Ligand profile

CHEMBL1392396

Bioactivity hit from ChEMBL on a similar protein.

Bound to: VK055_4646 — aminopeptidase B

Via homolog UniProt Q8IL11 Formula C₂₃H₂₂N₄O₅S
Mol. weight 466.52 Da
Permeability Check
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL1392396
UniProt (similar protein)
Q8IL11
Target protein
VK055_4646

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 466.52 Da
LogP (Crippen) 3.11
H-bond donors 1
H-bond acceptors 9
TPSA 96.73 Ų
Rotatable bonds 8
Aromatic rings 3 / 5
Heavy atoms 33
Fraction sp³ C 0.26
Formula C₂₃H₂₂N₄O₅S

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 96.7
  • −1 ≤ LogP ≤ 5 3.11
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 466.5
  • LogP ≤ 5 3.11
  • H-bond donors ≤ 5 1
  • H-bond acceptors ≤ 10 9
Veber's rules Pass
  • Rotatable bonds ≤ 10 8
  • TPSA ≤ 140 Ų 96.7
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
C=CCn1c(SCC(=O)NCc2ccc3c(c2)OCO3)nnc1C1COc2ccccc2O1
InChI 
InChI=1S/C23H22N4O5S/c1-2-9-27-22(20-12-29-16-5-3-4-6-18(16)32-20)25-26-23(27)33-13-21(28)24-11-15-7-8-17-19(10-15)31-14-30-17/h2-8,10,20H,1,9,11-14H2,(H,24,28)
InChIKey 
RVVAUORUXLSRNU-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_4646.

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)