icerguastat   Click here for help

GtoPdb Ligand ID: 13263

Synonyms: IFB-088 | IFB088 | Sephin-1 | Sephin1
Compound class: Synthetic organic
Comment: Icerguastat (IFB-088, Sephin1) selectively inhibits the regulatory subunit PPP1R15A within the PPP1R15A/PP1c phosphatase complex [2]. Inhibiting PPP1R15A results in reduced dephosphorylation of the translation initiation factor eIF2α, which rescues cells from proteostasis collapse. Structurally icerguastat is a guanabenz derivative but it has no α2-adrenerceptor agonist activity. Icerguastat is designed to maintain an active integrated stress response as a cytoprotective mechanism to combat the toxic effects of cellular stress [1].

icerguastat is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 76.76
Molecular weight 196.64
XLogP 1.47
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
Click here for help

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/)

✖
Canonical SMILES C1=CC(=C(C=C1)Cl)/C=N/N=C(N)N
Isomeric SMILES C1=CC=C(C(=C1)/C=N/N=C(N)N)Cl
InChI InChI=1S/C8H9ClN4/c9-7-4-2-1-3-6(7)5-12-13-8(10)11/h1-5H,(H4,10,11,13)/b12-5+
InChI Key PDWJALXSRRSUHR-LFYBBSHMSA-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/)
Download 2D Structure Click here for help
Canonical SMILES Download
Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel