Ligand profile

ZINC20624349

Virtual-screening candidate from ZINC.

Bound to: VK055_1548 — 3-phosphoshikimate 1-carboxyvinyltransferase

Via homolog UniProt P0A6D3 Formula C₂₁H₂₃NO₄
Tanimoto 0.54
Mol. weight 353.42 Da
Permeability High
PAINS Alert

Identifiers

Database identifiers and provenance.

Ligand ID
ZINC20624349
UniProt (similar protein)
P0A6D3
Tanimoto
0.544
Target protein
VK055_1548

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 353.42 Da
LogP (Crippen) 3.86
H-bond donors 1
H-bond acceptors 5
TPSA 59.00 Ų
Rotatable bonds 6
Aromatic rings 2 / 3
Heavy atoms 26
Fraction sp³ C 0.29
Formula C₂₁H₂₃NO₄

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 59.0
  • −1 ≤ LogP ≤ 5 3.86
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 353.4
  • LogP ≤ 5 3.86
  • H-bond donors ≤ 5 1
  • H-bond acceptors ≤ 10 5
Veber's rules Pass
  • Rotatable bonds ≤ 10 6
  • TPSA ≤ 140 Ų 59.0
PAINS Alert

Matches PAINS filter: mannich_A(296). May be a frequent false positive in HTS — review carefully.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
CCN(CC)Cc1c(O)ccc2c1O/C(=C\c1ccc(OC)cc1)C2=O
InChI 
InChI=1S/C21H23NO4/c1-4-22(5-2)13-17-18(23)11-10-16-20(24)19(26-21(16)17)12-14-6-8-15(25-3)9-7-14/h6-12,23H,4-5,13H2,1-3H3/b19-12-
InChIKey 
HJASBTALPVQHNR-UNOMPAQXSA-N

Provenance

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

Method
LigQ nearest_k
Query
CHEMBL334500
Homolog
P0A6D3

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_1548.

PDB 10

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

Ligand PDB entry

ChEMBL 14

Compounds with measured inhibitory activity on this target (higher pchembl = more potent).

Compound Potency (pchembl)

ZINC 49

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

Compound Similarity (Tanimoto)