You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:08:06 UTC
Update Date2020-09-27 19:18:25 UTC
HMDB IDHMDB0036065
Secondary Accession Numbers
  • HMDB36065
Metabolite Identification
Common Namealpha-Farnesene
Descriptionalpha-Farnesene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (3E,6E)-alpha-Farnesene, also known as trans-alpha-Farnesene, is a sweet, bergamot, and citrus tasting flavouring ingredient. (3E,6E)-alpha-Farnesene is a constituent of the natural coating of apples and pears and other fruit. It has been identified in gingers, cottonseeds, common oregano, sweet oranges, spearmints, guava, pomes, and pears. This could make (3E,6E)-alpha-farnesene a potential biomarker for the consumption of these foods.
Structure
Data?1601234304
Synonyms
ValueSource
(3E,6E)-alpha-FarneseneChEBI
(3E,6E)-a-FarneseneGenerator
(3E,6E)-Α-farneseneGenerator
a-FarneseneGenerator
Α-farneseneGenerator
(E,E)-FarneseneHMDB
trans-FarneseneHMDB
3,7,11-Trimethyl-(E,E)-1,3,6,10-dodecatetraeneHMDB
alpha-trans,trans-FarneseneHMDB
trans,trans-alpha-FarneseneHMDB
alpha-FarneseneMeSH
(3E,6E)-3,7,11-Trimethyl-1,3,6,10-dodecatetraeneHMDB
(E,E)-alpha-FarneseneHMDB
(E,E)-α-FarneseneHMDB
3,7,11-Trimethyl-1,3,6,10-dodecatetraeneHMDB
FarneseneHMDB
trans,trans-α-FarneseneHMDB
trans-2,6,10-Trimethyl-2,6,9,11-dodecatetraeneHMDB
trans-3,7,11-Trimethyl-1,3,6,10-dodecatetraeneHMDB
trans-alpha-FarneseneHMDB
trans-α-FarneseneHMDB
Chemical FormulaC15H24
Average Molecular Weight204.3511
Monoisotopic Molecular Weight204.187800768
IUPAC Name(3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene
Traditional Namefarnesene
CAS Registry Number502-61-4
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-VDQVFBMKSA-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:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
Polarizability26.86 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available154.30731661259
DarkChem[M-H]-PredictedNot Available154.14731661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0673-9800000000-2417bd57042b291e594e2016-09-22View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9300000000-3317cba9629f9379052f2015-03-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-3690000000-313b913d532cd4decec12016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pw9-9710000000-078e5a8d7e85822b7c0c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9100000000-3d3f85f913cafb612d5c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-6d4cdcd69849df029e452016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-e363a25bab51e774a5922016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kg9-4900000000-b4cda282a594b52f25392016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0190000000-fa0c676eabe0c49e322b2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0390000000-0d353a60a5a97cd9c1a32021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-4900000000-9f5bab6c0c653c72230e2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-060s-7910000000-05be940f3488abb12fe82021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7l-9300000000-a54209dd2c1271d1d7d72021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ru-9000000000-a7b8e3b259690a16a4412021-09-22View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014895
KNApSAcK IDC00003130
Chemspider ID4444849
KEGG Compound IDC09665
BioCyc IDCPD-8764
BiGG IDNot Available
Wikipedia LinkFarnesene
METLIN IDNot Available
PubChem Compound5281516
PDB IDNot Available
ChEBI ID10280
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
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.