Ligand profile

CHEMBL4640123

Bioactivity hit from ChEMBL on a similar protein.

Bound to: VK055_1677 — tyrosine phosphatase family protein

Via homolog UniProt I6WXK4 Formula C₂₀H₁₈N₂O₆
pchembl 7.24 ~57.5 nM
Mol. weight 382.37 Da
Permeability Check
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL4640123
UniProt (similar protein)
I6WXK4
pchembl
7.240 (~57.5 nM)
Target protein
VK055_1677

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 382.37 Da
LogP (Crippen) 1.67
H-bond donors 3
H-bond acceptors 6
TPSA 116.17 Ų
Rotatable bonds 3
Aromatic rings 2 / 2
Heavy atoms 28
Fraction sp³ C 0.15
Formula C₂₀H₁₈N₂O₆

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 116.2
  • −1 ≤ LogP ≤ 5 1.67
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 382.4
  • LogP ≤ 5 1.67
  • H-bond donors ≤ 5 3
  • H-bond acceptors ≤ 10 6
Veber's rules Pass
  • Rotatable bonds ≤ 10 3
  • TPSA ≤ 140 Ų 116.2
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
COC(=O)c1cc(C#Cc2cccc(NC(=O)C(=O)O)c2)c(N(C)C)cc1O
InChI 
InChI=1S/C20H18N2O6/c1-22(2)16-11-17(23)15(20(27)28-3)10-13(16)8-7-12-5-4-6-14(9-12)21-18(24)19(25)26/h4-6,9-11,23H,1-3H3,(H,21,24)(H,25,26)
InChIKey 
OVSBJBPGJKOFJT-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
1116964
Binding sites
PF13350

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_1677.

ChEMBL 75

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)