Showing Compound Card for Cannabichromanone (CDB005821)

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Record Information
Version1.0
Created at2020-04-27 16:59:55 UTC
Updated at2020-12-07 19:12:13 UTC
CannabisDB IDCDB005821
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabichromanone
DescriptionCannabichromanone (CBCN) 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. Cannabichromanone is one of more than 120 cannabinoid compounds that are known to occur in Cannabis plants (PMID: 6991645 ). Very little is known regarding cannabichromanone and only recently has its full spectroscopic data and absolute configuration been published (PMID: 19844597 ). Cannabichromanone has shown mild antimalarial and moderate antileishmanial activities, as well as radical scavenging activities in the DPPH assay (PMID: 19903367 , PMID: 19844597 ). Cannabichromanone 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 FormulaC20H28O4
Average Molecular Weight332.44
Monoisotopic Molecular Weight332.1988
IUPAC Name5-hydroxy-2,2-dimethyl-3-(3-oxobutyl)-7-pentyl-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name5-hydroxy-2,2-dimethyl-3-(3-oxobutyl)-7-pentyl-3H-1-benzopyran-4-one
CAS Registry Number56154-57-5
SMILES
CCCCCC1=CC(O)=C2C(=O)C(CCC(C)=O)C(C)(C)OC2=C1
InChI Identifier
InChI=1S/C20H28O4/c1-5-6-7-8-14-11-16(22)18-17(12-14)24-20(3,4)15(19(18)23)10-9-13(2)21/h11-12,15,22H,5-10H2,1-4H3
InChI KeyNHZMSIOYBVIOAF-UHFFFAOYSA-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
  • Chromone
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Ether
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Role

Industrial application:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.64ALOGPS
logP5.09ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)8.84ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity94.54 m³·mol⁻¹ChemAxon
Polarizability38.34 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCannabichromanone, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabichromanone, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabichromanone, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabichromanone, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabichromanone, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MSNot Available
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 Compound186690
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. Ahmed SA, Ross SA, Slade D, Radwan MM, Khan IA, Elsohly MA: Structure determination and absolute configuration of cannabichromanone derivatives from high potency Cannabis sativa. Tetrahedron Lett. 2008 Oct 13;49(42):6050-6053. doi: 10.1016/j.tetlet.2008.07.178. [PubMed:19844597 ]
  3. Bero J, Frederich M, Quetin-Leclercq J: Antimalarial compounds isolated from plants used in traditional medicine. J Pharm Pharmacol. 2009 Nov;61(11):1401-33. doi: 10.1211/jpp/61.11.0001. [PubMed:19903367 ]