Ligand profile

CHEMBL3355109

Bioactivity hit from ChEMBL on a similar protein.

Bound to: VK055_4646 — aminopeptidase B

Via homolog UniProt P28839 Formula C₂₀H₂₇N₂O₄P
pchembl 6.86 ~138.0 nM
Mol. weight 390.42 Da
Permeability Check
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL3355109
UniProt (similar protein)
P28839
pchembl
6.860 (~138.0 nM)
Target protein
VK055_4646

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 390.42 Da
LogP (Crippen) 2.58
H-bond donors 4
H-bond acceptors 4
TPSA 126.64 Ų
Rotatable bonds 10
Aromatic rings 2 / 2
Heavy atoms 27
Fraction sp³ C 0.35
Formula C₂₀H₂₇N₂O₄P

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 126.6
  • −1 ≤ LogP ≤ 5 2.58
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 390.4
  • LogP ≤ 5 2.58
  • H-bond donors ≤ 5 4
  • H-bond acceptors ≤ 10 4
Veber's rules Pass
  • Rotatable bonds ≤ 10 10
  • TPSA ≤ 140 Ų 126.6
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
NCc1ccc(CC(CP(=O)(O)C(N)CCc2ccccc2)C(=O)O)cc1
InChI 
InChI=1S/C20H27N2O4P/c21-13-17-8-6-16(7-9-17)12-18(20(23)24)14-27(25,26)19(22)11-10-15-4-2-1-3-5-15/h1-9,18-19H,10-14,21-22H2,(H,23,24)(H,25,26)
InChIKey 
XZFPYKBNMOQQLL-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
Curation
pdb_similarity_tanimoto
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)