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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:08:10 UTC
Update Date2020-03-11 15:04:47 UTC
HMDB IDHMDB0036066
Secondary Accession Numbers
  • HMDB36066
Metabolite Identification
Common Name(3Z,6E)-alpha-Farnesene
Description(3Z,6E)-alpha-Farnesene, also known as (Z,E)-alpha-farnesene or cis,trans-alpha-farnesene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (3Z,6E)-alpha-Farnesene is found in fats and oils. (3Z,6E)-alpha-Farnesene is a constituent of the oil of perilla (Perilla frutescens).
Structure
Data?1583939087
Synonyms
ValueSource
(Z,E)-a-FarneseneGenerator
(Z,E)-α-FarneseneGenerator
(3Z,6E)-3,7,11-Trimethyl-1,3,6,10-dodecatetraeneHMDB
(3Z,6E)-alpha-FarneseneHMDB
(3Z,6E)-α-FarneseneHMDB
(Z,E)-alpha-FarneseneHMDB
3,7,11-Trimethyl-1,3,6,10-dodecatetraeneHMDB
FarneseneHMDB
Zataroside AHMDB
alpha-FarneseneHMDB
cis,trans-alpha-FarneseneHMDB
cis,trans-α-FarneseneHMDB
Chemical FormulaC15H24
Average Molecular Weight204.3511
Monoisotopic Molecular Weight204.187800768
IUPAC Name(3Z,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene
Traditional Name(Z,E)-α-farnesene
CAS Registry Number26560-14-5
SMILES
CC(C)=CCC\C(C)=C\C\C=C(\C)C=C
InChI Identifier
InChI=1S/C15H24/c1-6-14(4)10-8-12-15(5)11-7-9-13(2)3/h6,9-10,12H,1,7-8,11H2,2-5H3/b14-10-,15-12+
InChI KeyCXENHBSYCFFKJS-OXYODPPFSA-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
  • Alkatetraene
  • Branched unsaturated hydrocarbon
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Acyclic olefin
  • Hydrocarbon
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0052 g/LALOGPS
logP5.7ALOGPS
logP5.14ChemAxon
logS-4.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity73.25 m³·mol⁻¹ChemAxon
Polarizability26.7 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-3690000000-313b913d532cd4decec1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pw9-9710000000-078e5a8d7e85822b7c0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9100000000-3d3f85f913cafb612d5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-6d4cdcd69849df029e45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-e363a25bab51e774a592Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kg9-4900000000-b4cda282a594b52f2539Spectrum
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 IDFDB014894
KNApSAcK IDC00035167
Chemspider ID4515350
KEGG Compound IDNot Available
BioCyc IDCPD-9338
BiGG IDNot Available
Wikipedia LinkFarnesene
METLIN IDNot Available
PubChem Compound5362889
PDB IDNot Available
ChEBI ID39238
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bicker W, Lammerhofer M, Lindner W: Direct high-performance liquid chromatographic method for enantioselective and diastereoselective determination of selected pyrethroic acids. J Chromatogr A. 2004 Apr 30;1035(1):37-46. [PubMed:15117072 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.