Ligand profile

8SW

Ligand co-crystallized with a similar protein (Protein Data Bank).

Bound to: KP13_05375 — Ferric enterobactin receptor

Via homolog PDB 5nc3 UniProt Q05098 Formula C₃₂H₃₂N₆O₁₂
Mol. weight 692.64 Da
Permeability Check
PAINS Alert

Identifiers

Database identifiers and provenance.

Ligand ID
8SW
PDB
5nc3
UniProt (similar protein)
Q05098
Target protein
KP13_05375

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 692.64 Da
LogP (Crippen) -1.77
H-bond donors 12
H-bond acceptors 12
TPSA 295.98 Ų
Rotatable bonds 14
Aromatic rings 3 / 3
Heavy atoms 50
Fraction sp³ C 0.19
Formula C₃₂H₃₂N₆O₁₂

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 296.0
  • −1 ≤ LogP ≤ 5 -1.77
Lipinski's Rule of Five Fail 3 violations
  • MW ≤ 500 Da 692.6
  • LogP ≤ 5 -1.77
  • H-bond donors ≤ 5 12
  • H-bond acceptors ≤ 10 12
Veber's rules Fail
  • Rotatable bonds ≤ 10 14
  • TPSA ≤ 140 Ų 296.0
PAINS Alert

Matches PAINS filter: catechol_A(92). May be a frequent false positive in HTS — review carefully.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
C#CCNC(=O)C(CNC(=O)C(CNC(=O)CNC(=O)c1cccc(c1O)O)NC(=O)c2cccc(c2O)O)NC(=O)c3cccc(c3O)O
InChI 
InChI=1S/C32H32N6O12/c1-2-12-33-31(49)20(38-30(48)18-8-5-11-23(41)27(18)45)14-35-32(50)19(37-29(47)17-7-4-10-22(40)26(17)44)13-34-24(42)15-36-28(46)16-6-3-9-21(39)25(16)43/h1,3-11,19-20,39-41,43-45H,12-15H2,(H,33,49)(H,34,42)(H,35,50)(H,36,46)(H,37,47)(H,38,48)
InChIKey 
XJMZSRWAQFOMTB-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
PDB
Binding sites
PF00593

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_05375.

PDB 12

Ligands co-crystallized with this protein (structural evidence).

Ligand PDB entry

ZINC 50

Virtual screening candidates selected by structural similarity to known actives (Tanimoto ≥ 0.5).

Compound Similarity (Tanimoto)