beta-Cubebene (CHEM025728)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:34:10 UTC
Update Date2016-11-09 01:18:08 UTC
Accession NumberCHEM025728
Identification
Common Namebeta-Cubebene
ClassSmall Molecule
DescriptionBeta-cubebene, also known as (-)-B-cubebene, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Beta-cubebene is a citrus and fruity tasting compound and can be found in a number of food items such as sweet basil, roman camomile, pot marjoram, and sweet bay, which makes beta-cubebene a potential biomarker for the consumption of these food products. Beta-cubebene can be found primarily in saliva. Piper cubeba, cubeb or tailed pepper is a plant in genus Piper, cultivated for its fruit and essential oil. It is mostly grown in Java and Sumatra, hence sometimes called Java pepper. The fruits are gathered before they are ripe, and carefully dried. Commercial cubebs consist of the dried berries, similar in appearance to black pepper, but with stalks attached – the "tails" in "tailed pepper". The dried pericarp is wrinkled, and its color ranges from grayish brown to black. The seed is hard, white and oily. The odor of cubebs is described as agreeable and aromatic and the taste as pungent, acrid, slightly bitter and persistent. It has been described as tasting like allspice, or like a cross between allspice and black pepper .
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Mass204.351 g/mol
Monoisotopic Mass204.188 g/mol
CAS Registry Number13744-15-5
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
SMILESCC(C)[C@@H]1CC[C@@H](C)[C@@]23CCC(=C)[C@@H]2[C@@H]13
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01rm-2900000000-dbacb878626acfeae4abSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1390000000-6a944b8e46ab50de2220Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-5940000000-af588cea8e1fb3c0a9d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pxr-9500000000-f65be015faf4afb50b4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-7e9c1e42af69f59fea70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-79206d02912ecd5353d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1910000000-9155330998fee11bfb19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-5590000000-3e03bee8035f33df3400Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9350000000-d48bf4c96f38a991dc20Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-0dac7d29bf1b8eb1d6a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0061853
FooDB IDFDB004832
Phenol Explorer IDNot Available
KNApSAcK IDC00003121
BiGG IDNot Available
BioCyc IDCPD-8803
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPiper cubeba
Chemspider ID84031
ChEBI ID10363
PubChem Compound ID93081
Kegg Compound IDC09648
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.
2. Kasali AA, Ekundayo O, Paul C, Konig WA: epi-Cubebanes from Solidago canadensis. Phytochemistry. 2002 Apr;59(8):805-10.
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.
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.
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.
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.
7. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
11. The lipid handbook with CD-ROM
12. Wikipedia: http://en.wikipedia.org/wiki/Beta-cubebene_synthase
13. MetaCyc: beta-cubebene biosynthesis: http://metacyc.org/META/NEW-IMAGE?type=PATHWAY&object=PWY-6290
14. UniProt B3TPQ6 : Beta-cubebene synthase: http://www.uniprot.org/uniprot/B3TPQ6
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=12587209
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=15241917
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=19370937
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=19449812
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=20401796
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=20433088