Showing Compound Card for Dehydrocannabifuran (CDB000440)

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Record Information
Version1.0
Created at2020-03-19 00:37:02 UTC
Updated at2020-11-18 16:35:10 UTC
CannabisDB IDCDB000440
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDehydrocannabifuran
DescriptionDehydrocannabifuran 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. Dehydrocannabifuran is one of more than 120 cannabinoid compounds that have been identified in cannabis plants (PMID: 6991645 ). Structurally it can be considered as the fully aromatized derivative of cannabielsoin (CBE). As CBE, dehydrocannabifuran 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: 10.1016/B978-0-12-800756-3.00002-8). Similarly to the case of cannabielsoin, the inclusion of dehydrocannabifuran as a Cannabis natural product is controversial, because it has been isolated and identified infrequently. Additionally, dehydrocannabifuran can be considered a derivative of cannabielsoin, which is most likely a product of the photo-oxidation of cannabidiol (CBD). Mention of dehydrocannabifuran in the scientific literature is very scarce and no reports on its biological activity exist. Dehydrocannabifuran is also found in cannabis smoke and is volatilized during the combustion of cannabis (DOI: 10.1007/978-1-59259-947-9_2).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC21H24O2
Average Molecular Weight308.42
Monoisotopic Molecular Weight308.1776
IUPAC Name10-methyl-5-pentyl-13-(prop-1-en-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),2(7),3,5,10,12-hexaen-3-ol
Traditional Name10-methyl-5-pentyl-13-(prop-1-en-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),2(7),3,5,10,12-hexaen-3-ol
CAS Registry Number56154-59-7
SMILES
CCCCCC1=CC(O)=C2C(OC3=C(C)C=CC(C(C)=C)=C23)=C1
InChI Identifier
InChI=1S/C21H24O2/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/h9-12,22H,2,5-8H2,1,3-4H3
InChI KeyNAGBBYZBIQVPIQ-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
  • Styrene
  • 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
logP7.06ALOGPS
logP6.69ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)8.8ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area33.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity95.66 m³·mol⁻¹ChemAxon
Polarizability37.47 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-MSDehydrocannabifuran, 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 Compound59444381
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 ]