Showing Compound Card for Cannabifuran (CDB000441)

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Record Information
Version1.0
Created at2020-03-19 00:37:06 UTC
Updated at2020-11-18 16:35:10 UTC
CannabisDB IDCDB000441
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabifuran
DescriptionCannabifuran (CBF) belongs to the class of organic compounds known as dibenzofurans. Dibenzofurans are compounds containing a dibenzofuran moiety, which consists of two benzene rings fused to a central furan ring. CBF is the reduced derivative of dehydrocannabifuran. As such it can be considered as a fully aromatized derivative of cannabielsoin (CBE). As CBE, cannabifuran is a molecule of mixed biosynthetic origin, in which its aromatic moiety (derived from olivetolic acid) occurs through the polyketide biosynthetic pathway while the prenylated sidechain derives from the MEP pathway of the terpenoids (DOI: 0.1016/B978-0-12-800756-3.00002-8). Similarly to the case of cannabielsoin, the inclusion of cannabifuran as a Cannabis natural product is controversial because it has been isolated and identified infrequently. Additionally, cannabifuran can be considered a derivative of cannabielsoin, which is most likely a product of the photo-oxidation of cannabidiol (CBD). Mention of cannabifuran in the scientific literature is very scarce and no reports on its biological activity exist. Cannabifuran is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (DOI: 10.1007/978-1-59259-947-9_2).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC21H26O2
Average Molecular Weight310.44
Monoisotopic Molecular Weight310.1933
IUPAC Name10-methyl-5-pentyl-13-(propan-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),2(7),3,5,10,12-hexaen-3-ol
Traditional Name13-isopropyl-10-methyl-5-pentyl-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),2(7),3,5,10,12-hexaen-3-ol
CAS Registry NumberNot Available
SMILES
CCCCCC1=CC(O)=C2C(OC3=C(C)C=CC(C(C)C)=C23)=C1
InChI Identifier
InChI=1S/C21H26O2/c1-5-6-7-8-15-11-17(22)20-18(12-15)23-21-14(4)9-10-16(13(2)3)19(20)21/h9-13,22H,5-8H2,1-4H3
InChI KeyVNGQMWZHHNCMLQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzofurans. Dibenzofurans are compounds containing a dibenzofuran moiety, which consists of two benzene rings fused to a central furan ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassDibenzofurans
Direct ParentDibenzofurans
Alternative Parents
Substituents
  • Dibenzofuran
  • Cumene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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
logP7ALOGPS
logP6.9ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)8.9ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area33.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity95.88 m³·mol⁻¹ChemAxon
Polarizability38.28 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-MSCannabifuran, 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
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 Compound9966466
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 ]