Showing Compound Card for Cannabichromene (CDB000007)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencestransporters (2) Show 6 proteinsXML
Show more...
Record Information
Version1.0
Created at2020-03-19 00:35:02 UTC
Updated at2022-12-13 20:57:25 UTC
CannabisDB IDCDB000007
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabichromene
DescriptionCannabichromene, also known as CBC, belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that include a 1-benzopyran moiety, a bicyclic compound made up of a benzene ring fused to a pyran ring, so that the oxygen atom is at the 1-position. Cannabichromene is a neutral compound. Cannabichromene (CBC), also called cannabichrome, cannanbichromene, pentylcannabichromene or cannabinochromene, is one of the hundreds of cannabinoids found in the cannabis plant and is therefore a phytocannabinoid. It bears structural similarity to other natural cannabinoids, including tetrahydrocannabinol (THC), tetrahydrocannabivarin (THCV), cannabidiol (CBD), and cannabinol (CBN), among others. CBC is a product of the decarboxylation of cannabichromenic acid (CBCA), which occurs over time or after reaching temperatures above 90 °C. CBCA is a product of the cyclization of the main cannabinoid precursor, cannabigerolic acid (CBGA). CBC and its derivatives are as abundant as cannabinols in cannabis. CBC is not scheduled by the Convention on Psychotropic Substances. CBC has shown interesting anti-inflammatory activities in pre-clinical trials (PMID: 20619971 ). CBC is non-psychoactive and does not affect the psychoactivity of THC (PMID: 16148455 ). CBC acts on the transient receptor potential cation channel subfamily V member 1 (TRPV1) and transient receptor potential ankyrin 1 (TRPA1) receptors, interfering with their ability to break down endocannabinoids (the bodies endogenous cannabinoids, such as anandamide and 2-arachidonoylglycerol, 2-AG, the endogenous agonist for the cannabinoid-1 receptor, CB1 and primary ligand for cannabinoid-2 receptor, CB2).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC21H30O2
Average Molecular Weight314.47
Monoisotopic Molecular Weight314.2246
IUPAC Name(2S)-2-methyl-2-(4-methylpent-3-en-1-yl)-7-pentyl-2H-chromen-5-ol
Traditional Name(2S)-2-methyl-2-(4-methylpent-3-en-1-yl)-7-pentylchromen-5-ol
CAS Registry Number20675-51-8
SMILES
CCCCCC1=CC(O)=C2C=C[C@](C)(CCC=C(C)C)OC2=C1
InChI Identifier
InChI=1S/C21H30O2/c1-5-6-7-10-17-14-19(22)18-11-13-21(4,23-20(18)15-17)12-8-9-16(2)3/h9,11,13-15,22H,5-8,10,12H2,1-4H3/t21-/m0/s1
InChI KeyUVOLYTDXHDXWJU-NRFANRHFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent1-benzopyrans
Alternative Parents
Substituents
  • 1-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
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
logP7.04ALOGPS
logP6.6ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)9.47ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity99.6 m³·mol⁻¹ChemAxon
Polarizability38.28 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCannabichromene, 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
Transporters
Protein NameGene NameLocusUniprot IDDetails
Transient receptor potential cation channel subfamily V member 1TRPV117p13.2Q8NER1 details
Transient receptor potential cation channel subfamily A member 1TRPA18q13O75762 details
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Transient receptor potential cation channel subfamily V member 1TRPV117p13.2Q8NER1 details
Cannabinoid receptor 1CNR16q14-q15P21554 details
Transient receptor potential cation channel subfamily A member 1TRPA18q13O75762 details
Cannabinoid receptor 2CNR21p36.11P34972 details
Transcriptional FactorsNot Available
Concentrations Data
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 Compound21668219
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. DeLong GT, Wolf CE, Poklis A, Lichtman AH: Pharmacological evaluation of the natural constituent of Cannabis sativa, cannabichromene and its modulation by Delta(9)-tetrahydrocannabinol. Drug Alcohol Depend. 2010 Nov 1;112(1-2):126-33. doi: 10.1016/j.drugalcdep.2010.05.019. [PubMed:20619971 ]
  2. Ilan AB, Gevins A, Coleman M, ElSohly MA, de Wit H: Neurophysiological and subjective profile of marijuana with varying concentrations of cannabinoids. Behav Pharmacol. 2005 Sep;16(5-6):487-96. doi: 10.1097/00008877-200509000-00023. [PubMed:16148455 ]

Transporters

Enzyme Details
1. Transient receptor potential cation channel subfamily V member 1
General function:
Involved in ion channel activity
Specific function:
Receptor-activated non-selective calcium permeant cation channel involved in detection of noxious chemical and thermal stimuli. Seems to mediate proton influx and may be involved in intracellular acidosis in nociceptive neurons. May be involved in mediation of inflammatory pain and hyperalgesia. Sensitized by a phosphatidylinositol second messenger system activated by receptor tyrosine kinases, which involves PKC isozymes and PCL
Gene Name:
TRPV1
Uniprot ID:
Q8NER1
Molecular weight:
94955.3
Enzyme Details
2. Transient receptor potential cation channel subfamily A member 1
General function:
Not Available
Specific function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function. Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes. Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)- tetrahydrocannabinol (THC), the psychoactive component of marijuana. Not involved in menthol sensation. May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular weight:
127485.8