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Structure Database (LMSD)

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Common Name

Resibufogenin

Systematic Name

3β-hydroxy-14β,15β-epoxy-5β-bufa-20,22-dienolide

Synonyms

Bufogenin
Respigon

LM ID

LMST01130031

Formula

C₂₄H₃₂O₄

Exact Mass

Calculate m/z

384.230061

Sum Composition

ST 24:5;O4

Status

Curated

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Classification

Biological Context

Resibufogenin is a cardiac glycoside first isolated from Bufonis venom that acts as an inhibitor of the Na+/K+-ATPase.¹ It exhibits cardiotonic, vasopressor, and respiratory stimulating actions in both animal and clinical models.² Resibufogenin has been used to antagonize the action of marinobufagenin in a rat experimental model of preeclampsia.³ Resibufogenin is also reported to have antiproliferative effects against cancer cells, inducing cell cycle arrest by suppressing the expression of cyclin D1.4

This information has been provided by Cayman Chemical

References

1. Puschett, J.B., Agunanne, E., and Uddin, M.N. Marinobufagenin, resibufogenin and preeclampsia. Biochim. Biophys. Acta 1802(12), 1246-1253 (2010).

2. Pamnani, M.B., Chen, S., Bryant, H.J., et al. Effects of three sodium-potassium adenosine triphosphatase inhibitors. Hypertension 18(3), 316-324 (1991).

3. Iwatsuki, K., Yusa, T., Kataoka, Y., et al. Experimental and clinical studies of resibufogenin. Tohoku J. Exp. Med. 86(2), 93-101 (1965).

4. Ichikawa, M., Sowa, Y., Iizumi, Y., et al. Resibufogenin induces G1-phase arrest through the proteasomal degradation of cyclin D1 in human malignant tumor cells. PLoS One 10(6), (2015).

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)

ATLJNLYIJOCWJE-CWMZOUAVSA-N

InChi (Click to copy)

InChI=1S/C24H32O4/c1-22-9-7-16(25)11-15(22)4-5-18-17(22)8-10-23(2)19(12-20-24(18,23)28-20)14-3-6-21(26)27-13-14/h3,6,13,15-20,25H,4-5,7-12H2,1-2H3/t15-,16+,17+,18-,19-,20-,22+,23-,24-/m1/s1

SMILES (Click to copy)

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