Showing Compound Card for cannabidihydrophenanthrene (CDB000330)

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Record Information
Version1.0
Created at2020-03-19 00:31:18 UTC
Updated at2020-11-18 16:35:04 UTC
CannabisDB IDCDB000330
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namecannabidihydrophenanthrene
DescriptionCannabidihydrophenanthrene, belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivatives where at least one ring C-C bond is substituted by hydrogenation. Cannabidihydrophenanthrene is neutral, hydrophobic molecule that is insoluble in water. Cannabidihydrophenanthrene is the only compound of its type isolated from cannabis. The isolation and identification of cannabidihydrophenanthrene was first reported from Thailand cannabis in 1979. In that same report the authors proposed that cannabidihydrophenanthrene could be biosynthetically derived from the spiro-compound cannabispiradienone, through a dienone-phenol rearrangement ( Ref:DOI ). Cannabidihydrophenanthrene is one of the non-cannabinoid phenols that have been isolated from cannabis plants (PMID: 6991645 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC15H14O3
Average Molecular Weight242.27
Monoisotopic Molecular Weight242.0943
IUPAC Name7-methoxy-9,10-dihydrophenanthrene-3,5-diol
Traditional Name7-methoxy-9,10-dihydrophenanthrene-3,5-diol
CAS Registry Number71135-80-3
SMILES
COC1=CC2=C(C(O)=C1)C1=CC(O)=CC=C1CC2
InChI Identifier
InChI=1S/C15H14O3/c1-18-12-6-10-3-2-9-4-5-11(16)7-13(9)15(10)14(17)8-12/h4-8,16-17H,2-3H2,1H3
InChI KeyPLHFLFWGPBWZHL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivative where at least one ring CC bond is substituted by hydrogenation.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassHydrophenanthrenes
Direct ParentHydrophenanthrenes
Alternative Parents
Substituents
  • Hydrophenanthrene
  • 1-naphthol
  • 2-naphthol
  • Naphthalene
  • Phenol ether
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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
logP2.72ALOGPS
logP3.42ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)9.13ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity69.9 m³·mol⁻¹ChemAxon
Polarizability26.17 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-MScannabidihydrophenanthrene, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScannabidihydrophenanthrene, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScannabidihydrophenanthrene, 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 Compound53438738
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. Pollastro F, Minassi A, Fresu LG: Cannabis Phenolics and their Bioactivities. Curr Med Chem. 2018;25(10):1160-1185. doi: 10.2174/0929867324666170810164636. [PubMed:28799497 ]