Ligand profile

CHEMBL1162041

Bioactivity hit from ChEMBL on a similar protein.

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

Via homolog UniProt P71716 Formula C₁₇H₁₈N₆O₉S
pchembl 6.86 ~138.0 nM
Mol. weight 482.43 Da
Permeability Check
PAINS Alert

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL1162041
UniProt (similar protein)
P71716
pchembl
6.860 (~138.0 nM)
Target protein
VK055_5117

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 482.43 Da
LogP (Crippen) -1.87
H-bond donors 6
H-bond acceptors 14
TPSA 232.24 Ų
Rotatable bonds 6
Aromatic rings 3 / 4
Heavy atoms 33
Fraction sp³ C 0.29
Formula C₁₇H₁₈N₆O₉S

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 232.2
  • −1 ≤ LogP ≤ 5 -1.87
Lipinski's Rule of Five Fail 2 violations
  • MW ≤ 500 Da 482.4
  • LogP ≤ 5 -1.87
  • H-bond donors ≤ 5 6
  • H-bond acceptors ≤ 10 14
Veber's rules Fail
  • Rotatable bonds ≤ 10 6
  • TPSA ≤ 140 Ų 232.2
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 
Nc1ncnc2c1ncn2[C@@H]1O[C@H](COS(=O)(=O)NC(=O)c2cccc(O)c2O)[C@@H](O)[C@H]1O
InChI 
InChI=1S/C17H18N6O9S/c18-14-10-15(20-5-19-14)23(6-21-10)17-13(27)12(26)9(32-17)4-31-33(29,30)22-16(28)7-2-1-3-8(24)11(7)25/h1-3,5-6,9,12-13,17,24-27H,4H2,(H,22,28)(H2,18,19,20)/t9-,12-,13-,17-/m1/s1
InChIKey 
DDOFAAYVEMVKLG-DMEFTLKTSA-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)