atabecestat   Click here for help

GtoPdb Ligand ID: 9963

Synonyms: JNJ-54861911 | JNJ-54861911-AAA | RSC-385896
PDB Ligand
Compound class: Synthetic organic
Comment: JNJ-54861911 was originally discovered at Shionogi in 2008 as a BACE1 inhibitor. Clinical development was progressed by Janssen as atabecestat [1]. The compound is orally active with good brain penetration and low P-gp substrate characteristic, which reflects in vivo Aβ reduction in brain and CSF for rat, monkey, and dog. However, serious elevations of liver enzymes were observed in the Phase 2b/3 study patients, causing the trial to be stopped in May 2018. The Phase 1 results were published in Sept 2018 [4].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 129.46
Molecular weight 367.09
XLogP 2.31
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES N#Cc1ccc(nc1)C(=O)Nc1ccc(c(c1)C1(C)C=CSC(=N1)N)F
Isomeric SMILES N#Cc1ccc(nc1)C(=O)Nc1ccc(c(c1)[C@]1(C)C=CSC(=N1)N)F
InChI InChI=1S/C18H14FN5OS/c1-18(6-7-26-17(21)24-18)13-8-12(3-4-14(13)19)23-16(25)15-5-2-11(9-20)10-22-15/h2-8,10H,1H3,(H2,21,24)(H,23,25)/t18-/m0/s1
InChI Key VLLFGVHGKLDDLW-SFHVURJKSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
N-[3-[(4S)-2-amino-4-methyl-1,3-thiazin-4-yl]-4-fluorophenyl]-5-cyanopyridine-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
10650 atabecestat
Synonyms Click here for help
JNJ-54861911 | JNJ-54861911-AAA | RSC-385896
Database Links Click here for help
GtoPdb PubChem SID 374883850
PubChem CID 68254185
RCSB PDB Ligand H3C
Search Google for chemical match using the InChIKey VLLFGVHGKLDDLW-SFHVURJKSA-N
Search Google for chemicals with the same backbone VLLFGVHGKLDDLW
Search PubMed clinical trials atabecestat
Search PubMed titles atabecestat
Search PubMed titles/abstracts atabecestat
Search UniChem for chemical match using the InChIKey VLLFGVHGKLDDLW-SFHVURJKSA-N
Search UniChem for chemicals with the same backbone VLLFGVHGKLDDLW