A resorcylic acid lactone
Related Products
Isomer(s)
17459(5Z)-7-Oxozeaenol
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(5E)-7-Oxozeaenol

Item No. 29840

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3S,5E,8S,9S,11E)-3,4,9,10-tetrahydro-8,9,16-trihydroxy-14-methoxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione
CAS Number
1198574-97-8
Synonyms
  • LL-Z 1640-2
Molecular Formula
C19H22O7
Formula Weight
362.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
COC1=CC(O)=C(C(O[C@@H](C)C/C=C/C([C@@H](O)[C@@H](O)C/C=C/2)=O)=O)C2=C1
InChi Code
InChI=1S/C19H22O7/c1-11-5-3-7-14(20)18(23)15(21)8-4-6-12-9-13(25-2)10-16(22)17(12)19(24)26-11/h3-4,6-7,9-11,15,18,21-23H,5,8H2,1-2H3/b6-4+,7-3+/t11-,15-,18+/m0/s1
InChi Key
NEQZWEXWOFPKOT-ULSULSEOSA-N
Origin
Fungus/Curvularia sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    (5E)-7-Oxozeaenol is a resorcylic acid lactone that has been found in the fungus MSX 63935 and has enzyme inhibitory and anticancer activities.1,2 It inhibits TGF-β-activated kinase 1 (TAK-1; IC50 = 1.3 µM).1 (5E)-7-Oxozeaenol inhibits proliferation of MCF-7, H460, SF-268, HT-29, and MDA-MB-435 human cancer cells with IC50 values of 4.9, 1.2, 5.6, 4.4, and 5.5 µM, respectively.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fakhouri, L., El-Elimat, T., Hurst, D.P., et al. Isolation, semisynthesis, covalent docking and transforming growth factor beta-activated kinase 1 (TAK1)-inhibitory activities of (5Z)-7-oxozeaenol analogues. Bioorg. Med. Chem. 23(21), 6993-6999 (2015).

    2. Ayers, S., Graf, T.N., Adcock, A.F., et al. Resorcylic acid lactones with cytotoxic and NF-κB inhibitory activities and their structure-activity relationships. J. Nat. Prod. 74(5), 1126-1131 (2011).