cantharidin (CHEBI:64213)

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ChEBI Name	cantharidin

ChEBI ID	CHEBI:64213

Definition	A monoterpenoid with an epoxy-bridged cyclic dicarboxylic anhydride structure secreted by many species of blister beetle, and most notably by the Spanish fly, Lytta vesicatoria. Natural toxin inhibitor of protein phosphatases 1 and 2A.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB0710248, eMolecules:2736475, eMolecules:36500365, ZINC000017611186

Download	Molfile XML SDF

Wikipedia	License
Cantharidin is an odorless, colorless fatty substance of the terpenoid class, which is secreted by many species of blister beetles. Its main current use in pharmacology is treating molluscum contagiosum and warts topically. It is a burn agent and poisonous in large doses, and has been historically used as aphrodisiacs (Spanish fly). In its natural form, cantharidin is secreted by the male blister beetle, and given to the female as a copulatory gift during mating. Afterwards, the female beetle covers her eggs with it as a defense against predators. Poisoning from cantharidin is a significant veterinary concern, especially in horses, but it can also be poisonous to humans if taken internally (where the source is usually experimental self-exposure). Externally, cantharidin is a potent vesicant (blistering agent), exposure to which can cause severe chemical burns. Properly dosed and applied, the same properties have also been used therapeutically, for instance, for treatment of skin conditions, such as molluscum contagiosum infection of the skin. Cantharidin is classified as an extremely hazardous substance in the United States, and is subject to strict reporting requirements by facilities that produce, store, or use it in significant quantities.
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Formula

C10H12O4

Net Charge

Average Mass

196.19990

Monoisotopic Mass

196.07356

InChI

InChI=1S/C10H12O4/c1-9-5-3-4-6(13-5)10(9,2)8(12)14-7(9)11/h5-6H,3-4H2,1-2H3/t5-,6+,9+,10-

InChIKey

DHZBEENLJMYSHQ-XCVPVQRUSA-N

SMILES

C[C@]12[C@@H]3CC[C@@H](O3)[C@@]1(C)C(=O)OC2=O

Roles Classification
Biological Role(s):	EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor Any EC 3.1.3.* (phosphoric monoester hydrolase) inhibitor that interferes with the action of phosphoprotein phosphatase (EC 3.1.3.16).

Application(s):	herbicide A substance used to destroy plant pests.

ChEBI Ontology
Outgoing	cantharidin (CHEBI:64213) has role EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor (CHEBI:37153) cantharidin (CHEBI:64213) has role herbicide (CHEBI:24527) cantharidin (CHEBI:64213) is a cyclic dicarboxylic anhydride (CHEBI:36609) cantharidin (CHEBI:64213) is a monoterpenoid (CHEBI:25409)

Incoming	cantharidic acid (CHEBI:78695) has functional parent cantharidin (CHEBI:64213)

IUPAC Name

(3aR,4S,7R,7aS)-3a,7a-dimethylhexahydro-4,7-epoxy-2-benzofuran-1,3-dione

Synonyms	Sources
1,2-Dimethyl-3,6-epoxyperhydrophthalic anhydride	ChemIDplus
Cantharidine	ChemIDplus
Cantharone	ChemIDplus
exo-1,2-cis-Dimethyl-3,6-epoxyhexahydrophthalic anhydride	ChemIDplus
Kantharidin	ChemIDplus

Citations

Last Modified

26 February 2016