Ligand profile

CHEMBL1444370

Bioactivity hit from ChEMBL on a similar protein.

Bound to: VK055_4646 — aminopeptidase B

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

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL1444370
UniProt (similar protein)
Q8IL11
Target protein
VK055_4646

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 358.46 Da
LogP (Crippen) 3.88
H-bond donors 2
H-bond acceptors 4
TPSA 90.19 Ų
Rotatable bonds 3
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 3.88
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 358.5
  • LogP ≤ 5 3.88
  • H-bond donors ≤ 5 2
  • H-bond acceptors ≤ 10 4
Veber's rules Pass
  • Rotatable bonds ≤ 10 3
  • 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 
N#Cc1c(NC(=O)C2CC=CCC2C(=O)O)sc2c1CCCCCC2
InChI 
InChI=1S/C19H22N2O3S/c20-11-15-12-7-3-1-2-4-10-16(12)25-18(15)21-17(22)13-8-5-6-9-14(13)19(23)24/h5-6,13-14H,1-4,7-10H2,(H,21,22)(H,23,24)
InChIKey 
BJRKVCNTDTWVOA-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)