Ligand profile

CHEMBL1454693

Bioactivity hit from ChEMBL on a similar protein.

Bound to: KP13_01981 — Chaperone protein dnaK

Via homolog UniProt P11021 Formula C₂₀H₂₄FN₃O₃S
Mol. weight 405.50 Da
Permeability High
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL1454693
UniProt (similar protein)
P11021
Target protein
KP13_01981

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 405.50 Da
LogP (Crippen) 3.24
H-bond donors 1
H-bond acceptors 4
TPSA 69.72 Ų
Rotatable bonds 5
Aromatic rings 2 / 3
Heavy atoms 28
Fraction sp³ C 0.35
Formula C₂₀H₂₄FN₃O₃S

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 69.7
  • −1 ≤ LogP ≤ 5 3.24
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 405.5
  • LogP ≤ 5 3.24
  • H-bond donors ≤ 5 1
  • H-bond acceptors ≤ 10 4
Veber's rules Pass
  • Rotatable bonds ≤ 10 5
  • TPSA ≤ 140 Ų 69.7
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
Cc1ccc(NC(=O)c2cc(S(=O)(=O)N(C)C)ccc2N2CCCC2)cc1F
InChI 
InChI=1S/C20H24FN3O3S/c1-14-6-7-15(12-18(14)21)22-20(25)17-13-16(28(26,27)23(2)3)8-9-19(17)24-10-4-5-11-24/h6-9,12-13H,4-5,10-11H2,1-3H3,(H,22,25)
InChIKey 
YDMCKWRFJWZPHV-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)