A fungal metabolite with diverse biological activities
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Cerulenin

Item No. 10005647

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2R,3S-epoxy-4-oxo-7,10-dodecadienamide
CAS Number
17397-89-6
Synonyms
  • Helicocerin
  • NSC 116069
Molecular Formula
C12H17NO3
Formula Weight
223.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2)(1:6): .2 mg/mlDMSO: 25 mg/mlEthanol: 20 mg/ml
SMILES
C/C=C/C/C=C/CCC([C@@H]1[C@H](C(N)=O)O1)=O
InChi Code
InChI=1S/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/b3-2+,6-5+/t10-,11-/m1/s1
InChi Key
GVEZIHKRYBHEFX-NQQPLRFYSA-N
Origin
Fungus/Cephalosporium caerulens
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $131

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    10 mg

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    50 mg

    $1,048

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    Product Description

    Cerulenin is a fungal metabolite originally isolated from C. caerulens that has diverse biological activities.1,2,3 It is active against a variety of bacteria, including B. subtilis, E. coli, B. megaterium, and B. anthracis (MICs = 12.5, 12.5, 50, and 50 µg/ml, respectively) and fungi, including strains of C. albicans, T. rubrum, and A. fumigatus (MICs = 0.8-3.7, 3.1-6.2 and 12.5-50 µg/ml, respectively).1 Cerulenin is an inhibitor of fatty acid synthase type I (FAS-I) and FAS-II (IC50s = 3 and 20 µM, respectively, for the E. coli enzymes).2 It inhibits fatty acid synthesis in a panel of human cancer cell lines, including breast, ovarian, and endometrial cancer cells, as well as reduces tumor growth in a OVCAR-3 mouse xenograft model.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Omura, S. The antibiotic cerulenin, a novel tool for biochemistry as an inhibitor of fatty acid synthesis. Bacteriol. Rev. 40(3), 681-697 (1976).

    2. Price, A.C., Choi, K.-H., Heath, R.J., et al. Inhibition of β-ketoacyl-acyl carrier protein synthases by thiolactomycin and cerulenin. Structure and mechanism. The Journal of Biological Chemisty 276(9), 6551-6559 (2001).

    3. Pizer, E.S., Wood, F.D., Heine, H.S., et al. Inhibition of fatty acid synthesis delays disease progression in a xenograft model of ovarian cancer. Cancer Res. 56(6), 1189-1193 (1996).