Showing Compound Card for Cannabinolic acid (CDB000028)

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Record Information
Version1.0
Created at2020-03-19 00:36:23 UTC
Updated at2020-12-07 19:07:25 UTC
CannabisDB IDCDB000028
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabinolic acid
DescriptionCannabinolic acid (CBNA), 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. It is one of the 120 cannabinoid compounds found in cannabis plants (PMID: 6991645 ). CBNA, belongs to a subclass of cannabis compounds known as cannabinols or CBNs. The best known and most abundant CBN is cannabinol. Cannabinolic acid is formed through the degradation THCA (Tetrahydrocannabinolic acid). CBNA was first isolated in 1965 (PMID: 5879350 ) and is a non-psychoactive compound. Heating can lead to the decarboxylation of CBNA resulting in the formation of the more psychoactive CBN.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Hydroxy-6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromene-2-carboxylateGenerator
Chemical FormulaC22H26O4
Average Molecular Weight354.45
Monoisotopic Molecular Weight354.1831
IUPAC Name1-hydroxy-6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromene-2-carboxylic acid
Traditional Namecannabinolic acid A
CAS Registry Number2808-39-1
SMILES
CCCCCC1=CC2=C(C(O)=C1C(O)=O)C1=C(C=CC(C)=C1)C(C)(C)O2
InChI Identifier
InChI=1S/C22H26O4/c1-5-6-7-8-14-12-17-19(20(23)18(14)21(24)25)15-11-13(2)9-10-16(15)22(3,4)26-17/h9-12,23H,5-8H2,1-4H3,(H,24,25)
InChI KeyKXKOBIRSQLNUPS-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
  • Hydroxybenzoic acid
  • Salicylic acid or derivatives
  • 2-benzopyran
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Vinylogous acid
  • Oxacycle
  • Carboxylic acid derivative
  • Ether
  • Carboxylic acid
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.47ALOGPS
logP6.72ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)2.85ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity102.99 m³·mol⁻¹ChemAxon
Polarizability40.76 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCannabinolic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabinolic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabinolic acid, 2 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
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.127 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.109 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.0936 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.141 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.111 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.134 mg/g dry wt
    • David S. Wishart,...
 details
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 Compound3081990
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Mechoulam R, Gaoni Y: Hashish. IV. The isolation and structure of cannabinolic cannabidiolic and cannabigerolic acids. Tetrahedron. 1965 May;21(5):1223-9. doi: 10.1016/0040-4020(65)80064-3. [PubMed:5879350 ]
  2. 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 ]