AKST4290   Click here for help

GtoPdb Ligand ID: 10653

Synonyms: AKST-4290 | ALK-4290 | ALK4290 | Example 11 [WO2012045803A1] | lazucirnon (proposed INN)
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: AKST4290 (formerly known as ALK4290) is a CCR3 antagonist that was developed by Alkahest as a novel oral therapy for wet age-related macular degeneration (AMD). It acts as a modulator of pathologic inflammation by inhibiting the CCR3/eotaxin axis and subsequent eosinophil accumulation. ALK4290 is now being repurposed for Parkinson's disease. The structure that is presented here was obtained from the NIH ChemIDplus chemical information resource, where it is listed as ALK4290. The structure matches example 11 that is claimed in patent WO2012045803A1 which was granted to Boehringer Ingelheim [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 85.85
Molecular weight 511.24
XLogP 2.96
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C([C@H]1CCC(=O)N1C1CCN(CC1)Cc1ccc(c(c1)C)Cl)Nc1nc(C)cc(c1)C(=O)N(C)C
Isomeric SMILES O=C([C@H]1CCC(=O)N1C1CCN(CC1)Cc1ccc(c(c1)C)Cl)Nc1nc(C)cc(c1)C(=O)N(C)C
InChI InChI=1S/C27H34ClN5O3/c1-17-13-19(5-6-22(17)28)16-32-11-9-21(10-12-32)33-23(7-8-25(33)34)26(35)30-24-15-20(14-18(2)29-24)27(36)31(3)4/h5-6,13-15,21,23H,7-12,16H2,1-4H3,(H,29,30,35)/t23-/m1/s1
InChI Key DWKNOLCXIFYNFV-HSZRJFAPSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
2-[[(2R)-1-[1-[(4-chloro-3-methylphenyl)methyl]piperidin-4-yl]-5-oxopyrrolidine-2-carbonyl]amino]-N,N,6-trimethylpyridine-4-carboxamide
Synonyms Click here for help
AKST-4290 | ALK-4290 | ALK4290 | Example 11 [WO2012045803A1] | lazucirnon (proposed INN)
Database Links Click here for help
CAS Registry No. 1251528-23-0 (source: PubChem)
ChEMBL Ligand CHEMBL3670800
GtoPdb PubChem SID 404859100
PubChem CID 59534386
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