Showing Compound Card for trans-trans-alpha-Farnesene (CDB000311)

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Record Information
Version1.0
Created at2020-03-19 00:30:18 UTC
Updated at2020-12-07 19:07:21 UTC
CannabisDB IDCDB000311
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Nametrans-trans-alpha-Farnesene
DescriptionTrans-trans-alpha-Farnesene, also known as (3E,6E)-alpha-Farnesene, belongs to the class of organic compounds known as sesquiterpenoids. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. The term farnesene refers to a set of six closely related chemical compounds (4 alpha-Farnesenes and 2 Beta-Farnesenes) which all are sesquiterpenes. α-Farnesene and β-Farnesene are isomers, differing by the location of one double bond. β-Farnesene is 7,11-dimethyl-3-methylene-1,6,10-dodecatriene while α-Farnesene is 3,7,11-trimethyl-1,3,6,10-dodecatetraene. There are four known Alpha-farnesene stereoisomers which differ about the geometry of two of its three internal double bonds (the stereoisomers of the third internal double bond are identical). (3E,6E)-alpha-Farnesene is one of the 4 isomers of Alpha-farnesene and is the most common isomer, Trans-trans-alpha-Farnesene is a hydrophobic, neutral molecule that is not water soluble. It has a woody, bergamot, green and citrus like aroma and a fresh, green, fruity taste. Trans-trans-alpha-Farnesene is used as a flavoring and perfuming agent. It is found in the coating of apples, and other fruits, and it is responsible for the characteristic green apple odour (doi:10.1038/2101260a0). (3E,6E)-alpha-Farnesene is found within a few different foods, such as gingers, cottonseeds, common oregano and sweet oranges. (3E,6E)-alpha-Farnesene has also been detected, but not quantified in, several different foods, such as apples, pears, spearmints, guava, and carrots. Trans-trans-alpha-farnesene is one of several sesquiterpenes that are found in cannabis plants (PMID: 6991645 ). It is also found in cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Weight204.35
Monoisotopic Molecular Weight204.1878
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:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9300000000-3317cba9629f9379052f2015-03-01View Spectrum
Predicted GC-MStrans-trans-alpha-Farnesene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0673-9800000000-2417bd57042b291e594eSpectrum
Predicted GC-MStrans-trans-alpha-Farnesene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MStrans-trans-alpha-Farnesene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-3690000000-313b913d532cd4decec12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pw9-9710000000-078e5a8d7e85822b7c0c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9100000000-3d3f85f913cafb612d5c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-6d4cdcd69849df029e452016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-e363a25bab51e774a5922016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kg9-4900000000-b4cda282a594b52f25392016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0190000000-fa0c676eabe0c49e322b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0390000000-0d353a60a5a97cd9c1a32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-4900000000-9f5bab6c0c653c72230e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-060s-7910000000-05be940f3488abb12fe82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7l-9300000000-a54209dd2c1271d1d7d72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ru-9000000000-a7b8e3b259690a16a4412021-09-22View Spectrum
NMR
TypeDescriptionView
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Bile acid receptorNR1H412q23.1Q96RI1 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Bile acid receptorNR1H412q23.1Q96RI1 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Bile acid receptorNR1H412q23.1Q96RI1 details
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Bile acid receptorNR1H412q23.1Q96RI1 details
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien Dawg (Indica dominant)Detected and Quantified4.22 +/- 0.27 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine Dream (Sativa dominant)Detected and Quantified3.57 +/- 0.17 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0036065
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. [PubMed:19932496 ]
  3. Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. [PubMed:17710406 ]

Enzymes

Enzyme Details
1. Bile acid receptor
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxylase gene (CYP7A1) through the induction of NR0B2 or FGF19 expression, via two distinct mechanisms. Activates the intestinal bile acid-binding protein (IBABP). Activates the transcription of bile salt export pump ABCB11 by directly recruiting histone methyltransferase CARM1 to this locus
Gene Name:
NR1H4
Uniprot ID:
Q96RI1
Molecular weight:
55913.9