You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Creation Date2006-08-13 16:33:07 UTC
Update Date2016-02-11 01:06:43 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameFarnesol
DescriptionFarnesol is a signaling molecule that is derived from farnesyl diphosphate, an intermediate in the isoprenoid/cholesterol biosynthetic pathway. Farnesol is a 15 carbon isoprenoid alcohol is the corresponding dephosphorylated form of the isoprenoid farnesyl diphosphate. Farnesol has a potential role in controlling the degradation of 3-hydroxy-3-methylglutaryl coenzyme A (HMGCoA) reductase (EC, NADPH-hydroxymethylglutaryl-CoA reductase). The enzyme is stabilized under conditions of cellular sterol depletion (e.g. statin-treated cells) and rapidly degraded in sterol-loaded cells. In mammalian cells, this enhanced degradation is dependent on the presence of both a sterol and a non-sterol derived from the isoprenoid pathway; farnesol, the dephosphorylated form of farnesyl diphosphate, can function as the non-sterol component. Farnesol has been shown to activate the farnesoid receptor (FXR), a nuclear receptor that forms a functional heterodimer with RXR. Thus, dephosphorylation of farnesyl diphosphate, an intermediate in the cholesterol synthetic pathway, might produce an active ligand for the FXR:RXR heterodimer. The physiological ligand for FXR remains to be identified; farnesol, may simply mimic the unidentified natural ligand(s). In addition, exogenous farnesol have an effect on several other physiological processes, including inhibition of phosphatidylcholine biosynthesis, induction of apoptosis, inhibition of cell cycle progression and actin cytoskeletal disorganization. Farnesol cellular availability is an important determinant of vascular tone in animals and humans, and provides a basis for exploring farnesyl metabolism in humans with compromised vascular function as well as for using farnesyl analogues as regulators of arterial tone in vivo. 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 an alcohol dehydrogenase (ADH), and that this activity resides in the mitochondrial and peroxisomal. Liver Endoplasmic reticulum and peroxisomal fractions are able to phosphorylate farnesol to Farnesyl diphosphate in a Cytosine triphosphate dependent fashion. (PMID: 9812197 , 8636420 , 9083051 , 9015362 ). Prenol is polymerized by dehydration reactions; when there are at least four isoprene units (n in the above formula is greater than or equal to four), the polymer is called a polyprenol. Polyprenols can contain up to 100 isoprene units (n=100) linked end to end with the hydroxyl group (-OH) remaining at the end. These isoprenoid alcohols are also called terpenols These isoprenoid alcohols are important in the acylation of proteins, carotenoids, and fat-soluble vitamins A, E and K. They are also building blocks for plant oils such as farnesol and geraniol. Prenol is also a building block of cholesterol (built from six isoprene units), and thus of all steroids. Prenol has sedative properities, it is probably GABA receptor allosteric modulator.When the isoprene unit attached to the alcohol is saturated, the compound is referred to as a dolichol. Dolichols are important as glycosyl carriers in the synthesis of polysaccharides.(Wikipedia).
Farnesyl alcoholHMDB
Chemical FormulaC15H26O
Average Molecular Weight222.3663
Monoisotopic Molecular Weight222.198365454
IUPAC Name(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
Traditional Name(E)-farnesol
CAS Registry Number4602-84-0
InChI Identifier
Chemical Taxonomy
DescriptionThis compound 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
  • Farsesane sesquiterpenoid
  • Sesquiterpenoid
  • Fatty alcohol
  • Fatty acyl
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
StatusDetected and Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
Experimental Properties
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.059 mg/mLALOGPS
pKa (Strongest Acidic)16.33ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity74.98 m3·mol-1ChemAxon
Polarizability28.7 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-000x-9800000000-0366097ae9a2af6bafceView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-001l-9800000000-eec57a93bb5862e554f1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-000x-8900000000-9c20df8f2d1959c137d7View in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-014l-9200000000-8e5fae6943a545e4bc0bView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
PathwaysNot Available
Normal Concentrations
BloodDetected and Quantified0.25 (0.0-0.5) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB014891
KNApSAcK IDC00003132
Chemspider ID392816
KEGG Compound IDC01126
BiGG IDNot Available
Wikipedia LinkFarnesol
NuGOwiki LinkHMDB04305
Metagene LinkHMDB04305
PubChem Compound445070
PDB IDNot Available
ChEBI ID16619
Synthesis ReferenceImai, Kunio; Marumo, Shingo. Stereochemistry of C-1 hydrogen exchange during 2,3-double bond trans-cis isomerization of farnesol by Helminthosporium sativum. Tetrahedron Letters (1974), (49/50), 4401-4.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Horn TL, Long L, Cwik MJ, Morrissey RL, Kapetanovic IM, McCormick DL: Modulation of hepatic and renal drug metabolizing enzyme activities in rats by subchronic administration of farnesol. Chem Biol Interact. 2005 Apr 15;152(2-3):79-99. [15840382 ]
  2. Hanley K, Wood L, Ng DC, He SS, Lau P, Moser A, Elias PM, Bikle DD, Williams ML, Feingold KR: Cholesterol sulfate stimulates involucrin transcription in keratinocytes by increasing Fra-1, Fra-2, and Jun D. J Lipid Res. 2001 Mar;42(3):390-8. [11254751 ]
  3. DeBarber AE, Bleyle LA, Roullet JB, Koop DR: Omega-hydroxylation of farnesol by mammalian cytochromes p450. Biochim Biophys Acta. 2004 Jun 1;1682(1-3):18-27. [15158752 ]
  4. Saidi S, Luitaud C, Rouabhia M: In vitro synergistic effect of farnesol and human gingival cells against Candida albicans. Yeast. 2006 Jul 15;23(9):673-87. [16845684 ]
  5. Hanley K, Komuves LG, Ng DC, Schoonjans K, He SS, Lau P, Bikle DD, Williams ML, Elias PM, Auwerx J, Feingold KR: Farnesol stimulates differentiation in epidermal keratinocytes via PPARalpha. J Biol Chem. 2000 Apr 14;275(15):11484-91. [10753967 ]
  6. Forman BM, Goode E, Chen J, Oro AE, Bradley DJ, Perlmann T, Noonan DJ, Burka LT, McMorris T, Lamph WW, Evans RM, Weinberger C: Identification of a nuclear receptor that is activated by farnesol metabolites. Cell. 1995 Jun 2;81(5):687-93. [7774010 ]
  7. Staines AG, Sindelar P, Coughtrie MW, Burchell B: Farnesol is glucuronidated in human liver, kidney and intestine in vitro, and is a novel substrate for UGT2B7 and UGT1A1. Biochem J. 2004 Dec 15;384(Pt 3):637-45. [15320866 ]
  8. Fayard E, Schoonjans K, Auwerx J: Xol INXS: role of the liver X and the farnesol X receptors. Curr Opin Lipidol. 2001 Apr;12(2):113-20. [11264982 ]
  9. 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. [8636420 ]
  10. 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. [9812197 ]
  11. 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. [9083051 ]
  12. 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. [9015362 ]


General function:
Involved in oxidoreductase activity
Specific function:
Oxidoreductase with a preference for NAD. Oxidizes all- trans-retinol and 13-cis-retinol to the corresponding aldehydes. Has higher activity towards CRBP-bound retinol than with free retinol. Oxidizes 3-alpha-hydroxysteroids. Oxidizes androstanediol and androsterone to dihydrotestosterone and androstanedione. Can also catalyze the reverse reaction
Gene Name:
Uniprot ID:
Molecular weight: