compound 9 [PMID: 26006010]

Ligand id: 9761

Name: compound 9 [PMID: 26006010]

Structure and Physico-chemical Properties

2D Structure
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Calculated Physico-chemical Properties
Hydrogen bond acceptors 9
Hydrogen bond donors 1
Rotatable bonds 10
Topological polar surface area 135.42
Molecular weight 610.28
XLogP 4.03
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
IUPAC Name
(E)-2-[(2S)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-methyl-4-[methyl(oxetan-3-yl)amino]pent-2-enenitrile
Comments
Compound 9 [PMID: 26006010] is a reversible BTK inhibitor that was designed to have a long target residency time with a resulting increase in the duration of in vivo target engagement, and with the overall aim of improving in vivo drug efficacy [1]. Compound 9 has a cysteine-reactive, inverted cyanoacrylamide scaffold structure that interacts with Cys481, a residue that lies outwith the catalytic domain of the enzyme but close to the ATP pocket (and is also a target of the irreversible inhibitor ibrutinib). It has good aqueous solubility and is orally bioavailable. Compound 9 may be PRN473 as described in [3], but PRN473's structure has not been formally disclosed.
Database Links
BindingDB Ligand 143185
ChEMBL Ligand CHEMBL3702836
GtoPdb PubChem SID 354702234
PubChem CID 73389638
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