Compound: cantharidin
SMILES: O=C1OC(=O)[C@]2([C@@]1([C@H]3O[C@@H]2CC3)C)C
InChIKey: DHZBEENLJMYSHQ-XCVPVQRUSA-N
Synonyms: cantharidin, 56-25-7, Cantharone, CANTHARIDINE, Cantharides camphor, Kantaridin, Kantharidin, Cantaridina, Cantharidinum, 1,2-Dimethyl-3,6-epoxyperhydrophthalic anhydride, exo-1,2-cis-Dimethyl-3,6-epoxyhexahydrophthalic anhydride, (3ar,4s,7r,7as)-3a,7a-dimethylhexahydro-4,7-epoxy-2-benzofuran-1,3-dione, IGL471WQ8P, NSC-61805, YCANTH, 2,3-Dimethyl-7-oxabicyclo(2.2.1)heptane-2,3-dicarboxylic anhydride, CHEBI:64213, 7-Oxabicyclo(2.2.1)heptane-2,3-dicarboxylic anhydride, 2,3-dimethyl-, Hexahydro-3aalpha,7aalpha-dimethyl-4beta,7beta-epoxyisobenzofuran-1,3-dione, (1S,2R,6S,7R)-2,6-dimethyl-4,10-dioxatricyclo(5.2.1.02,6)decane-3,5-dione, (1S,2R,6S,7R)-2,6-dimethyl-4,10-dioxatricyclo[5.2.1.02,6]decane-3,5-dione, RefChem:123249, CANTHARIDIN 0.7%, DTXCID601764425, 200-263-3, 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-, (3aalpha,4beta,7beta,7aalpha)-, DTXSID7041752, Cantharidin [USAN], NSC61805, 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-, (3aR,4S,7R,7aS)-rel-, MFCD00134968, CHEMBL48449, CAN [Alkaloid], NSC 61805, Kantharidin [German], Caswell No. 157, CCRIS 635, HSDB 2181, AI3-04021, EINECS 200-263-3, UNII-IGL471WQ8P, EPA Pesticide Chemical Code 013101, 3a,7a-Dimethylhexahydro-4,7-epoxyisobenzofuran-1,3-dione, BRN 0085302, CAS-56-25-7, NCGC00016247-01, Ycanth (TN), CANTHARIDIN [MI], Prestwick3_000885, CANTHARIDIN [INN], Cantharidin (JAN/USAN), CANTHARIDIN [IARC], (1R,2S,3R,6S)-1,2-Dimethyl-3,6-epoxycyclohexane-1,2-dicarboxylic anhydride, 2,3-dicarboxylic anhydride, 7a-Dimethylhexahydro-3a,4,7-epoxyisobenzofuran, CANTHARIDIN [VANDF], CANTHARIDINE [HSDB], NCIMech_000301, CANTHARIDIN [MART.], CANTHARIDINUM [HPUS], BSPBio_000670, CANTHARIDIN [WHO-DD], 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-, (3a-alpha,4-beta,7-beta,7a-alpha), 5-19-05-00051 (Beilstein Handbook Reference), orb421994, SCHEMBL152262, BPBio1_000738, orb2893612, orb3139388, SCHEMBL31628232, cid_6708701, GTPL13081, HMS2097B12, HMS3412J13, HMS3676J13, 1,6-epoxyperhydrophthalic anhydride, 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-, (3a.alpha.,4.beta.,7.beta.,7a.alpha.)-, HY-N0209, MSK40063, BDBM50090505, CCG-35382, CCG-36082, EBC-26179, WHO 11470, AKOS015895930, AC-7967, CS-4979, DB12328, FC29633, (1R,2S,6R,7S)-2,6-dimethyl-4,10-dioxatricyclo[5.2.1.02,6]decane-3,5-dione, 4,3-dione, hexahydro-3a,7a-dimethyl-, exo-1,6-epoxyhexahydrophthalic anhydride, NCGC00025212-02, NCGC00025212-03, NCGC00025212-04, NCGC00025212-05, NCGC00025212-31, AS-18735, NCI60_005413, VP-102 drug/device delivering cantharidin, WLN: T C555 A AO DVOVTJ C1 G1, AB00513946, Hexahydro-3a,7-epoxyisobenzofuran-1,3-dione, D11745, 7-Oxabicyclo[2.2.1]heptane-2, 2,3-dimethyl-, EN300-24727854, Q410884, SR-01000597585, SR-01000597585-1, BRD-K80684056-001-01-0, BRD-K80684056-001-04-4, BRD-K80684056-001-05-1, BRD-K80684056-001-06-9, Ycanth (0.7% solution, single-use topical applicator), Hexahydro-3a,7a-dimethyl-4,7-epoxyisobenzo-furan-1,3-dione, (3aR,4S,7R,7aS)-3a,7a-dimethylhexahydro-4,7-epoxyisobenzofuran-1,3-dione, (1R,2S,6R,7S)-2,6-Dimethyl-4,10-dioxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione, (1R,2S,6R,7S)-2,6-dimethyl-4,10-dioxatricyclo[5.2.1.0,2,6]decane-3,5-dione, (1R,5S,6R,9S)-rel-1,5-Dimethyl-3,10-dioxatricyclo[3.2.1.01,5]decane-2,4-dione, (1R,7S)-2,6-Dimethyl-4,10-dioxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione, (1S,2R,6S,7R)-2,6-Dimethyl-4,10-dioxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione, (1S,3S,4R,7R)-2,6-dimethyl-4,10-dioxa-tricyclo[5.2.1.0-2,6]decane-3,5-dione, 4,3-dione, hexahydro-3a,7a-dimethyl-, (3a.alpha.,4.beta.,7.beta.,7a.alpha.)-, HEXAHYDRO-3A.ALPHA.,7A.ALPHA.-DIMETHYL-4.BETA.,7.BETA.-EPOXYISOBENZOFURAN-1,3-DIONE
Theoretical properties:
molecular_formula: C10H12O4
molecular_weight: 196.20 g/mol
exact_mass: 196.07355886 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 0
heavy_atom_count: 14
topological_polar_surface_area: 52.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Orthorhombic plates, scales
color: Orthorhombic plates, scales
boiling_point: Sublimes at 230 °F (EPA, 1998)
melting_point: 424 °F (EPA, 1998)
solubility: Insol in cold water; somewhat sol in hot water; 1 g dissolves in 40 ml acetone, 65 ml chloroform; 1 g dissolves in 560 ml ether, 150 ml ethyl acetate; sol in oils.
Descriptions:
{"pubchem": "Cantharidin is 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. It has a role as a herbicide and an EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor. It is a monoterpenoid and a cyclic dicarboxylic anhydride.", "chebi": "A monoterpenoid with an epoxy-bridged cyclic dicarboxylic anhydride structure secreted by many species of blister beetle, and most notably by the Spanish fly, <em>Lytta vesicatoria</em>.  Natural toxin inhibitor of protein phosphatases 1 and 2A.", "chembl": "CANTHARIDIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "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, poisonous in large doses. It has been historically used as an aphrodisiac (in preparations sold under the name \"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.\nPoisoning from cantharidin is a significant veterinary concern, especially in horses, but cantharidin 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.\nCantharidin 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."}