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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:51:50 UTC
Update Date2022-03-07 02:54:17 UTC
HMDB IDHMDB0034932
Secondary Accession Numbers
  • HMDB34932
Metabolite Identification
Common NameFenchol
DescriptionFenchol, also known as endo-fenchol or fenchyl alcohol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Based on a literature review a small amount of articles have been published on Fenchol.
Structure
Data?1563862637
Synonyms
ValueSource
1,3,3-Trimethyl-2-norbornanolMeSH
endo-FencholMeSH
Fenchol, ((endo)-(+-))-isomerMeSH
Fenchol, ((exo)-(+-))-isomerMeSH
Fenchol, (1R-endo)-isomerMeSH
Fenchol, (1S-endo)-isomerMeSH
Fenchol, (1S-exo)-isomerMeSH
Fenchol, (endo)-isomerMeSH
Fenchol, (exo)-isomerMeSH
Fenchyl alcoholMeSH
1,3,3-trimethylbicyclo(2.2.1)Heptan-2-olHMDB
2-FenchanolHMDB
3,3-Dimethyl-8,9-dinorbornan-2-olHMDB
FEMA 2480HMDB
Fenchylic alcoholHMDB
FencholMeSH
Chemical FormulaC10H18O
Average Molecular Weight154.2493
Monoisotopic Molecular Weight154.135765198
IUPAC Name1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
Traditional Name(+)-fenchol
CAS Registry Number1632-73-1
SMILES
CC1(C)C2CCC(C)(C2)C1O
InChI Identifier
InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3
InChI KeyIAIHUHQCLTYTSF-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
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting Point35.00 to 40.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point201.00 to 202.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility461.4 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.550 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.87 g/LALOGPS
logP2.3ALOGPS
logP2.15ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-0.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.16 m³·mol⁻¹ChemAxon
Polarizability18.51 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]+131.62631661259
DarkChem[M-H]-126.84331661259
DeepCCS[M+H]+140.94730932474
DeepCCS[M-H]-137.81330932474
DeepCCS[M-2H]-174.7430932474
DeepCCS[M+Na]+150.1430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FencholCC1(C)C2CCC(C)(C2)C1O1551.9Standard polar33892256
FencholCC1(C)C2CCC(C)(C2)C1O1122.3Standard non polar33892256
FencholCC1(C)C2CCC(C)(C2)C1O1128.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fenchol,1TMS,isomer #1CC12CCC(C1)C(C)(C)C2O[Si](C)(C)C1196.3Semi standard non polar33892256
Fenchol,1TBDMS,isomer #1CC12CCC(C1)C(C)(C)C2O[Si](C)(C)C(C)(C)C1437.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Fenchol EI-B (Non-derivatized)splash10-001i-9000000000-03610ff0a989a69cf4782017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fenchol EI-B (Non-derivatized)splash10-001i-9100000000-2391ca66f3cd432bb0a22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fenchol EI-B (Non-derivatized)splash10-001i-9200000000-5ec7cae22ebff36623282017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fenchol EI-B (Non-derivatized)splash10-001i-9000000000-6704d50bcfa35df1f8862017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fenchol EI-B (Non-derivatized)splash10-001i-9100000000-97c1aaad48d62ad0ab302017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fenchol EI-B (Non-derivatized)splash10-001i-9200000000-de1f34c5e46838e35a672017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fenchol EI-B (Non-derivatized)splash10-001i-9000000000-03610ff0a989a69cf4782018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fenchol EI-B (Non-derivatized)splash10-001i-9100000000-2391ca66f3cd432bb0a22018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fenchol EI-B (Non-derivatized)splash10-001i-9200000000-5ec7cae22ebff36623282018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fenchol EI-B (Non-derivatized)splash10-001i-9000000000-6704d50bcfa35df1f8862018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fenchol EI-B (Non-derivatized)splash10-001i-9100000000-97c1aaad48d62ad0ab302018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fenchol EI-B (Non-derivatized)splash10-001i-9200000000-de1f34c5e46838e35a672018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fenchol GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9400000000-5297f0b29688722df06c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fenchol GC-MS (1 TMS) - 70eV, Positivesplash10-01x0-9520000000-7835ad73884f9d0dbde82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fenchol 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 - Fenchol 10V, Positive-QTOFsplash10-052r-0900000000-ed507d1b1719e12edbc12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenchol 20V, Positive-QTOFsplash10-052r-1900000000-0fe0191c4bde6f56fa8c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenchol 40V, Positive-QTOFsplash10-05aa-9500000000-f103d6927c834ced27782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenchol 10V, Negative-QTOFsplash10-0udi-0900000000-d7f7c5b94ca90ef600002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenchol 20V, Negative-QTOFsplash10-0udi-0900000000-4ebc0294913d58ac18f52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenchol 40V, Negative-QTOFsplash10-0fe0-2900000000-b92c9da7506b101aadc12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenchol 10V, Negative-QTOFsplash10-0udi-0900000000-d2363ae8d4dbdcccda802021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenchol 20V, Negative-QTOFsplash10-0udi-0900000000-d2363ae8d4dbdcccda802021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenchol 40V, Negative-QTOFsplash10-0udi-0900000000-459bafe52d5b103e88a62021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenchol 10V, Positive-QTOFsplash10-0a4i-3900000000-4094f7230adb483cf7e52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenchol 20V, Positive-QTOFsplash10-0a5c-6900000000-aabed757c552780da4722021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenchol 40V, Positive-QTOFsplash10-053i-9600000000-6fa6ff11a1ac49887bb32021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB013522
KNApSAcK IDC00052276
Chemspider ID14665
KEGG Compound IDC02344
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFenchol
METLIN IDNot Available
PubChem Compound15406
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1011531
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.