Ligand profile

CHEMBL592869

Bioactivity hit from ChEMBL on a similar protein.

Bound to: VK055_2229 — alkaline phosphatase H

Via homolog UniProt P10696 Formula C₁₄H₁₄N₂O₃S
pchembl 6.22 ~602.6 nM
Mol. weight 290.34 Da
Permeability High
PAINS Alert

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL592869
UniProt (similar protein)
P10696
pchembl
6.220 (~602.6 nM)
Target protein
VK055_2229

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 290.34 Da
LogP (Crippen) 2.48
H-bond donors 2
H-bond acceptors 6
TPSA 83.31 Ų
Rotatable bonds 4
Aromatic rings 2 / 2
Heavy atoms 20
Fraction sp³ C 0.21
Formula C₁₄H₁₄N₂O₃S

Drug-likeness

Descriptor-based ADME screening flags from SMILES. These are not experimental toxicity results.

Permeability proxy High

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 83.3
  • −1 ≤ LogP ≤ 5 2.48
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 290.3
  • LogP ≤ 5 2.48
  • H-bond donors ≤ 5 2
  • H-bond acceptors ≤ 10 6
Veber's rules Pass
  • Rotatable bonds ≤ 10 4
  • TPSA ≤ 140 Ų 83.3
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 
Cc1cc(C)nc(SCC(=O)c2ccc(O)c(O)c2)n1
InChI 
InChI=1S/C14H14N2O3S/c1-8-5-9(2)16-14(15-8)20-7-13(19)10-3-4-11(17)12(18)6-10/h3-6,17-18H,7H2,1-2H3
InChIKey 
JQXFBAGVXOGSNK-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
PF00245

External resources

Open this ligand in third-party databases and cheminformatics tools.

Other ligands for this protein

Quick navigation to other ligands bound to VK055_2229.

PDB 7

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

Ligand PDB entry

ChEMBL 26

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)