Description

5-Iodotubercidin (CAS No. 24386-93-4) is a highly specialized nucleoside analog with the molecular formula C₁₁H₁₃IN₄O₄. This compound, also known as 7-Deaza-7-iodoadenosine, is a potent and selective inhibitor of adenosine kinase (AK), making it invaluable for research in signal transduction, metabolic regulation, and neuroprotection studies. Its unique structure features an iodinated pyrrolo[2,3-d]pyrimidine ring linked to a ribofuranosyl moiety, ensuring high binding affinity and specificity. With purity ≥90% (solid form), this product is ideal for biochemical assays, cell-based research, and pharmacological investigations. Available in lyophilized or solution formats, it is rigorously tested for quality via HPLC, NMR, and MS to ensure reproducibility. Store at -20°C protected from light and moisture for optimal stability.

Properties

• CAS Number: 24386-93-4
• Complexity: 365
• IUPAC Name: (2R,3R,4S,5R)-2-(4-amino-5-iodo-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
• 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
• InChI Key: WHSIXKUPQCKWBY-IOSLPCCCSA-N
• Exact Mass: 391.99815
• Molecular Formula: C11H13IN4O4
• Molecular Weight: 392.15
• SMILES: C1=C(C2=C(N=CN=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N)I
• Topological: 127
• Monoisotopic Mass: 391.99815
• Synonyms: 5-Iodotubercidin, 24386-93-4, (2R,3R,4S,5R)-2-(4-AMINO-5-IODO-7H-PYRROLO[2,3-D]PYRIMIDIN-7-YL)-5-(HYDROXYMETHYL)TETRAHYDROFURAN-3,4-DIOL, 5′-iodotubericidin, NSC 113939, CHEBI:40167, DTXSID40865150, 5-iodo-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine, 7H-Pyrrolo(2,3-d)pyrimidin-4-amine, 5-iodo-7-beta-D-ribofuranosyl-, 5-iodo-7-(beta-D-ribofuranosyl)-7H-pyrrolo(2,3-d)pyrimidin-4-amine, (2R,3R,4S,5R)-2-(4-amino-5-iodo-7H-pyrrolo(2,3-d)pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol, DTXCID801509922, 5-iodotubericidin, 7-Deaza-7-iodoadenosine, 7-iodo-7-deazaadenosine, 7-iodotubercidin, (2R,3R,4S,5R)-2-(4-amino-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol, CHEMBL99203, 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, 5-iodo-7-b-D-ribofuranosyl-, 5-iodo-7-beta-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine, 5ID, 2zoq, 5-Iodotubercidine, MFCD00055131, 5-IODOTUBERCIDIN?, SCHEMBL319225, 5-Iodotubericidin, >=90%, solid, 7H-Pyrrolo[2,3-d]pyrimidin-4-amine,5-iodo-7-b-D-ribofuranosyl-, BDBM50375654, NSC 113939, 5-ITu, AKOS024456757, CS-0897, DB04604, ND09248, AC-27391, AS-71537, HY-15424, NS00069958, C74253, 7-Iodotubercidin;7-Deaza-7-iodo-D-adenosine;ITU, Q27095342, 4-amino-5-iodo-7-beta-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine, 5-Iodo-7-beta-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4- amine, 4-amino-5-iodo-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine, 2-(4-Amino-5-iodo-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol, (2R,3R,4S,5R)-2-(4-amino-5-iodo-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol, (2R,3R,4S,5R)-2-{4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-5-(hydroxymethyl)oxolane-3,4-diol

5-Iodotubercidin is widely used to study adenosine-mediated pathways, particularly in neuroscience and cardioprotection research. It inhibits adenosine kinase, elevating endogenous adenosine levels to modulate inflammation, ischemia-reperfusion injury, and synaptic plasticity. This compound is also employed in cancer research to investigate purine metabolism dysregulation. Its cell-permeable nature makes it suitable for in vitro and ex vivo models.

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