rupitasertib   Click here for help

GtoPdb Ligand ID: 12721

Synonyms: M-2698 | M2698 | MSC-2363318A | MSC2363318A
PDB Ligand
Compound class: Synthetic organic
Comment: M2698 is a dual inhibitor of the serine/threonine protein kinases, ribosomal protein S6 Kinase (p70S6K) and Akt (protein kinase B) [1]. It was designed for antitumour potential in cancers with dysregulated PI3K/Akt/mTOR (PAM) pathway signalling. The chemical structure for M2698 matches that of the INN rupitasertib (revealed in proposed INN list 130, Feb. 2024).
Click here for help

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.

✖

View interactive charts of activity data across species
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 83.08
Molecular weight 449.86
XLogP 0.81
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES C1=CC2=C(N=CN=C2C(=C1)C(=O)N)N[C@H](CN3CCC3)C4=CC=C(C(=C4)C(F)(F)F)Cl
Isomeric SMILES O=C(N)C1=CC=CC2=C1N=CN=C2N[C@H](CN3CCC3)C4=CC(C(F)(F)F)=C(Cl)C=C4
InChI InChI=1S/C21H19ClF3N5O/c22-16-6-5-12(9-15(16)21(23,24)25)17(10-30-7-2-8-30)29-20-14-4-1-3-13(19(26)31)18(14)27-11-28-20/h1,3-6,9,11,17H,2,7-8,10H2,(H2,26,31)(H,27,28,29)/t17-/m1/s1
InChI Key HXAUJHZZPCBFPN-QGZVFWFLSA-N
Classification Click here for help
Compound class Synthetic organic
International Nonproprietary Names Click here for help
INN number INN
12871 rupitasertib
Synonyms Click here for help
M-2698 | M2698 | MSC-2363318A | MSC2363318A
Database Links Click here for help
BindingDB Ligand 50574277
CAS Registry No. 1379545-95-5 (source: WHO INN record)
ChEMBL Ligand CHEMBL4871106
DrugBank Ligand DB15431
GtoPdb PubChem SID 483123269
PubChem CID 89808643
RCSB PDB Ligand 1SK
Search Google for chemical match using the InChIKey HXAUJHZZPCBFPN-QGZVFWFLSA-N
Search Google for chemicals with the same backbone HXAUJHZZPCBFPN
Search PubMed clinical trials rupitasertib
Search PubMed titles rupitasertib
Search PubMed titles/abstracts rupitasertib
UniChem Compound Search for chemical match using the InChIKey HXAUJHZZPCBFPN-QGZVFWFLSA-N
UniChem Connectivity Search for chemical match using the InChIKey HXAUJHZZPCBFPN-QGZVFWFLSA-N