A fungal metabolite
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Avrainvillamide

Item No. 31655

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,11,12,13,13aS,14-hexahydro-3,3,14,14-tetramethyl-8H,10H-7aS,12aS-(iminomethano)indolizino[6,7-h]pyrano[3,2-a]carbazole-8,16-dione 15-oxide
CAS Number
269741-97-1
Synonyms
  • CJ-17,665
Molecular Formula
C26H27N3O4
Formula Weight
445.5
Purity
≥90%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: solubleMethanol: soluble
λmax
214, 292 nm
SMILES
O=C1[C@@](C=C(C2=CC=C3C(C=CC(C)(C)O3)=C24)C5=[N]4=O)(NC6=O)[C@@](C5(C)C)([H])CC76N1CCC7
InChi Code
InChI=1S/C26H27N3O4/c1-23(2)10-8-15-17(33-23)7-6-14-16-12-26-18(24(3,4)20(16)29(32)19(14)15)13-25(21(30)27-26)9-5-11-28(25)22(26)31/h6-8,10,12,18H,5,9,11,13H2,1-4H3,(H,27,30)/t18-,25?,26-/m0/s1
InChi Key
ALXLLOQTGLPCFG-XLXODUMSSA-N
Origin
Fungus/Aspergillus sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    250 µg

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    Product Description

    Avrainvillamide is a fungal metabolite and monomeric form of stephacidin B (Item No. 31656) that has been found in A. ochraceus.1,2 It is active against S. aureus, S. pyogenes, and E. faecalis (MICs = 12.5, 12.5, and 25 µg/ml, respectively).2 Avrainvillamide inhibits the growth of LNCaP, BT-549, T47D, and MALME-3M cancer cells with GI50 values of 0.24, 0.62, 0.21, and 0.41 µM, respectively.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wulff, J.E., Herzon, S.B., Siegrist, R., et al. Evidence for the rapid conversion of stephacidin B into the electrophilic monomer avrainvillamide in cell culture. J. Am. Chem. Soc. 129(16), 4898-4899 (2007).

    2. Sugie, Y., Hirai, H., Inagaki, T., et al. A new antibiotic CJ-17,665 from Aspergillus ochraceus. J. Antibiot. 54(11), 911-916 (2001).