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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:57:59 UTC
Update Date2022-03-07 02:53:38 UTC
HMDB IDHMDB0033253
Secondary Accession Numbers
  • HMDB33253
Metabolite Identification
Common NameCurcumenone
DescriptionCurcumenone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on Curcumenone.
Structure
Data?1563862376
Synonyms
ValueSource
CurcumenoneMeSH
Chemical FormulaC15H22O2
Average Molecular Weight234.334
Monoisotopic Molecular Weight234.161979948
IUPAC Name1-methyl-7-(3-oxobutyl)-4-(propan-2-ylidene)bicyclo[4.1.0]heptan-3-one
Traditional Name1-methyl-7-(3-oxobutyl)-4-(propan-2-ylidene)bicyclo[4.1.0]heptan-3-one
CAS Registry Number100347-96-4
SMILES
CC(=O)CCC1C2CC(=C(C)C)C(=O)CC12C
InChI Identifier
InChI=1S/C15H22O2/c1-9(2)11-7-13-12(6-5-10(3)16)15(13,4)8-14(11)17/h12-13H,5-8H2,1-4H3
InChI KeyHUZJLWLCLJEXEL-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
  • Carabrane sesquiterpenoid
  • 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 effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point343.67 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility42.83 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.043 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP3.04ALOGPS
logP2.72ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)19.64ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity68.72 m³·mol⁻¹ChemAxon
Polarizability27.57 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]+155.44231661259
DarkChem[M-H]-154.37831661259
DeepCCS[M-2H]-189.6930932474
DeepCCS[M+Na]+164.6530932474
AllCCS[M+H]+155.332859911
AllCCS[M+H-H2O]+151.732859911
AllCCS[M+NH4]+158.632859911
AllCCS[M+Na]+159.632859911
AllCCS[M-H]-164.132859911
AllCCS[M+Na-2H]-164.532859911
AllCCS[M+HCOO]-165.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CurcumenoneCC(=O)CCC1C2CC(=C(C)C)C(=O)CC12C2411.1Standard polar33892256
CurcumenoneCC(=O)CCC1C2CC(=C(C)C)C(=O)CC12C1875.7Standard non polar33892256
CurcumenoneCC(=O)CCC1C2CC(=C(C)C)C(=O)CC12C1830.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Curcumenone,1TMS,isomer #1CC(=CCC1C2CC(=C(C)C)C(=O)CC12C)O[Si](C)(C)C2068.2Semi standard non polar33892256
Curcumenone,1TMS,isomer #1CC(=CCC1C2CC(=C(C)C)C(=O)CC12C)O[Si](C)(C)C1972.9Standard non polar33892256
Curcumenone,1TMS,isomer #2CC(=O)CCC1C2CC(=C(C)C)C(O[Si](C)(C)C)=CC12C1917.4Semi standard non polar33892256
Curcumenone,1TMS,isomer #2CC(=O)CCC1C2CC(=C(C)C)C(O[Si](C)(C)C)=CC12C1885.5Standard non polar33892256
Curcumenone,1TMS,isomer #3C=C(CCC1C2CC(=C(C)C)C(=O)CC12C)O[Si](C)(C)C2007.8Semi standard non polar33892256
Curcumenone,1TMS,isomer #3C=C(CCC1C2CC(=C(C)C)C(=O)CC12C)O[Si](C)(C)C1970.9Standard non polar33892256
Curcumenone,2TMS,isomer #1CC(=CCC1C2CC(=C(C)C)C(O[Si](C)(C)C)=CC12C)O[Si](C)(C)C2016.4Semi standard non polar33892256
Curcumenone,2TMS,isomer #1CC(=CCC1C2CC(=C(C)C)C(O[Si](C)(C)C)=CC12C)O[Si](C)(C)C2030.2Standard non polar33892256
Curcumenone,2TMS,isomer #2C=C(CCC1C2CC(=C(C)C)C(O[Si](C)(C)C)=CC12C)O[Si](C)(C)C1920.5Semi standard non polar33892256
Curcumenone,2TMS,isomer #2C=C(CCC1C2CC(=C(C)C)C(O[Si](C)(C)C)=CC12C)O[Si](C)(C)C2038.1Standard non polar33892256
Curcumenone,1TBDMS,isomer #1CC(=CCC1C2CC(=C(C)C)C(=O)CC12C)O[Si](C)(C)C(C)(C)C2308.8Semi standard non polar33892256
Curcumenone,1TBDMS,isomer #1CC(=CCC1C2CC(=C(C)C)C(=O)CC12C)O[Si](C)(C)C(C)(C)C2219.7Standard non polar33892256
Curcumenone,1TBDMS,isomer #2CC(=O)CCC1C2CC(=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC12C2151.7Semi standard non polar33892256
Curcumenone,1TBDMS,isomer #2CC(=O)CCC1C2CC(=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC12C2081.1Standard non polar33892256
Curcumenone,1TBDMS,isomer #3C=C(CCC1C2CC(=C(C)C)C(=O)CC12C)O[Si](C)(C)C(C)(C)C2256.9Semi standard non polar33892256
Curcumenone,1TBDMS,isomer #3C=C(CCC1C2CC(=C(C)C)C(=O)CC12C)O[Si](C)(C)C(C)(C)C2206.8Standard non polar33892256
Curcumenone,2TBDMS,isomer #1CC(=CCC1C2CC(=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC12C)O[Si](C)(C)C(C)(C)C2466.4Semi standard non polar33892256
Curcumenone,2TBDMS,isomer #1CC(=CCC1C2CC(=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC12C)O[Si](C)(C)C(C)(C)C2442.4Standard non polar33892256
Curcumenone,2TBDMS,isomer #2C=C(CCC1C2CC(=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC12C)O[Si](C)(C)C(C)(C)C2358.6Semi standard non polar33892256
Curcumenone,2TBDMS,isomer #2C=C(CCC1C2CC(=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC12C)O[Si](C)(C)C(C)(C)C2413.8Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Curcumenone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7920000000-7521392b1f7bd3d3a13b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Curcumenone 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 - Curcumenone 10V, Positive-QTOFsplash10-00kr-0290000000-44231713c7604901ad6e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumenone 20V, Positive-QTOFsplash10-0170-3930000000-21621f417134ecc8a0752016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumenone 40V, Positive-QTOFsplash10-0159-7900000000-ebb5437275fc9ee202a52016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumenone 10V, Negative-QTOFsplash10-001i-0090000000-cc1c2bfa5613282075f02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumenone 20V, Negative-QTOFsplash10-001i-4390000000-2c1883d4f4dc1f59ae002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumenone 40V, Negative-QTOFsplash10-0a4i-9320000000-2a8c666d152a109c02842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumenone 10V, Positive-QTOFsplash10-02ti-0950000000-2b38c731d12eef4039472021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumenone 20V, Positive-QTOFsplash10-0296-7900000000-9b02057600bf2fb4b97b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumenone 40V, Positive-QTOFsplash10-0006-9200000000-9e6d00d0883ea72de0362021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumenone 10V, Negative-QTOFsplash10-001i-0090000000-9087f47ed0ae51229a172021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumenone 20V, Negative-QTOFsplash10-001i-1490000000-66cee83414f465b42ca52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumenone 40V, Negative-QTOFsplash10-0ab9-1910000000-7cbd10787baf61ef72ea2021-09-25Wishart 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 IDFDB011275
KNApSAcK IDC00030068
Chemspider ID35013566
KEGG Compound IDC17492
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14632994
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1620311
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.