Ligand profile

CHEMBL238371

Bioactivity hit from ChEMBL on a similar protein.

Bound to: KP13_00085 — Regulatory protein uhpC

Via homolog UniProt O43826 Formula C₂₈H₂₀O₁₂
pchembl 8.30 ~5.0 nM
Mol. weight 548.46 Da
Permeability Check
PAINS Alert

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL238371
UniProt (similar protein)
O43826
pchembl
8.300 (~5.0 nM)
Target protein
KP13_00085

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 548.46 Da
LogP (Crippen) 2.31
H-bond donors 6
H-bond acceptors 10
TPSA 223.80 Ų
Rotatable bonds 9
Aromatic rings 3 / 4
Heavy atoms 40
Fraction sp³ C 0.14
Formula C₂₈H₂₀O₁₂

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 223.8
  • −1 ≤ LogP ≤ 5 2.31
Lipinski's Rule of Five Fail 2 violations
  • MW ≤ 500 Da 548.5
  • LogP ≤ 5 2.31
  • H-bond donors ≤ 5 6
  • H-bond acceptors ≤ 10 10
Veber's rules Fail
  • Rotatable bonds ≤ 10 9
  • TPSA ≤ 140 Ų 223.8
PAINS Alert

Matches PAINS filter: quinone_A(370). May be a frequent false positive in HTS — review carefully.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
O=C(O)CC(O)CCC(=O)c1cccc(O)c1C(=O)c1c(C(=O)O)c(O)cc2c1C(=O)c1c(O)cccc1C2=O
InChI 
InChI=1S/C28H20O12/c29-11(9-19(34)35)7-8-15(30)12-3-1-5-16(31)20(12)27(38)24-22-14(10-18(33)23(24)28(39)40)25(36)13-4-2-6-17(32)21(13)26(22)37/h1-6,10-11,29,31-33H,7-9H2,(H,34,35)(H,39,40)
InChIKey 
XFESZXMDORIFAO-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
Binding sites
PF07690

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_00085.

PDB 1

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

Ligand PDB entry

ChEMBL 6

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)