dapolsertib   Click here for help

GtoPdb Ligand ID: 13204

Synonyms: Example 26A [WO2014096388] | MEN1703 | SEL-24 | SEL24
Compound class: Synthetic organic
Comment: The chemical structure for dapolsertib was obtained from proposed INN list 130 (Feb. 2024). This matched to clinical lead SEL-24 (MEN1703) via PubChem, and to compound 26A in patent WO2014096388 [1]. The compound is proposed as dual pan-PIM/FLT3 kinase inhibitor for the treatment of acute myeloid leukemia.
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 3
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 70.77
Molecular weight 446.14
XLogP 3.73
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 CC(C)N1C2=CC(=C(C(=C2N=C1C3CCNCC3)[N+](=O)[O-])Br)Br
Isomeric SMILES CC(C)N1C2=CC(=C(C(=C2N=C1C3CCNCC3)[N+](=O)[O-])Br)Br
InChI InChI=1S/C15H18Br2N4O2/c1-8(2)20-11-7-10(16)12(17)14(21(22)23)13(11)19-15(20)9-3-5-18-6-4-9/h7-9,18H,3-6H2,1-2H3
InChI Key UOUBCIJIWDLRGM-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
5,6-dibromo-4-nitro-2-piperidin-4-yl-1-propan-2-ylbenzimidazole
International Nonproprietary Names Click here for help
INN number INN
12910 dapolsertib
Synonyms Click here for help
Example 26A [WO2014096388] | MEN1703 | SEL-24 | SEL24
Database Links Click here for help
CAS Registry No. 1616359-00-2 (source: WHO INN record)
ChEMBL Ligand CHEMBL4467168
GtoPdb PubChem SID 491299986
PubChem CID 76286825
Search Google for chemical match using the InChIKey UOUBCIJIWDLRGM-UHFFFAOYSA-N
Search Google for chemicals with the same backbone UOUBCIJIWDLRGM
Search PubMed clinical trials dapolsertib
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UniChem Compound Search for chemical match using the InChIKey UOUBCIJIWDLRGM-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey UOUBCIJIWDLRGM-UHFFFAOYSA-N