Showing Compound Card for gamma-Gurjunene (CDB000611)

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Record Information
Version1.0
Created at2020-03-19 00:46:35 UTC
Updated at2020-11-18 16:35:20 UTC
CannabisDB IDCDB000611
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namegamma-Gurjunene
Descriptionγ-Gurjunene, 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-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ). 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. γ-Gurjunene has been detected as a volatile component in cannabis plant samples ( PMID: 6991645 , 26657499 ). It was also identified in the shoots and nutlets of Carya illinoinensis (Pecan) (6.69% - 11.3% relative to total volatile compounds) (PMID: 21604354 ), the essential oil of Baccharis L. species (1.1 – 23.6% relative to total volatile compounds) (DOI: 10.1007/s00606-005-0296-6), the essential oil of Hypericum montbretii Spach (6.1-11.6% relative to total oil content) (DOI: 10.15547/ast.2018.03.050), the essential oil of Psidium L. (Guava) (PMID: 31286378 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC15H24
Average Molecular Weight204.36
Monoisotopic Molecular Weight204.1878
IUPAC Name(1S,3aS,4R,7R)-1,4-dimethyl-7-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulene
Traditional Name(1S,3aS,4R,7R)-1,4-dimethyl-7-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulene
CAS Registry Number22567-17-5
SMILES
C[C@H]1CC[C@H]2[C@H](C)CC[C@H](C=C12)C(C)=C
InChI Identifier
InChI=1S/C15H24/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h9,11-14H,1,5-8H2,2-4H3/t11-,12+,13-,14+/m1/s1
InChI KeyDUYRYUZIBGFLDD-RQJABVFESA-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
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP5.73ALOGPS
logP4.51ChemAxon
logS-4.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.53 m³·mol⁻¹ChemAxon
Polarizability26.27 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
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 Compound131705829
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Lukowski A, Maderek E, Giertych MJ, Karolewski P: Sex Ratio and Body Mass of Adult Herbivorous Beetles Depend on Time of Occurrence and Light Conditions. PLoS One. 2015 Dec 14;10(12):e0144718. doi: 10.1371/journal.pone.0144718. eCollection 2015. [PubMed:26657564 ]
  2. Corella-Madueno MA, Harris MK, Fu-Castillo AA, Martinez-Tellez MA, Valenzuela-Soto EM, Galvez-Ruiz JC, Vargas-Arispuro I: Volatiles emitted by Carya illinoinensis (Wang.) K. Koch as a prelude for semiochemical investigations to focus on Acrobasis nuxvorella Nuenzig (Lepidoptera: Pyralidae). Pest Manag Sci. 2011 Dec;67(12):1522-7. doi: 10.1002/ps.2205. Epub 2011 May 20. [PubMed:21604354 ]
  3. Vasconcelos LC, de Souza Santos E, de Oliveira Bernardes C, da Silva Ferreira MF, Ferreira A, Tuler AC, Carvalho JAM, Pinheiro PF, Praca-Fontes MM: Phytochemical analysis and effect of the essential oil of Psidium L. species on the initial development and mitotic activity of plants. Environ Sci Pollut Res Int. 2019 Sep;26(25):26216-26228. doi: 10.1007/s11356-019-05912-6. Epub 2019 Jul 8. [PubMed:31286378 ]
  4. Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. [PubMed:19932496 ]
  5. Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. [PubMed:17710406 ]
  6. 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 ]
  7. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]