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Structure Database (LMSD)

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Common Name

Telocinobufagin

Systematic Name

3β,5β,14β-trihydroxy-bufa-20,22-dienolide

Synonyms

Telocinobufogenin

LM ID

LMST01130025

Formula

C₂₄H₃₄O₅

Exact Mass

Calculate m/z

402.240626

Sum Composition

ST 24:4;O5

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

Telocinobufagin is a cardiotonic steroid that has been found in skin secretions of the toad B. rubescens and has diverse biological activities.^1,2,3,4 It inhibits human kidney Na+/K+-ATPase with an IC50 value of 44.2 nM.³ Telocinobufagin (9.9 μg/ml) increases contraction force in isolated frog ventricle strips by 30.2%.² It is cytotoxic to HL-60, HCT8, SF295, MDA-MB-435 cancer cells and human peripheral blood lymphocytes (IC50s = 0.06, 0.06, 0.03, 0.11, and 0.05 μM, respectively).⁴ Telocinobufagin is also active against E. coli and S. aureus (MICs = 64 and 128 μg/ml, respectively).²

This information has been provided by Cayman Chemical

References

1. Pavlovic, D. The role of cardiotonic steroids in the pathogenesis of cardiomyopathy in chronic kidney disease. Nephron Clin. Pract. 128(1-2), 11-21 (2014).

2. Cunha Filho, G.A., Schwartz, C.A., Resck, I.S., et al. Antimicrobial activity of the bufadienolides marinobufagin and telocinobufagin isolated as major components from skin secretion of the toad Bufo rubescens. Toxicon. 45(6), 777-782 (2005).

3. Touza, N.A., Pôças, E.S., Quintas, L.E.M., et al. Inhibitory effect of combinations of digoxin and endogenous cardiotonic steroids on Na+/K+-ATPase activity in human kidney membrane preparation. Life Sci. 88(1-2), 39-42 (2011).

4. G.A., C.-F., Resck, I.S., Cavalcanti, B.C., et al. Cytotoxic profile of natural and some modified bufadienolides from toad Rhinella schneideri parotoid gland secretion. Toxicon. 56(3), 339-348 (2010).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Duttaphrynus melanostictus (#30335)

Amphibia (#8292)

Isolation and structure of five new cancer cell growth inhibitory bufadienolides from the Chinese traditional drug Ch'an Su.,
J Nat Prod, 2001

Pubmed ID: 11575946

DOI: 10.1021/np0101088

String Representations

InChiKey (Click to copy)

PBSOJKPTQWWJJD-ZBDZJSKLSA-N

InChi (Click to copy)

InChI=1S/C24H34O5/c1-21-9-5-16(25)13-23(21,27)11-7-19-18(21)6-10-22(2)17(8-12-24(19,22)28)15-3-4-20(26)29-14-15/h3-4,14,16-19,25,27-28H,5-13H2,1-2H3/t16-,17+,18-,19+,21+,22+,23-,24-/m0/s1

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])(C5=COC(=O)C=C5)CC[C@]4(O)[C@]3([H])CC[C@]2(O)C[C@@H](O)C1