amcasertib   Click here for help

GtoPdb Ligand ID: 9924

Synonyms: BBI-503 | BBI503
Compound class: Synthetic organic
Comment: Amcasertib (BBI503) is a first-in-class, orally active, cancer stemness kinase inhibitor has been developed by Boston Biomedical for potential anticancer activity [1]. by targeting certain kinase enzymes it is reported to inhibit Nanog (NANOG; Q9H9S0) and other signalling pathways that control stem-cell replication, survival and differentiation. To date (April 2018) the only reports of BBI503 mechanism of action and clinical efficacy are in the form of meeting abstracts, and not in peer reviewed articles. Amcasertib is one of the chemical structures claimed in patent US8299106B2 [2], which were discussed as potential PDGFRα inhibitors therein.
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 10
Topological polar surface area 118.36
Molecular weight 539.24
XLogP 5.19
No. Lipinski's rules broken 1

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 CCN(CCNC(=O)c1c(C)[nH]c(c1C)C=C1C(=O)Nc2c1cc(cc2)c1csc(n1)c1ccccc1)CC
Isomeric SMILES CCN(CCNC(=O)c1c(C)[nH]c(c1C)C=C1C(=O)Nc2c1cc(cc2)c1csc(n1)c1ccccc1)CC
InChI InChI=1S/C31H33N5O2S/c1-5-36(6-2)15-14-32-30(38)28-19(3)26(33-20(28)4)17-24-23-16-22(12-13-25(23)34-29(24)37)27-18-39-31(35-27)21-10-8-7-9-11-21/h7-13,16-18,33H,5-6,14-15H2,1-4H3,(H,32,38)(H,34,37)
InChI Key QDWKGEFGLQMDAM-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/)
Download 2D Structure Click here for help
Canonical SMILES Download
Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel