Ligand profile

CHEMBL189620

Bioactivity hit from ChEMBL on a similar protein.

Bound to: HT085_RS00125 — prolyl oligopeptidase family serine peptidase

Via homolog UniProt Q9QUR6 Formula C₂₀H₂₅N₃O₂
pchembl 9.52 ~0.3 nM
Mol. weight 339.44 Da
Permeability High
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL189620
UniProt (similar protein)
Q9QUR6
pchembl
9.520 (~0.3 nM)
Target protein
HT085_RS00125

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 339.44 Da
LogP (Crippen) 2.51
H-bond donors 0
H-bond acceptors 3
TPSA 64.41 Ų
Rotatable bonds 5
Aromatic rings 1 / 3
Heavy atoms 25
Fraction sp³ C 0.55
Formula C₂₀H₂₅N₃O₂

Drug-likeness

Descriptor-based ADME screening flags from SMILES. These are not experimental toxicity results.

Permeability proxy High

Estimated from TPSA and LogP only: TPSA ≤ 90 Ų and −1 ≤ LogP ≤ 5 are treated as a favorable small-molecule permeability screen.

  • TPSA ≤ 90 Ų 64.4
  • −1 ≤ LogP ≤ 5 2.51
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 339.4
  • LogP ≤ 5 2.51
  • H-bond donors ≤ 5 0
  • H-bond acceptors ≤ 10 3
Veber's rules Pass
  • Rotatable bonds ≤ 10 5
  • TPSA ≤ 140 Ų 64.4
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
N#C[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)CCCc1ccccc1
InChI 
InChI=1S/C20H25N3O2/c21-15-17-10-5-13-22(17)20(25)18-11-6-14-23(18)19(24)12-4-9-16-7-2-1-3-8-16/h1-3,7-8,17-18H,4-6,9-14H2/t17-,18-/m0/s1
InChIKey 
SPXFAUXQZWJGCJ-ROUUACIJSA-N

Provenance

Annotation context from LigQ_2, the internal Target step that collects PDB, ChEMBL, and ZINC ligand evidence.

Method
LigQ nearest_k
Source
ChEMBL
Activity
Active
Curation
pdb_similarity_tanimoto
Binding sites
PF00326' 'PF02897

External resources

Open this ligand in third-party databases and cheminformatics tools.

Other ligands for this protein

Quick navigation to other ligands bound to HT085_RS00125.

PDB 2

Ligands co-crystallized with this protein (structural evidence).

Ligand PDB entry

ChEMBL 12

Compounds with measured inhibitory activity on this target (higher pchembl = more potent).

Compound Potency (pchembl)

ZINC 50

Virtual screening candidates selected by structural similarity to known actives (Tanimoto ≥ 0.5).

Compound Similarity (Tanimoto)