enexasogaol   Click here for help

GtoPdb Ligand ID: 9773

Synonyms: 6-Shogaol | [6]-shogaol | trans-6-shogaol
Immunopharmacology Ligand
Compound class: Natural product
Comment: Enexasogaol (6-Shogaol) is a bioactive phytochemical isolated from ginger (Zingiber officinale Roscoe). It has anti-inflammatory, analgesic and antioxidant properties [2-3,5-6].

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 46.53
Molecular weight 276.17
XLogP 4.11
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCCCCC=CC(=O)CCc1ccc(c(c1)OC)O
Isomeric SMILES CCCCC/C=C/C(=O)CCc1ccc(c(c1)OC)O
InChI InChI=1S/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3/b8-7+
InChI Key OQWKEEOHDMUXEO-BQYQJAHWSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Bioactivity Comments
As the PPAR-γ antagonist GW9662 can prevent 6-shogaol-induced inhibition of inflammatory mediator production, it is suggested that 6-shogaol may activate PPAR-γ [3]. Modulation of sodium channels has also been postulated as a mechanism of action [4]. In relation to amyloidogenesis, 6-shogaol is reported to upregulate the expression of Sortilin-related receptor 1 (SORL1), which in turn increases β-secretase APP cleaving enzyme (BACE), secreted APP-β and Aβ both in vitro (HT22 cells) and in vivo (transgenic mouse model of Alzheimer's disease) [1].