gunagratinib   Click here for help

GtoPdb Ligand ID: 11669

Synonyms: ICP-192 | ICP192
Compound class: Synthetic organic
Comment: The chemical structure for gunagratinib was obtained from WHO Proposed list 125. It mapped to PubChem CID 138734912, and from a web search it was identified as ICP-192, which is an irreversible pan-FGFR (fibroblast growth factor receptors) inhibitor that was developed by InnoCare Pharma for antitumuor potential (especially for tumours with FGF/FGFR gene aberrations). When we generated this ligand entry in August 2021, there was no published/peer reviewed report of ICP-192's pharmacology or biological activity. Phase 1 results were reported in a meeting abstract from the 2021 annual meeting of the American Society of Clinical Oncology DOI: 10.1200/JCO.2021.39.15_suppl.4092.

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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 6
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 111.71
Molecular weight 423.19
XLogP 2.44
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 C=CC(=O)N1CC[C@@H](C1)n1nc(c(c1NC)C(=O)N)C#Cc1cc(OC)cc(c1)OC
Isomeric SMILES CNc1c(c(nn1[C@H]1CCN(C1)C(=O)C=C)C#Cc1cc(cc(c1)OC)OC)C(=O)N
InChI InChI=1S/C22H25N5O4/c1-5-19(28)26-9-8-15(13-26)27-22(24-2)20(21(23)29)18(25-27)7-6-14-10-16(30-3)12-17(11-14)31-4/h5,10-12,15,24H,1,8-9,13H2,2-4H3,(H2,23,29)/t15-/m0/s1
InChI Key QFUIJOBJAQBGDH-HNNXBMFYSA-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
3-[2-(3,5-dimethoxyphenyl)ethynyl]-5-(methylamino)-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide
International Nonproprietary Names Click here for help
INN number INN
11714 gunagratinib
Synonyms Click here for help
ICP-192 | ICP192
Database Links Click here for help
CAS Registry No. 2211082-53-8 (source: WHO INN record)
GtoPdb PubChem SID 442878695
PubChem CID 138734912
Search Google for chemical match using the InChIKey QFUIJOBJAQBGDH-HNNXBMFYSA-N
Search Google for chemicals with the same backbone QFUIJOBJAQBGDH
Search PubMed clinical trials gunagratinib
Search PubMed titles gunagratinib
Search PubMed titles/abstracts gunagratinib
UniChem Compound Search for chemical match using the InChIKey QFUIJOBJAQBGDH-HNNXBMFYSA-N
UniChem Connectivity Search for chemical match using the InChIKey QFUIJOBJAQBGDH-HNNXBMFYSA-N

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MedChemExpress
Gunagratinib (links to external site)
Cat. No. HY-132817