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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:56:01 UTC
Update Date2020-03-31 18:40:00 UTC
HMDB IDHMDB0060356
Secondary Accession Numbers
  • HMDB60356
Metabolite Identification
Common Name2-trans,6-trans-Farnesal
Description2-trans,6-trans-Farnesal, also known as (2E,6E)-farnesal, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, 2-trans,6-trans-farnesal is considered to be an isoprenoid lipid molecule. 2-trans,6-trans-Farnesal is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866049
Synonyms
ValueSource
(2-trans,6-trans)-3,7,11-Trimethyldodeca-2,6,10-trienalChEBI
(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrienalChEBI
(2E,6E)-FarnesalChEBI
(e,e)-3,7,11-Trimethyl-2,6,10-dodecatrienalChEBI
e,e-FarnesalChEBI
FarnesalChEBI
trans,trans-2,6-FarnesalChEBI
trans,trans-FarnesalChEBI
trans-FarnesalChEBI
2-trans,6-trans-FarnesalChEBI
Chemical FormulaC15H24O
Average Molecular Weight220.356
Monoisotopic Molecular Weight220.182715393
IUPAC Name(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienal
Traditional NameE,E-farnesal
CAS Registry Number502-67-0
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\C=O
InChI Identifier
InChI=1S/C15H24O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11-12H,5-6,8,10H2,1-4H3/b14-9+,15-11+
InChI KeyYHRUHBBTQZKMEX-YFVJMOTDSA-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
  • Medium-chain aldehyde
  • Enal
  • Alpha,beta-unsaturated aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.033 g/LALOGPS
logP10(5.56) g/LALOGPS
logP10(4.32) g/LChemAxon
logS10(-3.8) g/LALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity73.93 m³·mol⁻¹ChemAxon
Polarizability28.24 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+156.86531661259
DarkChem[M-H]-152.55431661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-trans,6-trans-Farnesal GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-8910000000-6fceeb69758d37e309bb2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-trans,6-trans-Farnesal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-trans,6-trans-Farnesal Orbitrap 5V, positive-QTOFsplash10-00di-0390000000-657f36e374ebb8808c272020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-trans,6-trans-Farnesal Orbitrap 6V, positive-QTOFsplash10-00di-2890000000-0a4f6e8585575dafa1702020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-trans,6-trans-Farnesal Orbitrap 7V, positive-QTOFsplash10-0229-4950000000-acdd7ffcb4da681051582020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-trans,6-trans-Farnesal Orbitrap 8V, positive-QTOFsplash10-082a-5930000000-088e02c561f9f53fe0692020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-trans,6-trans-Farnesal Orbitrap 9V, positive-QTOFsplash10-06dj-6910000000-91730b247cc0357897212020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-trans,6-trans-Farnesal Orbitrap 11V, positive-QTOFsplash10-066r-9800000000-8cf27cc5267f4a6dccf72020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-trans,6-trans-Farnesal Orbitrap 14V, positive-QTOFsplash10-066r-9400000000-5e04261f084a43d235142020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-trans,6-trans-Farnesal Orbitrap 17V, positive-QTOFsplash10-066r-9300000000-f67fbf94ceed5805fbe12020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-trans,6-trans-Farnesal Orbitrap 21V, positive-QTOFsplash10-066u-9200000000-293d7522c83886695e8a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-trans,6-trans-Farnesal Orbitrap 25V, positive-QTOFsplash10-0ar3-9200000000-8de0a5fa9189611331e02020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-trans,6-trans-Farnesal Orbitrap 30V, positive-QTOFsplash10-05r3-9200000000-7e87afdfd792674d87432020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-trans,6-trans-Farnesal n/a 15V, positive-QTOFsplash10-0w2a-1940000000-2be454cf4cc48f7299622020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-trans,6-trans-Farnesal n/a 15V, positive-QTOFsplash10-0aor-0900000000-fb6da0f873a8f2e261412020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-trans,6-trans-Farnesal n/a 15V, positive-QTOFsplash10-05fu-4900000000-8ed2edbc1c823be73a312020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-trans,6-trans-Farnesal n/a 15V, positive-QTOFsplash10-0006-9100000000-044eb012cbedaa2529022020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-trans,6-trans-Farnesal n/a 15V, positive-QTOFsplash10-0a4i-2900000000-99939a6cb8c8c0fb61c22020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-trans,6-trans-Farnesal n/a 15V, positive-QTOFsplash10-004i-9000000000-316664545979ac5fe84e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-trans,6-trans-Farnesal n/a 15V, positive-QTOFsplash10-0002-1900000000-752a111bf98f3c3e77bd2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-trans,6-trans-Farnesal n/a 15V, positive-QTOFsplash10-014i-0900000000-8d5a34c76bb03428a6912020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-trans,6-trans-Farnesal 10V, Positive-QTOFsplash10-00di-1790000000-d6fa26be28ef2eaf429d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-trans,6-trans-Farnesal 20V, Positive-QTOFsplash10-0600-6920000000-98f532df8055b5d696152016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-trans,6-trans-Farnesal 40V, Positive-QTOFsplash10-0gb9-9200000000-1d5460348e4d5315c0782016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-trans,6-trans-Farnesal 10V, Negative-QTOFsplash10-014i-0090000000-ae58f757cade812b61002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-trans,6-trans-Farnesal 20V, Negative-QTOFsplash10-014i-0290000000-f1633db79a7dcddca9c02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-trans,6-trans-Farnesal 40V, Negative-QTOFsplash10-0ffx-5920000000-d8b1e1fb795bd6d4f4612016-08-03Wishart LabView Spectrum
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 IDFDB014515
KNApSAcK IDC00030246 C00035091
Chemspider ID4444210
KEGG Compound IDC03461
BioCyc ID2-TRANS6-TRANS-FARNESAL
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280598
PDB IDNot Available
ChEBI ID15894
Food Biomarker OntologyNot Available
VMH IDM00677
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Involved in the degradation of prenylated proteins. Cleaves the thioether bond of prenyl-L-cysteines, such as farnesylcysteine and geranylgeranylcysteine.
Gene Name:
PCYOX1
Uniprot ID:
Q9UHG3
Molecular weight:
56639.66
Reactions
Farnesylcysteine + Oxygen + Water → 2-trans,6-trans-Farnesal + L-Cysteine + Hydrogen peroxidedetails