Ligand profile

CHEMBL149394

Bioactivity hit from ChEMBL on a similar protein.

Bound to: VK055_1200 — major Facilitator Superfamily protein

Via homolog UniProt Q9NRA2 Formula C₂₁H₂₃NO₄
Mol. weight 353.42 Da
Permeability High
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL149394
UniProt (similar protein)
Q9NRA2
Target protein
VK055_1200

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 353.42 Da
LogP (Crippen) 4.02
H-bond donors 2
H-bond acceptors 3
TPSA 75.63 Ų
Rotatable bonds 6
Aromatic rings 2 / 3
Heavy atoms 26
Fraction sp³ C 0.33
Formula C₂₁H₂₃NO₄

Drug-likeness

Descriptor-based ADME screening flags from SMILES. These are not experimental toxicity results.

Permeability proxy High

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 75.6
  • −1 ≤ LogP ≤ 5 4.02
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 353.4
  • LogP ≤ 5 4.02
  • H-bond donors ≤ 5 2
  • H-bond acceptors ≤ 10 3
Veber's rules Pass
  • Rotatable bonds ≤ 10 6
  • TPSA ≤ 140 Ų 75.6
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
CC(C)C[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O
InChI 
InChI=1S/C21H23NO4/c1-13(2)11-19(20(23)24)22-21(25)26-12-18-16-9-5-3-7-14(16)15-8-4-6-10-17(15)18/h3-10,13,18-19H,11-12H2,1-2H3,(H,22,25)(H,23,24)/t19-/m0/s1
InChIKey 
CBPJQFCAFFNICX-IBGZPJMESA-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
Active
Binding sites
PF07690

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_1200.

PDB 1

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

Ligand PDB entry

ChEMBL 29

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)