An antifungal agent
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Heronamide C

Item No. 23644

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9S,10R-dihydroxy-7,15-dimethyl-20R-(2E,4E)-2,4-octadien-1-yl-,azacycloeicosa-3E,5E,7E,11Z,13E,15E,17E-heptaen-2-one
CAS Number
1257083-94-5
Molecular Formula
C29H39NO3
Formula Weight
449.6
Purity
≥90%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: solubleMethanol: unstable
SMILES
CC1=C/[C@H](O)[C@H](O)/C=C\C=C\C(C)=C/C=C/C[C@@H](C/C=C/C=C/CCC)NC(/C=C/C=C/1)=O
InChi Code
InChI=1S/C29H39NO3/c1-4-5-6-7-8-9-19-26-20-13-10-16-24(2)17-11-14-21-27(31)28(32)23-25(3)18-12-15-22-29(33)30-26/h6-18,21-23,26-28,31-32H,4-5,19-20H2,1-3H3,(H,30,33)/b7-6+,9-8+,13-10+,17-11+,18-12+,21-14-,22-15+,24-16-,25-23+/t26-,27-,28+/m1/s1
InChi Key
QUZNSWBEDCHESP-SSIUSDJISA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Heronamide C is a polyketide macrolactam antifungal agent produced by marine Actinomycetes.1 It inhibits the growth of and induces abnormal accumulation of cell wall material in wild-type fission yeast cells (MIC = 0.13-0.28 μM). Heronamide C lacks activity against Gram-positive bacteria and human HeLa and MDA-MB-231 cancer cell lines.2 However, it induces reversible morphological changes, including formation of large intracellular structures, in HeLa cells at a concentration of 20 μM.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fujita, K., Sugiyama, R., Nishimura, S., et al. Stereochemical assignment and biological evaluation of BE-14106 unveils the importance of one acetate unit for the antifungal activity of polyene macrolactams. J. Nat. Prod. 79(7), 1877-1880 (2016).

    2. Paju, R., Piggott, A.M., Conte, M.M., et al. Heronamides A-C, new polyketide macrolactams from an Australian marine-derived Streptomyces sp. A biosynthetic case for synchronized tandem electrocyclization. Org. Biomol. Chem. 8(20), 4682-4689 (2010).