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].
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 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
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 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
References
1. He L, Li S, Xie F, Cheng Z, Ran L, Liu X, Yu P. (2014)
LC-ESI-MS/MS determination of simotinib, a novel epidermal growth factor receptor tyrosine kinase inhibitor: application to a pharmacokinetic study.
J Chromatogr B Analyt Technol Biomed Life Sci, 947-948: 168-72. [PMID:24440798]
2. Zhu Q, Liu Z, Li P, Cheng Z. (2014)
Drug interaction studies reveal that simotinib upregulates intestinal absorption by increasing the paracellular permeability of intestinal epithelial cells.
Drug Metab Pharmacokinet, 29 (4): 317-24. [PMID:24522198]