Coriamyrtin (T3D4074)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2014-08-29 05:03:08 UTC
Update Date2014-12-24 20:26:37 UTC
Accession NumberT3D4074
Identification
Common NameCoriamyrtin
ClassSmall Molecule
DescriptionThe leaves and fruits of Coriaria myrtifolia contain coriamyrtin, a typical convulsant substance.
Compound Type
  • Ester
  • Ether
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC15H18O5
Average Molecular Mass278.300 g/mol
Monoisotopic Mass278.115 g/mol
CAS Registry Number2571-86-0
IUPAC Name(1'S,2R,2'R,3'S,5'R,7'R,9'S,12'R)-2'-hydroxy-7'-methyl-12'-(prop-1-en-2-yl)-4',10'-dioxaspiro[oxirane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]dodecane]-11'-one
Traditional Namecoriamyrtin
SMILES[H][C@@]12O[C@]1([H])[C@@]1(O)[C@@]3([H])C(=O)O[C@@]([H])(C[C@@]1(C)[C@@]21CO1)[C@@]3([H])C(C)=C
InChI IdentifierInChI=1S/C15H18O5/c1-6(2)8-7-4-13(3)14(5-18-14)10-11(20-10)15(13,17)9(8)12(16)19-7/h7-11,17H,1,4-5H2,2-3H3/t7-,8+,9+,10+,11-,13-,14+,15-/m0/s1
InChI KeyInChIKey=BWWDLKVKPVKBGJ-TWMZOSGRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Oxepane
  • Gamma butyrolactone
  • Oxane
  • Cyclic alcohol
  • Tertiary alcohol
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility13.4 g/LALOGPS
logP0.23ALOGPS
logP0.26ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)12.84ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.59 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity66.26 m³·mol⁻¹ChemAxon
Polarizability26.95 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-0aea41fd56036055c7752016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ti-1290000000-44deb1c9c6ed719dfc4b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-4930000000-b544a3f2366735da53e82016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-808669ed82604d0dac0d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-0090000000-cf71dcb24d4beab7688b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-6960000000-ecf6c832cc8fd5a41c202016-08-03View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityCoriamyrtin has inhibitory activity when modulating receptors of the central nervous system. In other words, coriamyrtin, as a picrotoxin-like sesquiterpene lactones found in Anamirta paniculata and A. cocculus, has a mode of anticonvulsive action as potent transmission inhibitors in the central nervous system. The presence of a hydroxyl group at C-6 could have a significant affinity for a γ-aminobutyric acid (GABA) effector chloride channel, an antagonist to the effects observed on γ-aminobutyric acid but not on alanine or taurine. These experiments were tested on primary afferent terminals and for the antagonism of presynaptic inhibition. Picrotoxin is a known antagonist of GABA-R in all its protein isoforms and R-Gly in the homomeric form. (1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID442189
ChEMBL IDNot Available
ChemSpider ID10252019
KEGG IDC09379
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkCoriaria myrtifolia
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Perez C, Becerra J, Manriquez-Navarro P, Aguayo LG, Fuentealba J, Guzman JL, Joseph-Nathan P, Jimenez V, Munoz MA, Silva M: Inhibitory activities on mammalian central nervous system receptors and computational studies of three sesquiterpene lactones from Coriaria ruscifolia subsp. ruscifolia. Chem Pharm Bull (Tokyo). 2011;59(2):161-5. [21297293 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available