A bacterial metabolite
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Product Categories

Product Type

Biochemicals
Natural Products
Microbial Metabolites

Research Area

Cancer

Spirohexenolide A

Item No. 25116

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3E,7Z,9R,11E,13E,14aR,17S,18aS)-6,9,10,14a,17,18-hexahydro-9-hydroxy-13,14a,16,17-tetramethyl-4,7-etheno-3,18a-methano-2H,18aH-1,5-benzodioxacyclohexadecin-2,19-dione
CAS Number
1193347-22-6
Molecular Formula
C25H28O5
Formula Weight
408.5
Purity
≥95%
Formulation (Request formulation change)
A solid
SMILES
O=C(/C(C(O1)=O)=C2C=C/C(CO\2)=C\[C@H](O)C/C=C/C(C)=C/3)[C@@]41[C@@]3(C)C=C(C)[C@@H](C)C4
InChi Code
InChI=1S/C25H28O5/c1-15-6-5-7-19(26)10-18-8-9-20(29-14-18)21-22(27)25(30-23(21)28)13-17(3)16(2)12-24(25,4)11-15/h5-6,8-12,17,19,26H,7,13-14H2,1-4H3/b6-5+,15-11+,18-10+,21-20-/t17-,19+,24+,25+/m0/s1
InChi Key
SWMOMSBFRQXQAA-AOCINJOHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    100 µg

    $222

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    500 µg

    $717

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    Cayman Chemical
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    Product Description

    Spirohexenolide A is a metabolite originally isolated from S. platensis.1 It inhibits growth in the NCI-60 cancer cell line panel (GI50s = 0.1-17 μM) with the RPMI-8226 multiple myeloma, HOP-92 lung, and SW620 colon cancer cell lines being most sensitive (GI50s = 254, 191, and 565 nM, respectively). Spirohexenolide A also binds to human macrophage migration inhibition factor (MIF; Kd = 35.9 μM) and inhibits MIF cellular uptake and lysosomal localization in HCT116 cells.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kang, M., Jones, B.D., Mandel, A.L., et al. Isolation, structure elucidation, and antitumor activity of spirohexenolides A and B. The Journal of Organic Chemistry 74(23), 9054-9061 (2009).

    2. Yu, W.-L., Jones, B.D., Kang, M., et al. Spirohexenolide A targets human macrophage migration inhibitory factor (hMIF). J. Nat. Prod. 76(5), 817-823 (2013).