DBPR112   Click here for help

GtoPdb Ligand ID: 12711

Synonyms: ABT-101 | ABT101 | compound 78 [PMID: 31560541] | DBPR-112
PDB Ligand
Compound class: Synthetic organic
Comment: DBPR112 (a.k.a. ABT-101) is an orally bioavailable, advanced inhibitor of the tyrosine kinase activity of epidermal growth factor receptors, EGFR and EGFR2 (HER2, ERBB2) [1]. It inhibits wild type and L858R/T790M double mutant EGFRs, and has demonstrated improved potency against EGFR and EGFR2 exon 20 insertion mutations compared to osimertinib. DBPR112 was designed for potential to treat advanced non-small cell lung cancer.
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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 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 8
Hydrogen bond donors 3
Rotatable bonds 11
Topological polar surface area 98.55
Molecular weight 533.62
XLogP 1.79
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 CN(C)C/C=C/C(=O)NC1=CC=CC(=C1)C2=C(C3=CC=CC=C3)OC4=C2C(=NC=N4)N[C@H](CO)C5=CC=CC=C5
Isomeric SMILES OC[C@H](C1=CC=CC=C1)NC2=NC=NC3=C2C(C4=CC=CC(NC(/C=C/CN(C)C)=O)=C4)=C(C5=CC=CC=C5)O3
InChI InChI=1S/C32H31N5O3/c1-37(2)18-10-17-27(39)35-25-16-9-15-24(19-25)28-29-31(36-26(20-38)22-11-5-3-6-12-22)33-21-34-32(29)40-30(28)23-13-7-4-8-14-23/h3-17,19,21,26,38H,18,20H2,1-2H3,(H,35,39)(H,33,34,36)/b17-10+/t26-/m1/s1
InChI Key NQAMTZUVRFRJCZ-VMMYIZNOSA-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
(E)-4-(dimethylamino)-N-[3-[4-[[(1S)-2-hydroxy-1-phenylethyl]amino]-6-phenylfuro[2,3-d]pyrimidin-5-yl]phenyl]but-2-enamide
Synonyms Click here for help
ABT-101 | ABT101 | compound 78 [PMID: 31560541] | DBPR-112
Database Links Click here for help
BindingDB Ligand 50530623
CAS Registry No. 1226549-49-0 (source: PubChem)
ChEMBL Ligand CHEMBL4521381
GtoPdb PubChem SID 483123259
PubChem CID 46212971
RCSB PDB Ligand CKO
Search Google for chemical match using the InChIKey NQAMTZUVRFRJCZ-VMMYIZNOSA-N
Search Google for chemicals with the same backbone NQAMTZUVRFRJCZ
UniChem Compound Search for chemical match using the InChIKey NQAMTZUVRFRJCZ-VMMYIZNOSA-N
UniChem Connectivity Search for chemical match using the InChIKey NQAMTZUVRFRJCZ-VMMYIZNOSA-N