Ligand profile

CHEMBL1917473

Bioactivity hit from ChEMBL on a similar protein.

Bound to: KP13_02224 — Protein fimH

Via homolog UniProt P08191 Formula C₁₆H₂₀N₄O₈
pchembl 6.95 ~112.2 nM
Mol. weight 396.36 Da
Permeability Check
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL1917473
UniProt (similar protein)
P08191
pchembl
6.950 (~112.2 nM)
Target protein
KP13_02224

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 396.36 Da
LogP (Crippen) -1.47
H-bond donors 4
H-bond acceptors 11
TPSA 173.23 Ų
Rotatable bonds 7
Aromatic rings 2 / 3
Heavy atoms 28
Fraction sp³ C 0.50
Formula C₁₆H₂₀N₄O₈

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 173.2
  • −1 ≤ LogP ≤ 5 -1.47
Lipinski's Rule of Five Pass 1 violation
  • MW ≤ 500 Da 396.4
  • LogP ≤ 5 -1.47
  • H-bond donors ≤ 5 4
  • H-bond acceptors ≤ 10 11
Veber's rules Fail
  • Rotatable bonds ≤ 10 7
  • TPSA ≤ 140 Ų 173.2
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
O=[N+]([O-])c1ccc(-n2cc(CCO[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)nn2)cc1
InChI 
InChI=1S/C16H20N4O8/c21-8-12-13(22)14(23)15(24)16(28-12)27-6-5-9-7-19(18-17-9)10-1-3-11(4-2-10)20(25)26/h1-4,7,12-16,21-24H,5-6,8H2/t12-,13-,14+,15+,16+/m1/s1
InChIKey 
DGNCIOKJDPOOAI-OWYFMNJBSA-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)