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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:04:07 UTC
Update Date2021-09-14 15:40:13 UTC
HMDB IDHMDB0036004
Secondary Accession Numbers
  • HMDB36004
Metabolite Identification
Common Namealpha-Cyperene
Descriptionalpha-Cyperene, also known as α-cyperene or 4-isopatchoulene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. alpha-Cyperene is possibly neutral.
Structure
Data?1563862806
Synonyms
ValueSource
(-)-CypereneKegg
a-CypereneGenerator
Α-cypereneGenerator
4-IsopatchouleneHMDB
4-PatchouleneHMDB
Cyperene IHMDB
Chemical FormulaC15H24
Average Molecular Weight204.3511
Monoisotopic Molecular Weight204.187800768
IUPAC Name4,10,11,11-tetramethyltricyclo[5.3.1.0¹,⁵]undec-4-ene
Traditional Name4,10,11,11-tetramethyltricyclo[5.3.1.0¹,⁵]undec-4-ene
CAS Registry Number2387-78-2
SMILES
CC1CCC2CC3=C(C)CCC13C2(C)C
InChI Identifier
InChI=1S/C15H24/c1-10-7-8-15-11(2)5-6-12(9-13(10)15)14(15,3)4/h11-12H,5-9H2,1-4H3
InChI KeyRTBLDXVIGWSICW-UHFFFAOYSA-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
  • Patchoulane 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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP10(5.51) g/LALOGPS
logP10(4.06) g/LChemAxon
logS10(-4.3) g/LALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity65.43 m³·mol⁻¹ChemAxon
Polarizability25.63 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+147.29331661259
DarkChem[M-H]-144.04231661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Cyperene GC-MS (Non-derivatized) - 70eV, Positivesplash10-004s-1900000000-7bbf691da8d283e794002017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Cyperene 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 - alpha-Cyperene 10V, Positive-QTOFsplash10-0a4i-0190000000-97ec58d6ef8d628611e02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Cyperene 20V, Positive-QTOFsplash10-0a4i-2980000000-dcd6f88c4c6f28310f152016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Cyperene 40V, Positive-QTOFsplash10-0a70-7900000000-e286e222c74eccbb91912016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Cyperene 10V, Negative-QTOFsplash10-0udi-0090000000-c771e488f23febc3ab432016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Cyperene 20V, Negative-QTOFsplash10-0udi-0090000000-1789b8be0d2e6d7d8c3c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Cyperene 40V, Negative-QTOFsplash10-0f79-1920000000-1be3791f327b6d13d38b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Cyperene 10V, Positive-QTOFsplash10-0a4i-0090000000-c084f3d998cc56a199d62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Cyperene 20V, Positive-QTOFsplash10-0a4i-0490000000-dbef4a8146d6207118e22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Cyperene 40V, Positive-QTOFsplash10-0a4i-5890000000-3d4c3454a1e76a4acff12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Cyperene 10V, Negative-QTOFsplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Cyperene 20V, Negative-QTOFsplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Cyperene 40V, Negative-QTOFsplash10-0udi-0090000000-69aa1e827c3f75733e162021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014815
KNApSAcK IDC00021283
Chemspider ID90221
KEGG Compound IDC17505
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound99856
PDB IDNot Available
ChEBI ID81141
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. 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.