Ligand profile

CHEMBL3818824

Bioactivity hit from ChEMBL on a similar protein.

Bound to: VK055_3709 — shikimate kinase family protein

Via homolog UniProt P56073 Formula C₁₆H₁₆O₅S
pchembl 6.25 ~562.3 nM
Mol. weight 320.37 Da
Permeability High
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL3818824
UniProt (similar protein)
P56073
pchembl
6.250 (~562.3 nM)
Target protein
VK055_3709

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 320.37 Da
LogP (Crippen) 1.92
H-bond donors 3
H-bond acceptors 5
TPSA 86.99 Ų
Rotatable bonds 4
Aromatic rings 2 / 3
Heavy atoms 22
Fraction sp³ C 0.31
Formula C₁₆H₁₆O₅S

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 87.0
  • −1 ≤ LogP ≤ 5 1.92
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 320.4
  • LogP ≤ 5 1.92
  • H-bond donors ≤ 5 3
  • H-bond acceptors ≤ 10 5
Veber's rules Pass
  • Rotatable bonds ≤ 10 4
  • TPSA ≤ 140 Ų 87.0
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
O=C(O)C1=C[C@@H](O)[C@@H](O)[C@H](OCc2ccc3sccc3c2)C1
InChI 
InChI=1S/C16H16O5S/c17-12-6-11(16(19)20)7-13(15(12)18)21-8-9-1-2-14-10(5-9)3-4-22-14/h1-6,12-13,15,17-18H,7-8H2,(H,19,20)/t12-,13-,15-/m1/s1
InChIKey 
NARPVYIWMVNSQH-UMVBOHGHSA-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
PF01202

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_3709.

PDB 7

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

Ligand PDB entry

ChEMBL 2

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)