BUFOTALIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H36O6
Molecular Weight	444.5604
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CC[C@]3([H])[C@]([H])(CC[C@]4(C)[C@H]([C@H](C[C@]34O)OC(C)=O)C5=COC(=O)C=C5)[C@@]1(C)CC[C@H](O)C2

InChI

InChIKey=VOZHMAYHYHEWBW-NVOOAVKYSA-N

InChI=1S/C26H36O6/c1-15(27)32-21-13-26(30)20-6-5-17-12-18(28)8-10-24(17,2)19(20)9-11-25(26,3)23(21)16-4-7-22(29)31-14-16/h4,7,14,17-21,23,28,30H,5-6,8-13H2,1-3H3/t17-,18+,19+,20-,21+,23+,24+,25-,26+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C26H36O6
Molecular Weight	444.5604
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25068992
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19055367

Bufotalin is a cardiotoxic bufanolide steroid, cardiac glycoside analogue, secreted by a number of toad species; a novel anti-osteoblastoma agent. Bufotalin is a traditional Chinese medicine prepared from the dried secretion of the auricular and skin glands of Bufo bufo gargarizans Cantor. Bufotalin has drawn attentions from both cancer biologists and oncologists due to its dramatic antitumor activities. It has been shown that bufotalin inhibits cancer cell growth and induces cancer cell apoptosis in vivo and in vitro.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
HepG2 16 Target ID: CHEMBL395 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22841670 \| https://www.ncbi.nlm.nih.gov/pubmed/19055367	Inhibitor 8297	0.5 µM [IC50]
transformed cell apoptotic process 108 Target ID: GO:0006927 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21887462 \| https://www.ncbi.nlm.nih.gov/pubmed/19055367	Activator 1430
A549 13 Target ID: CHEMBL392 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4050254	Inhibitor 8297	0.9 µM [IC50]
PC-3 15 Target ID: CHEMBL390 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23706005	Inhibitor 8297	34.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Liver cancer 53 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22841670	Primary		Basic research	Unknown Approved Use Unknown
Osteoblastoma 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25068992	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Microbial transformation of bufotalin by Alternaria alternata AS 3.4578.	2009	19180348
Bufotalin-induced apoptosis in osteoblastoma cells is associated with endoplasmic reticulum stress activation.	2014 Aug 15	25068992
[Bufadienolides from venom of Bufo bufo gargarizans].	2014 Mar	25204176

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 0.5–1 mg/kg, i.p. twice per day, for 7 days

Route of Administration: Intraperitoneal

In Vitro Use Guide

Bufotalin (1uM) inhibits MG-63 cell viability

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:00:04 GMT 2023` Edited by `admin` on `Sat Dec 16 10:00:04 GMT 2023`
Record UNII	EGL9670I6P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BUFOTALIN

Common Name

English

BUFA-20,22-DIENOLIDE, 16-(ACETYLOXY)-3,14-DIHYDROXY-, (3.BETA.,5.BETA.,16.BETA.)-

Common Name

English

NSC-89596

Code

English

3.BETA.,14,16.BETA.-TRIHYDROXY-5.BETA.-BUFA-20,22-DIENOLIDE 16-ACETATE

Common Name

English

BUFOTALIN [MI]

Common Name

English

Code System Code Type Description

WIKIPEDIA

Bufotalin