Ligand profile

CHEMBL4114663

Bioactivity hit from ChEMBL on a similar protein.

Bound to: VK055_0891 — beta-lactamase SHV-24

Via homolog UniProt P62593 Formula C₁₈H₁₇NO₅
pchembl 7.18 ~66.1 nM
Mol. weight 327.34 Da
Permeability High
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL4114663
UniProt (similar protein)
P62593
pchembl
7.180 (~66.1 nM)
Target protein
VK055_0891

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 327.34 Da
LogP (Crippen) 1.72
H-bond donors 0
H-bond acceptors 5
TPSA 72.91 Ų
Rotatable bonds 6
Aromatic rings 1 / 3
Heavy atoms 24
Fraction sp³ C 0.28
Formula C₁₈H₁₇NO₅

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 72.9
  • −1 ≤ LogP ≤ 5 1.72
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 327.3
  • LogP ≤ 5 1.72
  • H-bond donors ≤ 5 0
  • H-bond acceptors ≤ 10 5
Veber's rules Pass
  • Rotatable bonds ≤ 10 6
  • TPSA ≤ 140 Ų 72.9
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
C=CC/C(C=O)=C1\O[C@@H]2CC(=O)N2C1C(=O)OCc1ccccc1
InChI 
InChI=1S/C18H17NO5/c1-2-6-13(10-20)17-16(19-14(21)9-15(19)24-17)18(22)23-11-12-7-4-3-5-8-12/h2-5,7-8,10,15-16H,1,6,9,11H2/b17-13+/t15-,16?/m1/s1
InChIKey 
LSWFYHUYIAXPOB-MALCNQJZSA-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
324108
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)