Compound 12 [PMID:28626832]   

GtoPdb Ligand ID: 9823

Compound class: Synthetic organic
Comment: This work describes an approach to identify β-secretase 1 (BACE1) fragment binders. Assays, NMR and crystallographic studies with the soluble domain of BACE1 identified a unique binding mode for compound 12, a fragment that still occupies the active site while not making any interactions with catalytic Aspartic acid residues [1]. The very low IC50 of 0.5 mM is a consequence of being a fragment but this is unusual in having a PDB crystal structure 5MXD showing the novel active site interactions.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 0
Rotatable bonds 2
Topological polar surface area 32.26
Molecular weight 242.15
XLogP 3.58
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CN(c1nc(nc2c1cccc2)N1CCCC1)C
Isomeric SMILES CN(c1nc(nc2c1cccc2)N1CCCC1)C
InChI InChI=1S/C14H18N4/c1-17(2)13-11-7-3-4-8-12(11)15-14(16-13)18-9-5-6-10-18/h3-4,7-8H,5-6,9-10H2,1-2H3
InChI Key VONNLDQOEHSECV-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
IUPAC Name
N,N-dimethyl-2-pyrrolidin-1-ylquinazolin-4-amine
Comments
This work describes an approach to identify β-secretase 1 (BACE1) fragment binders. Assays, NMR and crystallographic studies with the soluble domain of BACE1 identified a unique binding mode for compound 12, a fragment that still occupies the active site while not making any interactions with catalytic Aspartic acid residues [1]. The very low IC50 of 0.5 mM is a consequence of being a fragment but this is unusual in having a PDB crystal structure 5MXD showing the novel active site interactions.
Database Links
GtoPdb PubChem SID 354702294
PubChem CID 52108499
RCSB PDB Ligand III
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