Showing Compound Card for Beta-Eudesmol (CDB000458)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-03-19 00:38:01 UTC
Updated at2020-11-18 16:35:11 UTC
CannabisDB IDCDB000458
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameBeta-Eudesmol
DescriptionBeta-Eudesmol, also known as beta-selinenol 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. 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. Beta-eudesmol is a green and wood tasting compound that can be found in a number of food items such as common walnut, sweet basil, ginkgo nuts, burdock, and ginger (PMID: 18242187 ). Beta-eudesmol has also been identified in Cannabis sativa extracts (PMID: 6991645 , 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R,4AR,8as)-decahydro-8-methylene-alpha,alpha,4a-trimethyl-2-naphthylmethanolChEBI
beta-SelinenolChEBI
(2R,4AR,8as)-decahydro-8-methylene-a,a,4a-trimethyl-2-naphthylmethanolGenerator
(2R,4AR,8as)-decahydro-8-methylene-α,α,4a-trimethyl-2-naphthylmethanolGenerator
b-SelinenolGenerator
Β-selinenolGenerator
b-EudesmolGenerator
Β-eudesmolGenerator
beta-Eudesmol, (2S-(2alpha,4aalpha,8abeta))-isomerMeSH
Eudesm-4(14)-en-11-olPhytoBank
(+)-beta-EudesmolPhytoBank
(+)-β-EudesmolPhytoBank
beta-EudesmolPhytoBank
Chemical FormulaC15H26O
Average Molecular Weight222.37
Monoisotopic Molecular Weight222.1984
IUPAC Name2-[(2R,4aR,8aS)-4a-methyl-8-methylidene-decahydronaphthalen-2-yl]propan-2-ol
Traditional Nameβ-eudesmol
CAS Registry Number473-15-4
SMILES
CC(C)(O)[C@@H]1CC[C@@]2(C)CCCC(=C)[C@@H]2C1
InChI Identifier
InChI=1S/C15H26O/c1-11-6-5-8-15(4)9-7-12(10-13(11)15)14(2,3)16/h12-13,16H,1,5-10H2,2-4H3/t12-,13+,15-/m1/s1
InChI KeyBOPIMTNSYWYZOC-VNHYZAJKSA-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
  • Tertiary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • 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
logP4.21ALOGPS
logP3.53ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)19.32ChemAxon
pKa (Strongest Basic)-0.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity68.36 m³·mol⁻¹ChemAxon
Polarizability27.56 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)splash10-0a4i-9600000000-bfbe0937cd5dc239880f2015-03-01View Spectrum
GC-MSBeta-Eudesmol, non-derivatized, GC-MS Spectrumsplash10-0a4l-9600000000-4d69e00253e73f0e361bSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - n/a 15V, positivesplash10-00di-0900000000-37710ebc1d0a882ecce82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 15V, positivesplash10-0a4i-1790000000-4b748160259df190b3ce2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0390000000-622feb5828bf8dd0f06b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0609-2930000000-1b5044feca732d2778ef2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014u-9700000000-4d2f04e8bc1ab5b7c8062016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-d313ddde27f9cb81f9012016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0229-0490000000-e0d2e1274c533a96c1de2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bta-1930000000-869158675ce2e4f6b83c2016-08-03View Spectrum
NMR
TypeDescriptionView
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Sensi StarDetected and Quantified0.21 mg/g dry wt
    • David S. Wishart,...
 details
Sensi Star (Pure Indica)Detected and Quantified0.39 +/- 0.00 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.35 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine Dream (Sativa dominant)Detected and Quantified0.53 +/- 0.02 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003839
KNApSAcK IDC00000164
Chemspider IDNot Available
KEGG Compound IDC09664
BioCyc IDCPD-11432
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91457
PDB IDNot Available
ChEBI ID10417
References
General References
  1. 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 ]
  2. 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 ]
  3. Yu F, Harada H, Yamasaki K, Okamoto S, Hirase S, Tanaka Y, Misawa N, Utsumi R: Isolation and functional characterization of a beta-eudesmol synthase, a new sesquiterpene synthase from Zingiber zerumbet Smith. FEBS Lett. 2008 Mar 5;582(5):565-72. doi: 10.1016/j.febslet.2008.01.020. Epub 2008 Jan 31. [PubMed:18242187 ]
  4. 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 ]
  5. 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 ]