alofanib   Click here for help

GtoPdb Ligand ID: 11622

Synonyms: RPT-835 | RPT835
Compound class: Synthetic organic
Comment: Alofanib (RPT835) is an allosteric inhibitor of the receptor tyrosine kinase, fibroblast growth factor receptor 2 (FGFR2) [1-4]. It inhibits phosphorylation of FGF receptor substrate 2α (FRS2α), but does not block FGF2-FGFR2 binding. Alofanib inhibits angiogenesis and was developed for antitumour potential.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

alofanib 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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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 6
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 147.88
Molecular weight 413.07
XLogP 4.21
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 [O-][N+](=O)c1cc(C)c(cc1NS(=O)(=O)c1cccc(c1)C(=O)O)c1cccnc1
Isomeric SMILES [O-][N+](=O)c1cc(C)c(cc1NS(=O)(=O)c1cccc(c1)C(=O)O)c1cccnc1
InChI InChI=1S/C19H15N3O6S/c1-12-8-18(22(25)26)17(10-16(12)14-5-3-7-20-11-14)21-29(27,28)15-6-2-4-13(9-15)19(23)24/h2-11,21H,1H3,(H,23,24)
InChI Key QUQGQIASFYWKAB-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. Khochenkov DA, Solomko ES, Peretolchina NM, Ryabaya OO, Stepanova EV. (2015)
Antiangiogenic Activity of Alofanib, an Allosteric Inhibitor of Fibroblast Growth Factor Receptor 2.
Bull Exp Biol Med, 160 (1): 84-7. [PMID:26597690]
2. Tsimafeyeu I, Daeyaert F, Joos JB, Aken KV, Ludes-Meyers J, Byakhov M, Tjulandin S. (2016)
Molecular Modeling, de novo Design and Synthesis of a Novel, Extracellular Binding Fibroblast Growth Factor Receptor 2 Inhibitor Alofanib (RPT835).
Med Chem, 12 (4): 303-17. [PMID:26732115]
3. Tsimafeyeu I, Ludes-Meyers J, Stepanova E, Daeyaert F, Khochenkov D, Joose JB, Solomko E, Van Akene K, Peretolchina N, Yin W et al.. (2016)
Targeting FGFR2 with alofanib (RPT835) shows potent activity in tumour models.
Eur J Cancer, 61: 20-8. [PMID:27136102]
4. Tyulyandina A, Harrison D, Yin W, Stepanova E, Kochenkov D, Solomko E, Peretolchina N, Daeyaert F, Joos JB, Van Aken K et al.. (2017)
Alofanib, an allosteric FGFR2 inhibitor, has potent effects on ovarian cancer growth in preclinical studies.
Invest New Drugs, 35 (2): 127-133. [PMID:27812884]