tovorafenib   Click here for help

GtoPdb Ligand ID: 9977

Synonyms: BIIB024 | example 10Da [US20090036419] | MLN-2480 | MLN2480 | TAK-580 | TAK580
PDB Ligand
Compound class: Synthetic organic
Comment: TAK-580 (MLN2480) is an investigational pan-RAF kinase inhibitor that was developed for anti-tumour potential against solid tumours, including gliomas, and common adult RAF mutant tumours (harbouring BRAF and CRAF fusions and mutations) that metastasise to the brain. It has been optimised for CNS penetration [2]. The chemical structure is claimed as example 10Da in patent US20090036419A1 [1]. Day One Biopharmaceuticals licensed this inhibitor from Sunesis Pharma in 2019, at which point it was re-named DAY101. The chemical structure of TAK-580 is identical to that which was submitted to the WHO for the INN tovorafenib (proposed INN list 126, Jan 2022).
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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
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 9
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 164.02
Molecular weight 505.01
XLogP 1.82
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 CC(c1ncc(s1)C(=O)Nc1ncc(c(c1)C(F)(F)F)Cl)NC(=O)c1ncnc(c1Cl)N
Isomeric SMILES C[C@H](c1ncc(s1)C(=O)Nc1ncc(c(c1)C(F)(F)F)Cl)NC(=O)c1ncnc(c1Cl)N
InChI InChI=1S/C17H12Cl2F3N7O2S/c1-6(28-15(31)12-11(19)13(23)27-5-26-12)16-25-4-9(32-16)14(30)29-10-2-7(17(20,21)22)8(18)3-24-10/h2-6H,1H3,(H,28,31)(H2,23,26,27)(H,24,29,30)/t6-/m1/s1
InChI Key VWMJHAFYPMOMGF-ZCFIWIBFSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(R)-2-(1-(6-amino-5-chloropyrimidine-4-carboxamido)ethyl)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)thiazole-5-carboxamide
International Nonproprietary Names Click here for help
INN number INN
11985 tovorafenib
Synonyms Click here for help
BIIB024 | example 10Da [US20090036419] | MLN-2480 | MLN2480 | TAK-580 | TAK580
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9657539
Reactome Reaction Reactome logo R-HSA-9653108
Other databases
CAS Registry No. 1096708-71-2 (source: PubChem)
ChEMBL Ligand CHEMBL3348923
GtoPdb PubChem SID 374883864
PubChem CID 25161177
RCSB PDB Ligand QOP
Search Google for chemical match using the InChIKey VWMJHAFYPMOMGF-ZCFIWIBFSA-N
Search Google for chemicals with the same backbone VWMJHAFYPMOMGF
Search PubMed clinical trials tovorafenib
Search PubMed titles tovorafenib
Search PubMed titles/abstracts tovorafenib
UniChem Compound Search for chemical match using the InChIKey VWMJHAFYPMOMGF-ZCFIWIBFSA-N
UniChem Connectivity Search for chemical match using the InChIKey VWMJHAFYPMOMGF-ZCFIWIBFSA-N