Identification
- Generic Name
- Farnesol
- DrugBank Accession Number
- DB02509
- Background
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)
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Farnesol (DB02509)
- Weight
- Average: 222.3663
Monoisotopic: 222.198365454 - Chemical Formula
- C15H26O
- Synonyms
- Not Available
- External IDs
- FEMA NO. 2478, (2Z,6Z)-
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UBile acid receptor agonistHumans UAmine oxidase [flavin-containing] B Not Available Humans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Alcohol / Aliphatic acyclic compound / Farsesane sesquiterpenoid / Fatty acyl / Fatty alcohol / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Primary alcohol / Sesquiterpenoid
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- farnesol (CHEBI:42680) / Acyclic farnesane sesquiterpenoids (LMPR0103010008)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- J03523NK03
- CAS number
- 4602-84-0
- 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
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
- PDB Entries
- 1dgp / 6dew
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) < 25 °C PhysProp boiling point (°C) 111 °C at 3.50E-01 mm Hg PhysProp - Predicted Properties
Property Value Source Water Solubility 0.0587 mg/mL ALOGPS logP 4.84 ALOGPS logP 4.16 ChemAxon logS -3.6 ALOGPS pKa (Strongest Acidic) 16.33 ChemAxon pKa (Strongest Basic) -2.2 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 20.23 Å2 ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 74.98 m3·mol-1 ChemAxon Polarizability 28.64 Å3 ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - 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 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available GC-MS Spectrum - GC-EI-TOF GC-MS splash10-052f-4900000000-1d9e975ae620e9a1e160 GC-MS Spectrum - GC-EI-TOF GC-MS splash10-052f-4900000000-0a9f94e6e357cca02a89 GC-MS Spectrum - GC-EI-TOF GC-MS splash10-052f-3900000000-75812c077a7a432c9c88 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- Khalil AA, Davies B, Castagnoli N Jr: Isolation and characterization of a monoamine oxidase B selective inhibitor from tobacco smoke. Bioorg Med Chem. 2006 May 15;14(10):3392-8. doi: 10.1016/j.bmc.2005.12.057. Epub 2006 Feb 3. [Article]
- Sari Y, Khalil A: Monoamine Oxidase Inhibitors Extracted from Tobacco Smoke as Neuroprotective Factors for Potential Treatment of Parkinson's Disease. CNS Neurol Disord Drug Targets. 2015;14(6):777-85. [Article]
Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:17