Ligand profile

CHEMBL590379

Bioactivity hit from ChEMBL on a similar protein.

Bound to: VK055_1452 — short chain dehydrogenase family protein

Via homolog UniProt P37058 Formula C₁₆H₁₂ClNO₃S
pchembl 7.33 ~46.8 nM
Mol. weight 333.80 Da
Permeability High
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL590379
UniProt (similar protein)
P37058
pchembl
7.330 (~46.8 nM)
Target protein
VK055_1452

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 333.80 Da
LogP (Crippen) 4.15
H-bond donors 1
H-bond acceptors 5
TPSA 63.33 Ų
Rotatable bonds 3
Aromatic rings 3 / 3
Heavy atoms 22
Fraction sp³ C 0.12
Formula C₁₆H₁₂ClNO₃S

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 63.3
  • −1 ≤ LogP ≤ 5 4.15
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 333.8
  • LogP ≤ 5 4.15
  • H-bond donors ≤ 5 1
  • H-bond acceptors ≤ 10 5
Veber's rules Pass
  • Rotatable bonds ≤ 10 3
  • TPSA ≤ 140 Ų 63.3
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
Cc1cccc(SCc2c(Cl)c(=O)oc3cc(O)ccc23)n1
InChI 
InChI=1S/C16H12ClNO3S/c1-9-3-2-4-14(18-9)22-8-12-11-6-5-10(19)7-13(11)21-16(20)15(12)17/h2-7,19H,8H2,1H3
InChIKey 
LGVQVMQXMHWBKN-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
Binding sites
PF00106

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_1452.

PDB 1

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)