Showing Compound Card for Cannabicitran (CDB000036)

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Record Information
Version1.0
Created at2020-03-19 00:37:14 UTC
Updated at2020-11-18 16:35:10 UTC
CannabisDB IDCDB000036
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabicitran
DescriptionCannabicitran 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. Cannabicitran possesses a tetracyclic skeleton, unique in the cannabinoid class of secondary metabolites. Interestingly, cannabicitran was first synthesized in 1971 ( Ref:DOI ) and later isolated from a natural cannabis source in 1974 (https://doi.org/10.1016/S0031-9422(00)91362-1) and its absolute configuration is still unknown (PMID: 6991645 ). No published data exists regarding cannabicitran’s biological or pharmacological activities. Cannabicitran is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC21H30O2
Average Molecular Weight314.47
Monoisotopic Molecular Weight314.2246
IUPAC Name(1S,4S,13S)-1,5,5-trimethyl-9-pentyl-6,15-dioxatetracyclo[9.3.1.0^{4,13}.0^{7,12}]pentadeca-7(12),8,10-triene
Traditional Name(1S,4S,13S)-1,5,5-trimethyl-9-pentyl-6,15-dioxatetracyclo[9.3.1.0^{4,13}.0^{7,12}]pentadeca-7(12),8,10-triene
CAS Registry NumberNot Available
SMILES
CCCCCC1=CC2=C3[C@H]4C[C@](C)(CC[C@@H]4C(C)(C)O2)OC3=C1
InChI Identifier
InChI=1S/C21H30O2/c1-5-6-7-8-14-11-17-19-15-13-21(4,23-18(19)12-14)10-9-16(15)20(2,3)22-17/h11-12,15-16H,5-10,13H2,1-4H3/t15-,16-,21-/m0/s1
InChI KeyIXJXRDCCQRZSDV-QYWGDWMGSA-N
Chemical Taxonomy
ClassificationNot classified
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
logP7.01ALOGPS
logP5.62ChemAxon
logS-6.8ALOGPS
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area18.46 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity93.86 m³·mol⁻¹ChemAxon
Polarizability38.51 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
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 Compound129360466
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 ]