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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:48:20 UTC
Update Date2021-09-14 15:45:25 UTC
HMDB IDHMDB0032182
Secondary Accession Numbers
  • HMDB32182
Metabolite Identification
Common NameCadinene
DescriptionCadinene is found in caraway. Cadinene is the trivial chemical name of a number of isomeric hydrocarbons that occur in a wide variety of essential oil-producing plants. They all share the cadalane skeleton (4-isopropyl-1,6-dimethyldecahydronaphthalene) and can be further subdivided in: cadinenes, muurolene, amorphenes, and bulgarenes. (Wikipedia ) According to the double bonds positions, they are also subdivided in alpha [e.g. 4,9-Cadinadiene], beta, gamma [e.g. 4,10(15)-Cadinadiene], delta [e.g. 1(10),4-Cadinadiene], epsilon, zeta 1 and zeta 2. Prominent stereo-isomers are: alpha-cadinene (FDB017447), gamma-cadinene (FDB017449), and delta-cadinene (FDB013710)
Structure
Data?1563862229
Synonyms
ValueSource
CadinaneHMDB
Chemical FormulaC15H28
Average Molecular Weight208.3828
Monoisotopic Molecular Weight208.219100896
IUPAC Name1,6-dimethyl-4-(propan-2-yl)-decahydronaphthalene
Traditional Name4-isopropyl-1,6-dimethyl-decahydronaphthalene
CAS Registry NumberNot Available
SMILES
CC(C)C1CCC(C)C2CCC(C)CC12
InChI Identifier
InChI=1S/C15H28/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h10-15H,5-9H2,1-4H3
InChI KeyFZZNNPQZDRVKLU-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
  • Sesquiterpenoid
  • Cadinane sesquiterpenoid
  • Polycyclic hydrocarbon
  • Saturated hydrocarbon
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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 Solubility0.00011 g/LALOGPS
logP10(5.7) g/LALOGPS
logP10(5.26) g/LChemAxon
logS10(-6.3) g/LALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity66.9 m³·mol⁻¹ChemAxon
Polarizability27.74 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+151.42231661259
DarkChem[M-H]-147.69931661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cadinene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uxu-2900000000-ca51e0e3716f9fb68c822017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cadinene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cadinene 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 - Cadinene 10V, Positive-QTOFsplash10-0a4i-0290000000-2bd0bacaff3f733f67512017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadinene 20V, Positive-QTOFsplash10-0pvi-3930000000-0fac628fb3506393b7d82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadinene 40V, Positive-QTOFsplash10-1000-4900000000-caee40d7d5623fa830d32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadinene 10V, Negative-QTOFsplash10-0a4i-0090000000-b058f2710b6d5ccd82402017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadinene 20V, Negative-QTOFsplash10-0a4i-0090000000-83f2c5a652672c08c8f32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadinene 40V, Negative-QTOFsplash10-054o-0910000000-1db3cdfb272e6eec28252017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadinene 10V, Negative-QTOFsplash10-0a4i-0090000000-637b60c1591aab7691312021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadinene 20V, Negative-QTOFsplash10-0a4i-0090000000-637b60c1591aab7691312021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadinene 40V, Negative-QTOFsplash10-0a4i-0290000000-159d099287c0758901912021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadinene 10V, Positive-QTOFsplash10-0a4j-9230000000-edc8fd39c41c45d7e2682021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadinene 20V, Positive-QTOFsplash10-052b-9100000000-fd62d662cf865b15ee7a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cadinene 40V, Positive-QTOFsplash10-0aov-9000000000-7f6b1c52ea9d151bfb2e2021-09-24Wishart 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 IDFDB009046
KNApSAcK IDC00003106
Chemspider ID31786
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCadinene
METLIN IDNot Available
PubChem Compound34540
PDB IDNot Available
ChEBI ID22976
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. (). EAFUS: Everything Added to Food in the United States.. .
  6. (). Klein H, Dressel J, Mayr H, with Azizur-Rahman. Diastereoselective synthesis of [beta]- and [gamma]2-muurolene: a carbocationic pathway from mono- to sesquiterpenes. Tetrahedron 1988;44(19):6041-6045. [Structure]. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.