Showing Compound Card for Canniprene (CDB000752)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (4) Show 8 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:54:56 UTC
Updated at2020-11-18 16:35:29 UTC
CannabisDB IDCDB000752
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCanniprene
DescriptionCanniprene, 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 leads to stilbenoids. Canniprene is also 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. Canniprene 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. Canniprene is neutral, hydrophobic molecule that is not water soluble. Canniprene is commonly found in the fan leaves of Cannabis sativa. The concentration of canniprene in the fan leaves of 160 strains of C. sativa has been measured and wide variations, ranging from traces to >0.2%, have been seen. Canniprene was first reported by Bosch and Salemink to be present in the methylene chloride extract of Mexican cannabis (PMID: 6991645 ). Canniprene exhibits good ant-nflammatory properties. Studies have shown that it potently inhibits the production of inflammatory eicosanoids via inhibition of the 5-lipoxygenase pathway. In particular, it limits the generation of prostaglandins via inhibition of the cyclooxygenase/microsomal prostaglandin E2 synthase pathway (PMID: 28165233 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC21H26O4
Average Molecular Weight342.44
Monoisotopic Molecular Weight342.1831
IUPAC Name3-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-6-methoxy-2-(3-methylbut-2-en-1-yl)phenol
Traditional Name3-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-6-methoxy-2-(3-methylbut-2-en-1-yl)phenol
CAS Registry Number70677-47-3
SMILES
COC1=CC(CCC2=C(CC=C(C)C)C(O)=C(OC)C=C2)=CC(O)=C1
InChI Identifier
InChI=1S/C21H26O4/c1-14(2)5-9-19-16(8-10-20(25-4)21(19)23)7-6-15-11-17(22)13-18(12-15)24-3/h5,8,10-13,22-23H,6-7,9H2,1-4H3
InChI KeyNGQFSSVGVDXEOE-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
logP4.51ALOGPS
logP5.32ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)9.39ChemAxon
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
Polarizability39.07 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-(2-isoprenyl-3-hydroxy-4-methoxyphenyl)ethyl]-5-methoxyphenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-[2-(2-isoprenyl-3-hydroxy-4-methoxyphenyl)ethyl]-5-methoxyphenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-[2-(2-isoprenyl-3-hydroxy-4-methoxyphenyl)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
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Prostaglandin E synthasePTGES9q34.3O14684 details
Arachidonate 5-lipoxygenaseALOX510q11.2P09917 details
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
Prostaglandin E synthase 2PTGES29q34.11Q9H7Z7 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Arachidonate 5-lipoxygenaseALOX510q11.2P09917 details
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Prostaglandin E synthase 2PTGES29q34.11Q9H7Z7 details
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. 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 ]
  2. Allegrone G, Pollastro F, Magagnini G, Taglialatela-Scafati O, Seegers J, Koeberle A, Werz O, Appendino G: The Bibenzyl Canniprene Inhibits the Production of Pro-Inflammatory Eicosanoids and Selectively Accumulates in Some Cannabis sativa Strains. J Nat Prod. 2017 Mar 24;80(3):731-734. doi: 10.1021/acs.jnatprod.6b01126. Epub 2017 Feb 6. [PubMed:28165233 ]

Enzymes

Enzyme Details
1. Prostaglandin E synthase
General function:
Involved in prostaglandin-E synthase activity
Specific function:
Catalyzes the oxidoreduction of prostaglandin endoperoxide H2 (PGH2) to prostaglandin E2 (PGE2).
Gene Name:
PTGES
Uniprot ID:
O14684
Molecular weight:
17102.135
Enzyme Details
2. Arachidonate 5-lipoxygenase
General function:
Involved in metal ion binding
Specific function:
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:
ALOX5
Uniprot ID:
P09917
Molecular weight:
77982.595
Enzyme Details
3. Prostaglandin G/H synthase 1
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
Enzyme Details
4. Prostaglandin E synthase 2
General function:
Involved in electron carrier activity
Specific function:
Isomerase that catalyzes the conversion of unstable intermediate of prostaglandin E2 H2 (PGH2) into the more stable prostaglandin E2 (PGE2) form. May also have transactivation activity toward IFN-gamma (IFNG), possibly via an interaction with CEBPB; however, the relevance of transcription activation activity remains unclear.
Gene Name:
PTGES2
Uniprot ID:
Q9H7Z7
Molecular weight:
21337.205