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

• ChemBase ID: 72787
• Molecular Formular: C10H12N4O3
• Molecular Mass: 236.22728
• Monoisotopic Mass: 236.09094026
• SMILES: [C@H]1(CC[C@@H](O1)n1c2c(nc1)c(=O)[nH]cn2)CO
• Canonical SMILES: OC[C@@H]1CC[C@@H](O1)n1cnc2c1nc[nH]c2=O
• InChI: InChI=1S/C10H12N4O3/c15-3-6-1-2-7(17-6)14-5-13-8-9(14)11-4-12-10(8)16/h4-7,15H,1-3H2,(H,11,12,16)/t6-,7+/m0/s1
• InChIKey: BXZVVICBKDXVGW-NKWVEPMBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2'3'-dideoxyinosine; @2'3'-dideoxyinosine
• Synonyms: ddIno; 2′,3′-Dideoxyinosine; 2',3'-Dideoxy-inosine; Didanosine; 2',3'-Dideoxyinosine; 9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one; 2'; 3'-dideoxyinosine; DDI; NSC 612049; Didanosine; 地丹诺辛

Database IDs

• CAS Number: 69655-05-6
• MDL Number: MFCD00077728
• Beilstein Number: 3619529
• PubChem SID: 162037708
• PubChem CID: 50599

CALCULATED PROPERTIES

• Acid pKa: 8.934663
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.86939377
• LogD (pH = 7.4): -0.88030183
• Log P: -0.8692472
• Molar Refractivity: 59.0272 cm^3
• Polarizability: 21.754555 Å^3
• Polar Surface Area: 88.74 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 172-174°C; 193-195 °C
• Optical Rotation: [α]20/D -27°, c = 1 in H2O
• Hydrophobicity(logP): -1.924

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: NM7460700
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (HPLC); 95%; 98%
• Salt Data: Free Base
• Impurities: ≤1% water
• Empirical Formula (Hill Notation): C10H12N4O3

DETAILS

Selleck Chemicals - S1702

Research Area: Infection
Biological Activity:
Didanosine(Videx, Videx EC) is a reverse transcriptase inhibitor with an IC50 of 0.49 μM. It is effective against HIV and used in combination with other antiretroviral drug therapy as part of highly active antiretroviral therapy (HAART). [1]

Sigma Aldrich - 362646

Packaging
100 mg in glass bottle

Sigma Aldrich - 36777

Other Notes
Experimental anti-retroviral agent1,2,3

Toronto Research Chemicals - D440950

Used as an antiviral.

REFERENCES

• http://en.wikipedia.org/wiki/Didanosine
• Dahlberg, J.E., et al.: Proc. Nat. Acad. Sci. U.S.A., 83, 1911 (1986)