Showing Compound Card for 4,7-Dimethoxy-1,2,5-trihydroxyphenanthrene (CDB000748)

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Record Information
Version1.0
Created at2020-03-19 00:54:40 UTC
Updated at2020-11-18 16:35:29 UTC
CannabisDB IDCDB000748
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name4,7-Dimethoxy-1,2,5-trihydroxyphenanthrene
Description4,7-dimethoxy-1,2,5-trihydroxyphenanthrene, also called 4,7-dimethoxyphenanthrene-1,2,5-triol, belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which one or more hydroxyl group is attached to it. Phenanthrenes are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzenes. 4,7-dimethoxy-1,2,5-trihydroxyphenanthrene is also classified as a phenanthrenoid. Phenanthrenoids are chemical compounds formed with a phenanthrene backbone. 4,7-dimethoxy-1,2,5-trihydroxyphenanthrene was first isolated from a high potency Cannabis sativa variety in 2008 (PMID: 18774146 )
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC16H14O5
Average Molecular Weight286.28
Monoisotopic Molecular Weight286.0841
IUPAC Name4,7-dimethoxyphenanthrene-1,2,5-triol
Traditional Name4,7-dimethoxyphenanthrene-1,2,5-triol
CAS Registry NumberNot Available
SMILES
COC1=CC(O)=C2C(C=CC3=C2C(OC)=CC(O)=C3O)=C1
InChI Identifier
InChI=1S/C16H14O5/c1-20-9-5-8-3-4-10-15(14(8)11(17)6-9)13(21-2)7-12(18)16(10)19/h3-7,17-19H,1-2H3
InChI KeyFBTSZZALORIKJQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassPhenanthrols
Direct ParentPhenanthrols
Alternative Parents
Substituents
  • Phenanthrol
  • 2-naphthol
  • 1-naphthol
  • Naphthalene
  • Phenol ether
  • Anisole
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Polyol
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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
logP2.68ALOGPS
logP2.73ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)8.65ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area79.15 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity77.83 m³·mol⁻¹ChemAxon
Polarizability29.14 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-MS4,7-Dimethoxy-1,2,5-trihydroxyphenanthrene, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,7-Dimethoxy-1,2,5-trihydroxyphenanthrene, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,7-Dimethoxy-1,2,5-trihydroxyphenanthrene, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,7-Dimethoxy-1,2,5-trihydroxyphenanthrene, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,7-Dimethoxy-1,2,5-trihydroxyphenanthrene, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,7-Dimethoxy-1,2,5-trihydroxyphenanthrene, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,7-Dimethoxy-1,2,5-trihydroxyphenanthrene, 3 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 Compound25172438
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Radwan MM, Elsohly MA, Slade D, Ahmed SA, Wilson L, El-Alfy AT, Khan IA, Ross SA: Non-cannabinoid constituents from a high potency Cannabis sativa variety. Phytochemistry. 2008 Oct;69(14):2627-33. doi: 10.1016/j.phytochem.2008.07.010. Epub 2008 Sep 4. [PubMed:18774146 ]