A sesquiterpene with diverse biological activities
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Mer-NF5003F

Item No. 29961

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1′R,2′R,4′aS,6′R,8′aS)-3′,4′,4′a,5′,6′,7′,8′,8′a-octahydro-4,6′-dihydroxy-2′,5′,5′,8′a-tetramethyl-spiro[benzofuran-2(3H),1′(2′H)-naphthalene]-6,7-dicarboxaldehyde
CAS Number
149598-70-9
Synonyms
  • F 1839M
  • NF 5003F
  • Stachybotrydial
Molecular Formula
C23H30O5
Formula Weight
386.5
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
O[C@@H]1CC[C@@]2(C)[C@](CC[C@@H](C)[C@@]23OC(C(C=O)=C(C=O)C=C4O)=C4C3)([H])C1(C)C
InChi Code
InChI=1S/C23H30O5/c1-13-5-6-18-21(2,3)19(27)7-8-22(18,4)23(13)10-15-17(26)9-14(11-24)16(12-25)20(15)28-23/h9,11-13,18-19,26-27H,5-8,10H2,1-4H3/t13-,18+,19-,22+,23-/m1/s1
InChi Key
WIGGVNIABVHHCS-QJAXDWLUSA-N
Origin
Fungus/Stachybotrys sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $267

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    5 mg

    $1,062

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    Product Description

    Mer-NF5003F is a sesquiterpene originally isolated from Stachybotrys with diverse biological activities.1,2,3 It inhibits avian myeloblastosis virus (AMV) protease (IC50 = 7.8 µM).1 Mer-NF5003F inhibits sialyltransferase 6N (ST6N), ST3O, and ST3N (IC50s = 0.61, 6.7, and 10 µg/ml, respectively), as well as fucosyltransferase (IC50 = 11.3 µg/ml).2 It is active against herpes simplex virus 1 (HSV-1) in vitro (IC50 = 4.32 µg/ml).3 Mer-NF5003F is also active against the multidrug-resistant P. falciparum strain K1 (IC50 = 0.85 µg/ml).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kaneto, R., Dobashi, K., Kojima, I., et al. Mer-NF5003B, E and F, novel sesquiterpenoids as avian myeloblastosis virus protease inhibitors produced by Stachybotrys sp. J. Antibiot. (Tokyo) 47(6), 727-730 (1994).

    2. Lin, T.-W., Chang, W.-W., Chen, C.-C., et al. Stachybotrydial, a potent inhibitor of fucosyltransferase and sialyltransferase. Biochem. Biophys. Res. Commun. 331(4), 953-957 (2005).

    3. Sawadjoon, S., Kittakoop, P., Isaka, M., et al. Antiviral and antiplasmodial spirodihydrobenzofuran terpenes from the fungus Stachybotrys nephrospora. Planta Med. 70(11), 1085-1087 (2004).