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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:06:49 UTC
Update Date2017-12-07 18:21:53 UTC
HMDB IDHMDB0060912
Secondary Accession Numbers
  • HMDB60912
Metabolite Identification
Common Name9-alpha,10-alpha-epoxyhexahydrocannabinol
Description9-alpha,10-alpha-epoxyhexahydrocannabinol is a metabolite of dronabinol. Dronabinol is the for a pure isomer of THC, (–)-trans-delta9-tetrahydrocannabinol, which is the main isomer found in cannabis. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
4-O-Acetyl-1,5-anhydro-2,3,6-trideoxy-3-trifluoroacetamidohex-1-enitolMeSH
AATTHMeSH
Chemical FormulaC21H30O3
Average Molecular Weight330.4611
Monoisotopic Molecular Weight330.219494826
IUPAC Name9,9,13-trimethyl-5-pentyl-8,14-dioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-2,4,6-trien-3-ol
Traditional Name9,9,13-trimethyl-5-pentyl-8,14-dioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-2,4,6-trien-3-ol
CAS Registry NumberNot Available
SMILES
CCCCCC1=CC(O)=C2C3C4OC4(C)CCC3C(C)(C)OC2=C1
InChI Identifier
InChI=1S/C21H30O3/c1-5-6-7-8-13-11-15(22)18-16(12-13)23-20(2,3)14-9-10-21(4)19(24-21)17(14)18/h11-12,14,17,19,22H,5-10H2,1-4H3
InChI KeyVSQGBNUBIDZRPJ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent2,2-dimethyl-1-benzopyrans
Alternative Parents
Substituents
  • 2,2-dimethyl-1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Oxepane
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0019 g/LALOGPS
logP5.6ALOGPS
logP5.12ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)9.9ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity95.42 m³·mol⁻¹ChemAxon
Polarizability39.6 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06dl-5393000000-d3cbbfbd6398e124a2a2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-008j-3019000000-a6c6e191d36386bbaee1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0119000000-6e8d5e495ba842352b0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06z0-4693000000-9a70297c6126bff36b13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9420000000-091575b50da2814dcdb3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-0a6ca3cf16464ed1e833View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0209000000-70499fa05a92fdc2463cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-1900000000-0447fd17ec6f5d063299View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      Phenol Explorer Compound IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound125763
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available