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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:13:06 UTC
Update Date2022-03-07 02:54:48 UTC
HMDB IDHMDB0036155
Secondary Accession Numbers
  • HMDB36155
Metabolite Identification
Common NameCurzerenone
DescriptionCurzerenone belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Based on a literature review a significant number of articles have been published on Curzerenone.
Structure
Data?1563862829
Synonyms
ValueSource
ZedoaroneHMDB
Chemical FormulaC15H18O2
Average Molecular Weight230.3022
Monoisotopic Molecular Weight230.13067982
IUPAC Name6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-4,5,6,7-tetrahydro-1-benzofuran-4-one
Traditional Name6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-5,7-dihydro-1-benzofuran-4-one
CAS Registry Number20493-56-5
SMILES
CC(=C)C1C(=O)C2=C(CC1(C)C=C)OC=C2C
InChI Identifier
InChI=1S/C15H18O2/c1-6-15(5)7-11-12(10(4)8-17-11)14(16)13(15)9(2)3/h6,8,13H,1-2,7H2,3-5H3
InChI KeyZVMJXSJCBLRAPD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
Substituents
  • Menthofuran monoterpenoid
  • Aromatic monoterpenoid
  • Bicyclic monoterpenoid
  • Benzofuran
  • Aryl ketone
  • Aryl alkyl ketone
  • Furan
  • Heteroaromatic compound
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point320.00 to 321.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1.44 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.315 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.041 g/LALOGPS
logP3.6ALOGPS
logP3.35ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)18.61ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area30.21 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity69.08 m³·mol⁻¹ChemAxon
Polarizability25.99 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]+152.44331661259
DarkChem[M-H]-149.8131661259
DeepCCS[M+H]+155.31630932474
DeepCCS[M-H]-152.95830932474
DeepCCS[M-2H]-186.19230932474
DeepCCS[M+Na]+161.40930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CurzerenoneCC(=C)C1C(=O)C2=C(CC1(C)C=C)OC=C2C2232.7Standard polar33892256
CurzerenoneCC(=C)C1C(=O)C2=C(CC1(C)C=C)OC=C2C1673.3Standard non polar33892256
CurzerenoneCC(=C)C1C(=O)C2=C(CC1(C)C=C)OC=C2C1612.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Curzerenone GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9530000000-5ce127ab411f7b319d4f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Curzerenone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Curzerenone 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 - Curzerenone 10V, Positive-QTOFsplash10-001i-0190000000-ac2e3fde2c9d43ceb56e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curzerenone 20V, Positive-QTOFsplash10-0fsm-6960000000-18f3d545eb8ff6645f892015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curzerenone 40V, Positive-QTOFsplash10-0uxr-9200000000-4000e91bc6bbbfebfe8b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curzerenone 10V, Negative-QTOFsplash10-004i-0090000000-98523e97b271e04856d42015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curzerenone 20V, Negative-QTOFsplash10-004i-0290000000-203d2685f68ba5b1b43e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curzerenone 40V, Negative-QTOFsplash10-007t-4910000000-c484fc471fbe855a0e552015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curzerenone 10V, Positive-QTOFsplash10-001i-0090000000-c656b3b03b821390fc7a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curzerenone 20V, Positive-QTOFsplash10-001i-7950000000-21dcf4dda75619d253592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curzerenone 40V, Positive-QTOFsplash10-000m-9200000000-e653b399f864f5e7132b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curzerenone 10V, Negative-QTOFsplash10-004i-0090000000-fb2ff0c6ce4213f1f3762021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curzerenone 20V, Negative-QTOFsplash10-004i-0290000000-b7fbbb4e9bc022dabbcc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curzerenone 40V, Negative-QTOFsplash10-01p9-3930000000-591264b61acf25ee00fd2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB015007
KNApSAcK IDC00011972
Chemspider ID4474745
KEGG Compound IDC16943
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCurzerenone
METLIN IDNot Available
PubChem Compound5315433
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1389501
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.