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bezisterim   Click here for help

GtoPdb Ligand ID: 13988

Synonyms: 17-ethynyl-5-androstene-3,7,17-triol | HE-3286 | HE3286 | NE-3107 | NE3107
Immunopharmacology Ligand
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
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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 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
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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 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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(3S,7R,8R,9S,10R,13S,14S,17R)-17-ethynyl-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,7,17-triol
International Nonproprietary Names Click here for help
INN number INN
12493 bezisterim
Synonyms Click here for help
17-ethynyl-5-androstene-3,7,17-triol | HE-3286 | HE3286 | NE-3107 | NE3107
Database Links Click here for help
ChEMBL Ligand CHEMBL4297284
DrugBank Ligand DB05212
GtoPdb PubChem SID 518520615
PubChem CID 16739648
Search Google for chemical match using the InChIKey JJKOQZHWYLMASZ-FJWDNACWSA-N
Search Google for chemicals with the same backbone JJKOQZHWYLMASZ
Search PubMed clinical trials bezisterim
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Search PubMed titles/abstracts bezisterim
UniChem Compound Search for chemical match using the InChIKey JJKOQZHWYLMASZ-FJWDNACWSA-N
UniChem Connectivity Search for chemical match using the InChIKey JJKOQZHWYLMASZ-FJWDNACWSA-N