Identification

Name
Farnesol
Accession Number
DB02509  (EXPT01466)
Type
Small Molecule
Groups
Experimental
Description

A colorless liquid extracted from oils of plants such as citronella, neroli, cyclamen, and tuberose. It is an intermediate step in the biological synthesis of cholesterol from mevalonic acid in vertebrates. It has a delicate odor and is used in perfumery. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)

Structure
Thumb
Synonyms
Not Available
External IDs
FEMA NO. 2478, (2Z,6Z)-
Categories
UNII
J03523NK03
CAS number
4602-84-0
Weight
Average: 222.3663
Monoisotopic: 222.198365454
Chemical Formula
C15H26O
InChI Key
CRDAMVZIKSXKFV-FBXUGWQNSA-N
InChI
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-
IUPAC Name
(2Z,6Z)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
SMILES
CC(C)=CCC\C(C)=C/CC\C(C)=C/CO

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAmine oxidase [flavin-containing] BNot AvailableHuman
UBile acid receptor
agonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

James Millis, "Production of farnesol and geranylgeraniol." U.S. Patent US20030092144, issued May 15, 2003.

US20030092144
General References
Not Available
External Links
KEGG Compound
C01493
PubChem Compound
1549107
PubChem Substance
46508260
ChemSpider
1266073
BindingDB
11021
ChEBI
42680
HET
FOH
Wikipedia
Farnesol
PDB Entries
1dgp / 2bk3 / 6eiz

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)< 25 °CPhysProp
boiling point (°C)111 °C at 3.50E-01 mm HgPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0587 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity74.98 m3·mol-1ChemAxon
Polarizability28.64 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9846
Blood Brain Barrier+0.9375
Caco-2 permeable+0.6445
P-glycoprotein substrateNon-substrate0.5851
P-glycoprotein inhibitor INon-inhibitor0.8865
P-glycoprotein inhibitor IINon-inhibitor0.5696
Renal organic cation transporterNon-inhibitor0.8179
CYP450 2C9 substrateNon-substrate0.791
CYP450 2D6 substrateNon-substrate0.8278
CYP450 3A4 substrateNon-substrate0.527
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9088
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.765
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.5055
BiodegradationReady biodegradable0.8931
Rat acute toxicity1.6146 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7838
hERG inhibition (predictor II)Non-inhibitor0.8377
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-052f-4900000000-1d9e975ae620e9a1e160
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-052f-4900000000-0a9f94e6e357cca02a89
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-052f-3900000000-75812c077a7a432c9c88
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound 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
Fatty alcohols / Primary alcohols / Hydrocarbon derivatives
Substituents
Farsesane sesquiterpenoid / Sesquiterpenoid / Fatty alcohol / Fatty acyl / Organic oxygen compound / Hydrocarbon derivative / Primary alcohol / Organooxygen compound / Alcohol / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
farnesol (CHEBI:42680) / Acyclic farnesane sesquiterpenoids (LMPR0103010008)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Primary amine oxidase activity
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Zinc ion binding
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-hydroxyla...
Gene Name
NR1H4
Uniprot ID
Q96RI1
Uniprot Name
Bile acid receptor
Molecular Weight
55913.915 Da
References
  1. Downie MM, Sanders DA, Maier LM, Stock DM, Kealey T: Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro. Br J Dermatol. 2004 Oct;151(4):766-75. [PubMed:15491415]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Primary amine oxidase activity
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da

Drug created on June 13, 2005 07:24 / Updated on October 01, 2018 13:20