Showing Compound Card for Cannithrene-2 (CDB000747)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-03-19 00:54:37 UTC
Updated at2020-11-18 16:35:29 UTC
CannabisDB IDCDB000747
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannithrene-2
DescriptionCannithrene-2, is one of two isomers of cannithrene (the other being canninthrene-1). It belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivatives where at least one ring carbon-carbon double bond has been reduced via hydrogenation. Phenanthrenes are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzenes. Hydrophenanthrenes in Cannabis are structurally derived from stilbenoids, which have undergone an additional cyclazation reaction to yield the phenanthrene skeleton. Cannithrene 1 and 2 were the first two dihydrophenanthrenes isolated from Cannabis (PMID: 28799497 ). Cannithrene 2 is a hydrophobic, neutral compound that is insoluble in water. So far, no biological activity has been associated with cannithrene 2. Cannithrene 2 is one of the non-cannabinoid compounds that have been identified in cannabis plants ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC16H16O4
Average Molecular Weight272.3
Monoisotopic Molecular Weight272.1049
IUPAC Name2,6-dimethoxy-9,10-dihydrophenanthrene-4,5-diol
Traditional Name2,6-dimethoxy-9,10-dihydrophenanthrene-4,5-diol
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(C(O)=C1)C1=C(O)C(OC)=CC=C1CC2
InChI Identifier
InChI=1S/C16H16O4/c1-19-11-7-10-4-3-9-5-6-13(20-2)16(18)15(9)14(10)12(17)8-11/h5-8,17-18H,3-4H2,1-2H3
InChI KeyJOPGVVOTXYNMIS-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
  • Naphthalene
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • 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
logP2.85ALOGPS
logP3.26ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)8.92ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity76.36 m³·mol⁻¹ChemAxon
Polarizability28.92 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-MSCannithrene-2, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannithrene-2, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannithrene-2, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-ef7de4d391b99f8c46fd2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0490000000-ed988b16accc0f1ee4702016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02bb-1790000000-f1739a582e42c99b90192016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-867f6aee25acb934d0312016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-76d4a75df389853757fe2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056s-0390000000-4671bc90fb23910197072016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-be7a06d3a99be6265fa32021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-72172f717bb9877b0ae32021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0940000000-8cbaa447eb4dd1f76dac2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-fa0ebf6f8073225621162021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-c19ecb967c82c4f234672021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0090000000-489a7d3a39991252ab2f2021-10-21View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0301762
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000638
KNApSAcK IDC00015535
Chemspider ID59696648
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound86021565
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. 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 ]