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YM-201636
![{PARAM:[Name]}()](https://resource.bocsci.com/structure/371942-69-7.gif)
| Category | Influenza Virus |
| CAS | 371942-69-7 |
| Description | YM201636 is an inhibitor of retroviral budding and PIKfyve-catalyzed PtdIns(3,5)P2 synthesis, can halt glucose entry by insulin in adipocytes. YM201636 almost completely inhibited basal and insulin-activated 2-deoxyglucose uptake at doses as low as 160 nM, with IC(50)=54+/-4 nM for the net insulin response. Insulin-induced GLUT4 translocation was partially inhibited at substantially higher doses, comparable to those required for inhibition of insulin-induced phosphorylation of Akt/PKB. In addition to PIKfyve, YM201636 also completely inhibited insulin-dependent activation of class IA PI 3-kinase. |
Product Information
| Synonyms | YM 201636; YM201636 |
| IUPAC Name | 6-amino-N-[3-(6-morpholin-4-yl-8-oxa-3,5,10-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-4-yl)phenyl]pyridine-3-carboxamide |
| Molecular Weight | 467.48 |
| Molecular Formula | C25H21N7O3 |
| Canonical SMILES | C1COCCN1C2=NC(=NC3=C2OC4=C3C=CC=N4)C5=CC(=CC=C5)NC(=O)C6=CN=C(C=C6)N |
| InChI | InChI=1S/C25H21N7O3/c26-19-7-6-16(14-28-19)24(33)29-17-4-1-3-15(13-17)22-30-20-18-5-2-8-27-25(18)35-21(20)23(31-22)32-9-11-34-12-10-32/h1-8,13-14H,9-12H2,(H2,26,28)(H,29,33) |
| InChIKey | YBPIBGNBHHGLEB-UHFFFAOYSA-N |
| Purity | >98% |
| Density | 1.4±0.1 g/cm3 |
| Solubility | In vitro: 10 mM in DMSO |
| Appearance | Light yellow to khaki (Solid) |
| Storage | Powder: -20°C: 3 years 4°C: 2 years In solvent: -80°C: 6 months -20°C: 1 month |
| Complexity | 738 |
| Exact Mass | 467.17058756 |
| Index Of Refraction | 1.751 |
| In Vitro | Acute treatment of cells with YM-201636 shows that the PIKfyve pathway is involved in the sorting of endosomal transport, with inhibition leading to the accumulation of a late endosomal compartment and blockade of retroviral exit. The yeast orthologue of PIKfyve, Fab1, is found to be insensitive to YM-201636 (IC50>5 μM). YM-201636 does not inhibit a type IIγ PtdInsP kinase even at 10 μM and inhibits a mouse type Iα PtdInsP kinase with an IC50>2 μM. YM-201636 almost completely inhibits basal and insulin-activated 2-deoxyglucose uptake at doses as low as 160 nM, with IC50=54 nM for the net insulin response. YM-201636 also completely inhibits insulin-dependent activation of class IA PI 3-kinase. At low doses (10-25 nM), YM-201636 inhibits preferentially PtdIns5P rather than PtdIns(3,5)P2 production, whereas at higher doses, the two products are similarly inhibited. YM-201636 at 160 nM inhibits PtdIns5P synthesis twice more effectively compared with PtdIns(3,5)P2 synthesis. MDCK cells treated with YM-201636 accumulate the tight junction protein claudin-1 intracellularly. YM-201636 treatment blocks the continuous recycling of claudin-1/claudin-2 and delays epithelial barrier formation. |
| PSA | 132.29000 |
| Target | PIKfyve: 33 nM (IC50) p110α: 3.3 μM (IC50) Autophagy |
| XLogP3-AA | 2.5 |
