Showing Compound Card for (+)-beta-Selinene (CDB000218)

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Record Information
Version1.0
Created at2020-03-19 00:25:06 UTC
Updated at2020-11-18 16:34:56 UTC
CannabisDB IDCDB000218
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(+)-beta-Selinene
Descriptionβ-Selinene or (+)-β-Selinene, also known as beta-eudesmene or b-selinene, belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. 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), 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. (+)-β-Selinene is a very hydrophobic molecule, practically insoluble in water, but readily soluble in organic solvents such as methanol and ethanol. The selinenes share the molecular formula C15H24 and they have been isolated from a variety of plant sources. β-Selinene has been detected in cannabis plants and their essential oils (PMID: 26836472 , 26657499 ). There are four known selinene isomers including α-, β-, γ-, and δ-Selinene. α-Selinene and β-selinene are the most common and are two of the principal components of the oil from celery seeds. γ-Selinene and δ-selinene are less common.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(4AR,7R,8as)-7-isopropenyl-4a-methyl-1-methylenedecahydronaphthaleneChEBI
[4AR-(4aalpha,7alpha,8abeta)]-decahydro-4a-methyl-1-methylene-7-(1-methylethenyl)-naphthaleneChEBI
beta-EudesmeneChEBI
beta-SelineneChEBI
[4AR-(4aalpha,7a,8abeta)]-decahydro-4a-methyl-1-methylene-7-(1-methylethenyl)-naphthaleneGenerator
[4AR-(4aalpha,7α,8abeta)]-decahydro-4a-methyl-1-methylene-7-(1-methylethenyl)-naphthaleneGenerator
b-EudesmeneGenerator
Β-eudesmeneGenerator
b-SelineneGenerator
Β-selineneGenerator
(+)-b-SelineneGenerator
(+)-Β-selineneGenerator
beta-Selinene, (4ar-(4aalpha,7beta,8aalpha))-isomerMeSH
beta-Selinene, ((4aalpha,7alpha,8abeta)-(+-))-isomerMeSH
beta-Selinene, (4as-(4aalpha,7beta,8abeta))-isomerMeSH
(+)-beta-SelinenePhytoBank
Eudesma-4(14),11-diene PhytoBank
Selina-4(14),11-dienePhytoBank
Chemical FormulaC15H24
Average Molecular Weight204.36
Monoisotopic Molecular Weight204.1878
IUPAC Name(4aR,7R,8aS)-4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-decahydronaphthalene
Traditional Nameβ-selinene
CAS Registry Number17066-67-0
SMILES
CC(=C)[C@@H]1CC[C@@]2(C)CCCC(=C)[C@@H]2C1
InChI Identifier
InChI=1S/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h13-14H,1,3,5-10H2,2,4H3/t13-,14+,15-/m1/s1
InChI KeyYOVSPTNQHMDJAG-QLFBSQMISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentEudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
Alternative Parents
Substituents
  • Eudesmane, isoeudesmane or cycloeudesmane 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
logP5.26ALOGPS
logP4.58ChemAxon
logS-4.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity66.38 m³·mol⁻¹ChemAxon
Polarizability26.03 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a4l-9700000000-33e5ff63b3cc971652972015-03-01View Spectrum
Predicted GC-MS(+)-beta-Selinene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-1900000000-ee20e3501745902ad88bSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1490000000-3ae6219ba8438ea1ca042017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bti-3920000000-e66f387d7d6d39cc5dae2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-6900000000-4c28a5c81853a6a2ffbf2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-4cbcb8fb131c575b04dd2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-b4dd4139bf34a165f4232017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1900000000-6292cb517b5a7bae000d2017-06-28View Spectrum
NMR
TypeDescriptionView
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.23 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.34 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.19 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.21 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.11 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.08 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00003186
Chemspider IDNot Available
KEGG Compound IDC09723
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound442393
PDB IDNot Available
ChEBI ID10443
References
General References
  1. Aizpurua-Olaizola O, Soydaner U, Ozturk E, Schibano D, Simsir Y, Navarro P, Etxebarria N, Usobiaga A: Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes. J Nat Prod. 2016 Feb 26;79(2):324-31. doi: 10.1021/acs.jnatprod.5b00949. Epub 2016 Feb 2. [PubMed:26836472 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Delgado-Povedano MM, Sanchez-Carnerero Callado C, Priego-Capote F, Ferreiro-Vera C: Untargeted characterization of extracts from Cannabis sativa L. cultivars by gas and liquid chromatography coupled to mass spectrometry in high resolution mode. Talanta. 2020 Feb 1;208:120384. doi: 10.1016/j.talanta.2019.120384. Epub 2019 Sep 25. [PubMed:31816756 ]