Canmetcon
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Record Information
Version1.0
Creation Date2016-05-19 01:30:51 UTC
Update Date2016-11-09 01:09:15 UTC
Accession NumberCHEM003964
Identification
Common NameCantharidin
ClassSmall Molecule
DescriptionCantharidin is an odorless, colorless terpene secreted by many species of blister beetles, including broadly in genus Epicauta, and in species Lytta vesicatoria . False blister beetles, cardinal beetles, and soldier beetles also produce cantharidin. Poisoning from the substance is a significant veterinary concern, especially in horses from the Epicauta species, but it can also be poisonous to humans if taken internally . Externally, cantharidin is a potent vesicant , exposure to which can cause severe chemical burns. Properly dosed and applied, the same properties have been used for effective topical medications for some conditions.
Contaminant Sources
  • Clean Air Act Chemicals
  • IARC Carcinogens Group 3
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
Synonyms
ValueSource
1,2-Dimethyl-3,6-epoxyperhydrophthalic anhydrideChEBI
CantharidineChEBI
CantharoneChEBI
exo-1,2-cis-Dimethyl-3,6-epoxyhexahydrophthalic anhydrideChEBI
KantharidinChEBI
CantharidesMeSH
Chemical FormulaC10H12O4
Average Molecular Mass196.202 g/mol
Monoisotopic Mass196.074 g/mol
CAS Registry Number56-25-7
IUPAC Name(1R,2S,6R,7S)-2,6-dimethyl-4,10-dioxatricyclo[5.2.1.0²,⁶]decane-3,5-dione
Traditional Namecantharidin
SMILES[H][C@]12CC[C@]([H])(O1)[C@]1(C)C(=O)OC(=O)[C@]21C
InChI IdentifierInChI=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-
InChI KeyDHZBEENLJMYSHQ-XCVPVQRUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassFurofurans
Sub ClassNot Available
Direct ParentFurofurans
Alternative Parents
Substituents
  • Furofuran
  • Dicarboxylic acid or derivatives
  • Oxolane
  • Carboxylic acid anhydride
  • Lactone
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility16.6 mg/mLALOGPS
logP1.1ALOGPS
logP1.06ChemAxon
logS-1.1ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.4 m3·mol-1ChemAxon
Polarizability18.54 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00010979
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCantharidin
Chemspider ID5731
ChEBI ID64213
PubChem Compound ID5944
Kegg Compound IDC16778
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. http://www.ncbi.nlm.nih.gov/pubmed/?term=20594813
2. http://www.ncbi.nlm.nih.gov/pubmed/?term=21595743
3. http://www.ncbi.nlm.nih.gov/pubmed/?term=21668865
4. http://www.ncbi.nlm.nih.gov/pubmed/?term=21907641
5. http://www.ncbi.nlm.nih.gov/pubmed/?term=21930197
6. http://www.ncbi.nlm.nih.gov/pubmed/?term=22001622
7. http://www.ncbi.nlm.nih.gov/pubmed/?term=22233030
8. http://www.ncbi.nlm.nih.gov/pubmed/?term=22351815
9. http://www.ncbi.nlm.nih.gov/pubmed/?term=22380659
10. http://www.ncbi.nlm.nih.gov/pubmed/?term=22402807
11. (1976) Cantharidin. IARC monographs on the evaluation of carcinogenic risk of chemicals to man;IARC Monogr Eval Carcinog Risk Chem Man;1976 ;10:79-84 (PMID: 791809)
12. Craven JD, Polak A (1954) Cantharidin Poisoning. British medical journal;Br Med J;1954 Dec;2(4901):1386-8 (PMID: 20788368)
13. (1954) CANTHARIDIN poisoning. British medical journal;Br Med J;1954 Dec;2(4901):1405-6 (PMID: 13209137)
14. OAKS WW, DITUNNO JF, MAGNANI T, LEVY HA, MILLS LC (1960) Cantharidin poisoning. Archives of internal medicine;Arch. Intern. Med.;1960 Apr;105:574-82 (PMID: 14428136)
15. Till JS, Majmudar BN (1981) Cantharidin poisoning. Southern medical journal;South. Med. J.;1981 Apr;74(4):444-7 (PMID: 7221663)
16. Pines A, Gapany M (1984) Cantharidin poisoning. Harefuah;Harefuah;1984 Mar;106(5):220 (PMID: 6724416)
17. KUSCHE E (1953) Cantharidin poisoning. Medizinische Monatsschrift;Med Monatsschr;1953 Apr;7(4):252-3 (PMID: 13086515)
18. Beasley VR, Wolf GA, Fischer DC, Ray AC, Edwards WC (1983) Cantharidin toxicosis in horses. Journal of the American Veterinary Medical Association;J. Am. Vet. Med. Assoc.;1983 Feb;182(3):283-4 (PMID: 6826454)
19. NICKOLLS LC, TEARE D (1954) Poisoning by cantharidin. British medical journal;Br Med J;1954 Dec;2(4901):1384-6 (PMID: 13209125)
20. Schmitz DG (1989) Cantharidin toxicosis in horses. Journal of veterinary internal medicine / American College of Veterinary Internal Medicine;J. Vet. Intern. Med.;1989 Oct-Dec;3(4):208-15 (PMID: 2685272)