sorafenib   Click here for help

GtoPdb Ligand ID: 5711

Synonyms: BAY 43-9006 | BAY-439006 | Nexavar®
Approved drug PDB Ligand
sorafenib is an approved drug (FDA (2005), EMA (2006))
Compound class: Synthetic organic
Comment: Sorafenib is a broad spectrum Type-2 kinase inhibitor targeting VEGFR2, VEGFR3, PDGFRβ, Flt3, and KIT and non-receptor kinases RAF1 and BRAF [8].
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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

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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 3
Rotatable bonds 9
Topological polar surface area 92.35
Molecular weight 464.09
XLogP 3.75
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 CNC(=O)c1nccc(c1)Oc1ccc(cc1)NC(=O)Nc1ccc(c(c1)C(F)(F)F)Cl
Isomeric SMILES CNC(=O)c1nccc(c1)Oc1ccc(cc1)NC(=O)Nc1ccc(c(c1)C(F)(F)F)Cl
InChI InChI=1S/C21H16ClF3N4O3/c1-26-19(30)18-11-15(8-9-27-18)32-14-5-2-12(3-6-14)28-20(31)29-13-4-7-17(22)16(10-13)21(23,24)25/h2-11H,1H3,(H,26,30)(H2,28,29,31)
InChI Key MLDQJTXFUGDVEO-UHFFFAOYSA-N
Bioactivity Comments
Sorafenib significantly inhibits neovascularization in xenograft models of human colon, breast, and non-small-cell lung cancer [8].
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
cyclin dependent kinase 8 Hs Inhibitor Inhibition 7.0 pKd - 2
⤷ pKd 7.0 (Kd 9.96x10-8 M) [2]
Description: CDK8/cyclin C.
cyclin dependent kinase 19 Hs Inhibitor Inhibition 7.0 pKd - 2
⤷ pKd 7.0 (Kd 1.03x10-7 M) [2]
Description: CDK19/cyclin C.
TNNI3 interacting kinase Hs Inhibitor Binding 6.6 pKd - 4,6
⤷ pKd 6.6 (Kd 2.8x10-7 M) [4,6]
Raf-1 proto-oncogene, serine/threonine kinase Hs Inhibitor Inhibition 8.2 pIC50 - 8
⤷ pIC50 8.2 (IC50 6x10-9 M) [8]
B-Raf proto-oncogene, serine/threonine kinase Hs Inhibitor Inhibition 7.7 pIC50 - 8
⤷ pIC50 7.7 (IC50 2.2x10-8 M) [8]
Selectivity at catalytic receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
kinase insert domain receptor Primary target of this compound Hs Inhibitor Inhibition 7.2 pKd - 3
⤷ pKd 7.2 (Kd 5.9x10-8 M) [3]
discoidin domain receptor tyrosine kinase 2 Hs Inhibitor Inhibition 8.0 pIC50 - 7
⤷ pIC50 8.0 (IC50 1x10-8 M) [7]
ret proto-oncogene Hs Inhibitor Inhibition 7.9 pIC50 - 7
⤷ pIC50 7.9 (IC50 1.4x10-8 M) [7]
fms related receptor tyrosine kinase 4 Mm Inhibitor Inhibition 7.7 pIC50 - 8
⤷ pIC50 7.7 (IC50 2x10-8 M) [8]
fms related receptor tyrosine kinase 3 Primary target of this compound Hs Inhibitor Inhibition 7.2 – 7.5 pIC50 - 8,10
⤷ pIC50 7.5 (IC50 3.3x10-8 M) [10]
pIC50 7.2 (IC50 5.8x10-8 M) [8]
platelet derived growth factor receptor beta Hs Inhibitor Inhibition 7.2 pIC50 - 10
⤷ pIC50 7.2 (IC50 5.7x10-8 M) [10]
platelet derived growth factor receptor beta Mm Inhibitor Inhibition 7.2 pIC50 - 8
⤷ pIC50 7.2 (IC50 5.7x10-8 M) [8]
KIT proto-oncogene, receptor tyrosine kinase Primary target of this compound Hs Inhibitor Inhibition 7.2 pIC50 - 8,10
⤷ pIC50 7.2 (IC50 6.8x10-8 M) [10]
pIC50 7.2 (IC50 6.8x10-8 M) [8]
kinase insert domain receptor Primary target of this compound Hs Inhibitor Inhibition 7.1 pIC50 - 8,10
⤷ pIC50 7.1 (IC50 9x10-8 M) [8]
pIC50 7.1 (IC50 9x10-8 M) [10]
fibroblast growth factor receptor 1 Hs Inhibitor Inhibition 6.2 pIC50 - 8,10
⤷ pIC50 6.2 (IC50 5.8x10-7 M) [10]
pIC50 6.2 (IC50 5.8x10-7 M) [8]
Ligand mentioned in the following text fields
Type III RTKs: PDGFR, CSFR, Kit, FLT3 receptor family comments