Showing Compound Card for Cannabinodiol (CDB000433)

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Record Information
Version1.0
Created at2020-03-19 00:36:44 UTC
Updated at2020-12-07 19:07:26 UTC
CannabisDB IDCDB000433
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabinodiol
DescriptionCannabinodiol (CBND) is a psychoactive cannabinoid (PMID: 30023762 ). It is present in Cannabis sativa plants at very low concentrations (doi:10.1016/0031-9422(77)80023-X). Cannabinodiol and Cannabinodivarin (CBVD) are the only two known members of the cannabinodiol class of cannabinoids (PMID: 6991645 ). CBND is the fully aromatized derivative of cannabidiol (CBD). Even though the oxidation of CBD to CBND seems to be a rational mechanism of conversion, it has not been proven experimentally. Oppositely, it has been experimentally demonstrated that CBD occurs through the photochemical reaction of cannabinol (CBN) with UV light, with the opening of the pyrane ring ( Ref:DOI ). Cannabinodiol is one of more than 120 cannabinoid compounds that are known to occur in cannabis (PMID: 6991645 ). Cannabinodiol is also found in cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC21H26O2
Average Molecular Weight310.44
Monoisotopic Molecular Weight310.1933
IUPAC Name5'-methyl-4-pentyl-2'-(prop-1-en-2-yl)-[1,1'-biphenyl]-2,6-diol
Traditional Name5'-methyl-4-pentyl-2'-(prop-1-en-2-yl)-[1,1'-biphenyl]-2,6-diol
CAS Registry NumberNot Available
SMILES
CCCCCC1=CC(O)=C(C(O)=C1)C1=C(C=CC(C)=C1)C(C)=C
InChI Identifier
InChI=1S/C21H26O2/c1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3/h9-13,22-23H,2,5-8H2,1,3-4H3
InChI KeyTWKHUZXSTKISQC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBiphenyls and derivatives
Direct ParentBiphenyls and derivatives
Alternative Parents
Substituents
  • Biphenyl
  • Phenylpropene
  • Styrene
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Toluene
  • Phenol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.79ALOGPS
logP6.85ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)9.11ChemAxon
pKa (Strongest Basic)-5.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.61 m³·mol⁻¹ChemAxon
Polarizability37.22 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCannabinodiol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabinodiol, 2 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 Compound11551346
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 ]
  2. Lewis MM, Yang Y, Wasilewski E, Clarke HA, Kotra LP: Chemical Profiling of Medical Cannabis Extracts. ACS Omega. 2017 Sep 30;2(9):6091-6103. doi: 10.1021/acsomega.7b00996. Epub 2017 Sep 22. [PubMed:30023762 ]