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About This Item

Empirical Formula (Hill Notation):
C30H38O11
CAS Number:
58812-37-6
Molecular Weight:
574.62
MDL number:
MFCD00210564
UNSPSC Code:
51111800
UNSPSC Code:
12352200
NACRES:
NA.77
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Quality Level

100

Assay

≥90% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

SMILES string

C[C@@]1([C@H]2OC(C)=O)[C@]3([C@]([H])(O3)C[C@H]1C4=COC=C4)[C@]5(C)[C@H](O)C[C@@]6([H])[C@@](C)([C@@H]7O)[C@H](OC(C)=O)C[C@H](O)[C@]6(CO7)[C@@]5([H])C2=O

InChI

1S/C30H38O11/c1-13(31)39-20-10-19(34)29-12-38-25(36)26(20,3)17(29)9-18(33)28(5)23(29)22(35)24(40-14(2)32)27(4)16(15-6-7-37-11-15)8-21-30(27,28)41-21/h6-7,11,16-21,23-25,33-34,36H,8-10,12H2,1-5H3/t16-,17-,18+,19-,20+,21+,23-,24-,25+,26+,27+,28+,29+,30+/m0/

InChI key

NAHTXVIXCMUDLF-RFNFAWMESA-N

Biochem/physiol Actions

Botulinum neurotoxin inhibitor; Inhibitor of anthrax Lethal Toxin-induced cell death; exhibits potent antiviral activity against SARS-CoV-2, SFTSV, and bunyavirus.
Toosendanin is a natural occuring triterpenoid recently found to be an inhibitor of botulinum neurotoxin and also found to be an inhibitor of anthrax Lethal Toxin (LT)-induced cell death. Anthrax toxin is composed of three proteins: the toxin B subunit protective antigen (PA), a zinc metalloprotease lethal factor (LF), and an adenylate cyclase edema factor (EF). PA and EF combine to form edema toxin (ET) while PA and LF combine to form lethal toxin (LT), which induces rapid caspase-1 dependent cell death in macrophages. Toosendanin had an IC50 of 56 nM (32 ng/ml) against LT, likely by inhibiting endocytosis and endosomal acidification. Toosendanin has also been found to suppress proliferation and induce apoptosis in a variety of human cancer cells, possibly mediated through JNK signaling pathway.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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