Showing Compound Card for Farnesol (CDB006149)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (3) Show 6 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:21:46 UTC
Updated at2020-12-07 19:06:55 UTC
CannabisDB IDCDB006149
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameFarnesol
DescriptionFarnesol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive (5-carbon) isoprene units. Thus, farnesol is considered to be an isoprenoid lipid molecule. Farnesol pyrophosphate (formed by the reaction of geranyl pyrophosphate reacts with isopentenyl pyrophosphate) is the building block of all acyclic sesquiterpenes. Two sesquiterpenes are paired to form squalene (a 30-carbon terpenoid), which is the precursor for all steroids in plants, animals, and fungi. Farnesol is a very hydrophobic molecule, practically insoluble in water but miscible with oil. Under standard conditions, it is a colorless liquid. Farnesol is present in many essential oils such as citronella, neroli, cyclamen, lemon grass, tuberose, rose, musk, balsam and tolu. It is widely used in perfumery to emphasize the odors of sweet floral perfumes. In addition to being a perfuming agent, farnesol is a natural pesticide for mites and is a pheromone for several other insects. It also exhibits anti-microbial activity. In fact, farnesol is used as a deodorant in cosmetic products because of its anti-bacterial activity (PMID: 18492144 ). Farnesol has also been shown to function as a chemopreventative and anti-tumor agent through the inhibition of phosphatidylcholine biosynthesis, the induction of apoptosis, inhibition of cell cycle progression and actin cytoskeletal disorganization (PMID: 19520495 ). These actions appear to be mediated through farnesol’s regulation/inhibition of 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) reductase and CTP:phosphocholine cytidylyltransferase alpha (CCTalpha). HMG-CoA is the rate-limiting enzyme in the mevalonate pathway and CCTalpha is the rate limiting enzyme in phosphatidylcholine biosynthesis (PMID: 19520495 ). Farnesol has also been shown to activate the farnesoid receptor (FXR), a nuclear receptor that forms a functional heterodimer with RXR (Retinoic X receptor). The physiological ligand for FXR remains to be identified; farnesol, may simply mimic the unidentified natural ligand(s). A possible metabolic fate for farnesol is its conversion to farnesoic acid, and then to farnesol-derived dicarboxylic acids (FDDCAs), which would then be excreted in the urine. Farnesol can also be oxidized to a prenyl aldehyde, presumably by mitochondrial or peroxisomal alcohol dehydrogenases (ADH). Liver endoplasmic reticulum and peroxisomal fractions are able to phosphorylate farnesol to farnesyl diphosphate in a cytosine triphosphate (CTP) dependent fashion. (PMID: 9812197 , 8636420 , 9083051 , 9015362 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2-cis,6-cis)-3,7,11-Trimethyldodeca-2,6,10-trien-1-olChEBI
(Z,Z)-FarnesolChEBI
cis,cis-FarnesolChEBI
FARNESOLChEBI
Chemical FormulaC15H26O
Average Molecular Weight222.37
Monoisotopic Molecular Weight222.1984
IUPAC Name(2Z,6Z)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
Traditional Name(Z,Z)-farnesol
CAS Registry Number16106-95-9
SMILES
CC(C)=CCC\C(C)=C/CC\C(C)=C/CO
InChI Identifier
InChI=1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3/b14-9-,15-11-
InChI KeyCRDAMVZIKSXKFV-FBXUGWQNSA-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
  • Fatty alcohol
  • Fatty acyl
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point283 - 284.00 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.84ALOGPS
logP4.16ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)16.33ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity74.98 m³·mol⁻¹ChemAxon
Polarizability28.64 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSFarnesol, non-derivatized, GC-MS Spectrumsplash10-052f-4900000000-1d9e975ae620e9a1e160Spectrum
GC-MSFarnesol, non-derivatized, GC-MS Spectrumsplash10-052f-4900000000-0a9f94e6e357cca02a89Spectrum
GC-MSFarnesol, non-derivatized, GC-MS Spectrumsplash10-052f-3900000000-75812c077a7a432c9c88Spectrum
Predicted GC-MSFarnesol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4u-9830000000-5e08d59a4cc2e87c9984Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-1590000000-88a1356fe7cab31719542017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avi-7930000000-81c18181dbd66735216a2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gi0-9400000000-e44ecbea8a96f84abd432017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0390000000-9beef594142e0da5de922017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-1980000000-3b9708ac6185abaf6d962017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05bf-4910000000-a8db2089f5647c8532ad2017-07-26View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Choline-phosphate cytidylyltransferase APCYT1A3q29P49585 details
3-hydroxy-3-methylglutaryl-coenzyme A reductaseHMGCR5q13.3-q14P04035 details
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 IDNot Available
DrugBank IDDB02509
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFarnesol
METLIN IDNot Available
PubChem Compound1549107
PDB IDNot Available
ChEBI ID42680
References
General References
  1. Kromidas L, Perrier E, Flanagan J, Rivero R, Bonnet I: Release of antimicrobial actives from microcapsules by the action of axillary bacteria. Int J Cosmet Sci. 2006 Apr;28(2):103-8. doi: 10.1111/j.1467-2494.2006.00283.x. [PubMed:18492144 ]
  2. Joo JH, Jetten AM: Molecular mechanisms involved in farnesol-induced apoptosis. Cancer Lett. 2010 Jan 28;287(2):123-35. doi: 10.1016/j.canlet.2009.05.015. Epub 2009 Jun 10. [PubMed:19520495 ]
  3. Edwards PA, Ericsson J: Signaling molecules derived from the cholesterol biosynthetic pathway: mechanisms of action and possible roles in human disease. Curr Opin Lipidol. 1998 Oct;9(5):433-40. doi: 10.1097/00041433-199810000-00007. [PubMed:9812197 ]
  4. Roullet JB, Xue H, Chapman J, McDougal P, Roullet CM, McCarron DA: Farnesyl analogues inhibit vasoconstriction in animal and human arteries. J Clin Invest. 1996 May 15;97(10):2384-90. doi: 10.1172/JCI118682. [PubMed:8636420 ]
  5. Bostedor RG, Karkas JD, Arison BH, Bansal VS, Vaidya S, Germershausen JI, Kurtz MM, Bergstrom JD: Farnesol-derived dicarboxylic acids in the urine of animals treated with zaragozic acid A or with farnesol. J Biol Chem. 1997 Apr 4;272(14):9197-203. doi: 10.1074/jbc.272.14.9197. [PubMed:9083051 ]
  6. Westfall D, Aboushadi N, Shackelford JE, Krisans SK: Metabolism of farnesol: phosphorylation of farnesol by rat liver microsomal and peroxisomal fractions. Biochem Biophys Res Commun. 1997 Jan 23;230(3):562-8. doi: 10.1006/bbrc.1996.6014. [PubMed:9015362 ]

Enzymes

Enzyme Details
1. Choline-phosphate cytidylyltransferase A
General function:
Involved in catalytic activity
Specific function:
Controls phosphatidylcholine synthesis.
Gene Name:
PCYT1A
Uniprot ID:
P49585
Molecular weight:
41730.67
Enzyme Details
2. 3-hydroxy-3-methylglutaryl-coenzyme A reductase
General function:
Involved in hydroxymethylglutaryl-CoA reductase (NADPH) activity
Specific function:
Transmembrane glycoprotein that is the rate-limiting enzyme in cholesterol biosynthesis as well as in the biosynthesis of nonsterol isoprenoids that are essential for normal cell function including ubiquinone and geranylgeranyl proteins.
Gene Name:
HMGCR
Uniprot ID:
P04035
Molecular weight:
97475.155
Enzyme Details
3. 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