc2c1nc[nH]c2=O
• InChI: InChI=1S/C10H12N4O4/c15-2-6-5(16)1-7(18-6)14-4-13-8-9(14)11-3-12-10(8)17/h3-7,15-16H,1-2H2,(H,11,12,17)/t5-,6+,7+/m0/s1
• InChIKey: VGONTNSXDCQUGY-RRKCRQDMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2'-deoxyinosine
• Synonyms: 9-(2-Deoxy-β-D-ribofuranosyl)hypoxanthine; 2′-Deoxyinosine; 9-(2-脱氧-β-D-呋喃核糖基)次黄嘌呤; 2′-脱氧肌苷

Database IDs

• CAS Number: 890-38-0
• EC Number: 212-964-1
• MDL Number: MFCD00005762
• Beilstein Number: 33517
• PubChem SID: 24893935; 162231676
• PubChem CID: 65058

CALCULATED PROPERTIES

• Acid pKa: 8.934634
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.5780466
• LogD (pH = 7.4): -1.5889554
• Log P: -1.5778999
• Molar Refractivity: 59.8211 cm^3
• Polarizability: 22.45079 Å^3
• Polar Surface Area: 108.97 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D -20±2°, c = 1% in H2O

Safety Information

• 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: ≥98%; ≥99.0% (HPLC); 99%
• Impurities: inosine, essentially free
• Empirical Formula (Hill Notation): C10H12N4O4
• Classification: Genuine Natural Compounds

DETAILS

Sigma Aldrich - D5287

Application
2′-Deoxyinosine is a nucleoside composed of hypoxanthine attached to 2′-deoxyribose via a β-N9-glycosidic bond. 2′-Deoxyinosine in DNA can arise from deamination of adenosine. 2′-deoxyinsine can be used as a model compound to study the chemistry of adduct formation and radical chemistry that may affect DNA structures. 2′-Deoxyinosine is used to produce hybridization-sensitive fluorescent DNA probes with self-avoidance ability.