Showing Compound Card for Cannabicyclolic acid (CDB000025)

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Record Information
Version1.0
Created at2020-03-19 00:36:05 UTC
Updated at2020-11-18 16:35:10 UTC
CannabisDB IDCDB000025
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabicyclolic acid
DescriptionCannabicyclolic acid, also known as cannabicyclolate or CBLA, belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof. Cannabicyclolic acid is a neutral compound . Cannabicyclolic acid or CBLA, has also been placed in the class of cannabis compounds known as Cannabicyclols. Cannabicyclolic acid (CBLA) is a non-psychoactive cannabinoid found in cannabis plants (PMID: 6991645 ). CBLA is a relatively rare or low-abundance compound in cannabis. It is thought to be a photo-oxidation or natural degradation product of cannabichromenic acid (CBCA). CBLA is not considered to be an original cannabinoid (PMID: 6991645 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(1AR)-1a,2,3,3a,8bbeta,8cbeta-hexahydro-1,1,3abeta-trimethyl-6-pentyl-8-hydroxy-1H-4-oxa-benzo[F]cyclobuta[CD]indene-7-carboxylateGenerator
Chemical FormulaC22H30O4
Average Molecular Weight358.48
Monoisotopic Molecular Weight358.2144
IUPAC Name(1S,9S,12R,14S)-3-hydroxy-9,13,13-trimethyl-5-pentyl-8-oxatetracyclo[7.4.1.0^{2,7}.0^{12,14}]tetradeca-2(7),3,5-triene-4-carboxylic acid
Traditional Name(1S,9S,12R,14S)-3-hydroxy-9,13,13-trimethyl-5-pentyl-8-oxatetracyclo[7.4.1.0^{2,7}.0^{12,14}]tetradeca-2(7),3,5-triene-4-carboxylic acid
CAS Registry NumberNot Available
SMILES
CCCCCC1=CC2=C([C@H]3[C@@H]4[C@@H](CC[C@]4(C)O2)C3(C)C)C(O)=C1C(O)=O
InChI Identifier
InChI=1S/C22H30O4/c1-5-6-7-8-12-11-14-16(19(23)15(12)20(24)25)18-17-13(21(18,2)3)9-10-22(17,4)26-14/h11,13,17-18,23H,5-10H2,1-4H3,(H,24,25)/t13-,17+,18+,22+/m1/s1
InChI KeyJVOHLEIRDMVLHS-NDONDOTQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentSalicylic acid and derivatives
Alternative Parents
Substituents
  • Chromane
  • Benzopyran
  • Salicylic acid or derivatives
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Vinylogous acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen 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
logP5.22ALOGPS
logP5.97ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)2.91ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity101.08 m³·mol⁻¹ChemAxon
Polarizability40.95 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCannabicyclolic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabicyclolic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabicyclolic 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
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 Compound101769204
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 ]