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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:48:34 UTC
Update Date2022-03-07 02:53:17 UTC
HMDB IDHMDB0032220
Secondary Accession Numbers
  • HMDB32220
Metabolite Identification
Common NameDihydronootkatone
DescriptionDihydronootkatone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on Dihydronootkatone.
Structure
Data?1563862233
SynonymsNot Available
Chemical FormulaC15H24O
Average Molecular Weight220.3505
Monoisotopic Molecular Weight220.18271539
IUPAC Name4a,8a-dimethyl-7-(prop-1-en-2-yl)-decahydronaphthalen-2-one
Traditional Name4a,8a-dimethyl-7-(prop-1-en-2-yl)-hexahydro-1H-naphthalen-2-one
CAS Registry Number20489-53-6
SMILES
CC(=C)C1CCC2(C)CCC(=O)CC2(C)C1
InChI Identifier
InChI=1S/C15H24O/c1-11(2)12-5-7-14(3)8-6-13(16)10-15(14,4)9-12/h12H,1,5-10H2,2-4H3
InChI KeyVESUMYPXHVXDJI-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
  • Valerane sequiterpene
  • Sesquiterpenoid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0078 g/LALOGPS
logP4.1ALOGPS
logP3.76ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.17 m³·mol⁻¹ChemAxon
Polarizability26.66 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+150.0331661259
DarkChem[M-H]-149.64431661259
DeepCCS[M+H]+155.30130932474
DeepCCS[M-H]-152.94330932474
DeepCCS[M-2H]-186.80630932474
DeepCCS[M+Na]+161.65430932474
AllCCS[M+H]+153.032859911
AllCCS[M+H-H2O]+149.232859911
AllCCS[M+NH4]+156.532859911
AllCCS[M+Na]+157.532859911
AllCCS[M-H]-160.532859911
AllCCS[M+Na-2H]-161.132859911
AllCCS[M+HCOO]-161.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DihydronootkatoneCC(=C)C1CCC2(C)CCC(=O)CC2(C)C12233.0Standard polar33892256
DihydronootkatoneCC(=C)C1CCC2(C)CCC(=O)CC2(C)C11653.3Standard non polar33892256
DihydronootkatoneCC(=C)C1CCC2(C)CCC(=O)CC2(C)C11713.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydronootkatone,1TMS,isomer #1C=C(C)C1CCC2(C)CCC(O[Si](C)(C)C)=CC2(C)C11808.3Semi standard non polar33892256
Dihydronootkatone,1TMS,isomer #1C=C(C)C1CCC2(C)CCC(O[Si](C)(C)C)=CC2(C)C11703.7Standard non polar33892256
Dihydronootkatone,1TMS,isomer #2C=C(C)C1CCC2(C)CC=C(O[Si](C)(C)C)CC2(C)C11822.5Semi standard non polar33892256
Dihydronootkatone,1TMS,isomer #2C=C(C)C1CCC2(C)CC=C(O[Si](C)(C)C)CC2(C)C11719.0Standard non polar33892256
Dihydronootkatone,1TBDMS,isomer #1C=C(C)C1CCC2(C)CCC(O[Si](C)(C)C(C)(C)C)=CC2(C)C12059.1Semi standard non polar33892256
Dihydronootkatone,1TBDMS,isomer #1C=C(C)C1CCC2(C)CCC(O[Si](C)(C)C(C)(C)C)=CC2(C)C11892.7Standard non polar33892256
Dihydronootkatone,1TBDMS,isomer #2C=C(C)C1CCC2(C)CC=C(O[Si](C)(C)C(C)(C)C)CC2(C)C12082.9Semi standard non polar33892256
Dihydronootkatone,1TBDMS,isomer #2C=C(C)C1CCC2(C)CC=C(O[Si](C)(C)C(C)(C)C)CC2(C)C11891.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dihydronootkatone GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-2920000000-73915c3917f1188e6a312017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydronootkatone 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 - Dihydronootkatone 10V, Positive-QTOFsplash10-00di-0290000000-65ba5df93ea0f198edea2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydronootkatone 20V, Positive-QTOFsplash10-00gl-2930000000-78e25d1021e02e37c52c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydronootkatone 40V, Positive-QTOFsplash10-016r-6900000000-e4773ce259c0d1c6f8d92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydronootkatone 10V, Negative-QTOFsplash10-014i-0090000000-e73b2e18005f1f84de872017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydronootkatone 20V, Negative-QTOFsplash10-014i-0090000000-9ad270217b913b72ca652017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydronootkatone 40V, Negative-QTOFsplash10-0udl-4940000000-01c7f38abc485a4995142017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydronootkatone 10V, Positive-QTOFsplash10-0fk9-0970000000-20e4a8a180ef3e0e09172021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydronootkatone 20V, Positive-QTOFsplash10-0002-0900000000-1d88774a0c12428d045f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydronootkatone 40V, Positive-QTOFsplash10-0006-9710000000-9978d158d3d86884d7b82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydronootkatone 10V, Negative-QTOFsplash10-014i-0090000000-4af4c4ee1c4acef7e18b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydronootkatone 20V, Negative-QTOFsplash10-014i-0090000000-4af4c4ee1c4acef7e18b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydronootkatone 40V, Negative-QTOFsplash10-014i-0290000000-e21425b8151949d615622021-09-23Wishart 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 IDFDB009290
KNApSAcK IDNot Available
Chemspider ID244192
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound277452
PDB IDNot Available
ChEBI IDNot Available
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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.