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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 23:26:18 UTC
Update Date2022-03-07 02:55:39 UTC
HMDB IDHMDB0038155
Secondary Accession Numbers
  • HMDB38155
Metabolite Identification
Common Namebeta-Bourbonene
Descriptionbeta-Bourbonene, also known as β-bourbonene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, beta-bourbonene is considered to be an isoprenoid. Based on a literature review a small amount of articles have been published on beta-Bourbonene.
Structure
Data?1601233760
Synonyms
ValueSource
b-BourboneneGenerator
Β-bourboneneGenerator
(-)-beta-BourbonenePhytoBank
(-)-β-BourbonenePhytoBank
beta-BourbonenePhytoBank
Chemical FormulaC15H24
Average Molecular Weight204.357
Monoisotopic Molecular Weight204.187800773
IUPAC Name(1S,2R,6S,7R,8S)-1-methyl-5-methylidene-8-(propan-2-yl)tricyclo[5.3.0.0^{2,6}]decane
Traditional Name(1S,2R,6S,7R,8S)-8-isopropyl-1-methyl-5-methylidenetricyclo[5.3.0.0^{2,6}]decane
CAS Registry Number5208-59-3
SMILES
[H][C@@]12CCC(=C)[C@]1([H])[C@@]1([H])[C@@H](CC[C@@]21C)C(C)C
InChI Identifier
InChI=1S/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)13(12)14(11)15/h9,11-14H,3,5-8H2,1-2,4H3/t11-,12+,13-,14+,15-/m0/s1
InChI KeyYIRAHEODBQONHI-ZQNQSHIBSA-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
  • Bourbonane sesquiterpenoid
  • 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point121.00 °C. @ 11.00 mm HgThe Good Scents Company Information System
Water Solubility0.14 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.128 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0024 g/LALOGPS
logP3.47ALOGPS
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
Polarizability25.84 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
DeepCCS[M-2H]-194.36230932474
DeepCCS[M+Na]+168.90330932474
AllCCS[M+H]+148.032859911
AllCCS[M+H-H2O]+144.232859911
AllCCS[M+NH4]+151.532859911
AllCCS[M+Na]+152.532859911
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-Bourbonene[H][C@@]12CCC(=C)[C@]1([H])[C@@]1([H])[C@@H](CC[C@@]21C)C(C)C1565.8Standard polar33892256
beta-Bourbonene[H][C@@]12CCC(=C)[C@]1([H])[C@@]1([H])[C@@H](CC[C@@]21C)C(C)C1401.6Standard non polar33892256
beta-Bourbonene[H][C@@]12CCC(=C)[C@]1([H])[C@@]1([H])[C@@H](CC[C@@]21C)C(C)C1393.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - beta-Bourbonene GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-4900000000-971a19356d2f3773b54b2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Bourbonene 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-Bourbonene 10V, Positive-QTOFsplash10-0a4i-1390000000-6cfb09d4bee8225adfb02016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Bourbonene 20V, Positive-QTOFsplash10-0a4i-4960000000-4abc8a9e131a79a0ff272016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Bourbonene 40V, Positive-QTOFsplash10-0pvi-9400000000-e58d05e1fcde39cbcf962016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Bourbonene 10V, Negative-QTOFsplash10-0udi-0090000000-46330ebe443a9c80ab502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Bourbonene 20V, Negative-QTOFsplash10-0udi-0090000000-3a394b7ae2cbfc8d1d122016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Bourbonene 40V, Negative-QTOFsplash10-000i-2910000000-70d27946e1464f9e40aa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Bourbonene 10V, Negative-QTOFsplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Bourbonene 20V, Negative-QTOFsplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Bourbonene 40V, Negative-QTOFsplash10-0udi-0090000000-61611159af8bfdbea87d2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Bourbonene 10V, Positive-QTOFsplash10-0aba-2930000000-d53c5b6b91bd5fa842c32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Bourbonene 20V, Positive-QTOFsplash10-00xr-8900000000-a134178d6fbd15c1f72f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Bourbonene 40V, Positive-QTOFsplash10-004l-9000000000-853aacd58544d4ca48c72021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB006026
KNApSAcK IDC00021884
Chemspider ID56330
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound62566
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1039751
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.