Showing Compound Card for Cannabitriol (CDB000435)

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Record Information
Version1.0
Created at2020-03-19 00:36:49 UTC
Updated at2020-11-18 16:35:10 UTC
CannabisDB IDCDB000435
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabitriol
DescriptionCannabitriol (CBT) was first isolated in 1966 and its structure was established in 1976 ( Ref:DOI PMID: 1253891 ). CBT shares the same basic skeleton of THC with the addition of two hydroxil groups and the isomerization of a double bond on the isoprenoid moiety. Little experimental data has been published in regards to the biological activities of CBT. It has been proposed that CBT is an intermediate in the aromatization of delta-9-THC to cannabinol (CBN) (PMID: 27722705 ). Cannabitriol has been described as one of the cannabinoids isolated from Cannabis sativa plants (PMID: 6991645 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC21H30O4
Average Molecular Weight346.47
Monoisotopic Molecular Weight346.2144
IUPAC Name(9S,10S)-6,6,9-trimethyl-3-pentyl-6H,7H,8H,9H,10H-cyclohexa[c]chromene-1,9,10-triol
Traditional Name(9S,10S)-6,6,9-trimethyl-3-pentyl-7H,8H,10H-cyclohexa[c]chromene-1,9,10-triol
CAS Registry Number74184-29-5
SMILES
CCCCCC1=CC(O)=C2C(OC(C)(C)C3=C2[C@H](O)[C@@](C)(O)CC3)=C1
InChI Identifier
InChI=1S/C21H30O4/c1-5-6-7-8-13-11-15(22)18-16(12-13)25-20(2,3)14-9-10-21(4,24)19(23)17(14)18/h11-12,19,22-24H,5-10H2,1-4H3/t19-,21-/m0/s1
InChI KeyZLYNXDIDWUWASO-FPOVZHCZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent2,2-dimethyl-1-benzopyrans
Alternative Parents
Substituents
  • 2,2-dimethyl-1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary alcohol
  • 1,2-diol
  • Secondary alcohol
  • Ether
  • Polyol
  • Oxacycle
  • 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
logP4.35ALOGPS
logP3.81ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)9.24ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.92 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity99.36 m³·mol⁻¹ChemAxon
Polarizability40.33 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCannabitriol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabitriol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabitriol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabitriol, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabitriol, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabitriol, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabitriol, 3 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 Compound156460
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. Chan WR, Magnus KE, Watson HA: The structure of cannabitriol. Experientia. 1976 Mar 15;32(3):283-4. doi: 10.1007/BF01940792. [PubMed:1253891 ]
  3. Hanus LO, Meyer SM, Munoz E, Taglialatela-Scafati O, Appendino G: Phytocannabinoids: a unified critical inventory. Nat Prod Rep. 2016 Nov 23;33(12):1357-1392. doi: 10.1039/c6np00074f. [PubMed:27722705 ]