hydroxyethylamine transition-state inhibitor 1   

GtoPdb Ligand ID: 8688

Compound class: Synthetic organic
Comment: A hydroxyethylamine transition-state mimetic inhibitor of BACE2 with a crystal structure. This compound was initially identified as a BACE1 inhibitor by Novartis [2]. A series of analogues is specified in a Novartis patent but without activity data [1].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 70.59
Molecular weight 504.24
XLogP 6.01
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES Cc1cccc(c1)CNCC(C(NC(=O)C1=Cc2ccccc2Oc2c1cccc2)Cc1ccccc1)O
Isomeric SMILES Cc1cccc(c1)CNC[C@H]([C@@H](NC(=O)C1=Cc2ccccc2Oc2c1cccc2)Cc1ccccc1)O
InChI InChI=1S/C33H32N2O3/c1-23-10-9-13-25(18-23)21-34-22-30(36)29(19-24-11-3-2-4-12-24)35-33(37)28-20-26-14-5-7-16-31(26)38-32-17-8-6-15-27(28)32/h2-18,20,29-30,34,36H,19,21-22H2,1H3,(H,35,37)/t29-,30+/m0/s1
InChI Key BNWZCXDHHPBQOX-XZWHSSHBSA-N
Classification
Compound class Synthetic organic
IUPAC Name
N-[(2S,3R)-3-hydroxy-4-[(3-methylphenyl)methylamino]-1-phenylbutan-2-yl]benzo[b][1]benzoxepine-6-carboxamide
Comments
A hydroxyethylamine transition-state mimetic inhibitor of BACE2 with a crystal structure. This compound was initially identified as a BACE1 inhibitor by Novartis [2]. A series of analogues is specified in a Novartis patent but without activity data [1].
Database Links
GtoPdb PubChem SID 252166888
PubChem CID 11963503
RCSB PDB Ligand DBO
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