bezisterim

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Ligands
bezisterim

GtoPdb Ligand ID: 13988

Synonyms: 17-ethynyl-5-androstene-3,7,17-triol | HE-3286 | HE3286 | NE-3107 | NE3107

Compound class: Synthetic organic

Comment: Bezisterim (NE3107 and formerly HE3286) is a synthetic, orally bioavailable analogue of the adrenal sterol metabolite androstenetriol. It can cross the blood-brain barrier. It has proposed anti-inflammatory and insulin-sensitising activities, which may be beneficial in treating the pathophysiology or symptom development in degenerative brain diseases such as Parkinson's and Alzheimer's, which are associated with chronic low-grade inflammation. The molecular target(s) of bezisterim are not fully resolved. Its anti-inflammatory and insulin-sensitising biological activities likely include modulation of pathways and networks that involve LDL receptor related protein 1 (Lrp1), Mapk3 (ERK1) and Mapk1 (ERK2) [8].

2D Structure

Physico-chemical Properties

Hydrogen bond acceptors	3
Hydrogen bond donors	3
Rotatable bonds	0
Topological polar surface area	60.69
Molecular weight	330.46
XLogP	2.06
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

Canonical SMILES	C#C[C@@]1(CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]4(C)CC[C@@H](CC4=C[C@@H]3O)O)O
Isomeric SMILES	C[C@]12CC[C@@H](CC1=C[C@@H]([C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C#C)O)C)O)O
InChI	InChI=1S/C21H30O3/c1-4-21(24)10-7-16-18-15(6-9-20(16,21)3)19(2)8-5-14(22)11-13(19)12-17(18)23/h1,12,14-18,22-24H,5-11H2,2-3H3/t14-,15-,16-,17-,18+,19-,20-,21-/m0/s1
InChI Key	JJKOQZHWYLMASZ-FJWDNACWSA-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/)