Tmic
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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
DescriptionA 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.
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
Description 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
  • Tetrahydrofuran
  • 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 g/LALOGPS
logP1.1ALOGPS
logP1.06ChemAxon
logS-1.1ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.4 m³·mol⁻¹ChemAxon
Polarizability18.54 ųChemAxon
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, Positivesplash10-0002-0900000000-2d4387a192fa4b019c2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-0f070c3ebeac7acf8ed2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9100000000-ece41192f3438759ec61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-2696ac6b96439730c8aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-04ead2e76b5e29626212View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9800000000-12d99cb03ca0677ff347View in MoNA
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 IDDB12328
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 IDNot Available
ChEBI ID64213
PubChem Compound ID5944
Kegg Compound IDC16778
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20594813
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21595743
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21668865
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21907641
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21930197
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22001622
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22233030
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22351815
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22380659
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22402807