Ligand profile

CHEMBL1592886

Bioactivity hit from ChEMBL on a similar protein.

Bound to: KP13_01981 — Chaperone protein dnaK

Via homolog UniProt P11021 Formula C₂₃H₂₃N₃O₅
Mol. weight 421.45 Da
Permeability Check
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL1592886
UniProt (similar protein)
P11021
Target protein
KP13_01981

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 421.45 Da
LogP (Crippen) 4.36
H-bond donors 1
H-bond acceptors 8
TPSA 98.77 Ų
Rotatable bonds 9
Aromatic rings 3 / 3
Heavy atoms 31
Fraction sp³ C 0.22
Formula C₂₃H₂₃N₃O₅

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 98.8
  • −1 ≤ LogP ≤ 5 4.36
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 421.5
  • LogP ≤ 5 4.36
  • H-bond donors ≤ 5 1
  • H-bond acceptors ≤ 10 8
Veber's rules Pass
  • Rotatable bonds ≤ 10 9
  • TPSA ≤ 140 Ų 98.8
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
COc1ccc(CNc2oc(/C=C/c3cc(OC)c(OC)c(OC)c3)nc2C#N)cc1
InChI 
InChI=1S/C23H23N3O5/c1-27-17-8-5-15(6-9-17)14-25-23-18(13-24)26-21(31-23)10-7-16-11-19(28-2)22(30-4)20(12-16)29-3/h5-12,25H,14H2,1-4H3/b10-7+
InChIKey 
CJVJWRZJICFBEL-JXMROGBWSA-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)