A bacterial metabolite
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.

Neoaureothin

Item No. 28091

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-methoxy-3,5-dimethyl-6-[(2R,4Z)-tetrahydro-4-[(2E,4E,6E)-2,4,6-trimethyl-7-(4-nitrophenyl)-2,4,6-heptatrien-1-ylidene]-2-furanyl]-4H-pyran-4-one
CAS Number
59795-94-7
Synonyms
  • NSC 260179
  • Spectinabilin
Molecular Formula
C28H31NO6
Formula Weight
477.6
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
λmax
268, 368 nm
SMILES
CC(/C=C1CO[C@@H](C(OC(OC)=C2C)=C(C)C2=O)C\1)=C\C(C)=C\C(C)=C\C3=CC=C([N+]([O-])=O)C=C3
InChi Code
InChI=1S/C28H31NO6/c1-17(11-18(2)13-22-7-9-24(10-8-22)29(31)32)12-19(3)14-23-15-25(34-16-23)27-20(4)26(30)21(5)28(33-6)35-27/h7-14,25H,15-16H2,1-6H3/b17-11+,18-13+,19-12+,23-14-/t25-/m1/s1
InChi Key
IZICQJAGBLBAMJ-QDYRYYKCSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature 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

    500 µg

    $314

    Add

    2.5 mg

    $1,098

    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

    Neoaureothin is a bacterial metabolite that has been found in Streptomyces.1 It is an androgen receptor (AR) antagonist that inhibits binding of dihydrotestosterone (DHT) to ARs (IC50 = 13 μM) and inhibits DHT-induced expression of prostate-specific antigen in LNCaP cells (IC50 = 1.75 nM). Neoaureothin is cytotoxic to A549, HCT116, and HepG2 cells (IC50s = 34.3, 47, and 37.2 μg/ml, respectively).2 It also has nematocidal activity against the pine wood nematode B. xylophilus (LC50 = 0.84 μg/ml) and increases survival of P. densiflora trees inoculated with B. xylophilus.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kawamura, T., Fujimaki, T., Hamanaka, N., et al. Isolation and structure elucidation of a novel androgen antagonist, arabilin, produced by Streptomyces sp. MK756-CF1. J. Antibiot. (Tokyo) 63(10), 601-605 (2010).

    2. Liu, C.X., Liu, S.H., Zhao, J.W., et al. A new spectinabilin derivative with cytotoxic activity from ant-derived Streptomyces sp. 1H-GS5. J. Asian Nat. Prod. Res. 19(9), 924-929 (2017).

    3. Liu, M.J., Hwang, B.S., Jin, C.Z., et al. Screening, isolation and evaluation of a nematicidal compound from actinomycetes against the pine wood nematode, Bursaphelenchus xylophilus. Pest. Manag. Sci. 75(6), 1585-1593 (2019).