PRN1008

Ligand id: 9993

Name: PRN1008

Structure and Physico-chemical Properties

2D Structure
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Calculated Physico-chemical Properties
Hydrogen bond acceptors 10
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 138.66
Molecular weight 665.32
XLogP 3.67
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
IUPAC Name
(E)-2-[(3R)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile
Synonyms
Example 31 [WO2014039899]
Comments
PRN1008 is an oral, reversible covalent inhibitor of Bruton's tyrosine kinase (BTK) [1]. The chemical structure of PRN1008 has not been formally disclosed, and there is some uncertainty of its precise stereochemistry evident in online resources. One possible structure is claimed as Example 31 in Principia Biopharma patent WO2014039899 [2] and this is depicted in PubChem CID 118325989 as the R form without E/Z specification. We show the (E,R) structure here. PRN1008 is speculatively the compound for which INN rilzabrutinib is being requested, although the IUPAC type name provided in INN proposed list 121 is unreadable by chemical structure parsers, and the accompanying CAS number (1575591-66-0) is as yet PubChem negative. CAS 1575591-66-0 specifies the R enantiomer but does not specify geometry of the rotatable double bond.
Database Links
BindingDB Ligand 143212
CAS Registry No. 1575596-29-0 (source: PubChem)
ChEMBL Ligand CHEMBL3702854
GtoPdb PubChem SID 374883880
PubChem CID 73388818
Search Google for chemical match using the InChIKey LCFFREMLXLZNHE-GBOLQPHISA-N
Search Google for chemicals with the same backbone LCFFREMLXLZNHE
Search UniChem for chemical match using the InChIKey LCFFREMLXLZNHE-GBOLQPHISA-N
Search UniChem for chemicals with the same backbone LCFFREMLXLZNHE