Showing Compound Card for delta-Cadinene (CDB000082)

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Record Information
Version1.0
Created at2020-03-18 23:24:06 UTC
Updated at2020-12-07 19:07:04 UTC
CannabisDB IDCDB000082
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namedelta-Cadinene
Description(+)-1(10),4-Cadinadiene, also known as delta-cadinene, one of the 4 isomers of Cadinene, belongs to the class of organic compounds known as sesquiterpenoids which are terpenes with three consecutive isoprene units. delta-Cadinene is an isoprenoid lipid molecule that is very hydrophobic, almost insoluble in water, soluble in alcohol and relatively neutral. Cadinene isomers were first isolated from oil of the wood of the Cade juniper, from which its name was derived. delta-Cadinene has a dry, thyme, herbal, and medicine taste ( Ref:DOI ). It is the trivial chemical name of several isomeric hydrocarbons that occur in a wide variety of essential oil-producing plants such as cannabis plants (PMID:6991645 ). 4-Cadinadiene occurs in the essential oils of all-spice, ylang-ylang, citronella, cubebs, and sweet flag. delta-Cadinadiene is found in highest concentrations in common oregano, hyssops, and lemon balms and in lower concentrations in sweet basils, spearmints, and winter savories. delta-Cadinene has also been detected in bread, macadamia nuts, common cabbages, moth beans, and half-highbush blueberries making delta-Cadinene a potential biomarker for the consumption of these foods. Delta-Cadinene has anti-cancer properties as it inhibited the growth of ovarian cancer cells (PMID: 26261482 ). 
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(1R,8AS)-4,7-dimethyl-1-isopropyl-1,2,3,5,6,8a-hexahydronaphthaleneChEBI
(1R,8AS)-4,7-dimethyl-1-(propan-2-yl)-1,2,3,5,6,8a-hexahydronaphthaleneKegg
(-)-Δ-cadineneGenerator
Chemical FormulaC15H24
Average Molecular Weight204.36
Monoisotopic Molecular Weight204.1878
IUPAC Name(1R,8aS)-4,7-dimethyl-1-(propan-2-yl)-1,2,3,5,6,8a-hexahydronaphthalene
Traditional Name(-)-delta-cadinene
CAS Registry Number483-76-1
SMILES
CC(C)[C@H]1CCC(C)=C2CCC(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,5-8H2,1-4H3/t13-,15-/m1/s1
InChI KeyFUCYIEXQVQJBKY-UKRRQHHQSA-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
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
logP4.92ALOGPS
logP4.4ChemAxon
logS-3.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity68.33 m³·mol⁻¹ChemAxon
Polarizability26.62 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
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.1 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID26606388
KEGG Compound IDC20182
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12306055
PDB IDNot Available
ChEBI ID63703
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. Hui LM, Zhao GD, Zhao JJ: delta-Cadinene inhibits the growth of ovarian cancer cells via caspase-dependent apoptosis and cell cycle arrest. Int J Clin Exp Pathol. 2015 Jun 1;8(6):6046-56. eCollection 2015. [PubMed:26261482 ]