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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:55:48 UTC
Update Date2021-09-14 15:45:27 UTC
HMDB IDHMDB0061848
Secondary Accession Numbers
  • HMDB0035816
  • HMDB35816
  • HMDB61848
Metabolite 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. 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. beta-Elemene can be found in herbs, spices, and root vegetables, which makes beta-elemene a potential biomarker for the consumption of these food products. It is a constituent of sweet flag, juniper oils, and Mentha species.
Structure
Data?1601238530
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 Weight204.3511
Monoisotopic Molecular Weight204.187800768
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
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.004 g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+152.04631661259
DarkChem[M-H]-148.55731661259
DeepCCS[M+H]+153.01330932474
DeepCCS[M-H]-150.61830932474
DeepCCS[M-2H]-184.38830932474
DeepCCS[M+Na]+159.43730932474
AllCCS[M+H]+147.632859911
AllCCS[M+H-H2O]+143.632859911
AllCCS[M+NH4]+151.232859911
AllCCS[M+Na]+152.232859911
AllCCS[M-H]-154.832859911
AllCCS[M+Na-2H]-155.632859911
AllCCS[M+HCOO]-156.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
beta-ElemeneCC(=C)[C@@H]1CC[C@@](C)(C=C)[C@@H](C1)C(C)=C1602.9Standard polar33892256
beta-ElemeneCC(=C)[C@@H]1CC[C@@](C)(C=C)[C@@H](C1)C(C)=C1406.3Standard non polar33892256
beta-ElemeneCC(=C)[C@@H]1CC[C@@](C)(C=C)[C@@H](C1)C(C)=C1409.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - beta-Elemene EI-B (Non-derivatized)splash10-055f-9300000000-0289c8de75fe9d63ecbe2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Elemene EI-B (Non-derivatized)splash10-0a5c-9300000000-5b0ee4d8b7869c2f11502017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Elemene EI-B (Non-derivatized)splash10-055f-9300000000-0289c8de75fe9d63ecbe2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Elemene EI-B (Non-derivatized)splash10-0a5c-9300000000-5b0ee4d8b7869c2f11502018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Elemene GC-EI-Q (Non-derivatized)splash10-00kf-9500000000-bf13cd3bd5550f5ba5c92020-07-08HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Elemene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0080-5900000000-01235238c52dcbb6dd6b2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Elemene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Elemene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Elemene 10V, Positive-QTOFsplash10-0a4i-1790000000-453c5a1555b65a45bbf62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Elemene 20V, Positive-QTOFsplash10-06ri-4910000000-01642b086e5ae7d47ddf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Elemene 40V, Positive-QTOFsplash10-0gb9-9300000000-8a8cfd7c816b632bb2302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Elemene 10V, Negative-QTOFsplash10-0udi-0090000000-c96ee5d6723e9d3e562c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Elemene 20V, Negative-QTOFsplash10-0udi-0190000000-650d4bfb37438f455f352016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Elemene 40V, Negative-QTOFsplash10-000i-1900000000-0f6b74b8fa42644d3cd02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Elemene 10V, Negative-QTOFsplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Elemene 20V, Negative-QTOFsplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Elemene 40V, Negative-QTOFsplash10-0zg0-0940000000-2cbeadbe4dfea2ed53832021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Elemene 10V, Positive-QTOFsplash10-059i-0910000000-4293e9b1be9fc1d09c272021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Elemene 20V, Positive-QTOFsplash10-05cr-9710000000-733055659972947a11712021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Elemene 40V, Positive-QTOFsplash10-00mo-9300000000-b061378f98f19194e1c52021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Li Z, Wang K, Chen YR, Wu XY, Su CY: [Studies on metabolite of beta-elemene in rat bile]. Yao Xue Xue Bao. 2000 Nov;35(11):829-31. [PubMed:11218859 ]
  2. Wang K, Su CY: [Pharmacokinetics and disposition of beta-elemene in rats]. Yao Xue Xue Bao. 2000 Oct;35(10):725-8. [PubMed:11372435 ]
  3. Zou L, Liu W, Yu L: [beta-elemene induces apoptosis of K562 leukemia cells]. Zhonghua Zhong Liu Za Zhi. 2001 May;23(3):196-8. [PubMed:11783084 ]
  4. Chen SL, You J, Wang GJ: [Supercritical fluid extraction of beta-elemene under lower pressure]. Se Pu. 2001 Mar;19(2):179-81. [PubMed:12541670 ]
  5. Wang K, Li Z, Chen YR, Wu XY, Li SY, Su CY: [Excretion of beta-elemene from rat respiratory tracts]. Yao Xue Xue Bao. 2005 Jan;40(1):54-6. [PubMed:15881328 ]
  6. Zhang BJ, Li WC, Liu XP: [The pharmacokinetics of long-circulating beta-elemene liposomes]. Zhong Yao Cai. 2012 Sep;35(9):1464-8. [PubMed:23451504 ]
  7. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  8. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  9. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  10. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  11. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  12. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  13. YUREN CHEN, 'BETA-ELEMENE, METHOD TO PREPARE THE SAME AND USES THEREOF.' U.S. Patent US20020155522, issued October 24, 2002. [Link]
  14. Yuren Chen, 'Beta-elemene, method to prepare the same and uses thereof.' U.S. Patent US20030216605, issued November 20, 2003. [Link]
  15. Lan Huang, 'Synthesis of beta-elemene, intermediates thereto, analogues and uses thereof.' U.S. Patent US20060014987, issued January 19, 2006. [Link]