A membrane-permeable antagonist of the inositol-1,4,5-triphosphate receptor
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Diastereomer(s)
10006797Araguspongin B
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Xestospongin C

Item No. 64950

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
[1R-(1R,4aR,11R,12aS,13S,16aS,23R,24aS)]-eicosahydro-5H,17H-1,23:11,13-diethano-2H,14H-[1,11]dioxacycloeicosino[2,3-b:12,13-b1]dipyridine
CAS Number
88903-69-9
Synonyms
  • Araguspongine E
  • XeC
Molecular Formula
C28H50N2O2
Formula Weight
446.7
Purity
≥90%
Formulation (Request formulation change)
A clear film
Solubility(Learn about Variance in Solubility)
Chloroform: SolubleEthyl Acetate: SolubleMethyl Acetate: Soluble
SMILES
[H][C@@]1(N2CCC3)[C@H]3CCCCCC[C@H]4O[C@]5([H])N(CCC[C@H]5CCCCCC[C@H](CC2)O1)CC4
InChi Code
InChI=1S/C28H50N2O2/c1-3-7-15-25-17-21-30-20-10-14-24(28(30)31-25)12-6-2-4-8-16-26-18-22-29-19-9-13-23(11-5-1)27(29)32-26/h23-28H,1-22H2/t23-,24+,25-,26-,27+,28+/m1/s1
InChi Key
PQYOPBRFUUEHRC-HCKQMYSWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 µg

    $120

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    50 µg

    $450

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    100 µg

    $780

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    250 µg

    $1,649

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    Product Description

    Xestospongin C is a marine natural product which was first isolated from Pacific basin sponges, and noted to have vasodilatory properties.1 Xestospongin C antagonizes the calcium-releasing action of inositol-1,4,5-trisphosphate (IP3) at the receptor level. Inositol phosphates are important signal transduction messengers acting via IP3 receptors to promote the mobilization of Ca2+ from intracellular stores. Xestospongin C blocks the increase in intracellular calcium in vascular smooth muscle cells completely at a concentration of 25 µM.2 Xestospongin C also inhibits the sarcoplasmic reticulum Ca2+ ATPase pump at concentrations of 700 nM.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nakagawa, M., and Endo, M. Structures of xestospongin A, B, C and D, novel vasodilative compounds from marine sponge, Xestospongia exigua. Tetrahedron Lett. 25(30), 3227-3230 (1984).

    2. Gafni, J., Munsch, J.A., Lam, T.H., et al. Xestospongins: Potent membrane permeable blockers of the inositol 1,4,5-triphosphate receptor. Neuron 19, 723-733 (1997).

    3. Castonguay, A., and Robitaille, R. Xestospongin C is a potent inhibitor of SERCA at a vertabrate synapse. Cell Calcium 32(1), 39-47 (2002).

    Product Citations

    Xian, H., Watari, K., Sanchez-Lopez, E., et al. Oxidized DNA fragments exit mitochondria via mPTP- and VDAC-dependent channels to activate NLRP3 inflammasome and interferon signaling. Immunity 55(8), 1370-1385 (2022).