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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:18:14 UTC
Update Date2022-03-07 02:55:10 UTC
HMDB IDHMDB0037061
Secondary Accession Numbers
  • HMDB37061
Metabolite Identification
Common Name(+)-4,11-Eudesmadien-3-one
Description(+)-4,11-Eudesmadien-3-one belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Based on a literature review a small amount of articles have been published on (+)-4,11-Eudesmadien-3-one.
Structure
Data?1563862971
Synonyms
ValueSource
(+)-alpha-CyperoneHMDB
(4AS-cis)-4,4a,5,6,7,8-hexahydro-1,4a-dimethyl-7-(1-methylethenyl)-2(3H)-naphthalenoneHMDB
Eudesma-4,11-dien-3-oneHMDB
Chemical FormulaC15H22O
Average Molecular Weight218.3346
Monoisotopic Molecular Weight218.167065326
IUPAC Name1,4a-dimethyl-7-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one
Traditional Name1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one
CAS Registry Number473-08-5
SMILES
CC(=C)C1CCC2(C)CCC(=O)C(C)=C2C1
InChI Identifier
InChI=1S/C15H22O/c1-10(2)12-5-7-15(4)8-6-14(16)11(3)13(15)9-12/h12H,1,5-9H2,2-4H3
InChI KeyKUFXJZXMWHNCEH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentEudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
Alternative Parents
Substituents
  • Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
  • Cyclohexenone
  • 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 effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point320.40 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1.84 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.220 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.084 g/LALOGPS
logP3.92ALOGPS
logP3.81ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.88 m³·mol⁻¹ChemAxon
Polarizability26.26 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]+152.59431661259
DarkChem[M-H]-149.21131661259
DeepCCS[M+H]+153.39230932474
DeepCCS[M-H]-151.03430932474
DeepCCS[M-2H]-184.68330932474
DeepCCS[M+Na]+159.61930932474
AllCCS[M+H]+151.232859911
AllCCS[M+H-H2O]+147.332859911
AllCCS[M+NH4]+154.832859911
AllCCS[M+Na]+155.832859911
AllCCS[M-H]-159.232859911
AllCCS[M+Na-2H]-159.632859911
AllCCS[M+HCOO]-160.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(+)-4,11-Eudesmadien-3-oneCC(=C)C1CCC2(C)CCC(=O)C(C)=C2C12403.5Standard polar33892256
(+)-4,11-Eudesmadien-3-oneCC(=C)C1CCC2(C)CCC(=O)C(C)=C2C11737.8Standard non polar33892256
(+)-4,11-Eudesmadien-3-oneCC(=C)C1CCC2(C)CCC(=O)C(C)=C2C11751.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(+)-4,11-Eudesmadien-3-one,1TMS,isomer #1C=C(C)C1CCC2(C)CC=C(O[Si](C)(C)C)C(C)=C2C11882.8Semi standard non polar33892256
(+)-4,11-Eudesmadien-3-one,1TMS,isomer #1C=C(C)C1CCC2(C)CC=C(O[Si](C)(C)C)C(C)=C2C11743.4Standard non polar33892256
(+)-4,11-Eudesmadien-3-one,1TBDMS,isomer #1C=C(C)C1CCC2(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)=C2C12103.0Semi standard non polar33892256
(+)-4,11-Eudesmadien-3-one,1TBDMS,isomer #1C=C(C)C1CCC2(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)=C2C11924.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - (+)-4,11-Eudesmadien-3-one EI-B (Non-derivatized)splash10-0006-7910000000-df760ddca07d59ed812c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (+)-4,11-Eudesmadien-3-one EI-B (Non-derivatized)splash10-0006-7910000000-df760ddca07d59ed812c2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-4,11-Eudesmadien-3-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udu-1910000000-187a975af82ec4d7f5882017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-4,11-Eudesmadien-3-one 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 - (+)-4,11-Eudesmadien-3-one 10V, Positive-QTOFsplash10-014i-0390000000-1c7b5876e297c2ba58b12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 20V, Positive-QTOFsplash10-0i29-2930000000-14df3115b7817b42780b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 40V, Positive-QTOFsplash10-0gbc-9700000000-29ed054963831bb24f022016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 10V, Negative-QTOFsplash10-014i-0090000000-a146fe81fc0bf2cb8ef62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 20V, Negative-QTOFsplash10-014i-0190000000-2213f64588ca34fc91602016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 40V, Negative-QTOFsplash10-0udi-2940000000-890ebe75f693b7df72512016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 10V, Positive-QTOFsplash10-014i-0980000000-ef0671ce0f33e777c3a92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 20V, Positive-QTOFsplash10-00kr-2920000000-8cb8c335175fdafdf9da2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 40V, Positive-QTOFsplash10-014i-9300000000-9eab3be47eb1086d69182021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 10V, Negative-QTOFsplash10-014i-0090000000-868e2fb00a2cfbf6c5292021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 20V, Negative-QTOFsplash10-014i-0090000000-868e2fb00a2cfbf6c5292021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 40V, Negative-QTOFsplash10-014i-0890000000-f634f2c34cc81095a09d2021-09-22Wishart 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 IDFDB016044
KNApSAcK IDC00012759
Chemspider ID240707
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound273568
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1441871
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.