beta-Sitosterol

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Ligands
beta-Sitosterol

GtoPdb Ligand ID: 13860

Synonyms: β-Sitosterol | azuprostat | clionasterol

Compound class: Natural product

Comment: Beta-Sitosterol is a phytosterol. It has been detected in plants including Solanum trilobatum, Sambucus chinensis and Erythrophleum fordii. Direct interaction with the farnesoid X receptor (FXR) has been determined by molecular docking, and confirmed by FXR activation in a luciferase reporter assay [2]. This action mediates a protective effect against hepatotoxicity and cholestasis in vivo.

2D Structure

Physico-chemical Properties

Hydrogen bond acceptors	1
Hydrogen bond donors	1
Rotatable bonds	6
Topological polar surface area	20.23
Molecular weight	414.71
XLogP	11.6
No. Lipinski's rules broken	1

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

Canonical SMILES	CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O)C(C)C
Isomeric SMILES	CC[C@H](CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)C(C)C
InChI	InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1
InChI Key	KZJWDPNRJALLNS-VJSFXXLFSA-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/)