Ligand profile

ZINC266927

Virtual-screening candidate from ZINC.

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

Via homolog UniProt P22636 Formula C₁₃H₁₃NO₃
Tanimoto 0.52
Mol. weight 231.25 Da
Permeability High
PAINS Alert

Identifiers

Database identifiers and provenance.

Ligand ID
ZINC266927
UniProt (similar protein)
P22636
Tanimoto
0.516
Target protein
VK055_0340

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 231.25 Da
LogP (Crippen) 2.50
H-bond donors 2
H-bond acceptors 3
TPSA 62.46 Ų
Rotatable bonds 2
Aromatic rings 2 / 2
Heavy atoms 17
Fraction sp³ C 0.15
Formula C₁₃H₁₃NO₃

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 62.5
  • −1 ≤ LogP ≤ 5 2.50
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 231.3
  • LogP ≤ 5 2.50
  • H-bond donors ≤ 5 2
  • H-bond acceptors ≤ 10 3
Veber's rules Pass
  • Rotatable bonds ≤ 10 2
  • TPSA ≤ 140 Ų 62.5
PAINS Alert

Matches PAINS filter: pyrrole_A(118). May be a frequent false positive in HTS — review carefully.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
Cc1ccc(C)n1-c1cc(C(=O)O)ccc1O
InChI 
InChI=1S/C13H13NO3/c1-8-3-4-9(2)14(8)11-7-10(13(16)17)5-6-12(11)15/h3-7,15H,1-2H3,(H,16,17)
InChIKey 
VGMWQYFVGDAXSK-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
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)