(2R,3S,5R)-2-{4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 171708
• Molecular Formular: C11H13IN4O4
• Molecular Mass: 392.14979
• Monoisotopic Mass: 391.99815292
• SMILES: [C@H]1(C([C@@H]([C@@H](O1)n1c2ncnc(c2c(c1)I)N)O)O)CO
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1cc(c2c1ncnc2N)I
• InChI: InChI=1S/C11H13IN4O4/c12-4-1-16(10-6(4)9(13)14-3-15-10)11-8(19)7(18)5(2-17)20-11/h1,3,5,7-8,11,17-19H,2H2,(H2,13,14,15)/t5-,7?,8+,11-/m1/s1
• InChIKey: WHSIXKUPQCKWBY-DWVWSIQXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5R)-2-{4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3S,5R)-2-{4-amino-5-iodopyrrolo[2,3-d]pyrimidin-7-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 4-Amino-5-iodo-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine; NSC 113939 5-Iodo-7-β-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine; 7-Iodotubercidin; 5-Iodotubercidin

Database IDs

• CAS Number: 24386-93-4
• PubChem SID: 164227618
• PubChem CID: 45039587

CALCULATED PROPERTIES

• Acid pKa: 12.455637
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.3952887
• LogD (pH = 7.4): -0.40726894
• Log P: -0.3495156
• Molar Refractivity: 78.7341 cm^3
• Polarizability: 30.722075 Å^3
• Polar Surface Area: 126.65 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White to Off-White Solid
• Melting Point: 216-217°C dec.

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Store tightly sealed at 4°C; Light Sensitive

DETAILS

Toronto Research Chemicals - I725000

An analogue of the antibiotic tubercidin, a pyrrolo[2,3-d]pyrimidine nucleoside antibiotic. A potent inhibitor of adenosine kinase from rat or guinea pig brain. Inhibits uptake of 3H-adenosine into brain slices.

REFERENCES

• Long, M., et al.: Biochem. Pharmacol., 71, 1671 (2006)
• Lehar, J., et al.: Mol. Sys. Biol., (2006)
• Bonilla-Santiago, R., et al.: Mol. Biochem. Parasitol., 162, 149 (2006)
• Caballero, J., et al.: Bioorg. Med. Chem., 16, 5103 (2006)