Ligand profile

CHEMBL1406195

Bioactivity hit from ChEMBL on a similar protein.

Bound to: VK055_4127 — phosphoglycerate kinase family protein

Via homolog UniProt P07378 Formula C₂₃H₂₀N₂O₃S
Mol. weight 404.49 Da
Permeability High
PAINS Alert

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL1406195
UniProt (similar protein)
P07378
Target protein
VK055_4127

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 404.49 Da
LogP (Crippen) 4.67
H-bond donors 2
H-bond acceptors 6
TPSA 75.35 Ų
Rotatable bonds 7
Aromatic rings 4 / 4
Heavy atoms 29
Fraction sp³ C 0.13
Formula C₂₃H₂₀N₂O₃S

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 75.4
  • −1 ≤ LogP ≤ 5 4.67
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 404.5
  • LogP ≤ 5 4.67
  • H-bond donors ≤ 5 2
  • H-bond acceptors ≤ 10 6
Veber's rules Pass
  • Rotatable bonds ≤ 10 7
  • TPSA ≤ 140 Ų 75.4
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(CSc1nc2ccccc2n1CCc1ccccc1)c1ccc(O)c(O)c1
InChI 
InChI=1S/C23H20N2O3S/c26-20-11-10-17(14-21(20)27)22(28)15-29-23-24-18-8-4-5-9-19(18)25(23)13-12-16-6-2-1-3-7-16/h1-11,14,26-27H,12-13,15H2
InChIKey 
NDLKOZVRJISFAO-UHFFFAOYSA-N

Provenance

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

Method
LigQ nearest_k
Source
ChEMBL
Activity
active
Binding sites
PF00162

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_4127.

PDB 4

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

Ligand PDB entry

ChEMBL 99

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

Compound Potency (pchembl)

ZINC 50

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

Compound Similarity (Tanimoto)