A fungal metabolite with diverse biological activities
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Penicillide

Item No. 26912

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
11-hydroxy-3-[(1S)-1-hydroxy-3-methylbutyl]-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]dioxocin-5-one
CAS Number
55303-92-9
Synonyms
  • Vermixocin A
Molecular Formula
C21H24O6
Formula Weight
372.4
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
SMILES
COC1=C2C(OC(C(O)=CC(C)=C3)=C3COC2=O)=CC=C1[C@@H](O)CC(C)C
InChi Code
InChI=1S/C21H24O6/c1-11(2)7-15(22)14-5-6-17-18(20(14)25-4)21(24)26-10-13-8-12(3)9-16(23)19(13)27-17/h5-6,8-9,11,15,22-23H,7,10H2,1-4H3/t15-/m0/s1
InChi Key
UOWGLBYIKHMCIS-HNNXBMFYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

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    1 mg

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    Product Description

    Penicillide is a fungal metabolite originally isolated from Penicillium that has diverse biological activities.1,2,3,4,5 It is an inhibitor of calpain 2/m-calpain (IC50 = 7.1 µM) and acyl-coenzyme A:cholesterol acyltransferase (ACAT; IC50 = 22.9 µM).2,3 It is also an antagonist of oxytocin receptors (IC50 = 67 µM).4 Penicillide inhibits RNA synthesis in P388 murine leukemia cells.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sassa, T., Niwa, G., Unno, H., et al. Structure of penicillide, a new metabolite produced by a Penicillium species. Tetrahedron Lett. 45, 3941-3942 (1974).

    2. Chung, M.-C., Lee, H.-J., Chun, H.K., et al. Penicillide, a nonpeptide calpain inhibitor, produced by Penicillium sp. F60760. J. Microbiol. Biotechnol. 8(2), 188-190 (1998).

    3. Kuroda, K., Morishita, Y., Saito, Y., et al. AS-186 compounds, new inhibitors of Acyl-CoA: Cholesterol acyltransferase from Penicillium asperosporum KYI635. J. Antibiot. 47(1), 16-22 (1994).

    4. Salituro, G.M., Pettibone, D.J., Clineschmidt, B.V., et al. Potent, non-peptidic oxytocin receptor antagonists from a natural source. Bioorg. Med. Chem. Lett. 3(2), 337-340 (1993).

    5. Proksa, B., Uhrín, D., Adamcová, J., et al. Vermixocins A and B, two novel metabolites from Penicillium vermiculatum. J. Antibiot. (Tokyo) 45(8), 1268-1272 (1992).