Ligand profile

CHEMBL4549821

Bioactivity hit from ChEMBL on a similar protein.

Bound to: HT085_RS00125 — prolyl oligopeptidase family serine peptidase

Via homolog UniProt Q9QUR6 Formula C₁₈H₂₃N₃O₂
pchembl 8.48 ~3.3 nM
Mol. weight 313.40 Da
Permeability High
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL4549821
UniProt (similar protein)
Q9QUR6
pchembl
8.480 (~3.3 nM)
Target protein
HT085_RS00125

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 313.40 Da
LogP (Crippen) 2.03
H-bond donors 1
H-bond acceptors 3
TPSA 73.20 Ų
Rotatable bonds 6
Aromatic rings 1 / 2
Heavy atoms 23
Fraction sp³ C 0.50
Formula C₁₈H₂₃N₃O₂

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 73.2
  • −1 ≤ LogP ≤ 5 2.03
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 313.4
  • LogP ≤ 5 2.03
  • H-bond donors ≤ 5 1
  • H-bond acceptors ≤ 10 3
Veber's rules Pass
  • Rotatable bonds ≤ 10 6
  • TPSA ≤ 140 Ų 73.2
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
C[C@H](NC(=O)CCCc1ccccc1)C(=O)N1CCC[C@H]1C#N
InChI 
InChI=1S/C18H23N3O2/c1-14(18(23)21-12-6-10-16(21)13-19)20-17(22)11-5-9-15-7-3-2-4-8-15/h2-4,7-8,14,16H,5-6,9-12H2,1H3,(H,20,22)/t14-,16-/m0/s1
InChIKey 
UVOXDQRATSEGCP-HOCLYGCPSA-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
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)