| Field | Specification |
|---|---|
| Target | |
| CAS no. | |
| Applications | |
| Source | Microbial — Aspergillus Species |
| Molecular weight | |
| Molecular formula | C40H36N6O4 |
| SMILES | |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
WIN-64821 is a secondary metabolite of Aspergillus species that acts as a neurokinin receptor antagonist, with Ki values of 0.24 μM (human astrocytoma cells), 0.26 μM (rat duodenum) and 15.2 μM (guinea pig forebrain) against the NK1, NK2 and NK3 receptors, respectively. It inhibits apamin-induced contraction of rat vas deferens, blocks substance P-induced contraction of guinea pig ileum, reduces Ca2+ efflux in human astrocytoma cells, and has been applied in analgesic and anti-inflammatory research[1][2]. Its molecular formula is C40H36N6O4, with a molecular weight of 664.77 g/mol.
Physical & Chemical Properties
| CAS Number | 150881-27-9 |
|---|---|
| Molecular Formula | C40H36N6O4 |
| Molecular Weight | 664.77 g/mol |
| Structure Classification | Ketones, Aldehydes, Acids |
| SMILES | O=C1N2[C@@]3([C@@](C=4C(N3)=CC=CC4)(C[C@]2(C(=O)N[C@H]1CC5=CC=CC=C5)[H])[C@@]67[C@@](N8[C@@](C6)(C(=O)N[C@@H](CC9=CC=CC=C9)C8=O)[H])(NC=%10C7=CC=CC%10)[H])[H] |
| Target | NK1R, NK2R, NK3R |
| Signaling Pathway | GPCR/G Protein; Neuronal Signaling; Metabolic Enzyme/Protease; Membrane Transporter/Ion Channel |
| Initial Source | Microbial — Aspergillus Species |
| Storage | Please store the product under the recommended conditions in the Certificate of Analysis. |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Biological Activity
IC50 & Target[1]
|
NK1R 0.24 μM (Ki) |
NK2R 0.26 μM (Ki) |
NK3R 15.2 μM (Ki) |
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
[1]. Oleynek JJ, et al. WIN 64821, a novel neurokinin antagonist produced by an Aspergillus sp. II. Biological activity. The Journal of Antibiotics. 1994 Apr 25;47(4):399-410.
[2]. Barrow CJ, et al. WIN 64821, a new competitive antagonist to substance P, isolated from an Aspergillus species: structure determination and solution conformation. The Journal of Organic Chemistry. 1993 Oct;58(22):6016-21.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with your institution's chemical hygiene plan.
In Vitro
In guinea pig ileal strips, WIN 64821 (10 minutes; 1-10 μM) is a competitive functional antagonist of contraction induced by substance P (SP), with a pA2 of 6.6 and a corresponding EC50 of 0.63 μM[1]. In human astrocytoma U-373 MG cells, WIN 64821 (0.01-10 μM) blocks substance P-induced 45Ca2+ efflux, with a mean IC50 of 0.6 μM; at 0.5 and 10 μM, it does not itself trigger 45Ca2+ efflux[1]. WIN 64821 inhibits NK2 functional model-induced twitch enhancement in rat vas deferens (an NK2 functional model); the mean IC50 is 3.4 μM, and basal twitch is minimally affected at concentrations up to 30 μM[1]. In human astrocytoma cells, WIN-64821 is a competitive antagonist of human NK1 receptors, with a Ki of 230 nM[2]. In normal human fetal tissues, WIN-64821 is a competitive antagonist of the human NK1 receptor, with a Ki of 0.74 μM[2]. In guinea pig submandibular gland membrane preparations, WIN-64821 is a competitive antagonist of the NK1 receptor, with a Ki of 0.6 μM[2].
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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