onfasprodil   Click here for help

GtoPdb Ligand ID: 12156

Compound class: Synthetic organic
Comment: Onfasprodil was identified from WHO proposed INN list 126 (Jan 2022) as a N-methyl-D-aspartate (NMDA) receptor antagonist. It acts as a negative allosteric modulator of the glutamate ionotropic receptor NMDA type subunit 2B (GRIN2B; GluN2B or NR2B) and is proposed as an intravenous, rapid onset antidepressant. Onfasprodil's chemical structure is claimed in patent US10239835B2 [1]. We predict that is onfasprodil Novartis' Phase 2 clinical lead MIJ821, although name-to-structure has not been disclosed.
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 3
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 65.82
Molecular weight 358.17
XLogP 2.28
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES Oc1ccc(nc1)[C@H](CN1C[C@@H]2[C@H](C1)CC(C2)Oc1ccccc1F)O
Isomeric SMILES C1[C@@H]2CN(C[C@@H]2CC1Oc1ccccc1F)C[C@@H](c1ncc(cc1)O)O
InChI InChI=1S/C20H23FN2O3/c21-17-3-1-2-4-20(17)26-16-7-13-10-23(11-14(13)8-16)12-19(25)18-6-5-15(24)9-22-18/h1-6,9,13-14,16,19,24-25H,7-8,10-12H2/t13-,14+,16?,19-/m0/s1
InChI Key NEFQLCKWVRZEJA-ZWVKXQFTSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
6-[(1S)-2-[(3aR,6aS)-5-(2-fluorophenoxy)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]-1-hydroxyethyl]pyridin-3-ol
Database Links Click here for help
BindingDB Ligand 370815
CAS Registry No. 1892581-29-1 (source: WHO INN record)
GtoPdb PubChem SID 472319278
PubChem CID 118981713
Search Google for chemical match using the InChIKey NEFQLCKWVRZEJA-ZWVKXQFTSA-N
Search Google for chemicals with the same backbone NEFQLCKWVRZEJA
UniChem Compound Search for chemical match using the InChIKey NEFQLCKWVRZEJA-ZWVKXQFTSA-N
UniChem Connectivity Search for chemical match using the InChIKey NEFQLCKWVRZEJA-ZWVKXQFTSA-N