Showing Compound Card for (-)-gamma-Cadinene (CDB000216)

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Record Information
Version1.0
Created at2020-03-19 00:25:00 UTC
Updated at2020-11-18 16:34:56 UTC
CannabisDB IDCDB000216
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(-)-gamma-Cadinene
Descriptiongamma-Cadinene or (-)-gamma-Cadinene is formally classified as a cyclic hydrocarbon. The name is derived from the Cade juniper (Juniperus oxycedrus L.) where cadinene isomers were first isolated. There are four known Cadinene isomers: α-, β-, γ-, and δ-Cadinene. gamma-Cadinene is possibly neutral. Although it is classified as a cyclic hydrocarbon, gamma-Cadinene is biochemically a bicyclic sesquiterpene as it synthesized from isoprene units. Sesquiterpenoides 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; PMID:17467679 ), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the cytosol (PMID: 23746261 ). 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. Gamma-Cadinene is one of the many sesquiterpenes found in cannabis plants and their essential oils (PMID:6991645 ). It is found in allspice fruit, allspice leaf, angelica seed oil, armoise oil from Morocco, ayou wood oil, basil leaf oil, basil oil, carrot seed oil from Spain, cascarilla bark oil, cedrela wood oil, ceylon cinnamon, cinnamon leaf and leaf oil, ceylon citronella oil, sweet orange peel oil, oregano oil from Mexico, oregano plant and shoot and oregano shoot oil ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Chemical FormulaC15H24
Average Molecular Weight204.36
Monoisotopic Molecular Weight204.1878
IUPAC Name(1R,4aS,8aS)-7-methyl-4-methylidene-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene
Traditional Namegamma-cadinene
CAS Registry Number39029-41-9
SMILES
CC(C)[C@H]1CCC(=C)[C@H]2CCC(C)=C[C@H]12
InChI Identifier
InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h9-10,13-15H,4-8H2,1-3H3/t13-,14-,15-/m1/s1
InChI KeyWRHGORWNJGOVQY-RBSFLKMASA-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
  • Cadinane sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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
logP4.48ALOGPS
logP4.51ChemAxon
logS-4.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.53 m³·mol⁻¹ChemAxon
Polarizability26.38 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(-)-gamma-Cadinene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01p5-2900000000-9b4c6cbe257f47e9d9feSpectrum
Predicted GC-MS(-)-gamma-Cadinene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0038207
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB097241
KNApSAcK IDC00030345 C00036278
Chemspider ID83342
KEGG Compound IDC19738
BioCyc IDCPD-12881
BiGG IDNot Available
Wikipedia LinkCadinenes
METLIN IDNot Available
PubChem Compound92313
PDB IDNot Available
ChEBI ID63203
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. Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. [PubMed:17467679 ]
  3. Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. [PubMed:23746261 ]