Showing Compound Card for 3,4'-Dihydroxy-5,3'-dimethoxy-5' isoprenyl bibenzyl (CDB000751)

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Record Information
Version1.0
Created at2020-03-19 00:54:51 UTC
Updated at2020-12-07 19:07:44 UTC
CannabisDB IDCDB000751
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name3,4'-Dihydroxy-5,3'-dimethoxy-5' isoprenyl bibenzyl
Description3,4'-dihydroxy-5,3'-dimethoxy-5'-isoprenyl bibenzyl, 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 the phenyl ring leads to stilbenoids. Stilbenoids were first detected and isolated from the stems of cannabis plants in 1982, from cannabis leaves in 1978 and from cannabis resin in 1986 ( Ref:DOI > Ref:DOI ). 3,4'-dihydroxy-5,3'-dimethoxy-5' isoprenyl bibenzyl is a derivative of Bibenzyl. Bibenzyl is a compound consisting to two benzene rings linked together via ethane. Bibenzyls typically form a white solid. Bibenzyl forms the central core of several natural products such as dihydrostilbenoids and isoquinoline alkaloids. 3,4'-dihydroxy-5,3'-dimethoxy-5'-isoprenyl bibenzyl is one of a small number of bibenzyls including 3,4'-dihydroxy-5-methoxybibenzyl and 3,3'-dihydroxy-5,4'-dimethoxy bibenzyl found in Cannabis sativa ( Ref:DOI > Ref:DOI ). Bibenzyls and bibenzyl derivatives exhibit anti-inflammatory and antineoplastic activities (PMID: 27310249 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC21H26O4
Average Molecular Weight342.44
Monoisotopic Molecular Weight342.1831
IUPAC Name5-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-methoxy-3-(3-methylbut-2-en-1-yl)phenol
Traditional Name5-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-methoxy-3-(3-methylbut-2-en-1-yl)phenol
CAS Registry NumberNot Available
SMILES
COC1=CC(O)=CC(CCC2=CC(CC=C(C)C)=C(OC)C(O)=C2)=C1
InChI Identifier
InChI=1S/C21H26O4/c1-14(2)5-8-17-9-15(12-20(23)21(17)25-4)6-7-16-10-18(22)13-19(11-16)24-3/h5,9-13,22-23H,6-8H2,1-4H3
InChI KeyZRAWGGRJVKXQIK-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
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.54ALOGPS
logP5.32ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)9.43ChemAxon
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
Polarizability38.87 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-MS3,4'-Dihydroxy-5,3'-dimethoxy-5' isoprenyl bibenzyl, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,4'-Dihydroxy-5,3'-dimethoxy-5' isoprenyl bibenzyl, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,4'-Dihydroxy-5,3'-dimethoxy-5' isoprenyl bibenzyl, 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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Zhou XM, Zheng CJ, Gan LS, Chen GY, Zhang XP, Song XP, Li GN, Sun CG: Bioactive Phenanthrene and Bibenzyl Derivatives from the Stems of Dendrobium nobile. J Nat Prod. 2016 Jul 22;79(7):1791-7. doi: 10.1021/acs.jnatprod.6b00252. Epub 2016 Jun 16. [PubMed:27310249 ]