Ligand profile

CHEMBL1162037

Bioactivity hit from ChEMBL on a similar protein.

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

Via homolog UniProt P71716 Formula C₁₈H₂₀N₆O₈S
pchembl 7.85 ~14.1 nM
Mol. weight 480.46 Da
Permeability Check
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL1162037
UniProt (similar protein)
P71716
pchembl
7.850 (~14.1 nM)
Target protein
VK055_5117

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 480.46 Da
LogP (Crippen) -1.27
H-bond donors 5
H-bond acceptors 13
TPSA 212.01 Ų
Rotatable bonds 6
Aromatic rings 3 / 4
Heavy atoms 33
Fraction sp³ C 0.33
Formula C₁₈H₂₀N₆O₈S

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 212.0
  • −1 ≤ LogP ≤ 5 -1.27
Lipinski's Rule of Five Pass 1 violation
  • MW ≤ 500 Da 480.5
  • LogP ≤ 5 -1.27
  • H-bond donors ≤ 5 5
  • H-bond acceptors ≤ 10 13
Veber's rules Fail
  • Rotatable bonds ≤ 10 6
  • TPSA ≤ 140 Ų 212.0
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
Cc1ccc(C(=O)NS(=O)(=O)OC[C@H]2O[C@@H](n3cnc4c(N)ncnc43)[C@H](O)[C@@H]2O)c(O)c1
InChI 
InChI=1S/C18H20N6O8S/c1-8-2-3-9(10(25)4-8)17(28)23-33(29,30)31-5-11-13(26)14(27)18(32-11)24-7-22-12-15(19)20-6-21-16(12)24/h2-4,6-7,11,13-14,18,25-27H,5H2,1H3,(H,23,28)(H2,19,20,21)/t11-,13-,14-,18-/m1/s1
InChIKey 
NMDBISLFAPBKLY-XWXWGSFUSA-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)