Record Information
Version1.0
Creation date2010-04-08 22:06:59 UTC
Update date2019-11-26 03:00:57 UTC
Primary IDFDB006096
Secondary Accession Numbers
  • FDB017449
Chemical Information
FooDB NameEpimuurolene
DescriptionGamma-cadinene, also known as D-G-cadinene or gamma-cadinene, (+)-isomer, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Gamma-cadinene is a wood tasting compound and can be found in a number of food items such as hyssop, lemon balm, sweet orange, and common sage, which makes gamma-cadinene a potential biomarker for the consumption of these food products. Gamma-cadinene can be found primarily in saliva. Chemically, the cadinenes are bicyclic sesquiterpenes. The term cadinene has sometimes also been used in a broad sense to refer to any sesquiterpene with the so-called cadalane (4-isopropyl-1,6-dimethyldecahydronaphthalene) carbon skeleton. Because of the large number of known double-bond and stereochemical isomers, this class of compounds has been subdivided into four subclasses based on the relative stereochemistry at the isopropyl group and the two bridgehead carbon atoms. The name cadinene is now properly used only for the first subclass below, which includes the compounds originally isolated from cade oil. Only one enantiomer of each subclass is depicted, with the understanding that the other enantiomer bears the same subclass name .
CAS Number483-74-9
Structure
Thumb
Synonyms
SynonymSource
D-gamma-CadineneChEBI
Epi-muuroleneChEBI
D-g-CadineneGenerator
D-Γ-cadineneGenerator
(+)-g-CadineneGenerator
(+)-Γ-cadineneGenerator
gamma-CadineneMeSH
gamma-Cadinene, (+)-isomerMeSH
gamma-Cadinene, (-)-isomerMeSH
gamma-Cadinene, (+)-gamma(1)-isomerMeSH
g-CadineneGenerator, HMDB
γ-cadineneGenerator, HMDB
1,2,3,4,4a,5,6,8a-octahydro-7-Methyl-4-methylene-1-(1-methylethyl)-(1S,4ar,8ar)-naphthaleneHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.0059 g/LALOGPS
logP4.48ALOGPS
logP4.51ChemAxon
logS-4.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.53 m³·mol⁻¹ChemAxon
Polarizability26.26 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H24
IUPAC name(1S,4aR,8aR)-7-methyl-4-methylidene-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene
InChI IdentifierInChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h9-10,13-15H,4-8H2,1-3H3/t13-,14-,15-/m0/s1
InChI KeyWRHGORWNJGOVQY-KKUMJFAQSA-N
Isomeric SMILES[H][C@@]12CCC(C)=C[C@@]1([H])[C@@H](CCC2=C)C(C)C
Average Molecular Weight204.3511
Monoisotopic Molecular Weight204.187800768
Classification
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
  • 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

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSEpimuurolene, non-derivatized, GC-MS Spectrumsplash10-03dl-7900000000-5735da8a4436cae8d6c5Spectrum
GC-MSEpimuurolene, non-derivatized, GC-MS Spectrumsplash10-03dl-7900000000-5735da8a4436cae8d6c5Spectrum
Predicted GC-MSEpimuurolene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01p5-2900000000-a648cf16712606029ec4Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-dc85480898a0884141d6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-93c533f1913690fe3979Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1910000000-cb52feba74ceaddb9360Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0590000000-152857a7341cf903230dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0490000000-2e5ae79ecdfa1abff465Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bta-3920000000-9e57207f76fd77fb69feSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gvt-6900000000-1be8491b4d6a6699abcbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1390000000-dec08090d83090223c29Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-4930000000-d018d03e18bf9231bbfaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9500000000-89d5115efd887002de1bSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDEPIMUUROLENE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).