fosifidancitinib   Click here for help

GtoPdb Ligand ID: 10637

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Fosifidancitinib is a Janus kinase (JAK) inhibitor that is claimed in Rigel Pharmaceuticals' patent WO2010085684A1 [1]. Strictly I-538 refers to the sodium salt but we represent the parent molecule in this entry. The chemical structure that was submitted to the WHO for the INN fosifidancitinib matches the structure of example I-538 (minus the sodium). Rigel declare two JAK inhibitor programmes on their pipeline webpage; one in partnership with Aclaris Therapeutics (ATI-501/ATI-502, oral and topical formulations respectively) for dermatological applications, and the second in partnership with AstraZeneca through which AZD0449 (R256) is being investigated as an inhalation asthma therapeutic. None of these investigational agents have published name to structure declarations.
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 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.

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Hydrogen bond acceptors 8
Hydrogen bond donors 4
Rotatable bonds 8
Topological polar surface area 170.78
Molecular weight 505.12
XLogP 1.45
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
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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.

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/)

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Canonical SMILES COc1cc(Nc2ncc(c(n2)Nc2ccc3c(c2)n(COP(=O)(O)O)c(=O)o3)C)cc(c1F)C
Isomeric SMILES COc1cc(Nc2ncc(c(n2)Nc2ccc3c(c2)n(COP(=O)(O)O)c(=O)o3)C)cc(c1F)C
InChI InChI=1S/C21H21FN5O7P/c1-11-6-14(8-17(32-3)18(11)22)25-20-23-9-12(2)19(26-20)24-13-4-5-16-15(7-13)27(21(28)34-16)10-33-35(29,30)31/h4-9H,10H2,1-3H3,(H2,29,30,31)(H2,23,24,25,26)
InChI Key JTUBTEKGIDQZMZ-UHFFFAOYSA-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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
[5-[[2-(4-fluoro-3-methoxy-5-methylanilino)-5-methylpyrimidin-4-yl]amino]-2-oxo-1,3-benzoxazol-3-yl]methyl dihydrogen phosphate
International Nonproprietary Names Click here for help
INN number INN
11231 fosifidancitinib
Database Links Click here for help
CAS Registry No. 1237168-58-9 (source: WHO INN record)
GtoPdb PubChem SID 404859084
PubChem CID 58071385
Search Google for chemical match using the InChIKey JTUBTEKGIDQZMZ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone JTUBTEKGIDQZMZ
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UniChem Compound Search for chemical match using the InChIKey JTUBTEKGIDQZMZ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey JTUBTEKGIDQZMZ-UHFFFAOYSA-N