simotinib   Click here for help

GtoPdb Ligand ID: 7640

Synonyms: AL 6802 | AL6802 | SIM 6802 | SIM6802
Approved drug
simotinib is an approved drug (China only)
Compound class: Synthetic organic
Comment: Simotinib is an oral, epidermal growth factor receptor tyrosine kinase inhibitor [1]. It was developed by Jiangsu Simcere Pharmaceutical Research Company in Nanjing, China. See also patent WO2010021918A1. Simotinib treatment is associated with serious adverse effects on gastrointestinal physiology [2].

simotinib is commercially available from our sponsors

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 1
Rotatable bonds 7
Topological polar surface area 77.97
Molecular weight 500.16
XLogP 3.3
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 COc1cc2ncnc(c2cc1OCCN1CC2(C3(C1)CC3)OCCO2)Nc1ccc(c(c1)Cl)F
Isomeric SMILES COc1cc2ncnc(c2cc1OCCN1CC2(C3(C1)CC3)OCCO2)Nc1ccc(c(c1)Cl)F
InChI InChI=1S/C25H26ClFN4O4/c1-32-21-12-20-17(23(29-15-28-20)30-16-2-3-19(27)18(26)10-16)11-22(21)33-7-6-31-13-24(4-5-24)25(14-31)34-8-9-35-25/h2-3,10-12,15H,4-9,13-14H2,1H3,(H,28,29,30)
InChI Key OXWUWXCJDBRCCG-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 (0)
IUPAC Name Click here for help
N-(3-chloro-4-fluorophenyl)-6-[2-(5,8-dioxa-10-azadispiro[2.0.4^{4}.3^{3}]undecan-10-yl)ethoxy]-7-methoxyquinazolin-4-amine
Synonyms Click here for help
AL 6802 | AL6802 | SIM 6802 | SIM6802
Database Links Click here for help
CAS Registry No. 944258-89-3 (source: Scifinder)
GtoPdb PubChem SID 223365975
PubChem CID 16735117
Search Google for chemical match using the InChIKey OXWUWXCJDBRCCG-UHFFFAOYSA-N
Search Google for chemicals with the same backbone OXWUWXCJDBRCCG
UniChem Compound Search for chemical match using the InChIKey OXWUWXCJDBRCCG-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey OXWUWXCJDBRCCG-UHFFFAOYSA-N

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MedChemExpress
Simotinib (links to external site)
Cat. No. HY-101820