Ligand profile

CHEMBL1513351

Bioactivity hit from ChEMBL on a similar protein.

Bound to: KP13_01981 — Chaperone protein dnaK

Via homolog UniProt P11021 Formula C₂₂H₂₂ClNO₃
Mol. weight 383.88 Da
Permeability Check
PAINS Alert

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL1513351
UniProt (similar protein)
P11021
Target protein
KP13_01981

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 383.88 Da
LogP (Crippen) 5.64
H-bond donors 2
H-bond acceptors 4
TPSA 50.72 Ų
Rotatable bonds 8
Aromatic rings 3 / 3
Heavy atoms 27
Fraction sp³ C 0.18
Formula C₂₂H₂₂ClNO₃

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 50.7
  • −1 ≤ LogP ≤ 5 5.64
Lipinski's Rule of Five Pass 1 violation
  • MW ≤ 500 Da 383.9
  • LogP ≤ 5 5.64
  • H-bond donors ≤ 5 2
  • H-bond acceptors ≤ 10 4
Veber's rules Pass
  • Rotatable bonds ≤ 10 8
  • TPSA ≤ 140 Ų 50.7
PAINS Alert

Matches PAINS filter: anil_OH_alk_A(8). May be a frequent false positive in HTS — review carefully.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
CCOc1cc(CNc2ccc(O)cc2)cc(Cl)c1OCc1ccccc1
InChI 
InChI=1S/C22H22ClNO3/c1-2-26-21-13-17(14-24-18-8-10-19(25)11-9-18)12-20(23)22(21)27-15-16-6-4-3-5-7-16/h3-13,24-25H,2,14-15H2,1H3
InChIKey 
LYONSKSTHIQELX-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
PF00012

External resources

Open this ligand in third-party databases and cheminformatics tools.

Other ligands for this protein

Quick navigation to other ligands bound to KP13_01981.

PDB 20

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)