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Identification
NameFarnesol
Accession NumberDB02509  (EXPT01466)
TypeSmall Molecule
GroupsExperimental
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
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number4602-84-0
WeightAverage: 222.3663
Monoisotopic: 222.198365454
Chemical FormulaC15H26O
InChI KeyCRDAMVZIKSXKFV-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassPrenol Lipids
SubclassSesquiterpenes
Direct parentSesquiterpenes
Alternative parentsFatty Alcohols; Polyamines; Primary Alcohols
Substituentspolyamine; primary alcohol; alcohol
Classification descriptionThis compound belongs to the sesquiterpenes. These are terpenes with three consecutive isoprene units.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9846
Blood Brain Barrier + 0.9375
Caco-2 permeable + 0.6445
P-glycoprotein substrate Non-substrate 0.5851
P-glycoprotein inhibitor I Non-inhibitor 0.8865
P-glycoprotein inhibitor II Non-inhibitor 0.5696
Renal organic cation transporter Non-inhibitor 0.8179
CYP450 2C9 substrate Non-substrate 0.791
CYP450 2D6 substrate Non-substrate 0.8278
CYP450 3A4 substrate Non-substrate 0.527
CYP450 1A2 substrate Non-inhibitor 0.9046
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.923
CYP450 2C19 substrate Non-inhibitor 0.9026
CYP450 3A4 substrate Non-inhibitor 0.9088
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.765
Ames test Non AMES toxic 0.9132
Carcinogenicity Non-carcinogens 0.5055
Biodegradation Ready biodegradable 0.8931
Rat acute toxicity 1.6146 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.7838
hERG inhibition (predictor II) Non-inhibitor 0.8377
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point< 25 °CPhysProp
boiling point111 °C at 3.50E-01 mm HgPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0587ALOGPS
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
Spectra
SpectraNot Available
References
Synthesis Reference

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

US20030092144
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC01493
PubChem Compound1549107
PubChem Substance46508260
ChemSpider1266073
BindingDB11021
ChEBI28600
ChEMBL
HETFOH
WikipediaFarnesol
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Amine oxidase [flavin-containing] B

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Amine oxidase [flavin-containing] B P27338 Details

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

Enzymes

1. Amine oxidase [flavin-containing] B

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Amine oxidase [flavin-containing] B P27338 Details
Comments
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:18