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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:55:16 UTC
Update Date2022-03-07 02:54:18 UTC
HMDB IDHMDB0034985
Secondary Accession Numbers
  • HMDB34985
Metabolite Identification
Common Name(+)-Fenchone
Description(+)-Fenchone belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, (+)-fenchone is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on (+)-Fenchone.
Structure
Data?1563862646
Synonyms
ValueSource
1,3,3-Trimethyl-2-norbornanoneChEBI
1,3,3-Trimethyl-2-norcamphanoneChEBI
1,3,3-Trimethylbicyclo[2.2.1]heptan-2-oneChEBI
(1R,4S)-(+)-FenchoneHMDB
(1R,4S)-1,3,3-trimethylbicyclo[2.2.1]Heptan-2-oneHMDB
(1R,4S)-Fenchan-2-oneHMDB
(1R,4S)-FenchoneHMDB
L-alpha-FenchoneHMDB
L-FenchoneHMDB
Fenchone, (1S)-isomerMeSH, HMDB
Fenchone, (+-)-isomerMeSH, HMDB
Fenchone, (1R)-isomerMeSH, HMDB
(+)-FenchoneKEGG
Chemical FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
IUPAC Name1,3,3-trimethylbicyclo[2.2.1]heptan-2-one
Traditional Namefenchone
CAS Registry Number7787-20-4
SMILES
CC1(C)C2CCC(C)(C2)C1=O
InChI Identifier
InChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3
InChI KeyLHXDLQBQYFFVNW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Fenchane monoterpenoid
  • Bicyclic monoterpenoid
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point5-6 °CNot Available
Boiling Point192.00 to 194.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility73.14 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.52Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.88 g/LALOGPS
logP2.54ALOGPS
logP3.06ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-7.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.54 m³·mol⁻¹ChemAxon
Polarizability17.85 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.31131661259
DarkChem[M-H]-130.60531661259
DeepCCS[M+H]+137.19530932474
DeepCCS[M-H]-133.36830932474
DeepCCS[M-2H]-170.86530932474
DeepCCS[M+Na]+146.40330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(+)-FenchoneCC1(C)C2CCC(C)(C2)C1=O1398.7Standard polar33892256
(+)-FenchoneCC1(C)C2CCC(C)(C2)C1=O1067.5Standard non polar33892256
(+)-FenchoneCC1(C)C2CCC(C)(C2)C1=O1071.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - (+)-Fenchone EI-B (Non-derivatized)splash10-001i-9000000000-39548fbec25228381f9b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (+)-Fenchone EI-B (Non-derivatized)splash10-001i-9000000000-a6f20ad638918f01e9752017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (+)-Fenchone EI-B (Non-derivatized)splash10-001i-9000000000-39548fbec25228381f9b2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (+)-Fenchone EI-B (Non-derivatized)splash10-001i-9000000000-a6f20ad638918f01e9752018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (+)-Fenchone GC-EI-Q (Non-derivatized)splash10-00lr-9000000000-6be6cc8fad0feab50dc42020-07-08HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-Fenchone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0043-9400000000-8a489af79633badeca622017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-Fenchone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00lr-9000000000-0490bda5c76f7c0af3bd2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Fenchone 10V, Positive-QTOFsplash10-0udi-0900000000-24a8ed13cef6845f9bec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Fenchone 20V, Positive-QTOFsplash10-0udi-5900000000-48ac2ef18d27307d28a42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Fenchone 40V, Positive-QTOFsplash10-00or-9200000000-a262db5efd11c7793ea72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Fenchone 10V, Negative-QTOFsplash10-0udi-0900000000-611d1944cb83d52bd4732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Fenchone 20V, Negative-QTOFsplash10-0udi-0900000000-aa8c9e54bea95cd3d9992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Fenchone 40V, Negative-QTOFsplash10-01c9-5900000000-7356fe255f32eabff21c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Fenchone 10V, Negative-QTOFsplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Fenchone 20V, Negative-QTOFsplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Fenchone 40V, Negative-QTOFsplash10-0udi-0900000000-2a5636c44361fc4733062021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Fenchone 10V, Positive-QTOFsplash10-0udi-2900000000-620886e230bbabe8a4ef2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Fenchone 20V, Positive-QTOFsplash10-0ue9-5900000000-b24f702346175a6b01002021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Fenchone 40V, Positive-QTOFsplash10-0043-9200000000-42f567566720679e24e52021-09-24Wishart 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 IDFDB014535
KNApSAcK IDC00011027
Chemspider ID13869
KEGG Compound IDC11387
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFenchone
METLIN IDNot Available
PubChem Compound14525
PDB IDNot Available
ChEBI ID4999
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1044072
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.