Showing Compound Card for Cannabistilbene IIb (CDB000754)

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Record Information
Version1.0
Created at2020-03-19 00:55:05 UTC
Updated at2020-11-18 16:35:29 UTC
CannabisDB IDCDB000754
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabistilbene IIb
DescriptionCannabistilbene IIb is one of 3 cannabistilbenes (the others being cannabistilbene IIa and cannabistilbene I) found in Cannabis savita. It 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 a common phenylpropene (C6-C3) skeleton building block. Cannabistilbene IIb belongs more formally to the class of the dihydrostilbenes. The introduction of one or more hydroxyl groups to a 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 ). Cannabistilbene IIb holds two hydroxyl groups (one is methylated) in ring A, both in a meta arrangement in relation to the C2 moiety. On the other hand, ring B holds one hydroxyl group in position 2 and two methoxyl groups in positions 3 and 4. Cannabistilbene IIb is a neutral, hydrophobic molecule that is insoluble in water. Cannabistilbene IIb is one of the non-cannabinoid phenolic compounds that are known to occur in the Cannabis plants (PMID: 28799497 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC17H20O5
Average Molecular Weight304.34
Monoisotopic Molecular Weight304.1311
IUPAC Name6-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2,3-dimethoxyphenol
Traditional Name6-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2,3-dimethoxyphenol
CAS Registry NumberNot Available
SMILES
COC1=CC(O)=CC(CCC2=CC=C(OC)C(OC)=C2O)=C1
InChI Identifier
InChI=1S/C17H20O5/c1-20-14-9-11(8-13(18)10-14)4-5-12-6-7-15(21-2)17(22-3)16(12)19/h6-10,18-19H,4-5H2,1-3H3
InChI KeyYFKXLCVZUWKRJH-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
  • Dimethoxybenzene
  • O-dimethoxybenzene
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • 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
logP2.85ALOGPS
logP3.43ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)9.49ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area68.15 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity83.75 m³·mol⁻¹ChemAxon
Polarizability32.69 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCannabistilbene IIb, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabistilbene IIb, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabistilbene IIb, 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. 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 ]