Ligand profile

ZINC5218089

Virtual-screening candidate from ZINC.

Bound to: VK055_0339 — 3-(3-hydroxy-phenyl)propionate/3-hydroxycinnamic acid hydroxylase

Via homolog UniProt Q54530 Formula C₂₂H₂₀O₉
Tanimoto 0.77
Mol. weight 428.39 Da
Permeability Check
PAINS Alert

Identifiers

Database identifiers and provenance.

Ligand ID
ZINC5218089
UniProt (similar protein)
Q54530
Tanimoto
0.772
Target protein
VK055_0339

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 428.39 Da
LogP (Crippen) 1.41
H-bond donors 5
H-bond acceptors 9
TPSA 161.59 Ų
Rotatable bonds 2
Aromatic rings 2 / 4
Heavy atoms 31
Fraction sp³ C 0.32
Formula C₂₂H₂₀O₉

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 161.6
  • −1 ≤ LogP ≤ 5 1.41
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 428.4
  • LogP ≤ 5 1.41
  • H-bond donors ≤ 5 5
  • H-bond acceptors ≤ 10 9
Veber's rules Fail
  • Rotatable bonds ≤ 10 2
  • TPSA ≤ 140 Ų 161.6
PAINS Alert

Matches PAINS filter: quinone_A(370). May be a frequent false positive in HTS — review carefully.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
CC[C@@]1(O)C[C@H](O)c2c(O)c3c(c(O)c2[C@@H]1C(=O)OC)C(=O)c1cccc(O)c1C3=O
InChI 
InChI=1S/C22H20O9/c1-3-22(30)7-10(24)12-13(16(22)21(29)31-2)20(28)14-15(19(12)27)18(26)11-8(17(14)25)5-4-6-9(11)23/h4-6,10,16,23-24,27-28,30H,3,7H2,1-2H3/t10-,16+,22+/m0/s1
InChIKey 
PYFOXRACBORDCT-JKBLZEGDSA-N

Provenance

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

Method
LigQ nearest_k
Query
VAK
Homolog
Q54530

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_0339.

PDB 5

Ligands co-crystallized with this protein (structural evidence).

Ligand PDB entry

ZINC 21

Virtual screening candidates selected by structural similarity to known actives (Tanimoto ≥ 0.5).

Compound Similarity (Tanimoto)