Squalene
Star0
This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Squalene
- DrugBank Accession Number
- DB11460
- Background
Squalene is originally obtained from shark liver oil. It is a natural 30-carbon isoprenoid compound and intermediate metabolite in the synthesis of cholesterol. It is not susceptible to lipid peroxidation and provides skin protection. It is ubiquitously distributed in human tissues where it is transported in serum generally in association with very low density lipoproteins. Squalene is investigated as an adjunctive cancer therapy.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
- Weight
- Average: 410.73
Monoisotopic: 410.39125161 - Chemical Formula
- C30H50
- Synonyms
- (all-E)-2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaene
- (E,E,E,E)-Squalene
- Spinacene
- Squalene
- Supraene
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.- Associated Conditions
- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Not Available
- Mechanism of action
- Not Available
- 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. View sample adverse effects data in our new Data Library!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
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Mixture Products
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Prenol lipids
- Sub Class
- Triterpenoids
- Direct Parent
- Triterpenoids
- Alternative Parents
- Branched unsaturated hydrocarbons / Unsaturated aliphatic hydrocarbons / Acyclic olefins
- Substituents
- Acyclic olefin / Aliphatic acyclic compound / Branched unsaturated hydrocarbon / Hydrocarbon / Olefin / Triterpenoid / Unsaturated aliphatic hydrocarbon / Unsaturated hydrocarbon
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- triterpene (CHEBI:15440) / Acyclic triterpenoids, Liner triterpenes (C00751) / Acyclic triterpenoids (LMPR0106010002)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 7QWM220FJH
- CAS number
- 111-02-4
- InChI Key
- YYGNTYWPHWGJRM-AAJYLUCBSA-N
- InChI
- InChI=1S/C30H50/c1-25(2)15-11-19-29(7)23-13-21-27(5)17-9-10-18-28(6)22-14-24-30(8)20-12-16-26(3)4/h15-18,23-24H,9-14,19-22H2,1-8H3/b27-17+,28-18+,29-23+,30-24+
- IUPAC Name
- (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
- SMILES
- CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)C
References
- General References
- Popjak G, Agnew WS: Squalene synthetase. Mol Cell Biochem. 1979 Oct 15;27(2):97-116. [Article]
- VILLALBA GOMEZ GM: [Squalene index]. Rev Sanid Asist Soc. 1956 May-Aug;21(3-4):155-69. [Article]
- Sato R, Hirano Y, Shimizu M: [Squalene synthase]. Nihon Rinsho. 2001 Feb;59 Suppl 2:161-6. [Article]
- Agnew WS: Squalene synthetase. Methods Enzymol. 1985;110:359-73. [Article]
- Smith TJ: Squalene: potential chemopreventive agent. Expert Opin Investig Drugs. 2000 Aug;9(8):1841-8. [Article]
- FLESCH P: Hair loss from squalene. Proc Soc Exp Biol Med. 1951 Apr;76(4):801-3. [Article]
- LANGDON RG, BLOCH K: The biosynthesis of squalene. J Biol Chem. 1953 Jan;200(1):129-34. [Article]
- Molbak K: [Squalene unlikely sinner]. Ugeskr Laeger. 2013 May 13;175(20):1444. [Article]
- Authors unspecified: SQUALENE, an essential nutrient? Nutr Rev. 1955 Nov;13(11):348-9. [Article]
- Samman N, Ignasiak T, Chen CJ, Strausz OP, Montgomery DS: Squalene in petroleum asphaltenes. Science. 1981 Sep 18;213(4514):1381-3. [Article]
- Kanter JL, Narayana S, Ho PP, Catz I, Warren KG, Sobel RA, Steinman L, Robinson WH: Lipid microarrays identify key mediators of autoimmune brain inflammation. Nat Med. 2006 Jan;12(1):138-43. Epub 2005 Dec 11. [Article]
- de Jong A, Cheng TY, Huang S, Gras S, Birkinshaw RW, Kasmar AG, Van Rhijn I, Pena-Cruz V, Ruan DT, Altman JD, Rossjohn J, Moody DB: CD1a-autoreactive T cells recognize natural skin oils that function as headless antigens. Nat Immunol. 2014 Feb;15(2):177-85. doi: 10.1038/ni.2790. Epub 2013 Dec 22. [Article]
- Kelly GS: Squalene and its potential clinical uses. Altern Med Rev. 1999 Feb;4(1):29-36. [Article]
- External Links
- KEGG Compound
- C00751
- PubChem Compound
- 638072
- PubChem Substance
- 347827980
- ChemSpider
- 553635
- 10014
- ChEBI
- 15440
- ChEMBL
- CHEMBL458402
- ZINC
- ZINC000006845904
- PDBe Ligand
- SQL
- Wikipedia
- Squalene
- PDB Entries
- 3wqj / 4fbz / 4md1 / 4md2 / 4omk / 7wwd / 7z0e
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Emulsion Intramuscular Injection, suspension Intramuscular Capsule, liquid filled Oral Capsule Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.000502 mg/mL ALOGPS logP 8.64 ALOGPS logP 10.42 Chemaxon logS -5.9 ALOGPS Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 0 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 0 Å2 Chemaxon Rotatable Bond Count 15 Chemaxon Refractivity 144.62 m3·mol-1 Chemaxon Polarizability 56.17 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key GC-MS Spectrum - GC-MS GC-MS splash10-001i-9600000000-280b7ccaed0215f0937c Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available GC-MS Spectrum - EI-B GC-MS splash10-015i-9500000000-63fc959bf17e2f6e0381 Mass Spectrum (Electron Ionization) MS splash10-0159-9610000000-aaf0145da95343082ae1 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 13C NMR Spectrum 1D NMR Not Applicable
Drug created at February 25, 2016 18:56 / Updated at June 07, 2022 22:57