Epicubenol (CHEM030657)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:03:46 UTC
Update Date2016-11-09 01:19:07 UTC
Accession NumberCHEM030657
Identification
Common NameEpicubenol
ClassSmall Molecule
Description1alpha-4-Cadinen-1-ol is found in cloves. 1alpha-4-Cadinen-1-ol is a constituent of oil of cubeb pepper (Piper cubeba).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Epi-cubenolHMDB
CubenolMeSH
EpicubenolMeSH
Chemical FormulaC15H26O
Average Molecular Mass222.366 g/mol
Monoisotopic Mass222.198 g/mol
CAS Registry Number19912-67-5
IUPAC Name4,7-dimethyl-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-4a-ol
Traditional Name1-isopropyl-4,7-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-4a-ol
SMILESCC(C)C1CCC(C)C2(O)CCC(C)=CC12
InChI IdentifierInChI=1S/C15H26O/c1-10(2)13-6-5-12(4)15(16)8-7-11(3)9-14(13)15/h9-10,12-14,16H,5-8H2,1-4H3
InChI KeyCOGPRPSWSKLKTF-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
  • Tertiary alcohol
  • Cyclic alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • 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 Solubility0.064 g/LALOGPS
logP3.76ALOGPS
logP3.69ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)-0.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity69.28 m³·mol⁻¹ChemAxon
Polarizability27.83 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-0aor-2910000000-111512c6fafa742b0facSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fvr-3190000000-f83e568356ec58491bc1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0290000000-7a35d479ddbd4829d3c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0c00-3970000000-407486e1357e1d16db16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9600000000-a24dc5d1649ce4073f2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-b0d0833ab0c8f145798eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0190000000-c25e09e4d431e8dc0445Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0920000000-0006e1a4c1269d380023Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0290000000-b06de3f5e5ed0416b4e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-3930000000-8960ad0fa5b9de2038b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9100000000-28be6d1d486ec4131fcfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-ab61d8a2af41e6ed2e49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-ab61d8a2af41e6ed2e49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kmi-0950000000-9acd7bb562666d7a8a7bSpectrum
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 IDHMDB0037031
FooDB IDFDB016012
Phenol Explorer IDNot Available
KNApSAcK IDC00033734
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID453462
ChEBI IDNot Available
PubChem Compound ID519857
Kegg Compound IDNot Available
YMDB IDYMDB15978
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Cane DE, Ke N: Epicubenol synthase. Origin of the oxygen atom of a bacterial sesquiterpene alcohol. Bioorg Med Chem Lett. 2000 Jan 17;10(2):105-7.
2. Takei M, Umeyama A, Arihara S: Epicubenol and Ferruginol induce DC from human monocytes and differentiate IL-10-producing regulatory T cells in vitro. Biochem Biophys Res Commun. 2005 Nov 18;337(2):730-8. Epub 2005 Sep 26.
3. Catalan CA, de Heluani CS, Kotowicz C, Gedris TE, Herz W: A linear sesterterpene, two squalene derivatives and two peptide derivatives from Croton hieronymi. Phytochemistry. 2003 Sep;64(2):625-9.
4. Cole RA, Haber WA, Lawton RO, Setzer WN: Leaf essential oil composition of three species of Myrcianthes from Monteverde, Costa Rica. Chem Biodivers. 2008 Jul;5(7):1327-34. doi: 10.1002/cbdv.200890120.
5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
6. 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.
7. 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.
8. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
9. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
10. The lipid handbook with CD-ROM