compound 9 [PMID: 26006010]   Click here for help

GtoPdb Ligand ID: 9761

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: 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.
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2D Structure
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Physico-chemical Properties
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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
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Canonical SMILES N#CC(=CC(N(C1COC1)C)(C)C)C(=O)N1CCCC1Cn1nc(c2c1ncnc2N)c1ccc(cc1F)Oc1ccccc1
Isomeric SMILES N#C/C(=C\C(N(C1COC1)C)(C)C)/C(=O)N1CCC[C@H]1Cn1nc(c2c1ncnc2N)c1ccc(cc1F)Oc1ccccc1
InChI InChI=1S/C33H35FN8O3/c1-33(2,40(3)23-18-44-19-23)15-21(16-35)32(43)41-13-7-8-22(41)17-42-31-28(30(36)37-20-38-31)29(39-42)26-12-11-25(14-27(26)34)45-24-9-5-4-6-10-24/h4-6,9-12,14-15,20,22-23H,7-8,13,17-19H2,1-3H3,(H2,36,37,38)/b21-15+/t22-/m0/s1
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
Database Links Click here for help
BindingDB Ligand 143185
ChEMBL Ligand CHEMBL3702836
GtoPdb PubChem SID 354702234
PubChem CID 73389638
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