NOOTKATONE (CHEM006927)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:19:28 UTC
Update Date2016-11-09 01:09:50 UTC
Accession NumberCHEM006927
Identification
Common NameNOOTKATONE
ClassSmall Molecule
DescriptionA sesquiterpenoid that is 4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one which is substituted by methyl groups at positions 4 and 4a, and by an isopropenyl group at position 6 (the 4R,4aS,6R stereoisomer).
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
NootkatoneChEBI
Nootkatone, (4R-(4alpha,4aalpha,6beta))-isomerMeSH
Chemical FormulaC15H22O
Average Molecular Mass218.340 g/mol
Monoisotopic Mass218.167 g/mol
CAS Registry Number4674-50-4
IUPAC Name(4R,4aS,6R)-4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one
Traditional Namenootkatone
SMILESC[C@@H]1CC(=O)C=C2CC[C@H](C[C@@]12C)C(C)=C
InChI IdentifierInChI=1S/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3/t11-,12-,15+/m1/s1
InChI KeyWTOYNNBCKUYIKC-JMSVASOKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentEremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
Alternative Parents
Substituents
  • Eremophilane sesquiterpenoid
  • Cyclohexenone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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 Solubility0.029 g/LALOGPS
logP3.89ALOGPS
logP3.7ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)18.91ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity68.07 m³·mol⁻¹ChemAxon
Polarizability26.24 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, Positivesplash10-0fbi-2910000000-4441ef38f470fcf0d466Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0290000000-efcbb2df0a794f23f014Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-2940000000-125f96d262572db6c141Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9600000000-37f6a34d2bf3f9d79f1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-56b8036ffd3b6ade2127Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0190000000-92a574b59137108bfbf1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1940000000-37dd30fa03887c2c0103Spectrum
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 IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00016987
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNootkatone
Chemspider IDNot Available
ChEBI ID81377
PubChem Compound ID1268142
Kegg Compound IDC17914
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11441443
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15962787
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16272746
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19333595
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19630428
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21354294
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22238870
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22308777
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23025184
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24704449
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24747046
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=24938835
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=25189516
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=25326849