Ligand profile

ZINC28294429

Virtual-screening candidate from ZINC.

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

Via homolog UniProt Q6J1Z6 Formula C₁₅H₁₅N₃O₇
Tanimoto 0.55
Mol. weight 349.30 Da
Permeability Check
PAINS Alert

Identifiers

Database identifiers and provenance.

Ligand ID
ZINC28294429
UniProt (similar protein)
Q6J1Z6
Tanimoto
0.545
Target protein
VK055_2653

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 349.30 Da
LogP (Crippen) 1.87
H-bond donors 3
H-bond acceptors 8
TPSA 150.21 Ų
Rotatable bonds 7
Aromatic rings 2 / 2
Heavy atoms 25
Fraction sp³ C 0.20
Formula C₁₅H₁₅N₃O₇

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 150.2
  • −1 ≤ LogP ≤ 5 1.87
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 349.3
  • LogP ≤ 5 1.87
  • H-bond donors ≤ 5 3
  • H-bond acceptors ≤ 10 8
Veber's rules Fail
  • Rotatable bonds ≤ 10 7
  • TPSA ≤ 140 Ų 150.2
PAINS Alert

Matches PAINS filter: mannich_A(296). May be a frequent false positive in HTS — review carefully.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
O=[N+]([O-])c1ccc(O)c(CN(CO)Cc2cc([N+](=O)[O-])ccc2O)c1
InChI 
InChI=1S/C15H15N3O7/c19-9-16(7-10-5-12(17(22)23)1-3-14(10)20)8-11-6-13(18(24)25)2-4-15(11)21/h1-6,19-21H,7-9H2
InChIKey 
AWPZWNSOUAZQFU-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)