Structure Database (LMSD)
Common Name
Squalene
Systematic Name
Squalene
Synonyms
3D model of Squalene
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Level 4 Class
Biological Context
Squalene is a biosynthetic precursor to all steroids and a terpene originally isolated from shark liver oil.1,2 Squalene is produced in mammals by condensation of two farnesyl diphosphate molecules by squalene synthase and then oxidized to squalene epoxide for use in the biosynthesis of lanosterol , cholesterol, and other steroids.1 An oil-in-water emulsion of squalene synergistically increases adaptive immune responses to glucopyranosyl lipid adjuvant (GLA), a toll-like receptor 4 (TLR4) agonist, compared with an aqueous formulation of GLA.3 Formulations containing squalene have been used as adjuvants in vaccines and as hair and skin conditioning agents.
This information has been provided by Cayman Chemical
References
3. Kubota, B. The chemical composition of squalene. Tokyo Kagaku Kaishi 39, 879-907 (1918).
Reactions
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Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
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String Representations
InChiKey (Click to copy)
YYGNTYWPHWGJRM-AAJYLUCBSA-N
InChi (Click to copy)
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+
SMILES (Click to copy)
C(C)(CCC=C(C)C)=CCC/C(/C)=C/CCC=C(C)CCC=C(C)CCC=C(C)C
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
30
Rings
0
Aromatic Rings
0
Rotatable Bonds
15
Van der Waals Molecular Volume
511.72
Topological Polar Surface Area
0.00
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
0
logP
10.60
Molar Refractivity
140.06
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Created at
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Updated at
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