A fungal metabolite with potassium channel inhibitory and antiviral activities
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Nalanthalide

Item No. 29724

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-[[(1R,4aR,5S,6S,8aR)-6-(acetyloxy)decahydro-5,8a-dimethyl-2-methylene-5-(4-methyl-3-penten-1-yl)-1-naphthalenyl]methyl]-2-methoxy-5,6-dimethyl-4H-pyran-4-one
CAS Number
145603-76-5
Synonyms
  • (–)-Nalanthalide
Molecular Formula
C30H44O5
Formula Weight
484.7
Purity
≥70%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Dichloromethane: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
C=C1CC[C@]([C@@](CC/C=C(C)/C)(C)[C@@H](OC(C)=O)CC2)([H])[C@@]2(C)[C@@H]1CC3=C(OC)OC(C)=C(C)C3=O
InChi Code
InChI=1S/C30H44O5/c1-18(2)11-10-15-30(8)25-13-12-19(3)24(29(25,7)16-14-26(30)35-22(6)31)17-23-27(32)20(4)21(5)34-28(23)33-9/h11,24-26H,3,10,12-17H2,1-2,4-9H3/t24-,25-,26+,29-,30+/m1/s1
InChi Key
RVADBFKZGNOVDI-PELMAWFUSA-N
Origin
Fungus/Unidentified sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $303

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    Product Description

    Nalanthalide is a diterpenoid pyrone fungal metabolite that has been found in Nalanthamala and has potassium channel inhibitory and antiviral activities.1 It inhibits binding of the potassium channel inhibitor charybdotoxin (Item No. 24115) to Jurkat cell membranes (IC50 = 3 µM) and inhibits rubidium efflux from CHO cells expressing the voltage-gated potassium (Kv) channel Kv1.3 (IC50 = 3.9 µM). Nalanthalide depolarizes T cells in vitro with an EC50 value of 500 nM. It also inhibits HIV-1 integrase activity with IC50 values of 10 and 25 µM in coupled and strand transfer assays, respectively.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Goetz, M.A., Zink, D.L., Dezeny, G., et al. Diterpenoid pyrones, novel blockers of the voltage-gated potassium channel Kv1.3 from fungal fermentations. Tetrahedron Lett. 42(7), 1255-1257 (2001).

    2. Singh, S.B., Jayasuriya, H., Dewey, R., et al. Isolation, structure, and HIV-1-integrase inhibitory activity of structurally diverse fungal metabolites. J. Ind. Microbiol. Biotechnol. 30(12), 721-731 (2003).