Showing Compound Card for 2,4(10)-Thujadien (CDB000705)

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Record Information
Version1.0
Created at2020-03-19 00:52:07 UTC
Updated at2020-11-18 16:35:27 UTC
CannabisDB IDCDB000705
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2,4(10)-Thujadien
Description2,4(10)-Thujadien, also known as Dehydrosabinene, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 2,4(10)-Thujadien with the molecular formula C10H14 has a strained ring system with a cyclopentane ring fused to a cyclopropane ring. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes in plants is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. 2,4(10)-Thujadien is a naturally occurring monoterpene found in a variety of plants such as cumin and carawy planted in the Middle East (PMID: 17258753 ). 2,4(10)-Thujadien or dihydrosabinene is a dehyrogenation product of Sabinene. Sabinene is isolated from the essential oils of a variety of plants including holm oak (Quercus ilex) and Norway spruce (Picea abies). Sabinene is one of the chemical compounds that contributes to the spiciness of black pepper and is a major constituent of carrot seed oil. 2,4(10)-Thujadien is also one of the terpenoids found in cannabis plants (PMID: 6991645 ). There are more than 140 known terpenes in cannabis and the combination of these terepenoids produces the skunky, fruity odor characteristic of C. savita.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC10H14
Average Molecular Weight134.22
Monoisotopic Molecular Weight134.1096
IUPAC Name(1S,5S)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hex-2-ene
Traditional Name(1S,5S)-1-isopropyl-4-methylidenebicyclo[3.1.0]hex-2-ene
CAS Registry NumberNot Available
SMILES
CC(C)[C@]12C[C@H]1C(=C)C=C2
InChI Identifier
InChI=1S/C10H14/c1-7(2)10-5-4-8(3)9(10)6-10/h4-5,7,9H,3,6H2,1-2H3/t9-,10-/m0/s1
InChI KeyLBVRQJWOZIMWNY-UWVGGRQHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
  • Thujane monoterpenoid
  • 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
logP3.5ALOGPS
logP2.5ChemAxon
logS-3.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.77 m³·mol⁻¹ChemAxon
Polarizability16.54 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
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 Compound162891376
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Jalali-Heravi M, Zekavat B, Sereshti H: Use of gas chromatography-mass spectrometry combined with resolution methods to characterize the essential oil components of Iranian cumin and caraway. J Chromatogr A. 2007 Mar 2;1143(1-2):215-26. doi: 10.1016/j.chroma.2007.01.042. Epub 2007 Jan 18. [PubMed:17258753 ]
  2. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  3. 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 ]