Ligand profile

CHEMBL4865920

Bioactivity hit from ChEMBL on a similar protein.

Bound to: KP13_02224 — Protein fimH

Via homolog UniProt P08191 Formula C₂₀H₂₇N₃O₈
pchembl 7.25 ~56.2 nM
Mol. weight 437.45 Da
Permeability Check
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL4865920
UniProt (similar protein)
P08191
pchembl
7.250 (~56.2 nM)
Target protein
KP13_02224

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 437.45 Da
LogP (Crippen) -0.06
H-bond donors 5
H-bond acceptors 10
TPSA 167.39 Ų
Rotatable bonds 10
Aromatic rings 2 / 3
Heavy atoms 31
Fraction sp³ C 0.55
Formula C₂₀H₂₇N₃O₈

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 167.4
  • −1 ≤ LogP ≤ 5 -0.06
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 437.4
  • LogP ≤ 5 -0.06
  • H-bond donors ≤ 5 5
  • H-bond acceptors ≤ 10 10
Veber's rules Fail
  • Rotatable bonds ≤ 10 10
  • TPSA ≤ 140 Ų 167.4
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
O=C(O)CCCCCOc1cccc(-c2cn([C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)nn2)c1
InChI 
InChI=1S/C20H27N3O8/c24-11-15-17(27)18(28)19(29)20(31-15)23-10-14(21-22-23)12-5-4-6-13(9-12)30-8-3-1-2-7-16(25)26/h4-6,9-10,15,17-20,24,27-29H,1-3,7-8,11H2,(H,25,26)/t15-,17-,18+,19+,20+/m1/s1
InChIKey 
MIKGICXPWUAHFK-LGKHCZOZSA-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
Curation
pdb_similarity_tanimoto
Binding sites
PF09160

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_02224.

PDB 25

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)