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APT-101   Click here for help

GtoPdb Ligand ID: 14335

Synonyms: APT101 | compound 423 [WO2017100558A1] | compound 52 [PMID: 35594649]
Compound class: Synthetic organic
Comment: APT-101 (APIE Therapeutics) is an orally bioavailable small molecule that acts as an apelin receptor (APLNR; APJ) agonist [2]. It activates the apelin/apelin receptor pathway to trigger the repair of pulmonary vascular endothelial cell breakdown that drives damage in fibrotic and sclerotic lung diseases [3,5-8].
We obtained the IUPAC descriptor for the molecule from the FDA Orphan Drug register. This chemical structure was first claimed in a patent series from RTI International [4], and is a structure match for compound 52 in [2].
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 7
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 85.24
Molecular weight 542.54
XLogP 4.32
No. Lipinski's rules broken 1

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 C1CCC(C1)N2C(=CC(=N2)C(=O)N[C@@H](CCN3CCCC(C3)(F)F)CC(=O)O)C4=C(C=CC=C4)C(F)(F)F
Isomeric SMILES C1(CCCC1)N2N=C(C=C2C3=C(C=CC=C3)C(F)(F)F)C(=O)N[C@H](CC(=O)O)CCN4CC(CCC4)(F)F
InChI InChI=1S/C26H31F5N4O3/c27-25(28)11-5-12-34(16-25)13-10-17(14-23(36)37)32-24(38)21-15-22(35(33-21)18-6-1-2-7-18)19-8-3-4-9-20(19)26(29,30)31/h3-4,8-9,15,17-18H,1-2,5-7,10-14,16H2,(H,32,38)(H,36,37)/t17-/m0/s1
InChI Key HSTYVOXQTWCRDM-KRWDZBQOSA-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
(S)-3-(1-Cyclopentyl-5-(2-(trifluoromethyl)phenyl)-1H-pyrazole-3-carboxamido)-5-(3,3-difluoropiperidin-1-yl)pentanoic acid
Synonyms Click here for help
APT101 | compound 423 [WO2017100558A1] | compound 52 [PMID: 35594649]
Database Links Click here for help
CAS Registry No. 2100848-01-7 (source: PubChem)
PubChem CID 129226407
Search Google for chemical match using the InChIKey HSTYVOXQTWCRDM-KRWDZBQOSA-N
Search Google for chemicals with the same backbone HSTYVOXQTWCRDM
UniChem Compound Search for chemical match using the InChIKey HSTYVOXQTWCRDM-KRWDZBQOSA-N
UniChem Connectivity Search for chemical match using the InChIKey HSTYVOXQTWCRDM-KRWDZBQOSA-N