Showing Compound Card for Cannabinol-C4 (CDB000031)

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Record Information
Version1.0
Created at2020-03-19 00:36:34 UTC
Updated at2020-12-07 19:07:26 UTC
CannabisDB IDCDB000031
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabinol-C4
DescriptionCannabinol-C4, also known as CBN-C4, 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. Cannabinol-C4 also belongs to the class of cannabis compounds known as cannabinols or CBNs. The best known and most abundant CBN is cannabinol or cannabinol-C5 (CBN or CBN-C5). CBN has a 5-carbon aliphatic chain attached to its phenol group, while CBN-C4 has a 4-carbon aliphatic chain. Other CBNs have 1, 2 or 3 carbon atom chains. These shorter chain cannabinols are even less abundant than CBN-C5. Cannabinols are mildly psychoactive cannabinoids found only in trace amounts (PMID: 1221432 ) and are mostly found in aged cannabis (PMID:26870049 ). Pharmacologically relevant quantities are formed as a metabolite of tetrahydrocannabinol (THC) (PMID: 1140243 ). Cannabinols act as partial agonists of the CB1 receptors but tend to have higher affinities to CB2 receptors. The relative activity and CB1/CB2 affinity of CBN-C4 versus CBN-C5 has not been determined. Cannabinol-C4 is one of more than 120 cannabinoid compounds that can be found in cannabis plants (PMID: 6991645 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC20H24O2
Average Molecular Weight296.41
Monoisotopic Molecular Weight296.1776
IUPAC Name3-butyl-6,6,9-trimethyl-6H-benzo[c]chromen-1-ol
Traditional Name3-butyl-6,6,9-trimethylbenzo[c]chromen-1-ol
CAS Registry NumberNot Available
SMILES
CCCCC1=CC2=C(C(O)=C1)C1=C(C=CC(C)=C1)C(C)(C)O2
InChI Identifier
InChI=1S/C20H24O2/c1-5-6-7-14-11-17(21)19-15-10-13(2)8-9-16(15)20(3,4)22-18(19)12-14/h8-12,21H,5-7H2,1-4H3
InChI KeyGGVVJZIANMUEJO-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentDibenzopyrans
Alternative Parents
Substituents
  • Dibenzopyran
  • 2-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP6.08ALOGPS
logP5.97ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)9.32ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity91.14 m³·mol⁻¹ChemAxon
Polarizability35.57 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCannabinol-C4, 1 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
Receptors
Protein NameGene NameLocusUniprot IDDetails
Cannabinoid receptor 1CNR16q14-q15P21554 details
Cannabinoid receptor 2CNR21p36.11P34972 details
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 Compound59444392
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Karniol IG, Shirakawa I, Takahashi RN, Knobel E, Musty RE: Effects of delta9-tetrahydrocannabinol and cannabinol in man. Pharmacology. 1975;13(6):502-12. doi: 10.1159/000136944. [PubMed:1221432 ]
  2. Andre CM, Hausman JF, Guerriero G: Cannabis sativa: The Plant of the Thousand and One Molecules. Front Plant Sci. 2016 Feb 4;7:19. doi: 10.3389/fpls.2016.00019. eCollection 2016. [PubMed:26870049 ]
  3. McCallum ND, Yagen B, Levy S, Mechoulam R: Cannabinol: a rapidly formed metabolite of delta-1- and delta-6-tetrahydrocannabinol. Experientia. 1975 May 15;31(5):520-1. doi: 10.1007/bf01932433. [PubMed:1140243 ]
  4. 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 ]