olafertinib   Click here for help

GtoPdb Ligand ID: 9863

Synonyms: CK101 | CK‐101 | Example 153 [US20170050936A1] | RX-518 | RX518
Compound class: Synthetic organic
Comment: Olafertinib (CK‐101) is an orally available third-generation, selective inhibitor of epidermal growth factor receptor (EGFR) harbouring activating mutations (e.g. the resistance mutation T790M, the L858R mutation and the exon 19 deletion (del 19) mutation). It is an irreversible (covalent binding) inhibitor with minimal activity towards the wild type EGFR. The chemical structure is claimed as Example 153 in patent US20170050936A1 [2].
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 8
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 93.62
Molecular weight 530.22
XLogP 4.09
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 OCCN1CCN(CC1)c1ccc(c(c1F)F)Nc1ncc2c(n1)c(ccc2)c1cccc(c1)NC(=O)C=C
Isomeric SMILES OCCN1CCN(CC1)c1ccc(c(c1F)F)Nc1ncc2c(n1)c(ccc2)c1cccc(c1)NC(=O)C=C
InChI InChI=1S/C29H28F2N6O2/c1-2-25(39)33-21-7-3-5-19(17-21)22-8-4-6-20-18-32-29(35-28(20)22)34-23-9-10-24(27(31)26(23)30)37-13-11-36(12-14-37)15-16-38/h2-10,17-18,38H,1,11-16H2,(H,33,39)(H,32,34,35)
InChI Key IDRGFNPZDVBSSE-UHFFFAOYSA-N
References
1. FDA. 
N-(3-(2-(2,3-difluoro-4-(4-(2-hydroxyethyl)piperazin-1-yl)phenylamino)quinazolin-8-yl)phenyl)acrylamide.
Accessed on 22/03/2018. Modified on 22/03/2018. FDA Orphan Drug Designations and Approvals, https://www.accessdata.fda.gov/scripts/opdlisting/oopd/detailedIndex.cfm?cfgridkey=599817
2. Qian X, Zhu Y-L. (2017)
Certain chemical entities, compositions, and methods.
Patent number: US20170050936A1. Assignee: NeuPharma Inc.. Priority date: 23/08/2013. Publication date: 23/02/2017.