[(2S,5R)-5-(6-amino-9H-purin-9-yl)oxolan-2-yl]methanol

• ChemBase ID: 103189
• Molecular Formular: C10H13N5O2
• Molecular Mass: 235.24252
• Monoisotopic Mass: 235.10692468
• SMILES: n1c2c(ncnc2n(c1)[C@@H]1O[C@@H](CC1)CO)N
• Canonical SMILES: OC[C@@H]1CC[C@@H](O1)n1cnc2c1ncnc2N
• InChI: InChI=1S/C10H13N5O2/c11-9-8-10(13-4-12-9)15(5-14-8)7-2-1-6(3-16)17-7/h4-7,16H,1-3H2,(H2,11,12,13)/t6-,7+/m0/s1
• InChIKey: WVXRAFOPTSTNLL-NKWVEPMBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2S,5R)-5-(6-amino-9H-purin-9-yl)oxolan-2-yl]methanol
• IUPAC Traditional name: adenosine, 2',3'-dideoxy-
• Synonyms: 2′,3′-Dideoxyadenosine; 2',3'-Dideoxyadenosine; NSC 98700; Dideoxy Adenosine; ((2S,5R)-5-(6-Amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methanol; DDA; 2',3'-DIDEOXYADENOSINE

Database IDs

• CAS Number: 4097-22-7
• EC Number: 223-853-2
• MDL Number: MFCD00010534
• Beilstein Number: 619924
• PubChem SID: 162090349; 24893397
• PubChem CID: 20039

CALCULATED PROPERTIES

• Acid pKa: 14.672701
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.5999503
• LogD (pH = 7.4): -0.48338678
• Log P: -0.48167303
• Molar Refractivity: 60.891 cm^3
• Polarizability: 23.18721 Å^3
• Polar Surface Area: 99.08 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 181-184 °C(lit.); 181-184°C
• Optical Rotation: [α]20/D -29±2°, c = 1% in H2O

Safety Information

• Storage Condition: 0°C
• RTECS: AU7358900
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... DCK(1633)

Product Information

• Purity: ≥97% (HPLC); ≥99.0% (HPLC); 97-98%; 98%
• Impurities: ≤1% water
• Empirical Formula (Hill Notation): C10H13N5O2

DETAILS

MP Biomedicals - 02150879

Crystalline
Purity: 97-98%

Sigma Aldrich - D1285

包装
5, 25 mg in poly bottle
Application
2′,3′-Dideoxyadenosine (ddA), a specific adenylyl cyclase inhibitor, is useful in biological process and pathway studies involving adenylyl cyclase activity and cAMP pool modulation.

Sigma Aldrich - 36769

Other Notes
Used as experimental anti-viral agent.; Inhibition of HTLV-III/LAV DNA synthesis and mRNA expression in T cells by completely blocking reverse transcription from viral RNA to viral DNA1,2

Toronto Research Chemicals - D439850

A potent anti-HIV agent.

REFERENCES

• Pearlman, D., et al.: J. Mol. Biol., 220, 457 (1991)
• Cappellacci, L., et al.: J. Med. Chem., 45, 1196 (1991)