Showing Compound Card for Cannabielsoin (CDB000027)

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Record Information
Version1.0
Created at2020-03-19 00:36:20 UTC
Updated at2020-11-18 16:35:10 UTC
CannabisDB IDCDB000027
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabielsoin
DescriptionCannabielsoin (CBE) is a phytocannabinoid and a part of the 120 cannabinoid compounds found in cannabis plants (PMID: 6991645 ). Cannabielsoin is a molecule of mixed biosynthetic origin, in which its aromatic moiety (derived from olivetolic acid) occurs through the polyketide biosynthetic pathway while the prenylated sidechain derives from the MEP pathway of the terpenoids (DOI: 10.1016/B978-0-12-800756-3.00002-8). Thus, cannabielsoin can be considered a polyketide, a monoterpenoid and a resorcinol derivative, due to the meta arrangement of its two hydroxil groups (one of them in the form of an ether) on the bencene ring. Similarly, to the case of the cannabielsoic acids, the inclusion of cannabielsoin as a cannabis natural product is controversial because it has been isolated and identified infrequently. Additionally, cannabielsoin is most likely a product of the photo-oxidation of cannabidiol (CBD). It has also been detected as a metabolite from CBD in mammals (PMID: 1806944 ), suggesting that CBE is not a natural product but more likely an artifact. However, cannabielsoin has been repeatedly mentioned in the literature as a natural cannabinoid and is therefore considered a cannabinoid.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Cannabielsoin aKegg
CBEKegg
Chemical FormulaC21H30O3
Average Molecular Weight330.47
Monoisotopic Molecular Weight330.2195
IUPAC Name(1R,9S,10S,13R)-10-methyl-5-pentyl-13-(prop-1-en-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-2,4,6-triene-3,10-diol
Traditional Name(1R,9S,10S,13R)-10-methyl-5-pentyl-13-(prop-1-en-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-2,4,6-triene-3,10-diol
CAS Registry Number52025-76-0
SMILES
CCCCCC1=CC(O)=C2[C@@H]3[C@H](OC2=C1)[C@@](C)(O)CC[C@H]3C(C)=C
InChI Identifier
InChI=1S/C21H30O3/c1-5-6-7-8-14-11-16(22)19-17(12-14)24-20-18(19)15(13(2)3)9-10-21(20,4)23/h11-12,15,18,20,22-23H,2,5-10H2,1,3-4H3/t15-,18+,20-,21-/m0/s1
InChI KeyRBEAVAMWZAJWOI-MTOHEIAKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
Substituents
  • Aromatic monoterpenoid
  • P-menthane monoterpenoid
  • Coumaran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Cyclic alcohol
  • Tertiary alcohol
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • 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
logP5.01ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)9.89ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity96.95 m³·mol⁻¹ChemAxon
Polarizability38.96 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCannabielsoin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabielsoin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabielsoin, 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 IDC20218
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162113
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. Yamamoto I, Gohda H, Narimatsu S, Watanabe K, Yoshimura H: Cannabielsoin as a new metabolite of cannabidiol in mammals. Pharmacol Biochem Behav. 1991 Nov;40(3):541-6. doi: 10.1016/0091-3057(91)90360-e. [PubMed:1806944 ]