Ligand profile

ZINC142447986

Virtual-screening candidate from ZINC.

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

Via homolog UniProt P22636 Formula C₉H₉NO₅
Tanimoto 0.53
Mol. weight 211.17 Da
Permeability Check
PAINS Alert

Identifiers

Database identifiers and provenance.

Ligand ID
ZINC142447986
UniProt (similar protein)
P22636
Tanimoto
0.533
Target protein
VK055_0340

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 211.17 Da
LogP (Crippen) -0.09
H-bond donors 4
H-bond acceptors 4
TPSA 106.86 Ų
Rotatable bonds 3
Aromatic rings 1 / 1
Heavy atoms 15
Fraction sp³ C 0.11
Formula C₉H₉NO₅

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 106.9
  • −1 ≤ LogP ≤ 5 -0.09
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 211.2
  • LogP ≤ 5 -0.09
  • H-bond donors ≤ 5 4
  • H-bond acceptors ≤ 10 4
Veber's rules Pass
  • Rotatable bonds ≤ 10 3
  • TPSA ≤ 140 Ų 106.9
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(O)CNC(=O)c1ccc(O)c(O)c1
InChI 
InChI=1S/C9H9NO5/c11-6-2-1-5(3-7(6)12)9(15)10-4-8(13)14/h1-3,11-12H,4H2,(H,10,15)(H,13,14)
InChIKey 
QVGDKHUNWDVPOR-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)