Ligand profile

CHEMBL3647122

Bioactivity hit from ChEMBL on a similar protein.

Bound to: VK055_2471 — UDP-3-O-[3-hydroxymyristoyl] N-acetylglucosaminedeacetylase

Via homolog UniProt P47205 Formula C₂₀H₂₂N₂O₄S
pchembl 9.62 ~0.2 nM
Mol. weight 386.47 Da
Permeability Check
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL3647122
UniProt (similar protein)
P47205
pchembl
9.620 (~0.2 nM)
Target protein
VK055_2471

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 386.47 Da
LogP (Crippen) 2.78
H-bond donors 2
H-bond acceptors 5
TPSA 107.26 Ų
Rotatable bonds 6
Aromatic rings 2 / 2
Heavy atoms 27
Fraction sp³ C 0.30
Formula C₂₀H₂₂N₂O₄S

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 107.3
  • −1 ≤ LogP ≤ 5 2.78
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 386.5
  • LogP ≤ 5 2.78
  • H-bond donors ≤ 5 2
  • H-bond acceptors ≤ 10 5
Veber's rules Pass
  • Rotatable bonds ≤ 10 6
  • TPSA ≤ 140 Ų 107.3
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
Cc1cc(CCC(C)(C(=O)NO)S(C)(=O)=O)ccc1-c1ccc(C#N)cc1
InChI 
InChI=1S/C20H22N2O4S/c1-14-12-15(10-11-20(2,19(23)22-24)27(3,25)26)6-9-18(14)17-7-4-16(13-21)5-8-17/h4-9,12,24H,10-11H2,1-3H3,(H,22,23)
InChIKey 
DBSXYZNRCVYIOL-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
Activity
269022
Binding sites
PF03331

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_2471.

PDB 41

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

Ligand PDB entry

ChEMBL 99

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)