Showing Compound Card for 8,9-Dihydroxy-delta-6a-tetrahydrocannabinol (CDB000035)

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Record Information
Version1.0
Created at2020-03-19 00:36:55 UTC
Updated at2020-11-18 16:35:10 UTC
CannabisDB IDCDB000035
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name8,9-Dihydroxy-delta-6a-tetrahydrocannabinol
Description8,9-Dihydroxy-delta-6a-tetrahydrocannabinol belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. 8,9-Dihydroxy-delta-6a-tetrahydrocannabinol, also belongs to the subclass of cannabis compounds known as Cannabitriols. 8,9-Dihydroxy-delta-6a-tetrahydrocannabinol is one of more than 120 cannabinoid compounds that are known in cannabis plant (PMID: 6991645 ). It was first characterized in the hexane extract of an Indian variant of Cannabis sativa L. in 1978 (DOI: 10.1007/BF01922908).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC21H30O4
Average Molecular Weight346.47
Monoisotopic Molecular Weight346.2144
IUPAC Name(8S,9R)-6,6,9-trimethyl-3-pentyl-6H,7H,8H,9H,10H-cyclohexa[c]chromene-1,8,9-triol
Traditional Name(8S,9R)-6,6,9-trimethyl-3-pentyl-7H,8H,10H-cyclohexa[c]chromene-1,8,9-triol
CAS Registry NumberNot Available
SMILES
CCCCCC1=CC(O)=C2C(OC(C)(C)C3=C2C[C@@](C)(O)[C@@H](O)C3)=C1
InChI Identifier
InChI=1S/C21H30O4/c1-5-6-7-8-13-9-16(22)19-14-12-21(4,24)18(23)11-15(14)20(2,3)25-17(19)10-13/h9-10,18,22-24H,5-8,11-12H2,1-4H3/t18-,21+/m0/s1
InChI KeyWEVYNIJDEFFKLF-GHTZIAJQSA-N
Chemical Taxonomy
Description 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
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary alcohol
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Polyol
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.86ALOGPS
logP3.65ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)9.35ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.92 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity99.51 m³·mol⁻¹ChemAxon
Polarizability40.64 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS8,9-Dihydroxy-delta-6a-tetrahydrocannabinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8,9-Dihydroxy-delta-6a-tetrahydrocannabinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8,9-Dihydroxy-delta-6a-tetrahydrocannabinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8,9-Dihydroxy-delta-6a-tetrahydrocannabinol, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8,9-Dihydroxy-delta-6a-tetrahydrocannabinol, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8,9-Dihydroxy-delta-6a-tetrahydrocannabinol, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8,9-Dihydroxy-delta-6a-tetrahydrocannabinol, 3 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]