asengeprast   Click here for help

GtoPdb Ligand ID: 13202

Synonyms: example 27 [WO2018144620] | FT-011 | FT011 | SHP-627
Compound class: Synthetic organic
Comment: Asengeprast is the INN for a G protein-coupled receptor 68 (GPR68) antagonist with anti-inflammatory potential. We obtained the chemical structure and proposed mechanism of action from INN proposed list 130 (released Feb. 2024). This structure matched to clinical lead FT001 via PubChem, which has proposed anti-inflammatory and anti-fibrotic actions that may be of benefit across a range of human diseases [1-3,6]. Asengeprast's structure was claimed in patent WO2018144620 in 2019 [4].
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 CDK toolkit. 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 6
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 84.86
Molecular weight 351.35
XLogP 1.75
No. Lipinski's rules broken 0
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.

✖
Canonical SMILES C#CCOC1=CC=C(/C=C/C(=O)NC2=C(C=CC=C2)C(=O)O)C=C1OC
Isomeric SMILES COC1=C(C=CC(=C1)/C=C/C(=O)NC2=CC=CC=C2C(=O)O)OCC#C
InChI InChI=1S/C20H17NO5/c1-3-12-26-17-10-8-14(13-18(17)25-2)9-11-19(22)21-16-7-5-4-6-15(16)20(23)24/h1,4-11,13H,12H2,2H3,(H,21,22)(H,23,24)/b11-9+
InChI Key UIWZIDIJCUEOMT-PKNBQFBNSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
2-[[(E)-3-(3-methoxy-4-prop-2-ynoxyphenyl)prop-2-enoyl]amino]benzoic acid
International Nonproprietary Names Click here for help
INN number INN
13056 asengeprast
Synonyms Click here for help
example 27 [WO2018144620] | FT-011 | FT011 | SHP-627
Database Links Click here for help
CAS Registry No. 1001288-58-9 (source: WHO INN record)
ChEMBL Ligand CHEMBL1075834
GtoPdb PubChem SID 491299984
PubChem CID 23648966
Search Google for chemical match using the InChIKey UIWZIDIJCUEOMT-PKNBQFBNSA-N
Search Google for chemicals with the same backbone UIWZIDIJCUEOMT
Search PubMed clinical trials asengeprast
Search PubMed titles asengeprast
Search PubMed titles/abstracts asengeprast
UniChem Compound Search for chemical match using the InChIKey UIWZIDIJCUEOMT-PKNBQFBNSA-N
UniChem Connectivity Search for chemical match using the InChIKey UIWZIDIJCUEOMT-PKNBQFBNSA-N