Showing Compound Card for Iso-cannabispiradienone (CDB000758)

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Record Information
Version1.0
Created at2020-03-19 00:55:18 UTC
Updated at2020-12-07 19:07:44 UTC
CannabisDB IDCDB000758
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameIso-cannabispiradienone
DescriptionIso-cannabispiradienone 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. Iso-cannabispirdienone is also classified as a phenol and as a spiroindane. 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. Isocannabispiradienone is a non-cannabinoid spiroindane and one of the spiroindane compounds found in cannabis plants. Spiroindane compounds were first isolated and identified as cannabis constituents in 1976. The structure of Iso-cannabispiradienone is similar to cannabispiradienone except the positions of hydroxy and methoxy groups on benzene ring. Isocannabispiradienone exists as a colourless amorphous solid ( Ref:DOI ). It is a neutral, hydrophobic molecule that is insoluble in water. Cannabispiradienones may have anti-inflammatory activities (PMID: 26101147 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC15H14O3
Average Molecular Weight242.27
Monoisotopic Molecular Weight242.0943
IUPAC Name5'-hydroxy-7'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-indene]-2,5-dien-4-one
Traditional Name5'-hydroxy-7'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-indene]-2,5-dien-4-one
CAS Registry NumberNot Available
SMILES
COC1=CC(O)=CC2=C1C1(CC2)C=CC(=O)C=C1
InChI Identifier
InChI=1S/C15H14O3/c1-18-13-9-12(17)8-10-2-5-15(14(10)13)6-3-11(16)4-7-15/h3-4,6-9,17H,2,5H2,1H3
InChI KeyYDQGBHYBGYGBPF-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassIndanes
Sub ClassNot Available
Direct ParentIndanes
Alternative Parents
Substituents
  • Indane
  • Phenol ether
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Cyclic ketone
  • Ketone
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.55ALOGPS
logP2.79ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)9.54ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.24 m³·mol⁻¹ChemAxon
Polarizability25.17 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-MSIso-cannabispiradienone, 1 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 Compound101802953
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Granica S, Piwowarski JP, Randazzo A, Schneider P, Zyzynska-Granica B, Zidorn C: Novel stilbenoids, including cannabispiradienone glycosides, from Tragopogon tommasinii (Asteraceae, Cichorieae) and their potential anti-inflammatory activity. Phytochemistry. 2015 Sep;117:254-266. doi: 10.1016/j.phytochem.2015.06.018. Epub 2015 Jun 19. [PubMed:26101147 ]