Ligand profile

ZINC43190941

Virtual-screening candidate from ZINC.

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

Via homolog UniProt Q6J1Z6 Formula C₂₀H₁₄N₄O₈
Tanimoto 0.53
Mol. weight 438.35 Da
Permeability Check
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
ZINC43190941
UniProt (similar protein)
Q6J1Z6
Tanimoto
0.529
Target protein
VK055_2653

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 438.35 Da
LogP (Crippen) 3.42
H-bond donors 4
H-bond acceptors 8
TPSA 184.94 Ų
Rotatable bonds 6
Aromatic rings 3 / 3
Heavy atoms 32
Fraction sp³ C 0.00
Formula C₂₀H₁₄N₄O₈

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 184.9
  • −1 ≤ LogP ≤ 5 3.42
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 438.4
  • LogP ≤ 5 3.42
  • H-bond donors ≤ 5 4
  • H-bond acceptors ≤ 10 8
Veber's rules Fail
  • Rotatable bonds ≤ 10 6
  • TPSA ≤ 140 Ų 184.9
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
O=C(Nc1ccc(NC(=O)c2cc([N+](=O)[O-])ccc2O)cc1)c1cc([N+](=O)[O-])ccc1O
InChI 
InChI=1S/C20H14N4O8/c25-17-7-5-13(23(29)30)9-15(17)19(27)21-11-1-2-12(4-3-11)22-20(28)16-10-14(24(31)32)6-8-18(16)26/h1-10,25-26H,(H,21,27)(H,22,28)
InChIKey 
PMVDLQNBBYTGBU-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)