Cannabis Compound Database: Showing Compound Card for trans-trans-alpha-Farnesene (CDB000311)

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Record Information

Version

1.0

Created at

2020-03-19 00:30:18 UTC

Updated at

2020-12-07 19:07:21 UTC

CannabisDB ID

CDB000311

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

trans-trans-alpha-Farnesene

Description

Trans-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. Œ±-Farnesene and Œ≤-Farnesene are isomers, differing by the location of one double bond. Œ≤-Farnesene is 7,11-dimethyl-3-methylene-1,6,10-dodecatriene while¬†Œ±-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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(3E,6E)-alpha-Farnesene	ChEBI
(3E,6E)-a-Farnesene	Generator
(3E,6E)-Α-farnesene	Generator
a-Farnesene	Generator
Α-farnesene	Generator
(E,E)-Farnesene	HMDB
trans-Farnesene	HMDB
3,7,11-Trimethyl-(E,E)-1,3,6,10-dodecatetraene	HMDB
alpha-trans,trans-Farnesene	HMDB
trans,trans-alpha-Farnesene	HMDB
alpha-Farnesene	MeSH
(3E,6E)-3,7,11-Trimethyl-1,3,6,10-dodecatetraene	HMDB
(E,E)-alpha-Farnesene	HMDB
(E,E)-α-Farnesene	HMDB
3,7,11-Trimethyl-1,3,6,10-dodecatetraene	HMDB
Farnesene	HMDB
trans,trans-α-Farnesene	HMDB
trans-2,6,10-Trimethyl-2,6,9,11-dodecatetraene	HMDB
trans-3,7,11-Trimethyl-1,3,6,10-dodecatetraene	HMDB
trans-alpha-Farnesene	HMDB
trans-α-Farnesene	HMDB

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.35

Monoisotopic Molecular Weight

204.1878

IUPAC Name

(3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene

Traditional Name

farnesene

CAS Registry Number

502-61-4

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 Key

CXENHBSYCFFKJS-VDQVFBMKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Alkatetraene
Branched unsaturated hydrocarbon
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Acyclic olefin
Hydrocarbon
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha-farnesene (CHEBI:10280 )
Farnesenes (C09665 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Extracellular

Subcellular:

Biofluid and excreta:

Feces

Role

Industrial application:

Personal care products:

Perfuming agent

Food and nutrition:

Flavoring agent

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.7	ALOGPS
logP	5.14	ChemAxon
logS	-4.6	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	73.25 m³·mol⁻¹	ChemAxon
Polarizability	26.86 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0006-9300000000-3317cba9629f9379052f	2015-03-01	View Spectrum
Predicted GC-MS	trans-trans-alpha-Farnesene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0673-9800000000-2417bd57042b291e594e	Spectrum
Predicted GC-MS	trans-trans-alpha-Farnesene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	trans-trans-alpha-Farnesene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-3690000000-313b913d532cd4decec1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pw9-9710000000-078e5a8d7e85822b7c0c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxr-9100000000-3d3f85f913cafb612d5c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-6d4cdcd69849df029e45	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0190000000-e363a25bab51e774a592	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kg9-4900000000-b4cda282a594b52f2539	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0190000000-fa0c676eabe0c49e322b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0390000000-0d353a60a5a97cd9c1a3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-4900000000-9f5bab6c0c653c72230e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-060s-7910000000-05be940f3488abb12fe8	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a7l-9300000000-a54209dd2c1271d1d7d7	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05ru-9000000000-a7b8e3b259690a16a441	2021-09-22	View Spectrum

NMR

Type	Description		View

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Bile acid receptor	NR1H4	12q23.1	Q96RI1	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Bile acid receptor	NR1H4	12q23.1	Q96RI1	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Bile acid receptor	NR1H4	12q23.1	Q96RI1	details
Taste receptor type 1 member 3	TAS1R3	1p36.33	Q7RTX0	details
Taste receptor type 1 member 2	TAS1R2	1p36.13	Q8TE23	details

Transcriptional Factors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Bile acid receptor	NR1H4	12q23.1	Q96RI1	details

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg (Indica dominant)	Detected and Quantified	4.22 +/- 0.27 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream (Sativa dominant)	Detected and Quantified	3.57 +/- 0.17 mg/g dry wt	David S. Wishart,...	details

External Links

HMDB ID

HMDB0036065

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Farnesene

METLIN ID

Not Available

PubChem Compound

5281516

PDB ID

Not Available

ChEBI ID

10280

References

General References

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 ]
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 ]
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

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

Structure for CDB000311 (trans-trans-alpha-Farnesene)

Enzymes