Showing Compound Card for (z)-beta-Farnesen (CDB000310)

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Record Information
Version1.0
Created at2020-03-19 00:30:16 UTC
Updated at2020-12-07 19:07:21 UTC
CannabisDB IDCDB000310
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(z)-beta-Farnesen
Descriptionβ-Farnesene, also known as (Z)-β-farnesene or β-cis-farnesene, belongs to the class of organic compounds known as sesquiterpenoids. These 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-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. β-Farnesene is 7,11-dimethyl-3-methylene-1,6,10-dodecatriene. beta-Farnesene exists as two stereoisomers about the geometry of its central double bond. β-Farnesene has one naturally occurring isomer. The E isomer is a constituent of various essential oils. It is also released by aphids as an alarm pheremone upon death to warn away other aphids. Several plants, including potato species, have been shown to emit this terpenoid as a natural insect repellent. β-Farnesene is a sweet, citrus, and green tasting compound. β-Farnesene has been detected as a volatile component in cannabis plant samples and essential oils (PMID: 6991645 ; PMID: 26657499 ). 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
(6Z)-7,11-Dimethyl-3-methylene-1,6,10-dodecatrieneChEBI
(Z)-beta-FarneseneChEBI
beta-(Z)-FarneseneChEBI
beta-cis-FarneseneChEBI
(Z)-b-FarneseneGenerator
(Z)-Β-farneseneGenerator
b-(Z)-FarneseneGenerator
Β-(Z)-farneseneGenerator
b-cis-FarneseneGenerator
Β-cis-farneseneGenerator
b-FarneseneGenerator
Β-farneseneGenerator
7,11-Dimethyl-3-methylene-1,6,10-dodecatrieneHMDB
cis-b-FarneseneGenerator
cis-Β-farneseneGenerator
beta-FarneseneMeSH
Chemical FormulaC15H24
Average Molecular Weight204.35
Monoisotopic Molecular Weight204.1878
IUPAC Name(6Z)-7,11-dimethyl-3-methylidenedodeca-1,6,10-triene
Traditional Name(Z)-β-farnesene
CAS Registry Number28973-97-9
SMILES
CC(C)=CCC\C(C)=C/CCC(=C)C=C
InChI Identifier
InChI=1S/C15H24/c1-6-14(4)10-8-12-15(5)11-7-9-13(2)3/h6,9,12H,1,4,7-8,10-11H2,2-3,5H3/b15-12-
InChI KeyJSNRRGGBADWTMC-QINSGFPZSA-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
logP5.2ChemAxon
logS-4.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity72.18 m³·mol⁻¹ChemAxon
Polarizability26.75 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)splash10-00kf-9200000000-8fe9965c757993a3da3c2015-03-01View Spectrum
Predicted GC-MS(z)-beta-Farnesen, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06dr-9800000000-0cf1a88b3286d23cfee8Spectrum
Predicted GC-MS(z)-beta-Farnesen, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2590000000-97aec58a39dbd95191c22016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0api-9820000000-5cfce39fed14f59cb32c2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9100000000-b58552bbf4bf6991f2392016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-8679dd3e5f4e50a4cded2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-6ebdcd800d0f42496ce22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kg9-4900000000-74d9a26b7a0e990038eb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0290000000-452458c093084cfa46782021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00mn-5900000000-43455a50f927d4e736852021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-060s-9710000000-994d4c690288900708592021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7l-9300000000-4a11eb2cdd00336af5af2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lgl-9100000000-0525b6ed5a080a68463b2021-09-25View 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
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Bile acid receptorNR1H412q23.1Q96RI1 details
Concentrations Data
Not Available
HMDB IDHMDB0035913
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014702
KNApSAcK IDC00029350
Chemspider ID4476201
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFarnesene
METLIN IDNot Available
PubChem Compound5317319
PDB IDNot Available
ChEBI ID39242
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 ]
  4. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

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