andamertinib   Click here for help

GtoPdb Ligand ID: 13732

Synonyms: compound 206 [WO2018228446A1] | PLB-1004 | PLB1004
Compound class: Synthetic organic
Comment: The chemical structure for andamertinib was derived from WHO proposed INN list 132 (Feb 2025), in which it is listed as an epidermal growth factor receptor (EGFR) tyrosine kinase inhibitor with antineoplastic potential. This generated a SMILES match via PubChem to a compound (206) that is claimed in patent WO2018228446A1 (Beijing Adamadle Biotechnology) [2]. Information provided in a clinical trials document (NCT06574347) indicates that andamertinib is a synonym for the clinical candidate PLB1004. PLB1004 is disclosed as an irreversible EGFR inhibitor that is designed to target EGFR with Ex20 insertion mutations [1] (this publication confirms the name to structure match). It is claimed that PLB1004 can cross the blood-brain barrier, meaning that it offers potential to reach metastatic lesions in the brain.
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 11
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 106.39
Molecular weight 568.67
XLogP 1.71
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)NC1=C(C=C(C(=C1)NC2=NC=NC(=C2)C3=CC4=C(C=C3)N(C)N=C4)OC)N5CCC(CC5)N6CC(C6)OC
Isomeric SMILES COC1=CC(=C(C=C1NC2=NC=NC(=C2)C=3C=C4C=NN(C4=CC3)C)NC(C=C)=O)N5CCC(CC5)N6CC(C6)OC
InChI InChI=1S/C31H36N8O3/c1-5-31(40)36-25-13-26(29(42-4)15-28(25)38-10-8-22(9-11-38)39-17-23(18-39)41-3)35-30-14-24(32-19-33-30)20-6-7-27-21(12-20)16-34-37(27)2/h5-7,12-16,19,22-23H,1,8-11,17-18H2,2-4H3,(H,36,40)(H,32,33,35)
InChI Key KKPCZGCBAIJCOU-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/)
References
1. Liu D, Li Q, Yan S, Zhang X, Li W, Wang F, Gao L, Geng F, Zhou H, Ye P et al.. (2025)
Pharmacokinetics, mass balance, and metabolism of [14C]PLB1004, a selective and irreversible EGFR-TKI in humans.
Cancer Chemother Pharmacol, 95 (1): 19. [PMID:39776242]
2. Zhang P, Shi H, Lan W, Song Z. (2018)
Aminopyrimidine compound, preparation method therefor and use thereof.
Patent number: WO2018228446A1. Assignee: Beijing Adamadle Biotechnology. Priority date: 13/06/2018. Publication date: 20/12/2018.