Ligand profile

CHEMBL1587393

Bioactivity hit from ChEMBL on a similar protein.

Bound to: VK055_2794 — pepA Transcriptional Repressor, Aminopeptidase A/I

Via homolog UniProt Q8IL11 Formula C₁₉H₂₂N₂O₃S
Mol. weight 358.46 Da
Permeability Check
PAINS Alert

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL1587393
UniProt (similar protein)
Q8IL11
Target protein
VK055_2794

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 358.46 Da
LogP (Crippen) 3.74
H-bond donors 2
H-bond acceptors 4
TPSA 90.19 Ų
Rotatable bonds 4
Aromatic rings 1 / 3
Heavy atoms 25
Fraction sp³ C 0.53
Formula C₁₉H₂₂N₂O₃S

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 90.2
  • −1 ≤ LogP ≤ 5 3.74
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 358.5
  • LogP ≤ 5 3.74
  • H-bond donors ≤ 5 2
  • H-bond acceptors ≤ 10 4
Veber's rules Pass
  • Rotatable bonds ≤ 10 4
  • TPSA ≤ 140 Ų 90.2
PAINS Alert

Matches PAINS filter: thiophene_amino_C(7). May be a frequent false positive in HTS — review carefully.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
CCC1CCc2c(sc(NC(=O)C3CC=CCC3C(=O)O)c2C#N)C1
InChI 
InChI=1S/C19H22N2O3S/c1-2-11-7-8-12-15(10-20)18(25-16(12)9-11)21-17(22)13-5-3-4-6-14(13)19(23)24/h3-4,11,13-14H,2,5-9H2,1H3,(H,21,22)(H,23,24)
InChIKey 
KQWSFSCGHQOOKF-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
PF00883

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_2794.

PDB 10

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)