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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:55:55 UTC
Update Date2022-03-07 03:17:48 UTC
HMDB IDHMDB0061853
Secondary Accession Numbers
  • HMDB61853
Metabolite Identification
Common Namebeta-Cubebene
Descriptionbeta-Cubebene, also known as β-cubebene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. beta-Cubebene is possibly neutral.
Structure
Data?1563866239
Synonyms
ValueSource
(-)-beta-CubebeneChEBI
(3AS-(3aalpha,3bbata,4beta,7alpha,7as*))-octahydro-7-methyl-3-methylene-4-(1-methylethyl)-1Hcyclopenta(1,3)cyclopropa(1,2)benzeneChEBI
(-)-b-CubebeneGenerator
(-)-Β-cubebeneGenerator
(3AS-(3aalpha,3bbata,4b,7a,7as*))-octahydro-7-methyl-3-methylene-4-(1-methylethyl)-1Hcyclopenta(1,3)cyclopropa(1,2)benzeneGenerator
(3AS-(3aalpha,3bbata,4β,7α,7as*))-octahydro-7-methyl-3-methylene-4-(1-methylethyl)-1Hcyclopenta(1,3)cyclopropa(1,2)benzeneGenerator
b-CubebeneGenerator
Β-cubebeneGenerator
(3AS-(3aalpha,3bbata,4b,7a,7aa*))-octahydro-7-methyl-3-methylene-4-(1-methylethyl)-1Hcyclopenta(1,3)cyclopropa(1,2)benzeneHMDB
(3AS-(3aalpha,3bbata,4S,7R,7as*))-octahydro-7-methyl-3-methylene-4-(1-methylethyl)-1H-cyclopenta(1,3)cyclopropa(1,2)benzeneHMDB
Chemical FormulaC15H24
Average Molecular Weight204.3511
Monoisotopic Molecular Weight204.187800768
IUPAC Name(1R,5S,6R,7S,10R)-10-methyl-4-methylidene-7-(propan-2-yl)tricyclo[4.4.0.0¹,⁵]decane
Traditional Name(-)-β-cubebene
CAS Registry Number13744-15-5
SMILES
CC(C)[C@@H]1CC[C@@H](C)[C@@]23CCC(=C)[C@@H]2[C@@H]13
InChI Identifier
InChI=1S/C15H24/c1-9(2)12-6-5-11(4)15-8-7-10(3)13(15)14(12)15/h9,11-14H,3,5-8H2,1-2,4H3/t11-,12+,13-,14-,15+/m1/s1
InChI KeyFSRZGYRCMPZNJF-KHMAMNHCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • 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
Disposition

Biological location

Source

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 Solubility0.0024 g/LALOGPS
logP3.49ALOGPS
logP4.15ChemAxon
logS-4.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity64.7 m³·mol⁻¹ChemAxon
Polarizability26.11 ųChemAxon
Number of Rings3ChemAxon
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]+151.2431661259
DarkChem[M-H]-149.13931661259
DeepCCS[M-2H]-195.83430932474
DeepCCS[M+Na]+171.06930932474
AllCCS[M+H]+148.032859911
AllCCS[M+H-H2O]+144.132859911
AllCCS[M+NH4]+151.632859911
AllCCS[M+Na]+152.632859911
AllCCS[M-H]-157.932859911
AllCCS[M+Na-2H]-158.332859911
AllCCS[M+HCOO]-158.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
beta-CubebeneCC(C)[C@@H]1CC[C@@H](C)[C@@]23CCC(=C)[C@@H]2[C@@H]131621.4Standard polar33892256
beta-CubebeneCC(C)[C@@H]1CC[C@@H](C)[C@@]23CCC(=C)[C@@H]2[C@@H]131409.8Standard non polar33892256
beta-CubebeneCC(C)[C@@H]1CC[C@@H](C)[C@@]23CCC(=C)[C@@H]2[C@@H]131412.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - beta-Cubebene GC-MS (Non-derivatized) - 70eV, Positivesplash10-01rm-2900000000-dbacb878626acfeae4ab2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Cubebene 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-Cubebene 10V, Positive-QTOFsplash10-0a4i-1390000000-6a944b8e46ab50de22202016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cubebene 20V, Positive-QTOFsplash10-0a4i-5940000000-af588cea8e1fb3c0a9d02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cubebene 40V, Positive-QTOFsplash10-0pxr-9500000000-f65be015faf4afb50b4f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cubebene 10V, Negative-QTOFsplash10-0udi-0090000000-7e9c1e42af69f59fea702016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cubebene 20V, Negative-QTOFsplash10-0udi-0190000000-79206d02912ecd5353d42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cubebene 40V, Negative-QTOFsplash10-000i-1910000000-9155330998fee11bfb192016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cubebene 10V, Positive-QTOFsplash10-0a4i-5590000000-3e03bee8035f33df34002021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cubebene 20V, Positive-QTOFsplash10-0a4l-9350000000-d48bf4c96f38a991dc202021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cubebene 40V, Positive-QTOFsplash10-0006-9000000000-0dac7d29bf1b8eb1d6a92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cubebene 10V, Negative-QTOFsplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cubebene 20V, Negative-QTOFsplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cubebene 40V, Negative-QTOFsplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-22Wishart 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 IDFDB004832
KNApSAcK IDC00003121
Chemspider ID84031
KEGG Compound IDC09648
BioCyc IDCPD-8803
BiGG IDNot Available
Wikipedia LinkPiper cubeba
METLIN IDNot Available
PubChem Compound93081
PDB IDNot Available
ChEBI ID10363
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. Debrauwere J, Verzele M: Constituents of peppers: IV. The hydrocarbons of pepper essential oil. J Chromatogr Sci. 1976 Jun;14(6):296-8. [PubMed:1270568 ]
  2. Kasali AA, Ekundayo O, Paul C, Konig WA: epi-Cubebanes from Solidago canadensis. Phytochemistry. 2002 Apr;59(8):805-10. [PubMed:11937158 ]
  3. Sajjadi SE, Ghannadi A, Sajjadi SE, Ghannadi A: Volatile oil composition of the aerial parts of Ajuga orientalis L. from Iran. Z Naturforsch C. 2004 Mar-Apr;59(3-4):166-8. [PubMed:15241917 ]
  4. Nickavar B, Amin G, Yosefi M: Volatile constituents of the flower and fruit oils of Pittosporum tobira (Thunb.) Ait. grown in Iran. Z Naturforsch C. 2004 Mar-Apr;59(3-4):174-6. [PubMed:15241919 ]
  5. Skalicka-Wozniak K, Ludwiczuk A, Widelski J, Filipe JJ, Asakawa Y, Glowniak K: Volatile constituents of Ocimum minimum herb cultivated in Portugal. Nat Prod Commun. 2009 Oct;4(10):1383-6. [PubMed:19911576 ]
  6. Park SY, Park SJ, Park NJ, Joo WH, Lee SJ, Choi YW: alpha-Iso-cubebene exerts neuroprotective effects in amyloid beta stimulated microglia activation. Neurosci Lett. 2013 Oct 25;555:143-8. doi: 10.1016/j.neulet.2013.09.053. Epub 2013 Sep 30. [PubMed:24090820 ]
  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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  12. Wikipedia [Link]
  13. MetaCyc: beta-cubebene biosynthesis [Link]
  14. UniProt B3TPQ6 : Beta-cubebene synthase [Link]