Ligand profile

CHEMBL589396

Bioactivity hit from ChEMBL on a similar protein.

Bound to: VK055_1452 — short chain dehydrogenase family protein

Via homolog UniProt P37058 Formula C₁₇H₁₅NO₃
pchembl 8.10 ~7.9 nM
Mol. weight 281.31 Da
Permeability High
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL589396
UniProt (similar protein)
P37058
pchembl
8.100 (~7.9 nM)
Target protein
VK055_1452

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 281.31 Da
LogP (Crippen) 2.99
H-bond donors 1
H-bond acceptors 4
TPSA 63.33 Ų
Rotatable bonds 3
Aromatic rings 3 / 3
Heavy atoms 21
Fraction sp³ C 0.18
Formula C₁₇H₁₅NO₃

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 63.3
  • −1 ≤ LogP ≤ 5 2.99
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 281.3
  • LogP ≤ 5 2.99
  • H-bond donors ≤ 5 1
  • H-bond acceptors ≤ 10 4
Veber's rules Pass
  • Rotatable bonds ≤ 10 3
  • TPSA ≤ 140 Ų 63.3
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
Cc1cccc(CCc2cc(=O)oc3cc(O)ccc23)n1
InChI 
InChI=1S/C17H15NO3/c1-11-3-2-4-13(18-11)6-5-12-9-17(20)21-16-10-14(19)7-8-15(12)16/h2-4,7-10,19H,5-6H2,1H3
InChIKey 
LDCRVNBWINORDP-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
Binding sites
PF00106

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_1452.

PDB 1

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)