An HIV-1 integrase inhibitor
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Metabolite(s)
25454Epiequisetin
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Equisetin

Item No. 18196

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3E,5S)-5-(hydroxymethyl)-3-[hydroxy[(1S,2R,4aS,6R,8aR)-1,2,4a,5,6,7,8,8a-octahydro-1,6-dimethyl-2-(1E)-1-propen-1-yl-1-naphthalenyl]methylene]-1-methyl-2,4-pyrrolidinedione
CAS Number
57749-43-6
Molecular Formula
C22H31NO4
Formula Weight
373.5
Purity
≥99%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: Soluble
SMILES
C/C=C/[C@H](C=C1)[C@](/C(O)=C2C([C@H](CO)N(C)C/2=O)=O)(C)[C@@]3([H])[C@@]1([H])C[C@H](C)CC3
InChi Code
InChI=1S/C22H31NO4/c1-5-6-15-9-8-14-11-13(2)7-10-16(14)22(15,3)20(26)18-19(25)17(12-24)23(4)21(18)27/h5-6,8-9,13-17,24,26H,7,10-12H2,1-4H3/b6-5+,20-18+/t13-,14-,15-,16-,17+,22-/m1/s1
InChi Key
QNQBPPQLRODXET-AIMHRHHOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Equisetin is a fungal metabolite that has been isolated from Fusarium.1,2 It inhibits HIV-1 integrase 3’ end-processing and strand transfer activities.3 Equisetin inhibits the ATPase activity of rat liver mitochondria and mitoplasts stimulated by 2,4-dinitrophenol (Dnp) in a concentration-dependent manner (IC50 = ~8 nM per mg of protein for both).4 It also inhibits ADP-stimulated respiration and the mitochondrial transport of ATP, inorganic phosphate, and succinate. Epiequisetin is phytotoxic and inhibits the germination of various seeds and growth of young seedlings.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Desjardins, A.E., and Proctor, R.H. Molecular biology of Fusarium mycotoxins. Int. J. Food Microbiol. 119(1-2), 47-50 (2007).

    2. Patham, B., Duffy, J., Lane, A., et al. Post-translational import of protein into the endoplasmic reticulum of a trypanosome: An in vitro system for discovery of anti-trypanosomal chemical entities. Biochem. J. 419(2), 507-517 (2009).

    3. Singh, S.B., Zink, D.L., Goetz, M.A., et al. Equisetin and a novel opposite stereochemical homolog phomasetin, two fungal metabolites as inhibitors of HIV-1 integrase. Tetrahedron Lett. 39(16), 2243-2246 (1998).

    4. König, T., Kapus, A., and Sarkadi, B. Effects of equisetin on rat liver mitochondria: Evidence for inhibition of substrate anion carriers of the inner membrane. J. Bioenerg. Biomembr. 25(5), 537-545 (1993).

    5. Wheeler, M.H., Stipanovic, R.D., and Puckhaber, L.S. Phytotoxicity of equisetin and epi-equisetin isolated from Fusarium equiseti and F. pallidoroseum. Mycol. Res. 103(8), 967-973 (1999).