asciminib   Click here for help

GtoPdb Ligand ID: 8962

Synonyms: ABL-001 | ABL001 | Example 9 [1]
PDB Ligand
Compound class: Synthetic organic
Comment: Asciminib (ABL001) is a negative allosteric modulator of BCR-ABL1 [1,4,7-8], that induces the kinase to adopt an autoinhibitory, and thereby inactive, conformation [2]. The compound is the result of a structure-guided medicinal chemistry program targeting the vestigial myristoyl pocket of the ABL1 kinase. The acronym STAMP inhibitor is used to descrobe this class of compound, which specifically targets the ABL myristoyl pocket. The structure of ABL001 was disclosed at the American Society of Hematology's (ASH) 57th Annual Meeting and Exposition in Orlando, Florida (Dec., 2015)- see Abstract 1565. Mechanisms by which resistance to asciminib can develop are reported by Qiang et al. (2017) [6], including the development of T315I (confers resistance to ponatinib)-inclusive compound mutations. Combining ponatinib + asciminib has been shown to be effective against such compind mutations
Asciminib-based PROTACs have been reported [9].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 103.37
Molecular weight 449.11
XLogP 4.3
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OC1CCN(C1)c1ncc(cc1c1ccn[nH]1)C(=O)Nc1ccc(cc1)OC(Cl)(F)F
Isomeric SMILES O[C@@H]1CCN(C1)c1ncc(cc1c1ccn[nH]1)C(=O)Nc1ccc(cc1)OC(Cl)(F)F
InChI InChI=1S/C20H18ClF2N5O3/c21-20(22,23)31-15-3-1-13(2-4-15)26-19(30)12-9-16(17-5-7-25-27-17)18(24-10-12)28-8-6-14(29)11-28/h1-5,7,9-10,14,29H,6,8,11H2,(H,25,27)(H,26,30)/t14-/m1/s1
InChI Key VOVZXURTCKPRDQ-CQSZACIVSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
N-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3R)-3-hydroxypyrrolidin-1-yl]-5-(1H-pyrazol-5-yl)pyridine-3-carboxamide
International Nonproprietary Names Click here for help
INN number INN
10267 asciminib
Synonyms Click here for help
ABL-001 | ABL001 | Example 9 [1]
Database Links Click here for help
CAS Registry No. 1492952-76-7 (source: WHO INN record)
GtoPdb PubChem SID 310264743
PubChem CID 72165228
RCSB PDB Ligand AY7
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