Ligand profile

ZINC17158509

Virtual-screening candidate from ZINC.

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

Via homolog UniProt Q6J1Z6 Formula C₁₄H₁₀N₄O₆
Tanimoto 0.58
Mol. weight 330.26 Da
Permeability Check
PAINS Alert

Identifiers

Database identifiers and provenance.

Ligand ID
ZINC17158509
UniProt (similar protein)
Q6J1Z6
Tanimoto
0.581
Target protein
VK055_2653

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 330.26 Da
LogP (Crippen) 2.37
H-bond donors 2
H-bond acceptors 8
TPSA 151.46 Ų
Rotatable bonds 5
Aromatic rings 2 / 2
Heavy atoms 24
Fraction sp³ C 0.00
Formula C₁₄H₁₀N₄O₆

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 151.5
  • −1 ≤ LogP ≤ 5 2.37
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 330.3
  • LogP ≤ 5 2.37
  • H-bond donors ≤ 5 2
  • H-bond acceptors ≤ 10 8
Veber's rules Fail
  • Rotatable bonds ≤ 10 5
  • TPSA ≤ 140 Ų 151.5
PAINS Alert

Matches PAINS filter: hzone_phenol_A(479). May be a frequent false positive in HTS — review carefully.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
O=[N+]([O-])c1ccc(O)c(/C=N\N=C/c2cc([N+](=O)[O-])ccc2O)c1
InChI 
InChI=1S/C14H10N4O6/c19-13-3-1-11(17(21)22)5-9(13)7-15-16-8-10-6-12(18(23)24)2-4-14(10)20/h1-8,19-20H/b15-7-,16-8-
InChIKey 
ULNJZDPQMMBRNH-DUGOVBPYSA-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)