Showing Compound Card for gamma-elemene (CDB000309)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-03-19 00:30:12 UTC
Updated at2020-12-07 19:07:20 UTC
CannabisDB IDCDB000309
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namegamma-elemene
DescriptionGamma-Elemene, also known as g-elemene, belongs to the class of organic compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. More formally, gamma-elemene is a cyclohexane substituted at positions 1, 1, 2, and 4 by methyl, vinyl, isopropenyl and isopropylidene groups, respectively. There are four known elemene isomers including α-, β-, γ-, and δ-elemene. The elemenes contribute to the floral aromas of some plants and are used as pheromones by some insects. Gamma-elemene is found in many essential plant oils including wormwood leaf oil, peppermint oil, pepper tree leaf oil, parsley leaf oil, orange peel oil, lime oil, juniper berry oil, hinoki leaf oil, angelica root oil, and angelica seed oil. Gamma-elemene is also one of the many sesquiterpenes found in cannabis plants (PMID: 6991645 ). Gamma-elemene has been shown to exhibit good insecticidal activity against the crop pest Spodoptera litura (tobacco cutworm or cotton leafworm) and could be useful as an eco-friendly biopesticide (PMID:28634795 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-gamma-ElemeneChEBI
(+)-g-ElemeneGenerator
(+)-Γ-elemeneGenerator
g-ElemeneGenerator
Γ-elemeneGenerator
Chemical FormulaC15H24
Average Molecular Weight204.36
Monoisotopic Molecular Weight204.1878
IUPAC Name(1S,2S)-1-ethenyl-1-methyl-2-(prop-1-en-2-yl)-4-(propan-2-ylidene)cyclohexane
Traditional Name(1S,2S)-1-ethenyl-1-methyl-2-(prop-1-en-2-yl)-4-(propan-2-ylidene)cyclohexane
CAS Registry NumberNot Available
SMILES
CC(C)=C1CC[C@@](C)(C=C)[C@@H](C1)C(C)=C
InChI Identifier
InChI=1S/C15H24/c1-7-15(6)9-8-13(11(2)3)10-14(15)12(4)5/h7,14H,1,4,8-10H2,2-3,5-6H3/t14-,15+/m0/s1
InChI KeyBQSLMQNYHVFRDT-LSDHHAIUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic 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
logP5.09ALOGPS
logP4.64ChemAxon
logS-4.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity69.03 m³·mol⁻¹ChemAxon
Polarizability25.8 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSgamma-elemene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0019-4900000000-fb790115baaf4a3d1616Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1890000000-450e146224ccff06d6172016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07br-3910000000-61daee527832bc1811302016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9300000000-84044dadf41caec7632f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-6bfd709831d5599e9c1e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0290000000-b951c20dccfd334852ad2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1900000000-9c9cef0e084401e873e92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-022i-0900000000-b8727734b8bc280cd8072021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-9710000000-8f184d721121df33f4dc2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-069u-9300000000-dc6712d7b870be6f2b3a2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zg0-0940000000-75fae33c5b380ac995912021-10-21View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
GabriolaDetected and Quantified0.18 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.05 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0302493
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004787
KNApSAcK IDC00012012
Chemspider ID4937571
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID132656
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. Benelli G, Govindarajan M, AlSalhi MS, Devanesan S, Maggi F: High toxicity of camphene and gamma-elemene from Wedelia prostrata essential oil against larvae of Spodoptera litura (Lepidoptera: Noctuidae). Environ Sci Pollut Res Int. 2018 Apr;25(11):10383-10391. doi: 10.1007/s11356-017-9490-7. Epub 2017 Jun 20. [PubMed:28634795 ]