LIPID MAPS

Structure Database (LMSD)

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Common Name

Digitoxigenin

Systematic Name

3-β,14β-dihydroxy-5-β-card-20(22)-enolide

Synonyms

LM ID

LMST01120001

Formula

C₂₃H₃₄O₄

Exact Mass

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374.24571

Sum Composition

ST 23:3;O4

Status

Curated

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Classification

Biological Context

Digitoxigenin is a cardenolide and aglycone constituent of digitoxin, an extract from the foxglove plant, D. purpurea. It elicits cardiac contraction and cardiotonic effects by inhibiting the Na+/K+ ATPase via binding at the digitalis receptor site with nanomolar potency.^1,2 Digitoxigenin is highly cytotoxic, inhibiting Na+/K+ ATPase-dependent protein synthesis, and has been examined for use as an antitumor compound.³

This information has been provided by Cayman Chemical

References

1. Balzan, S., D'Urso, G., Ghione, S., et al. Selective inhibition of human erythrocyte Na+/K+ ATPase by cardiac glycosides and by a mammalian digitalis like factor. Life Sci. 67(16), 1921-1928 (2000).

2. Katz, A., Lifshitz, Y., Bab-Dinitz, E., et al. Selectivity of digitalis glycosides for isoforms of human Na,K-ATPase. The Journal of Biological Chemisty 285(25), 19582-19592 (2010).

3. Perne, A., Muellner, M.K., Steinrueck, M., et al. Cardiac glycosides induce cell death in human cells by inhibiting general protein synthesis. PLoS One 4(12), 1-9 (2009).

String Representations

InChiKey (Click to copy)

XZTUSOXSLKTKJQ-CESUGQOBSA-N

InChi (Click to copy)

InChI=1S/C23H34O4/c1-21-8-5-16(24)12-15(21)3-4-19-18(21)6-9-22(2)17(7-10-23(19,22)26)14-11-20(25)27-13-14/h11,15-19,24,26H,3-10,12-13H2,1-2H3/t15-,16+,17-,18+,19-,21+,22-,23+/m1/s1

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])(C5COC(=O)C=5)CC[C@]4(O)[C@]3([H])CC[C@]2([H])C[C@@H](O)C1