Squalene

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Squalene
Accession Number
DB11460
Type
Small Molecule
Groups
Vet approved
Description

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.

Structure
Thumb
Synonyms
  • (all-e)-2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaene
  • Spinacene
  • Supraene
Categories
UNII
7QWM220FJH
CAS number
111-02-4
Weight
Average: 410.73
Monoisotopic: 410.39125161
Chemical Formula
C30H50
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
[H]C(=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])C(=C(/[H])C([H])([H])C([H])([H])C(=C(/[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])\C([H])([H])[H])\C([H])([H])[H]

Pharmacology

Indication
Not Available
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
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

General References
  1. Popjak G, Agnew WS: Squalene synthetase. Mol Cell Biochem. 1979 Oct 15;27(2):97-116. [PubMed:41173]
  2. VILLALBA GOMEZ GM: [Squalene index]. Rev Sanid Asist Soc. 1956 May-Aug;21(3-4):155-69. [PubMed:13379961]
  3. Sato R, Hirano Y, Shimizu M: [Squalene synthase]. Nihon Rinsho. 2001 Feb;59 Suppl 2:161-6. [PubMed:11351567]
  4. Agnew WS: Squalene synthetase. Methods Enzymol. 1985;110:359-73. [PubMed:3894879]
  5. Smith TJ: Squalene: potential chemopreventive agent. Expert Opin Investig Drugs. 2000 Aug;9(8):1841-8. [PubMed:11060781]
  6. FLESCH P: Hair loss from squalene. Proc Soc Exp Biol Med. 1951 Apr;76(4):801-3. [PubMed:14844354]
  7. LANGDON RG, BLOCH K: The biosynthesis of squalene. J Biol Chem. 1953 Jan;200(1):129-34. [PubMed:13034767]
  8. Molbak K: [Squalene unlikely sinner]. Ugeskr Laeger. 2013 May 13;175(20):1444. [PubMed:23833782]
  9. Authors unspecified: SQUALENE, an essential nutrient? Nutr Rev. 1955 Nov;13(11):348-9. [PubMed:13266257]
  10. Samman N, Ignasiak T, Chen CJ, Strausz OP, Montgomery DS: Squalene in petroleum asphaltenes. Science. 1981 Sep 18;213(4514):1381-3. [PubMed:17732574]
  11. 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. [PubMed:16341241]
  12. 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. [PubMed:24362891]
  13. Kelly GS: Squalene and its potential clinical uses. Altern Med Rev. 1999 Feb;4(1):29-36. [PubMed:9988781]
External Links
KEGG Compound
C00751
PubChem Compound
638072
PubChem Substance
347827980
ChemSpider
553635
ChEBI
15440
ChEMBL
CHEMBL458402
HET
SQL
Wikipedia
Squalene
PDB Entries
3wqj / 4fbz / 4md1 / 4md2 / 4omk

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
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000502 mg/mLALOGPS
logP8.64ALOGPS
logP10.42ChemAxon
logS-5.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity144.62 m3·mol-1ChemAxon
Polarizability56.17 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MSGC-MSsplash10-001i-9600000000-280b7ccaed0215f0937c
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-015i-9500000000-63fc959bf17e2f6e0381
Mass Spectrum (Electron Ionization)MSsplash10-0159-9610000000-aaf0145da95343082ae1
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
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

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
Triterpenoid / Branched unsaturated hydrocarbon / Unsaturated aliphatic hydrocarbon / Unsaturated hydrocarbon / Olefin / Acyclic olefin / Hydrocarbon / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
triterpene (CHEBI:15440) / Acyclic triterpenoids, Liner triterpenes (C00751) / Acyclic triterpenoids (LMPR0106010002)

Drug created on February 25, 2016 11:56 / Updated on November 02, 2018 07:10