Ligand profile

CHEMBL396889

Bioactivity hit from ChEMBL on a similar protein.

Bound to: VK055_0891 — beta-lactamase SHV-24

Via homolog UniProt P62593 Formula C₁₇H₁₈BNO₄S
pchembl 6.60 ~251.2 nM
Mol. weight 343.21 Da
Permeability High
PAINS Alert

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL396889
UniProt (similar protein)
P62593
pchembl
6.600 (~251.2 nM)
Target protein
VK055_0891

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 343.21 Da
LogP (Crippen) 2.21
H-bond donors 3
H-bond acceptors 6
TPSA 70.95 Ų
Rotatable bonds 6
Aromatic rings 3 / 3
Heavy atoms 24
Fraction sp³ C 0.18
Formula C₁₇H₁₈BNO₄S

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 71.0
  • −1 ≤ LogP ≤ 5 2.21
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 343.2
  • LogP ≤ 5 2.21
  • H-bond donors ≤ 5 3
  • H-bond acceptors ≤ 10 6
Veber's rules Pass
  • Rotatable bonds ≤ 10 6
  • TPSA ≤ 140 Ų 71.0
PAINS Alert

Matches PAINS filter: anil_di_alk_C(246). May be a frequent false positive in HTS — review carefully.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
COc1ccc(NCc2ccc3sc(B(O)O)cc3c2)cc1OC
InChI 
InChI=1S/C17H18BNO4S/c1-22-14-5-4-13(9-15(14)23-2)19-10-11-3-6-16-12(7-11)8-17(24-16)18(20)21/h3-9,19-21H,10H2,1-2H3
InChIKey 
IQEFBPFYMDWCHP-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
PF13354

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_0891.

PDB 44

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)