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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-03-07 21:32:52 UTC
Update Date2019-07-23 07:13:02 UTC
HMDB IDHMDB0059849
Secondary Accession Numbers
  • HMDB59849
Metabolite Identification
Common Name(Z)-Farnesol
Description(Z)-Farnesol, also known as (2Z,6E)-farnesol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, (Z)-farnesol is considered to be an isoprenoid lipid molecule (Z)-Farnesol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563865982
Synonyms
ValueSource
(2-cis,6-trans)-3,7,11-Trimethyldodeca-2,6,10-trien-1-olChEBI
(2Z,6E)-FarnesolChEBI
(Z,e)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-olChEBI
(Z,e)-FarnesolChEBI
2-cis,6-trans-FarnesolChEBI
cis,trans-FarnesolChEBI
(2-cis,6-trans)-FarnesolHMDB
(2Z,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-1-olHMDB
Chemical FormulaC15H26O
Average Molecular Weight222.3663
Monoisotopic Molecular Weight222.198365454
IUPAC Name(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
Traditional Name(Z,E)-farnesol
CAS Registry NumberNot Available
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C/CO
InChI Identifier
InChI=1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3/b14-9+,15-11-
InChI KeyCRDAMVZIKSXKFV-PVMFERMNSA-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
  • Farsesane sesquiterpenoid
  • Sesquiterpenoid
  • Fatty alcohol
  • Fatty acyl
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.059 g/LALOGPS
logP4.84ALOGPS
logP4.16ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)16.33ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity74.98 m³·mol⁻¹ChemAxon
Polarizability28.88 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0avr-8930000000-641aa7a0528c963eca89Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05xr-9860000000-2eeca721058a47519afdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-1590000000-88a1356fe7cab3171954Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avi-7930000000-81c18181dbd66735216aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gi0-9400000000-e44ecbea8a96f84abd43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0390000000-9beef594142e0da5de92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-1980000000-3b9708ac6185abaf6d96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05bf-4910000000-a8db2089f5647c8532adSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDFDB014760
KNApSAcK IDNot Available
Chemspider ID1266074
KEGG Compound IDC03220
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1549108
PDB IDNot Available
ChEBI ID16774
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.