Ligand profile

ZINC1685914

Virtual-screening candidate from ZINC.

Bound to: VK055_0340 — 2,3-dihydroxyphenylpropionate/2, 3-dihydroxicinnamic acid 1,2-dioxygenase

Via homolog UniProt P22636 Formula C₁₃H₁₂NO₃⁺
Tanimoto 0.50
Mol. weight 230.24 Da
Permeability High
PAINS Alert

Identifiers

Database identifiers and provenance.

Ligand ID
ZINC1685914
UniProt (similar protein)
P22636
Tanimoto
0.500
Target protein
VK055_0340

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 230.24 Da
LogP (Crippen) 1.27
H-bond donors 2
H-bond acceptors 3
TPSA 61.41 Ų
Rotatable bonds 3
Aromatic rings 2 / 2
Heavy atoms 17
Fraction sp³ C 0.08
Formula C₁₃H₁₂NO₃⁺

Drug-likeness

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

Permeability proxy High

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 61.4
  • −1 ≤ LogP ≤ 5 1.27
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 230.2
  • LogP ≤ 5 1.27
  • H-bond donors ≤ 5 2
  • H-bond acceptors ≤ 10 3
Veber's rules Pass
  • Rotatable bonds ≤ 10 3
  • TPSA ≤ 140 Ų 61.4
PAINS Alert

Matches PAINS filter: catechol_A(92). May be a frequent false positive in HTS — review carefully.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
O=C(C[n+]1ccccc1)c1ccc(O)c(O)c1
InChI 
InChI=1S/C13H11NO3/c15-11-5-4-10(8-12(11)16)13(17)9-14-6-2-1-3-7-14/h1-8H,9H2,(H-,15,16,17)/p+1
InChIKey 
WHVFPQYXJQZEFV-UHFFFAOYSA-O

Provenance

Annotation context from LigQ_2, the internal Target step that collects PDB, ChEMBL, and ZINC ligand evidence.

Method
LigQ nearest_k
Query
DHB
Homolog
P22636

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_0340.

PDB 2

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)