Showing Compound Card for Cannabistilbene IIa (CDB000753)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-03-19 00:54:58 UTC
Updated at2020-11-18 16:35:29 UTC
CannabisDB IDCDB000753
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabistilbene IIa
DescriptionCannabistilbene IIa is one of 3 cannabistilbenes (the others being cannabistilbene IIb 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 IIa 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 IIa 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 3 and two methoxyl groups in positions 2 and 4. Cannabistilbene IIa is a neutral, hydrophobic molecule that is insoluble in water. Cannabistilbene IIa 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 FormulaC16H18O4
Average Molecular Weight274.32
Monoisotopic Molecular Weight274.1205
IUPAC Name3-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-methoxyphenol
Traditional Name3-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-methoxyphenol
CAS Registry NumberNot Available
SMILES
COC1=CC(O)=CC(CCC2=CC=CC(O)=C2OC)=C1
InChI Identifier
InChI=1S/C16H18O4/c1-19-14-9-11(8-13(17)10-14)6-7-12-4-3-5-15(18)16(12)20-2/h3-5,8-10,17-18H,6-7H2,1-2H3
InChI KeyRSTDNUBRTQLVBF-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
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.03ALOGPS
logP3.59ChemAxon
logS-3.8ALOGPS
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 Count5ChemAxon
Refractivity77.28 m³·mol⁻¹ChemAxon
Polarizability29.52 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 IIa, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zmi-7357900000-a0e01cada67ae6bcc544Spectrum
Predicted GC-MSCannabistilbene IIa, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-0930000000-a7dd8175b172ad607b6fSpectrum
Predicted GC-MSCannabistilbene IIa, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0290000000-0bda3da156d7a73e81cd2019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0940000000-76eb5f440df1d81ca5152019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059i-3910000000-465bea19e32fd827eba72019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-9e09855e0ce450e3ef6f2019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-faef6ebdadde0f824b912019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1490000000-e614cf1abf6be132d3172019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-b55215739aea26b5370d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0390000000-fc5ace8ac8a70fd6c7632021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-0980000000-df1f0de916c2586d86672021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0390000000-a18db050d8777b3fc5fb2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abi-2920000000-656cbf840b01cff8dbc72021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00y0-4940000000-8ea3ff9e7a1afcb5c1c72021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0129945
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 Compound642896
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Andre CM, Hausman JF, Guerriero G: Cannabis sativa: The Plant of the Thousand and One Molecules. Front Plant Sci. 2016 Feb 4;7:19. doi: 10.3389/fpls.2016.00019. eCollection 2016. [PubMed:26870049 ]
  2. 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 ]