LIPID MAPS

Structure Database (LMSD)

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Common Name

Cinobufotalin

Systematic Name

3β,5β-dihydroxy-16β-acetoxy-14β,15β-epoxy-bufa-20,22-dienolide

Synonyms

CINOBUFOTLIN

LM ID

LMST01130034

Formula

C₂₆H₃₄O₇

Exact Mass

Calculate m/z

458.230456

Sum Composition

ST 26:6;O7

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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View NP-MRD ID(NMR) spectrum

Classification

Biological Context

Cinobufotalin is a steroid glycoside originally isolated from the Asiatic toad (B. gargarizans) and has diverse biological activities.^1,2 It reduces SRC-3 protein levels in MCF-7 breast cancer cells when used at concentrations ranging from 10 to 100 nM.¹ Cinobufotalin (1 μM) reduces Na+/K+ pump activity, viability, and cell attachment of C7-MDCK cells.² It reduces expression of the epithelial-mesenchymal (EMT) markers E-cadherin, vimentin, ZEB1, and Slug in and migration and invasion of PC3 cells.³ Cinobufotalin (0.1-10 μM) is cytotoxic to A549, H460, and HTB-58 lung cancer cells.⁴ In vivo, cinobufotalin (1 and 5 mg/kg) reduces tumor volume and increases survival in an A549 mouse xenograft model.

This information has been provided by Cayman Chemical

References

1. Kai, S., Lu, J.-H., Hui, P.-P., et al. Pre-clinical evaluation of cinobufotalin as a potential anti-lung cancer agent. Biochem. Biophys. Res. Commun. 452(3), 768-774 (2014).

2. Chen, L., Mai, W., Chen, M., et al. Arenobufagin inhibits prostate cancer epithelial-mesenchymal transition and metastasis by down-regulating β-catenin. Pharmacol. Res. 123, 130-142 (2017).

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. J. Biol. Chem. 280(1), 832-839 (2005).

4. 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).

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)

KBKUJJFDSHBPPA-ZNCGZLKOSA-N

InChi (Click to copy)

InChI=1S/C26H34O7/c1-14(27)32-21-20(15-4-5-19(29)31-13-15)24(3)10-7-17-18(26(24)22(21)33-26)8-11-25(30)12-16(28)6-9-23(17,25)2/h4-5,13,16-18,20-22,28,30H,6-12H2,1-3H3/t16-,17-,18+,20-,21+,22+,23+,24+,25-,26+/m0/s1

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])(C5=COC(=O)C=C5)[C@@H](OC(=O)C)[C@H]5O[C@@]45[C@]3([H])CC[C@]2(O)C[C@@H](O)C1