CAS Number24386-93-4
SynonymsMFCD00055131; 5-Iodo-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine; 5-Iodotubercidin; 5-Iodotubericidin
Molecular FormulaC11H13IN4O4
Molecular Weight392.15
Purity≥85%
Density2.5±0.1 g/cm3
Boiling Point701.5±60.0 °C at 760 mmHg
Melting Point216-217ºC dec.
Appearancesolid
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 24386-93-4 |
| Catalog No. | 2A-1174478 |
| Chinese Name | 5-碘代杀结核菌素 |
| Synonyms | MFCD00055131; 5-Iodo-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine; 5-Iodotubercidin; 5-Iodotubericidin |
| Molecular Formula | C11H13IN4O4 |
| Molecular Weight | 392.15 |
| Purity | ≥85 |
| Density | 2.5±0.1 g/cm3 |
| Boiling Point | 701.5±60.0 °C at 760 mmHg |
| Melting Point | 216-217ºC dec. |
| Appearance | solid |
| Water Solubility | 0.1 M HCl: 0.7 mg/mL |
| Storage Condition | 2-8℃ |
| Application | 5-Iodotubercidin is a potent adenosine kinase inhibitor with an IC50 value of 26 nM. |
| HTC | 2934999090 |
| PubChem ID | 329815331 |
| MDL Number | MFCD00055131 |
| SMILES | Nc1ncnc2n(cc(I)c12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O |
| 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 |
| NACRES Code | NA.77 |
| UNSPSC | 12352202 |
| MSDS | msds/174831_1_24386_93_4.pdf |
| Use of | 5-Iodotubercidin is a potent adenosine kinase inhibitor with IC50 of 26 nM. Properties Articles37 Name 5-iodotubercidin Synonym More Synonyms 5-Iodotubercidin Biological Activity Description 5-Iodotubercidin is a potent adenosine kinase inhibitor with IC50 of 26 nM. Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> Adenosine Kinase Signaling Pathways >> Neuronal Signaling >> Adenosine Kinase Research Areas >> Cancer IC50: 26 nM (adenosine kinase) In Vitro 5-Iodotubercidin (40 μM) enhances the rate of phosphorylase inactivation and shortens the lag before the activation of glycogen synthase. 5-Iodotubercidin (50 μM) antagonizes the effects of glucagon and vasopressin, but does not affect the basal concentration of free calcium in single hepatocytes[1]. 5-Iodotubercidin (20 μM) causes an important decrease in ATP concentration, and a concomitant smaller increase in AMP concentration. 5-Iodotubercidin decreases the activity of ACC and the rates of synthesis of fatty acids and cholesterol. In line with the iodotubercidin-mediated inhibition of ACC, 5-iodotubercidin induces a marked decrease in the intracellular concentration of malonyl-CoA[3]. 5-Iodotubercidin causes a strong decrease in the immunofluorescence levels of P-T3-H3, and depletion of P-T3-H3 is complete at 10 µM 5-5-iodotubercidin[4]. References [1]. Massillon D, et al. Identification of the glycogenic compound 5-iodotubercidin as a general protein kinase inhibitor. Biochem J. 1994 Apr 1;299 (Pt 1):123-8. [2]. Ugarkar BG, et al. Adenosine kinase inhibitors. 1. Synthesis, enzyme inhibition, and antiseizure activity of 5-iodotubercidin analogues. J Med Chem. 2000 Jul 27;43(15):2883-93. [3]. García-Villafranca J, et al. Effects of 5-iodotubercidin on hepatic fatty acid metabolism mediated by the inhibition of acetyl-CoA carboxylase. Biochem Pharmacol. 2002 Jun 1;63(11):1997-2000. [4]. De Antoni A, et al. A small-molecule inhibitor of Haspin alters the kinetochore functions of Aurora B. J Cell Biol. 2012 Oct 15;199(2):269-84. [5]. Acharya MM, et al. Adenosine Kinase Inhibition Protects against Cranial Radiation-Induced Cognitive Dysfunction. Front Mol Neurosci. 2016 Jun 3;9:42. Chemical & Physical Properties Molecular Formula C11H13IN4O4 Exact Mass 391.998138 PSA 126.65000 Index of Refraction 1.919 InChIKey WHSIXKUPQCKWBY-IOSLPCCCSA-N Safety Information Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter Hazard Codes Xi RIDADR NONH for all modes of transport WGK Germany 3 HS Code 2934999090 Synthetic Route (2R,3R,4R,5R)-2... CAS#:480439-89-2 5-Iodotubercidin CAS#:24386-93-4 Literature: Seela, Frank; Ming, Xin Tetrahedron, 2007 , vol. 63, # 39 p. 9850 - 9861 7H-Pyrrolo[2,3-... CAS#:24386-91-2 5-Iodotubercidin CAS#:24386-93-4 Literature: Zhang, Liangren; Zhang, Yunlong; Li, Xianghui; Zhang, Lihe Bioorganic and Medicinal Chemistry, 2002 , vol. 10, # 4 p. 907 - 912 4-Chloro-5-iodo... CAS#:123148-78-7 5-Iodotubercidin CAS#:24386-93-4 Literature: Tetrahedron, , vol. 63, # 39 p. 9850 - 9861 Precursor & DownStream Precursor 5 CAS#:24386-91-2 7H-Pyrrolo[2,3-... CAS#:123148-78-7 4-Chloro-5-iodo... CAS#:291535-38-1 4-chloro-5-iodo... CAS#:217309-46-1 (3aR,6R,6aR)-6-... DownStream 0 |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Product name: Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
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