Showing Compound Card for Beta-Elemene (CDB000469)

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Record Information
Version1.0
Created at2020-03-19 00:38:36 UTC
Updated at2020-12-07 19:07:27 UTC
CannabisDB IDCDB000469
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameBeta-Elemene
DescriptionBeta-Elemene belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Sesquiterpenes 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. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively. Elemenes are a group of closely related natural chemical compounds found in a variety of plants, with Beta-Elemene being one of the 4 isomers of Elemene. The elemenes contribute to the floral aromas of some plants and are a part of the composition of Cannabis sativa (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1S,2S,4R)-(-)-1-Methyl-1-vinyl-2,4-diisopropenylcyclohexaneChEBI
(1S,2S,4R)-1-Methyl-2,4-di(prop-1-en-2-yl)-1-vinylcyclohexaneChEBI
(1S,2S,4R)-2,4-Diisopropenyl-1-methyl-1-vinylcyclohexaneChEBI
2,4-Diisopropenyl-1-methyl-1-vinylcyclohexaneChEBI
beta-ElemenChEBI
Levo-beta-elemeneChEBI
b-ElemenGenerator
Β-elemenGenerator
Levo-b-elemeneGenerator
Levo-β-elemeneGenerator
b-ElemeneGenerator
Β-elemeneGenerator
(-)-b-ElemeneHMDB
(-)-beta-ElemeneHMDB
beta-ElemeneChEBI
(-)-β-ElemeneGenerator
(1S,2S,4R)-1-Ethenyl-1-methyl-2,4-bis(1-methylethenyl)cyclohexanePhytoBank
(±)-beta-ElemenePhytoBank
(±)-β-ElemenePhytoBank
Chemical FormulaC15H24
Average Molecular Weight204.35
Monoisotopic Molecular Weight204.1878
IUPAC Name(1S,2S,4R)-1-ethenyl-1-methyl-2,4-bis(prop-1-en-2-yl)cyclohexane
Traditional Nameβ-elemene
CAS Registry Number515-13-9
SMILES
CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@@H](C1)C(C)=C
InChI Identifier
InChI=1S/C15H24/c1-7-15(6)9-8-13(11(2)3)10-14(15)12(4)5/h7,13-14H,1-2,4,8-10H2,3,5-6H3/t13-,14+,15-/m1/s1
InChI KeyOPFTUNCRGUEPRZ-QLFBSQMISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentElemane sesquiterpenoids
Alternative Parents
Substituents
  • Elemane sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.4ALOGPS
logP4.74ChemAxon
logS-4.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity68.23 m³·mol⁻¹ChemAxon
Polarizability25.97 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSBeta-Elemene, non-derivatized, GC-MS Spectrumsplash10-055f-9300000000-0289c8de75fe9d63ecbeSpectrum
GC-MSBeta-Elemene, non-derivatized, GC-MS Spectrumsplash10-0a5c-9300000000-5b0ee4d8b7869c2f1150Spectrum
GC-MSBeta-Elemene, non-derivatized, GC-MS Spectrumsplash10-055f-9300000000-0289c8de75fe9d63ecbeSpectrum
GC-MSBeta-Elemene, non-derivatized, GC-MS Spectrumsplash10-0a5c-9300000000-5b0ee4d8b7869c2f1150Spectrum
GC-MSBeta-Elemene, non-derivatized, GC-MS Spectrumsplash10-00kf-9500000000-bf13cd3bd5550f5ba5c9Spectrum
Predicted GC-MSBeta-Elemene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0080-5900000000-01235238c52dcbb6dd6bSpectrum
Predicted GC-MSBeta-Elemene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBeta-Elemene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1790000000-453c5a1555b65a45bbf62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06ri-4910000000-01642b086e5ae7d47ddf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9300000000-8a8cfd7c816b632bb2302016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-c96ee5d6723e9d3e562c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-650d4bfb37438f455f352016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1900000000-0f6b74b8fa42644d3cd02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zg0-0940000000-2cbeadbe4dfea2ed53832021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-059i-0910000000-4293e9b1be9fc1d09c272021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05cr-9710000000-733055659972947a11712021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-9300000000-b061378f98f19194e1c52021-09-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0061848
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014577
KNApSAcK IDC00007453
Chemspider ID5293588
KEGG Compound IDC17094
BioCyc IDCPD-8232
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6918391
PDB IDNot Available
ChEBI ID62855
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. 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 ]