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
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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 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.

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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
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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.

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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
References
1. Deliyanti D, Zhang Y, Khong F, Berka DR, Stapleton DI, Kelly DJ, Wilkinson-Berka JL. (2015)
FT011, a Novel Cardiorenal Protective Drug, Reduces Inflammation, Gliosis and Vascular Injury in Rats with Diabetic Retinopathy.
PLoS One, 10 (7): e0134392. [PMID:26222724]
2. Gilbert RE, Zhang Y, Williams SJ, Zammit SC, Stapleton DI, Cox AJ, Krum H, Langham R, Kelly DJ. (2012)
A purpose-synthesised anti-fibrotic agent attenuates experimental kidney diseases in the rat.
PLoS One, 7 (10): e47160. [PMID:23071743]
3. Lau X, Zhang Y, Kelly DJ, Stapleton DI. (2013)
Attenuation of Armanni-Ebstein lesions in a rat model of diabetes by a new anti-fibrotic, anti-inflammatory agent, FT011.
Diabetologia, 56 (3): 675-9. [PMID:23242170]
4. Miller T, Papaioannou N. (2019)
Anti-fibrotic compounds.
Patent number: WO2018144620A9. Assignee: Shire Human Genetic Therapies, Inc.. Priority date: 31/01/2018. Publication date: 24/01/2019.
5. Zammit SC, Cox AJ, Gow RM, Zhang Y, Gilbert RE, Krum H, Kelly DJ, Williams SJ. (2009)
Evaluation and optimization of antifibrotic activity of cinnamoyl anthranilates.
Bioorg Med Chem Lett, 19 (24): 7003-6. [PMID:19879136]
6. Zhang Y, Edgley AJ, Cox AJ, Powell AK, Wang B, Kompa AR, Stapleton DI, Zammit SC, Williams SJ, Krum H et al.. (2012)
FT011, a new anti-fibrotic drug, attenuates fibrosis and chronic heart failure in experimental diabetic cardiomyopathy.
Eur J Heart Fail, 14 (5): 549-62. [PMID:22417655]