(+)-Xestospongin A

Cayman Chemical Item Number 10006794

Araguspongin D; XeA (CAS 88840-02-2)

(+)-Xestospongin A (CAS 88840-02-2)

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Description

Xestospongins are marine natural products first isolated from pacific basin sponges, and noted to have vasodilatory properties.1 Inositol phosphates (IPs) are important signal transduction messengers acting via IP3 receptors to promote the mobilization of Ca2+ from intracellular stores.2 XestosponginA antagonizes the calcium-releasing action of inositol-1,4,5-trisphosphate at the receptor level in cerebral microsomes, with an IC50 of 2.5 µM.3 It is thus about ten times less potent than XestosponginC as an antagonist of the IP3 receptor.

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 Majerus, P.W. Inositol phosphate biochemistry. Annu Rev Biochem 61 225-250 (1992).

3 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).

Synonyms
  • Araguspongin D
  • XeA
Formal Name [1R-​(1R*,​4aR*,​11R*,​12aS*,​13R*,​16aR*,​23R*,​24aS*)]-​eicosahydro-​5H,​17H-​1,​23:11,​13-​diethano-​2H,​14H-​[1,​11]dioxacyclo-​eicosino[2,​3-​b:12,​13-​b’]dipyridine
CAS Number 88840-02-2
Molecular Formula C28H50N2O2
Formula Weight 446.7
Formulation A solution in acetone
Purity >90%
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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[H]​[C@@]​12N(CCC[C@H]​2CCCCCC[C@H]​3O[C@]​4([H]​)​[C@@H]​(CCCN4CC3)​CCCCCC5)​CC[C@@H]​5O1
InCHI Code
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​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
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PQYOPBRFUUEHRC-BXZOIBFVSA-N

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Size Price Quantity Subtotal
50 µg $165.00 $0.00
100 µg $314.00 $0.00
250 µg $743.00 $0.00
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Pricing updated 2014-04-23. Prices are subject to change without notice.

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Related Products

Araguspongin B
SKF 96365 (hydrochloride)
Xestospongin C

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