Showing Compound Card for Cannabivarin (CDB000032)

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Record Information
Version1.0
Created at2020-03-19 00:36:36 UTC
Updated at2020-11-18 16:35:10 UTC
CannabisDB IDCDB000032
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabivarin
DescriptionCannabivarin (CBV), also known as Cannabivarol, 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. CBV is considered a non-psychoactive cannabinoid. It does not produce the euphoric side effects found in THC. Minor amounts of CBV are found in the hemp varieties of Cannabis sativa. CBV 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 CBV has a 3-carbon aliphatic chain. Other CBNs have 1, 2 or 4 carbon atom chains. These shorter chain cannabinols are even less abundant than CBN-C5. CBV is an oxidation product of tetrahydrocannabivarin (THCV, THV). CBV 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 FormulaC19H22O2
Average Molecular Weight282.38
Monoisotopic Molecular Weight282.162
IUPAC Name6,6,9-trimethyl-3-propyl-6H-benzo[c]chromen-1-ol
Traditional Namecannabivarin
CAS Registry Number33745-21-0
SMILES
CCCC1=CC(O)=C2C(OC(C)(C)C3=C2C=C(C)C=C3)=C1
InChI Identifier
InChI=1S/C19H22O2/c1-5-6-13-10-16(20)18-14-9-12(2)7-8-15(14)19(3,4)21-17(18)11-13/h7-11,20H,5-6H2,1-4H3
InChI KeySVTKBAIRFMXQQF-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
  • 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
logP5.61ALOGPS
logP5.52ChemAxon
logS-4.9ALOGPS
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 Count2ChemAxon
Refractivity86.53 m³·mol⁻¹ChemAxon
Polarizability33.48 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCannabivarin, 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 LinkCannabivarin
METLIN IDNot Available
PubChem Compound622545
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 ]