Ligand profile

ZINC536953409

Virtual-screening candidate from ZINC.

Bound to: VK055_2653 — 3,4-dihydroxyphenylacetate 2,3-dioxygenase

Via homolog UniProt Q6J1Z6 Formula C₁₂H₈ClNO₃
Tanimoto 0.55
Mol. weight 249.65 Da
Permeability High
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
ZINC536953409
UniProt (similar protein)
Q6J1Z6
Tanimoto
0.548
Target protein
VK055_2653

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 249.65 Da
LogP (Crippen) 3.62
H-bond donors 1
H-bond acceptors 3
TPSA 63.37 Ų
Rotatable bonds 2
Aromatic rings 2 / 2
Heavy atoms 17
Fraction sp³ C 0.00
Formula C₁₂H₈ClNO₃

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 63.4
  • −1 ≤ LogP ≤ 5 3.62
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 249.7
  • LogP ≤ 5 3.62
  • H-bond donors ≤ 5 1
  • H-bond acceptors ≤ 10 3
Veber's rules Pass
  • Rotatable bonds ≤ 10 2
  • TPSA ≤ 140 Ų 63.4
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
O=[N+]([O-])c1ccc(-c2ccc(O)c(Cl)c2)cc1
InChI 
InChI=1S/C12H8ClNO3/c13-11-7-9(3-6-12(11)15)8-1-4-10(5-2-8)14(16)17/h1-7,15H
InChIKey 
JWTHYLHZHLXPMV-UHFFFAOYSA-N

Provenance

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

Method
LigQ nearest_k
Query
4NC
Homolog
Q6J1Z6

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_2653.

PDB 3

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

Ligand PDB entry

ZINC 49

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

Compound Similarity (Tanimoto)