Showing Compound Card for Beta-cannabispiranol (CDB000760)

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Record Information
Version1.0
Created at2020-03-19 00:55:25 UTC
Updated at2020-11-18 16:35:29 UTC
CannabisDB IDCDB000760
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameBeta-cannabispiranol
DescriptionCannabispiranol belongs to the class of organic compounds known as indanes. Indanes are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring. Cannapispiranol is also classified as a spiroindane compound. Spiroindane compounds were first isolated and identified as cannabis constituents in 1976. Spiroindane compounds are indane compounds that include two rings which share a single atom (usually a carbon). The simplest example of this type of compound is Spiro[2.2]pentane. Cannapispiranol can also be formally classified as a phenol. There are two known cannabispiranol isomers including Alpha- and Beta-cannabispiranol which differ in the configuration of the hydroxy group on C-4'. The hydroxy group in Beta-cannabispiranol faces "up" and it faces "down" in Alpha-cannabispiranol. Cannabispiranol is an extremely weak basic (essentially neutral) compound (based on its pKa). Cannabispiranol is one of six spirans that have been isolated from Cannabis sativa (DOI: 10.1039/P19820001477). These six spirans have same skeleton of 2 benzene rings and 1 cyclopentane. 
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC15H20O3
Average Molecular Weight248.32
Monoisotopic Molecular Weight248.1412
IUPAC Name(1r,4s)-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-indene]-4,7'-diol
Traditional Name(1r,4s)-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-indene]-4,7'-diol
CAS Registry Number64052-90-0
SMILES
COC1=CC2=C(C(O)=C1)[C@@]1(CC2)CC[C@H](O)CC1
InChI Identifier
InChI=1S/C15H20O3/c1-18-12-8-10-2-5-15(14(10)13(17)9-12)6-3-11(16)4-7-15/h8-9,11,16-17H,2-7H2,1H3/t11-,15-
InChI KeyZFFYHYZOCYEEPL-FUKZOUPISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indan-1-spirocyclohexanes. These are organic aromatic compounds containing a cyclohexane moiety linked to the 1-position of an indane moiety in a spiro configuration.
KingdomOrganic compounds
Super ClassBenzenoids
ClassIndanes
Sub ClassIndan-1-spirocyclohexanes
Direct ParentIndan-1-spirocyclohexanes
Alternative Parents
Substituents
  • Indan-1-spirocyclohexane
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Cyclic alcohol
  • Secondary alcohol
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.26ALOGPS
logP2.59ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)10.11ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity70.08 m³·mol⁻¹ChemAxon
Polarizability27.77 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-MScannabispiranol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScannabispiranol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScannabispiranol, 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 ID33823754
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Appendino G, Gibbons S, Giana A, Pagani A, Grassi G, Stavri M, Smith E, Rahman MM: Antibacterial cannabinoids from Cannabis sativa: a structure-activity study. J Nat Prod. 2008 Aug;71(8):1427-30. doi: 10.1021/np8002673. Epub 2008 Aug 6. [PubMed:18681481 ]
  2. Molnar J, Petri I, Berek I, Shoyama Y, Nishioka I: The effects of cannabinoids and cannabispiro compounds on Escherichia coli adhesion to tissue culture cells and on leukocyte functions in vitro. Acta Microbiol Hung. 1987;34(3-4):233-40. [PubMed:3329437 ]