compound 2 [PMID: 22911925]   Click here for help

GtoPdb Ligand ID: 6950

Synonyms: compound 37 [PMID: 22468684] [1]
PDB Ligand
Compound class: Synthetic organic
Comment: A hydroxyethylamine-based inhibitor of BACE1 from Amgen capable of lowering Aβ levels in the brains of rats after oral administration [2]. Also has a PDB structure [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 13
Topological polar surface area 133.84
Molecular weight 592.31
XLogP 5.33
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES COC(C(=O)NC(C(CNC1CC2(CCC2)Oc2c1cc(cn2)CC(C)(C)C)O)Cc1cccc(c1)c1nccs1)C
Isomeric SMILES CO[C@@H](C(=O)N[C@H]([C@@H](CN[C@H]1CC2(CCC2)Oc2c1cc(cn2)CC(C)(C)C)O)Cc1cccc(c1)c1nccs1)C
InChI InChI=1S/C33H44N4O4S/c1-21(40-5)29(39)37-26(16-22-8-6-9-24(14-22)31-34-12-13-42-31)28(38)20-35-27-18-33(10-7-11-33)41-30-25(27)15-23(19-36-30)17-32(2,3)4/h6,8-9,12-15,19,21,26-28,35,38H,7,10-11,16-18,20H2,1-5H3,(H,37,39)/t21-,26+,27+,28-/m1/s1
InChI Key IUSARDYWEPUTPN-OZBXUNDUSA-N
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Compound class Synthetic organic
IUPAC Name Click here for help
(2R)-N-[(2S,3R)-4-{[(4'S)-6'-(2,2-dimethylpropyl)-3',4'-dihydrospiro[cyclobutane-1,2'-pyrano[2,3-b]pyridine]-4'-yl]amino}-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide
Synonyms Click here for help
compound 37 [PMID: 22468684] [1]
Database Links Click here for help
ChEMBL Ligand CHEMBL2181911
GtoPdb PubChem SID 178103532
PubChem CID 60202321
RCSB PDB Ligand 0K9
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SynPHARM 79000 (in complex with beta-secretase 1)