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Record Information
Version4.0
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

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 Solubility0.033 g/LALOGPS
logP5.56ALOGPS
logP4.32ChemAxon
logS-3.8ALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-8910000000-6fceeb69758d37e309bbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-00di-0390000000-657f36e374ebb8808c27Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-00di-2890000000-0a4f6e8585575dafa170Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-0229-4950000000-acdd7ffcb4da68105158Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-082a-5930000000-088e02c561f9f53fe069Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-06dj-6910000000-91730b247cc035789721Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-066r-9800000000-8cf27cc5267f4a6dccf7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-066r-9400000000-5e04261f084a43d23514Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 17V, positivesplash10-066r-9300000000-f67fbf94ceed5805fbe1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 21V, positivesplash10-066u-9200000000-293d7522c83886695e8aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 25V, positivesplash10-0ar3-9200000000-8de0a5fa9189611331e0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, positivesplash10-05r3-9200000000-7e87afdfd792674d8743Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 15V, positivesplash10-0w2a-1940000000-2be454cf4cc48f729962Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 15V, positivesplash10-0aor-0900000000-fb6da0f873a8f2e26141Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 15V, positivesplash10-05fu-4900000000-8ed2edbc1c823be73a31Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 15V, positivesplash10-0006-9100000000-044eb012cbedaa252902Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 15V, positivesplash10-0a4i-2900000000-99939a6cb8c8c0fb61c2Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 15V, positivesplash10-004i-9000000000-316664545979ac5fe84eSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 15V, positivesplash10-0002-1900000000-752a111bf98f3c3e77bdSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 15V, positivesplash10-014i-0900000000-8d5a34c76bb03428a691Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1790000000-d6fa26be28ef2eaf429dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0600-6920000000-98f532df8055b5d69615Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9200000000-1d5460348e4d5315c078Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-ae58f757cade812b6100Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0290000000-f1633db79a7dcddca9c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ffx-5920000000-d8b1e1fb795bd6d4f461Spectrum
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 ID
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