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Structure Database (LMSD)

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Common Name

Strophanthidin

Systematic Name

3β,5,14-trihydroxy-19-oxo-5β-card-20(22)-enolide

Synonyms

5beta-Hydroxy-19-oxodigitoxigenin
Convallatoxigenin
Corchorgenin
Corchorin
Corchoside A aglycon
Corchsularin
Erysimupicrone
Strophanthidin K
Strophanthidine

LM ID

LMST01120005

Formula

C₂₃H₃₂O₆

Exact Mass

Calculate m/z

404.21989

Sum Composition

ST 23:4;O6

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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Classification

Biological Context

Strophanthidin is a cardenolide that has been found in A. schimperi and has diverse biological activities.^1,2,3,4 It is an inhibitor of N-acetyltransferase (IC50 = ~1.2 µM).¹ Strophanthidin (1 µM) reduces maximal Na+/K+-ATPase pump activity and cell attachment and increases cell death in MDCK-C7 cells.² It decreases the levels of steroid receptor coactivator 3 (SRC-3) in MCF-7 breast cancer cells when used at a concentration of 500 nM.³ Strophanthidin (50 µM) increases calcium efflux and sarcoplasmic reticulum calcium levels in a voltage-clamp assay using isolated and perfused guinea pig hearts.⁴

This information has been provided by Cayman Chemical

References

1. Wang, Y., Lonard, D.M., Yu, Y., et al. Bufalin is a potent small-molecule inhibitor of the steroid receptor coactivators SRC-3 and SRC-1. Cancer Res. 74(5), 1506-1517 (2014).

2. González-García, C., Ceña, V., and Klein, D.C. Characterization of the α+-like Na+,K+-ATPase which mediates ouabain inhibition of adrenergic induction of N-acetyltransferase (EC 2.3.1.87) activity: Studies with isolated pinealocytes. Mol. Pharmacol. 32(6), 792-797 (1987).

3. Akimova, O.A., Bagrov, A.Y., Lopina, O.D., et al. Cardiotonic steroids differentially affect intracellular Na+ and [Na+]i/[K+]i-independent signaling in C7-MDCK cells. The Journal of Biological Chemisty 280(1), 832-839 (2005).

4. Bennett, D.L., O'Neill, S.C., and Eisner, D.A. Strophanthidin-induced gain of Ca2+ occurs during diastole and not systole in guinea-pig ventricular myocytes. Pflugers Arch. 437(5), 731-736 (1999).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Strophanthus kombe (#992788)

Magnoliopsida (#3398)

The crystal structure of strophanthidin, a cardioactive steroid, C23H32O6.1/2H2O,
Acta Cryst B, 1973

DOI: 10.1107/S0567740873005625

String Representations

InChiKey (Click to copy)

ODJLBQGVINUMMR-HZXDTFASSA-N

InChi (Click to copy)

InChI=1S/C23H32O6/c1-20-6-3-17-18(4-8-22(27)11-15(25)2-7-21(17,22)13-24)23(20,28)9-5-16(20)14-10-19(26)29-12-14/h10,13,15-18,25,27-28H,2-9,11-12H2,1H3/t15-,16+,17-,18+,20+,21-,22-,23-/m0/s1

SMILES (Click to copy)

C1[C@@]2(C=O)[C@](O)(CC[C@]3([H])[C@]2([H])CC[C@@]2(C)[C@]3(O)CC[C@]2([H])C2=CC(=O)OC2)C[C@@H](O)C1