Showing Compound Card for Cannabistilbene I (CDB000477)

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Record Information
Version1.0
Created at2020-03-19 00:39:02 UTC
Updated at2020-12-07 19:07:27 UTC
CannabisDB IDCDB000477
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabistilbene I
DescriptionCannabistilbene I, also known as DMMBD, 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. Cannabistilbene I holds two hydroxyl groups (one is methylated) in ring A, both in a meta arrangement in relation to the C2 moiety. Ring B holds one hydroxyl group in para position and is prenylated in the meta position. Cannabistilbene I is a new dihydrostilbene and was obtained as a light oil. Cannabis stilbenoids were first detected and isolated from leaves in 1978, from stem in 1982, and from resin in 1986 ( Ref:DOI ). Cannabis stilbenoids exhibit antibacterial, anti-inflammatory, antioxidant activities. Cannabistilbene I is one of several non-cannabinoid phenolic compounds that are known to occur in the Cannabis plants (PMID: 28799497 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3,4'-Dihydroxy-5-methoxy-3'-(3-methylbut-2-enyl)dihydrostilbeneMeSH
DMMBDMeSH
Chemical FormulaC20H24O3
Average Molecular Weight312.41
Monoisotopic Molecular Weight312.1725
IUPAC Name4-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-(3-methylbut-2-en-1-yl)phenol
Traditional Name4-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-(3-methylbut-2-en-1-yl)phenol
CAS Registry Number91925-76-7
SMILES
COC1=CC(CCC2=CC(CC=C(C)C)=C(O)C=C2)=CC(O)=C1
InChI Identifier
InChI=1S/C20H24O3/c1-14(2)4-8-17-10-15(7-9-20(17)22)5-6-16-11-18(21)13-19(12-16)23-3/h4,7,9-13,21-22H,5-6,8H2,1-3H3
InChI KeyPPIQDICARGCSMB-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
Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.73ALOGPS
logP5.47ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)9.29ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity95.06 m³·mol⁻¹ChemAxon
Polarizability36.37 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-MSCannabistilbene I, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabistilbene I, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabistilbene I, 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 Compound146349
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 ]