lunresertib   Click here for help

GtoPdb Ligand ID: 13211

Synonyms: (Rac)-RP-6306
PDB Ligand
Compound class: Synthetic organic
Comment: Lunresertib (RP-6306) is the first lead candidate in the class of protein kinase, membrane associated tyrosine/threonine 1 (PKMYT1) inhibitors to be advanced for clinical evaluation [3]. It is orally bioavailable and selective for PKMYT1, and it is active in appropriate preclinical xenograft models of solid tumours [1]. PKMYT1 is a negative regulator of CDK1 [2], and its inhibition induces activation of CDK1 selectively in CCNE1-overexpressing cells; CCNE1 being a chromosome 19q12 locus that is amplified in multiple tumour types and which is a marker of poor prognosis and/or insensitivity to cytotoxic oncotherapies. As a monotherapy lunresertib induces synthetic lethality in combination with CCNE1 amplification (or alongside inactivating mutations in FBXW7 and PPP2R1A).

Structure note: the INN record for lunresertib does not specify the (S) stereo specification that is declared in the original disclosure of RP-6306's chemical structure [3]. We depict the racaemic mixture with no defined stereo centers.

lunresertib 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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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 3
Rotatable bonds 2
Topological polar surface area 104.94
Molecular weight 324.38
XLogP 1.05
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 CC1=CC=C(C(=C1N2C(=C(C3=C2N=C(C)C(=C3)C)C(=O)N)N)C)O
Isomeric SMILES CC1=C(C(=C(C=C1)O)C)N2C(=C(C3=C2N=C(C(=C3)C)C)C(=O)N)N
InChI InChI=1S/C18H20N4O2/c1-8-5-6-13(23)10(3)15(8)22-16(19)14(17(20)24)12-7-9(2)11(4)21-18(12)22/h5-7,23H,19H2,1-4H3,(H2,20,24)
InChI Key ARBRHWRTXPWZGN-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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
2-amino-1-(3-hydroxy-2,6-dimethylphenyl)-5,6-dimethylpyrrolo[2,3-b]pyridine-3-carboxamide
International Nonproprietary Names Click here for help
INN number INN
13035 lunresertib
Synonyms Click here for help
(Rac)-RP-6306
Database Links Click here for help
BindingDB Ligand 50598851
CAS Registry No. 2719793-90-3 (source: WHO INN record)
ChEMBL Ligand CHEMBL5199076
GtoPdb PubChem SID 491299993
PubChem CID 156869388
RCSB PDB Ligand QGI
Search Google for chemical match using the InChIKey ARBRHWRTXPWZGN-UHFFFAOYSA-N
Search Google for chemicals with the same backbone ARBRHWRTXPWZGN
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UniChem Compound Search for chemical match using the InChIKey ARBRHWRTXPWZGN-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey ARBRHWRTXPWZGN-UHFFFAOYSA-N

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MedChemExpress
lunresertib (links to external site)
Cat. No. HY-145817A
(Rac)-lunresertib (links to external site)
Cat. No. HY-145817
(R)-lunresertib (links to external site)
Cat. No. HY-145817B