Ligand profile

ZINC1602813

Virtual-screening candidate from ZINC.

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

Via homolog UniProt P22636 Formula C₁₂H₁₇NO₃
Tanimoto 0.52
Mol. weight 223.27 Da
Permeability High
PAINS Alert

Identifiers

Database identifiers and provenance.

Ligand ID
ZINC1602813
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 223.27 Da
LogP (Crippen) 1.62
H-bond donors 2
H-bond acceptors 4
TPSA 60.77 Ų
Rotatable bonds 5
Aromatic rings 1 / 1
Heavy atoms 16
Fraction sp³ C 0.42
Formula C₁₂H₁₇NO₃

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 60.8
  • −1 ≤ LogP ≤ 5 1.62
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 223.3
  • LogP ≤ 5 1.62
  • H-bond donors ≤ 5 2
  • H-bond acceptors ≤ 10 4
Veber's rules Pass
  • Rotatable bonds ≤ 10 5
  • TPSA ≤ 140 Ų 60.8
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 
CCN(CC)CC(=O)c1ccc(O)c(O)c1
InChI 
InChI=1S/C12H17NO3/c1-3-13(4-2)8-12(16)9-5-6-10(14)11(15)7-9/h5-7,14-15H,3-4,8H2,1-2H3
InChIKey 
YYBGWGLGOFFORL-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)