ifidancitinib   Click here for help

GtoPdb Ligand ID: 10638

Synonyms: A-301 | ATI-50002 | ATI-502
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: The chemical structure that was submitted to the WHO for the INN ifidancitinib matches one of the that are claimed as Janus kinase (JAK) inhibitors in Rigel Pharmaceuticals' patent WO2012015972A1 [1]. Structurally ifidancitinib is identical to fosifidancitinib (fosifidancitinib) but without the phosphate group. The closest structural match in the patent is example I-221 but this has deuterium iotopes replacing some of the hydrogens on methylanilino group. This compound has been matched to ATI-502 which was developed as a topical agent for dermatological applications.
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 4
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 105.07
Molecular weight 395.14
XLogP 3.11
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 COc1cc(Nc2ncc(c(n2)Nc2ccc3c(c2)[nH]c(=O)o3)C)cc(c1F)C
Isomeric SMILES COc1cc(Nc2ncc(c(n2)Nc2ccc3c(c2)[nH]c(=O)o3)C)cc(c1F)C
InChI InChI=1S/C20H18FN5O3/c1-10-6-13(8-16(28-3)17(10)21)24-19-22-9-11(2)18(26-19)23-12-4-5-15-14(7-12)25-20(27)29-15/h4-9H,1-3H3,(H,25,27)(H2,22,23,24,26)
InChI Key OYFMQDVLFYKOPZ-UHFFFAOYSA-N
References
1. Chen Y, Ding P, Heckrodt TJ, Li H, Mcmurtrie DJ, Singh R, Taylor V, Yen R. (2012)
Compositions and methods for inhibition of the JAK pathway.
Patent number: WO2012015972A1. Assignee: Rigel Pharmaceuticals. Priority date: 28/07/2010. Publication date: 02/02/2012.