Ligand profile

CHEMBL1537

Bioactivity hit from ChEMBL on a similar protein.

Bound to: VK055_4371 — sugar (and other) transporter family protein

Via homolog UniProt O88909 Formula C₂₀H₂₃N₅O₆S
Mol. weight 461.50 Da
Permeability Check
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL1537
UniProt (similar protein)
O88909
Target protein
VK055_4371

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 461.50 Da
LogP (Crippen) 0.09
H-bond donors 4
H-bond acceptors 6
TPSA 148.15 Ų
Rotatable bonds 5
Aromatic rings 1 / 4
Heavy atoms 32
Fraction sp³ C 0.45
Formula C₂₀H₂₃N₅O₆S

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 148.1
  • −1 ≤ LogP ≤ 5 0.09
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 461.5
  • LogP ≤ 5 0.09
  • H-bond donors ≤ 5 4
  • H-bond acceptors ≤ 10 6
Veber's rules Fail
  • Rotatable bonds ≤ 10 5
  • TPSA ≤ 140 Ų 148.1
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](NC(=O)N3CCNC3=O)c3ccccc3)C(=O)N2[C@H]1C(=O)O
InChI 
InChI=1S/C20H23N5O6S/c1-20(2)13(17(28)29)25-15(27)12(16(25)32-20)22-14(26)11(10-6-4-3-5-7-10)23-19(31)24-9-8-21-18(24)30/h3-7,11-13,16H,8-9H2,1-2H3,(H,21,30)(H,22,26)(H,23,31)(H,28,29)/t11-,12-,13+,16-/m1/s1
InChIKey 
JTWOMNBEOCYFNV-NFFDBFGFSA-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
PF00083

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_4371.

ChEMBL 35

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)