A mycotoxin with diverse biological activities
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Viridicatumtoxin

Item No. 25480

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,7'aR,11'aR,12'R)-rel-(-)-7',7'a,8',11',11'a,12'-hexahydro-5',6',7'a,10',11'a,12'-hexahydroxy-3'-methoxy-2,6,6-trimethyl-7',8'-dioxo-spiro[2-cyclohexene-1,2'(1'H)-cyclopenta[de]naphthacene]-9'-carboxamide
CAS Number
39277-41-3
Synonyms
  • NSC 159628
Molecular Formula
C30H31NO10
Formula Weight
565.6
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O[C@@H]1[C@]2(O)[C@](C(C(C(N)=O)=C(O)C2)=O)(O)C(C3=C(O)C4=C(O)C=C(OC)C5=C4C(C[C@]56C(C)(C)CCC=C6C)=C31)=O
InChi Code
InChI=1S/C30H31NO10/c1-11-6-5-7-27(2,3)28(11)9-12-16-18(13(32)8-15(41-4)21(16)28)22(34)20-17(12)23(35)29(39)10-14(33)19(26(31)38)24(36)30(29,40)25(20)37/h6,8,23,32-35,39-40H,5,7,9-10H2,1-4H3,(H2,31,38)/t23-,28+,29-,30+/m0/s1
InChi Key
SUWQGLGDFGHZNH-VQCLQPKNSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    1 mg

    $250

    Add

    5 mg

    $1,050

    Add
    Cayman Chemical
    Visit Our Environmental Toxicology Resource Center

    Explore additional resources to study natural toxins, pollutants including PFAS and 6-PPD-Q, and their biological effects.

    ENVIRONMENTAL TOXICOLOGY TOOLS & SERVICES
    Product Description

    Viridicatumtoxin in a mycotoxin originally isolated from Penicillium that has diverse biological activities, including antimicrobial, cytotoxic, and toxic properties.1,2,3 It inhibits the growth of B. subtilis, M. luteus, C. perfringens, B. fragilis, and methicillin-resistant S. aureus (MRSA; MICs = 0.39-1.56 µg/ml), as well as C. albicans, S. cerevisiae, M. racemosus, A. niger, and P. chrysogenum (MICs = 6.2-25 µg/ml), but has no activity against M. smegmatis, E. coli, K. pneumoniae, P. aeruginosa, or S. marcescens (MICs = >100 µg/ml).3 Viridicatumtoxin inhibits the production of polyprenyl alcohols by S. aureus undecaprenyl pyrophosphate (UPP) synthase, E. coli octaprenyl pyrophosphate synthase (OPS), and S. cerevisiae dehydrodolichyl pyrophosphate (DedoIPP) synthase in vitro (IC50s = 3.1, 21, and 71 µM, respectively). It has cytotoxic effects against human Jurkat T (IC50 = 4.92 µM), chronic lymphocytic leukemia (CLL; LC50 = 0.7-3.5 nM), and bone marrow-derived HS-5 stromal cells.2,3 Viridicatumtoxin is toxic to rats and mice when administered intraperitoneally (LD50s = 80 and 90 mg/kg, respectively) and to rats when administered via gastric intubation (LD50 = 122.4 mg/kg), but not to rats or mice when administered orally or through subcutaneous injection.1,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hutchinson, R.D., Steyn, P.S., and Van Rensburg, S.J. Viridicatumtoxin, a new mycotoxin from Penicillium viridicatum Westling. Toxicol. Appl. Pharmacol. 24(30), 507-509 (1973).

    2. Bladt, T.T., Dürr, C., Knudsen, P.B., et al. Bio-activity and dereplication-based discovery of ophiobolins and other fungal secondary metabolites targeting leukemia cells. Molecules 18(12), 14629-14650 (2013).

    3. Inokoshi, J., Nakamura, Y., Komada, S., et al. Inhibition of bacterial undecaprenyl pyrophosphate synthase by small fungal molecules. J. Antibiot. (Tokyo) 69(11), 798-805 (2016).

    4. Bendele, A.M., Carlton, W.W., Nelson, G.E., et al. Viridicatumtoxin mycotoxicosis in mice and rats. Toxicol. Lett. 22(3), 287-291 (1984).