Ligand profile

OSA

Ligand co-crystallized with a similar protein (Protein Data Bank).

Bound to: VK055_3709 — shikimate kinase family protein

Via homolog PDB 3n2e UniProt P56073 Formula C₂₀H₁₅N₃O₈S₂
Mol. weight 489.49 Da
Permeability Check
PAINS Alert

Identifiers

Database identifiers and provenance.

Ligand ID
OSA
PDB
3n2e
UniProt (similar protein)
P56073
Target protein
VK055_3709

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 489.49 Da
LogP (Crippen) 3.90
H-bond donors 5
H-bond acceptors 9
TPSA 199.94 Ų
Rotatable bonds 4
Aromatic rings 4 / 4
Heavy atoms 33
Fraction sp³ C 0.00
Formula C₂₀H₁₅N₃O₈S₂

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 199.9
  • −1 ≤ LogP ≤ 5 3.90
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 489.5
  • LogP ≤ 5 3.90
  • H-bond donors ≤ 5 5
  • H-bond acceptors ≤ 10 9
Veber's rules Fail
  • Rotatable bonds ≤ 10 4
  • TPSA ≤ 140 Ų 199.9
PAINS Alert

Matches PAINS filter: azo_A(324). May be a frequent false positive in HTS — review carefully.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
c1cc2c(cc1N)cc(c(c2O)/N=N/c3ccc4c(c3)cc(cc4O)S(=O)(=O)O)S(=O)(=O)O
InChI 
InChI=1S/C20H15N3O8S2/c21-12-1-3-16-10(5-12)8-18(33(29,30)31)19(20(16)25)23-22-13-2-4-15-11(6-13)7-14(9-17(15)24)32(26,27)28/h1-9,24-25H,21H2,(H,26,27,28)(H,29,30,31)/b23-22+
InChIKey 
ZSHNSNDVNDUHIM-GHVJWSGMSA-N

Provenance

Annotation context from LigQ_2, the internal Target step that collects PDB, ChEMBL, and ZINC ligand evidence.

Method
LigQ nearest_k
Source
PDB
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 6

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

Ligand PDB entry

ChEMBL 3

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)