obefazimod   Click here for help

GtoPdb Ligand ID: 11698

Synonyms: ABX-464 | ABX464 | MMV1581032 | SPL-464
Compound class: Synthetic organic
Comment: We obtained the chemical structure for obefazimod from WHO Proposed list 125 of July 2021. This mapped to PubChem CID 49846599, with the association to ABX464, a first-in-class, clinical-stage, oral small molecule immunomodulator [2]. ABX464 was originally developed for antiviral potential (associated via ChEMBL to the Medicines for Malaria Venture (MMV) compound MMV1581032), but was redeployed for chronic inflammatory diseases because of its potent anti-inflammatory effects in preclinical testing. ABX464 is reported to bind to the RNA cap-binding complex, which modulates both viral and cellular RNA biogenesis [1].
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 2
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 34.15
Molecular weight 338.04
XLogP 5.85
No. Lipinski's rules broken 1
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 Clc1cccc2c1nc(cc2)Nc1ccc(cc1)OC(F)(F)F
Isomeric SMILES Clc1cccc2ccc(nc12)Nc1ccc(cc1)OC(F)(F)F
InChI InChI=1S/C16H10ClF3N2O/c17-13-3-1-2-10-4-9-14(22-15(10)13)21-11-5-7-12(8-6-11)23-16(18,19)20/h1-9H,(H,21,22)
InChI Key OZOGDCZJYVSUBR-UHFFFAOYSA-N
References
1. Tazi J, Begon-Pescia C, Campos N, Apolit C, Garcel A, Scherrer D. (2021)
Specific and selective induction of miR-124 in immune cells by the quinoline ABX464: a transformative therapy for inflammatory diseases.
Drug Discov Today, 26 (4): 1030-1039. [PMID:33387693]
2. Vautrin A, Manchon L, Garcel A, Campos N, Lapasset L, Laaref AM, Bruno R, Gislard M, Dubois E, Scherrer D et al.. (2019)
Both anti-inflammatory and antiviral properties of novel drug candidate ABX464 are mediated by modulation of RNA splicing.
Sci Rep, 9 (1): 792. [PMID:30692590]
3. Vermeire S, Hébuterne X, Tilg H, De Hertogh G, Gineste P, Steens JM, ABX464 Investigators. (2021)
Induction and Long-term Follow-up With ABX464 for Moderate-to-severe Ulcerative Colitis: Results of Phase IIa Trial.
Gastroenterology, 160 (7): 2595-2598.e3. [PMID:33662385]