Ligand profile

CHEMBL4168282

Bioactivity hit from ChEMBL on a similar protein.

Bound to: VK055_5117 — 2,3-dihydroxybenzoate-AMP ligase

Via homolog UniProt P71716 Formula C₁₉H₁₉N₇O₆S
pchembl 6.92 ~120.2 nM
Mol. weight 473.47 Da
Permeability Check
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL4168282
UniProt (similar protein)
P71716
pchembl
6.920 (~120.2 nM)
Target protein
VK055_5117

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 473.47 Da
LogP (Crippen) -1.15
H-bond donors 5
H-bond acceptors 11
TPSA 198.34 Ų
Rotatable bonds 5
Aromatic rings 4 / 5
Heavy atoms 33
Fraction sp³ C 0.26
Formula C₁₉H₁₉N₇O₆S

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 198.3
  • −1 ≤ LogP ≤ 5 -1.15
Lipinski's Rule of Five Pass 1 violation
  • MW ≤ 500 Da 473.5
  • LogP ≤ 5 -1.15
  • H-bond donors ≤ 5 5
  • H-bond acceptors ≤ 10 11
Veber's rules Fail
  • Rotatable bonds ≤ 10 5
  • TPSA ≤ 140 Ų 198.3
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
Nc1ncnc2c1ncn2[C@@H]1O[C@H](CNS(=O)(=O)c2c[nH]c3ccccc3c2=O)[C@@H](O)[C@H]1O
InChI 
InChI=1S/C19H19N7O6S/c20-17-13-18(23-7-22-17)26(8-24-13)19-16(29)15(28)11(32-19)5-25-33(30,31)12-6-21-10-4-2-1-3-9(10)14(12)27/h1-4,6-8,11,15-16,19,25,28-29H,5H2,(H,21,27)(H2,20,22,23)/t11-,15-,16-,19-/m1/s1
InChIKey 
PRFXKDATEQMALE-LUTMRVPUSA-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
PF00501' 'PF13193

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_5117.

PDB 7

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

Ligand PDB entry

ChEMBL 81

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)