Showing Compound Card for 3-[2-(3-Isoprenyl-4-hydroxy-5-methoxy-phenyl)ethyl]-5-methoxyphenol (CDB000328)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-03-19 00:31:11 UTC
Updated at2020-11-18 16:35:04 UTC
CannabisDB IDCDB000328
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name3-[2-(3-Isoprenyl-4-hydroxy-5-methoxy-phenyl)ethyl]-5-methoxyphenol
Description3-[2-(3-isoprenyl-4-hydroxy-5-methoxy-phenyl)ethyl]-5-methoxyphenol, belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Stilbenoids can be produced by plants and bacteria. Stilbenoids are secondary metabolites present in Cannabis sativa. 3-[2-(3-isoprenyl-4-hydroxy-5-methoxy-phenyl)ethyl]-5-methoxyphenol is one of several dihydrostilbene or noncannabinoid stilbenoids found in the cannabis plant. It was first reported by Bosch and Salemink to be present in the methylene chloride extract of Mexican cannabis and identified as a cannabis constituent in 1978 (PMID: 6991645 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC21H26O4
Average Molecular Weight342.44
Monoisotopic Molecular Weight342.1831
IUPAC Name4-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-methoxy-6-(3-methylbut-2-en-1-yl)phenol
Traditional Name4-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-methoxy-6-(3-methylbut-2-en-1-yl)phenol
CAS Registry NumberNot Available
SMILES
COC1=CC(CCC2=CC(CC=C(C)C)=C(O)C(OC)=C2)=CC(O)=C1
InChI Identifier
InChI=1S/C21H26O4/c1-14(2)5-8-17-9-15(12-20(25-4)21(17)23)6-7-16-10-18(22)13-19(11-16)24-3/h5,9-13,22-23H,6-8H2,1-4H3
InChI KeyMTPFJBMNZHSOND-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP4.53ALOGPS
logP5.32ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity101.53 m³·mol⁻¹ChemAxon
Polarizability39.35 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3-[2-(3-Isoprenyl-4-hydroxy-5-methoxy-phenyl)ethyl]-5-methoxyphenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-[2-(3-Isoprenyl-4-hydroxy-5-methoxy-phenyl)ethyl]-5-methoxyphenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-[2-(3-Isoprenyl-4-hydroxy-5-methoxy-phenyl)ethyl]-5-methoxyphenol, 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 Compound10427486
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 ]