Ligand profile

ZINC5568338

Virtual-screening candidate from ZINC.

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

Via homolog UniProt Q6J1Z6 Formula C₁₃H₉N₃O₆
Tanimoto 0.54
Mol. weight 303.23 Da
Permeability Check
PAINS Alert

Identifiers

Database identifiers and provenance.

Ligand ID
ZINC5568338
UniProt (similar protein)
Q6J1Z6
Tanimoto
0.543
Target protein
VK055_2653

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 303.23 Da
LogP (Crippen) 2.66
H-bond donors 2
H-bond acceptors 7
TPSA 139.10 Ų
Rotatable bonds 4
Aromatic rings 2 / 2
Heavy atoms 22
Fraction sp³ C 0.00
Formula C₁₃H₉N₃O₆

Drug-likeness

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

Permeability proxy Check

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 139.1
  • −1 ≤ LogP ≤ 5 2.66
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 303.2
  • LogP ≤ 5 2.66
  • H-bond donors ≤ 5 2
  • H-bond acceptors ≤ 10 7
Veber's rules Pass
  • Rotatable bonds ≤ 10 4
  • TPSA ≤ 140 Ų 139.1
PAINS Alert

Matches PAINS filter: imine_phenol_A(3). May be a frequent false positive in HTS — review carefully.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
O=[N+]([O-])c1ccc(/N=C/c2cc([N+](=O)[O-])ccc2O)c(O)c1
InChI 
InChI=1S/C13H9N3O6/c17-12-4-2-9(15(19)20)5-8(12)7-14-11-3-1-10(16(21)22)6-13(11)18/h1-7,17-18H/b14-7+
InChIKey 
BUIYECCAUPUSOV-VGOFMYFVSA-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)