Ligand profile

ZINC3850719

Virtual-screening candidate from ZINC.

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

Via homolog UniProt Q54530 Formula C₂₁H₁₈O₈
Tanimoto 0.79
Mol. weight 398.37 Da
Permeability Check
PAINS Alert

Identifiers

Database identifiers and provenance.

Ligand ID
ZINC3850719
UniProt (similar protein)
Q54530
Tanimoto
0.789
Target protein
VK055_0339

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 398.37 Da
LogP (Crippen) 1.32
H-bond donors 4
H-bond acceptors 8
TPSA 141.36 Ų
Rotatable bonds 1
Aromatic rings 2 / 4
Heavy atoms 29
Fraction sp³ C 0.29
Formula C₂₁H₁₈O₈

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 141.4
  • −1 ≤ LogP ≤ 5 1.32
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 398.4
  • LogP ≤ 5 1.32
  • H-bond donors ≤ 5 4
  • H-bond acceptors ≤ 10 8
Veber's rules Fail
  • Rotatable bonds ≤ 10 1
  • TPSA ≤ 140 Ų 141.4
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 
COC(=O)[C@@H]1c2cc3c(c(O)c2[C@@H](O)C[C@@]1(C)O)C(=O)c1c(O)cccc1C3=O
InChI 
InChI=1S/C21H18O8/c1-21(28)7-12(23)14-9(16(21)20(27)29-2)6-10-15(19(14)26)18(25)13-8(17(10)24)4-3-5-11(13)22/h3-6,12,16,22-23,26,28H,7H2,1-2H3/t12-,16-,21+/m0/s1
InChIKey 
WCKNDRCJQZCZLO-LBJGKRIESA-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)