GLPG4716   Click here for help

GtoPdb Ligand ID: 11617

Synonyms: compound 9 [PMID: 33078933]
PDB Ligand
Compound class: Synthetic organic
Comment: GLPG4716 (formerly OATD-01) is a first-in-class, orally bioavailable inhibitor of the chitinase enzymes chitinase 1 (chitotriosidase; CHIT1) and AMCase (chitinase acidic; CHIA) [1]. Galapagos have in-licensed the rights to develop this compound from OncoArendi/Molecure. GLPG4716 was developed as a treatment for respiratory diseases, having demonstrated efficacy in in vivo models of asthma and pulmonary fibrosis, and sarcoidosis. In mid-2022 the Galapagos/Molecure partnership was terminated and all rights for OATD-01 were returned to Molecure.
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Ligand Activity Visualisation Charts

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View interactive charts of activity data across species
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 4
Topological polar surface area 83.3
Molecular weight 390.19
XLogP 4.53
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[C@@H]1OC[C@@H](N(C1)C1CCN(CC1)c1nnc([nH]1)N)Cc1ccc(cc1)Cl
Isomeric SMILES C[C@@H]1OC[C@@H](N(C1)C1CCN(CC1)c1nnc([nH]1)N)Cc1ccc(cc1)Cl
InChI InChI=1S/C19H27ClN6O/c1-13-11-26(17(12-27-13)10-14-2-4-15(20)5-3-14)16-6-8-25(9-7-16)19-22-18(21)23-24-19/h2-5,13,16-17H,6-12H2,1H3,(H3,21,22,23,24)/t13-,17-/m0/s1
InChI Key STWVLEKJQQRGMO-GUYCJALGSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
3-[4-[(2S,5S)-5-[(4-chlorophenyl)methyl]-2-methylmorpholin-4-yl]piperidin-1-yl]-1H-1,2,4-triazol-5-amine
Synonyms Click here for help
compound 9 [PMID: 33078933]
Database Links Click here for help
GtoPdb PubChem SID 442878651
PubChem CID 126642132
RCSB PDB Ligand QGB
Search Google for chemical match using the InChIKey STWVLEKJQQRGMO-GUYCJALGSA-N
Search Google for chemicals with the same backbone STWVLEKJQQRGMO
UniChem Compound Search for chemical match using the InChIKey STWVLEKJQQRGMO-GUYCJALGSA-N
UniChem Connectivity Search for chemical match using the InChIKey STWVLEKJQQRGMO-GUYCJALGSA-N