firmonertinib   Click here for help

GtoPdb Ligand ID: 10477

Synonyms: alflutinib (pseudo INN) | ASK120067 | AST-2818 | AST2818 | example 3 [US10072002B2] | furmonertinib | Ivesa®
Approved drug
firmonertinib is an approved drug (China (2021))
Compound class: Synthetic organic
Comment: Firmonertinib (AST2818; formerly furmonertinib) is a receptor tyrosine kinase inhibitor that targets mutant forms of the EGFR more effectively than the wild type receptor kinase, with notable potency vs. the T790M resistance mutation. Firmonertinib is the formal WHO INN. It has an irreversible binding mode. AST2818's chemical structure is claimed as example 3 in Shanghai Allist Pharmaceuticals' patent US10072002B2 [2]. Note that AST2818 is administered clinically as the mesylate.
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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Click here for structure editor
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 2
Rotatable bonds 13
Topological polar surface area 100.44
Molecular weight 568.25
XLogP 5.22
No. Lipinski's rules broken 2

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)Nc1cc(Nc2nccc(n2)c2cn(c3c2cccc3)C)c(nc1N(CCN(C)C)C)OCC(F)(F)F
Isomeric SMILES C=CC(=O)Nc1cc(Nc2nccc(n2)c2cn(c3c2cccc3)C)c(nc1N(CCN(C)C)C)OCC(F)(F)F
InChI InChI=1S/C28H31F3N8O2/c1-6-24(40)33-21-15-22(26(41-17-28(29,30)31)36-25(21)38(4)14-13-37(2)3)35-27-32-12-11-20(34-27)19-16-39(5)23-10-8-7-9-18(19)23/h6-12,15-16H,1,13-14,17H2,2-5H3,(H,33,40)(H,32,34,35)
InChI Key GHKOONMJXNWOIW-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
Approved drug? Yes (China (2021))
IUPAC Name Click here for help
N-[2-[2-(dimethylamino)ethyl-methylamino]-5-[[4-(1-methylindol-3-yl)pyrimidin-2-yl]amino]-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]prop-2-enamide
Synonyms Click here for help
alflutinib (pseudo INN) | ASK120067 | AST-2818 | AST2818 | example 3 [US10072002B2] | furmonertinib | Ivesa®
Database Links Click here for help
CAS Registry No. 1869057-83-9 (source: WHO INN record)
ChEMBL Ligand CHEMBL4297258
GtoPdb PubChem SID 385612236
PubChem CID 118861389
Search Google for chemical match using the InChIKey GHKOONMJXNWOIW-UHFFFAOYSA-N
Search Google for chemicals with the same backbone GHKOONMJXNWOIW
UniChem Compound Search for chemical match using the InChIKey GHKOONMJXNWOIW-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey GHKOONMJXNWOIW-UHFFFAOYSA-N