Showing Compound Card for dehydrocannabispiran (CDB000324)

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Record Information
Version1.0
Created at2020-03-19 00:30:58 UTC
Updated at2020-11-18 16:35:04 UTC
CannabisDB IDCDB000324
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namedehydrocannabispiran
DescriptionDehydrocannabispiran or (R)-2′,3′-Dihydro-7′-hydroxy-5′-methoxyspiro[2-cyclohexene-1,1′-[1H]inden]-4-one 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. Dehydrocannabispiran is also classified as a spiroindane compound. Spiroindanes 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. Dehydrocannabispiran is neutral, hydrophobic molecule that is insoluble in water. Dehydrocannabispiran is one of several spiroindane, non-cannabinoid phenols that are known in cannabis plants. It was first identified from the dried leaves of a South African C. savita variant grown in France in 1976 (DOI: 10.1016/0040-4020(76)80149-4). A year later it was isolated from the South African cannabis variant grown in Mississippi and was named as dehydrocannabispiran (DOI: 10.1016/0040-4020(77)80249-4). Dehydrocannabispiran was also identified in the Japanese Kumamoto strain (DOI:10.1248/cpb.26.3641). Its structure resembles a synthetic compound which was found to potentiate the estrogenic activity of Stilbestrol (DOI: 10.1016/0040-4020(77)80249-4, PMID: 1255671 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC15H16O3
Average Molecular Weight244.29
Monoisotopic Molecular Weight244.1099
IUPAC Name(1S)-7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-inden]-2-en-4-one
Traditional Name(1S)-7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-inden]-2-en-4-one
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(C(O)=C1)[C@@]1(CC2)CCC(=O)C=C1
InChI Identifier
InChI=1S/C15H16O3/c1-18-12-8-10-2-5-15(14(10)13(17)9-12)6-3-11(16)4-7-15/h3,6,8-9,17H,2,4-5,7H2,1H3/t15-/m1/s1
InChI KeyMVYJADZNMQXLJB-OAHLLOKOSA-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
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Cyclohexenone
  • 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
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
logP2.85ALOGPS
logP2.8ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.33ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity70.14 m³·mol⁻¹ChemAxon
Polarizability26.22 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-MSdehydrocannabispiran, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSdehydrocannabispiran, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSdehydrocannabispiran, 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 IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound134714927
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Bailey DJ, Doggett NS, Ng LY, Qazi T: Potentiation of the estrogenic activity of stilbestrol by spiro (cyclohexane-1,2'-indan)-1',4-dione. J Med Chem. 1976 Mar;19(3):438-9. doi: 10.1021/jm00225a024. [PubMed:1255671 ]