Ligand profile

CHEMBL589376

Bioactivity hit from ChEMBL on a similar protein.

Bound to: VK055_0681 — alpha/beta hydrolase fold family protein

Via homolog UniProt P34913 Formula C₂₀H₁₉Cl₂N₃O₂
pchembl 9.36 ~0.4 nM
Mol. weight 404.30 Da
Permeability High
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL589376
UniProt (similar protein)
P34913
pchembl
9.360 (~0.4 nM)
Target protein
VK055_0681

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 404.30 Da
LogP (Crippen) 4.62
H-bond donors 1
H-bond acceptors 3
TPSA 65.36 Ų
Rotatable bonds 4
Aromatic rings 2 / 3
Heavy atoms 27
Fraction sp³ C 0.30
Formula C₂₀H₁₉Cl₂N₃O₂

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 65.4
  • −1 ≤ LogP ≤ 5 4.62
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 404.3
  • LogP ≤ 5 4.62
  • H-bond donors ≤ 5 1
  • H-bond acceptors ≤ 10 3
Veber's rules Pass
  • Rotatable bonds ≤ 10 4
  • TPSA ≤ 140 Ų 65.4
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
N#Cc1ccccc1OC1CCN(C(=O)NCc2ccc(Cl)cc2Cl)CC1
InChI 
InChI=1S/C20H19Cl2N3O2/c21-16-6-5-15(18(22)11-16)13-24-20(26)25-9-7-17(8-10-25)27-19-4-2-1-3-14(19)12-23/h1-6,11,17H,7-10,13H2,(H,24,26)
InChIKey 
BBUGXHIGCLAOLZ-UHFFFAOYSA-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
PF00561

External resources

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

Other ligands for this protein

Quick navigation to other ligands bound to VK055_0681.

PDB 99

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

Ligand PDB entry

ChEMBL 99

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)