fosizensertib   Click here for help

GtoPdb Ligand ID: 13806

Synonyms: compound 19 [WO2023018643A1]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: The chemical structure for fosizensertib was derived from WHO proposed INN list 132 (Feb 2025), in which it is listed as a receptor-interacting serine/threonine protein kinase 1 (RIPK1) inhibitor. This generated a SMILES match via PubChem to a compound (19) claimed in patent WO2023018643A1 (AbbVie) [1]. This appears to be a phosphate prodrug, that is dephosphorylated in vivo, to the active metabolite compound 2. In the absence of formal structure disclosure (March 2025) we hypothesise that this is likely to be the INN for AbbVie's oral ulcerative colitis lead ABBV-668.
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 9
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 124.84
Molecular weight 490.4
XLogP 0.92
No. Lipinski's rules broken 0

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
Click here for help

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/)

✖
Canonical SMILES CN(C[C@H](CC1=CC=CC=C1)OP(=O)(O)O)C(=O)C2=CC(=CN=C2)C#CC3=CN(C(F)F)N=C3
Isomeric SMILES P(=O)(O[C@H](CN(C(=O)C=1C=NC=C(C1)C#CC=2C=NN(C2)C(F)F)C)CC3=CC=CC=C3)(O)O
InChI InChI=1S/C22H21F2N4O5P/c1-27(15-20(33-34(30,31)32)10-16-5-3-2-4-6-16)21(29)19-9-17(11-25-13-19)7-8-18-12-26-28(14-18)22(23)24/h2-6,9,11-14,20,22H,10,15H2,1H3,(H2,30,31,32)/t20-/m0/s1
InChI Key AJSWMXIMACDPCV-FQEVSTJZSA-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/)
References
1. Cusack KP, Hoemann MZ, Kinsman DA, Osman S, Stambuli JP, Argiriadi MA, O'reilly C, Dexter H, Fordyce E, St.Gallay S. (2023)
Nicotinamide ripk1 inhibitors.
Patent number: WO2023018643A1. Assignee: Abbvie Inc.. Priority date: 08/08/2022. Publication date: 16/02/2023.