Ligand profile

ZINC16997814

Virtual-screening candidate from ZINC.

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

Via homolog UniProt Q6J1Z6 Formula C₂₀H₁₄N₄O₆
Tanimoto 0.53
Mol. weight 406.35 Da
Permeability Check
PAINS Alert

Identifiers

Database identifiers and provenance.

Ligand ID
ZINC16997814
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 406.35 Da
LogP (Crippen) 4.42
H-bond donors 2
H-bond acceptors 8
TPSA 151.46 Ų
Rotatable bonds 6
Aromatic rings 3 / 3
Heavy atoms 30
Fraction sp³ C 0.00
Formula C₂₀H₁₄N₄O₆

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 4.42
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 406.4
  • LogP ≤ 5 4.42
  • H-bond donors ≤ 5 2
  • H-bond acceptors ≤ 10 8
Veber's rules Fail
  • Rotatable bonds ≤ 10 6
  • TPSA ≤ 140 Ų 151.5
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(O)c(/N=C\c2ccc(/C=N/c3cc([N+](=O)[O-])ccc3O)cc2)c1
InChI 
InChI=1S/C20H14N4O6/c25-19-7-5-15(23(27)28)9-17(19)21-11-13-1-2-14(4-3-13)12-22-18-10-16(24(29)30)6-8-20(18)26/h1-12,25-26H/b21-11-,22-12+
InChIKey 
KQNVPCLMARLCKC-ZCJKAFFOSA-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)