Ligand profile

CHEMBL4299749

Bioactivity hit from ChEMBL on a similar protein.

Bound to: VK055_5117 — 2,3-dihydroxybenzoate-AMP ligase

Via homolog UniProt P71716 Formula C₂₄H₃₃N₉O₆S
pchembl 7.84 ~14.5 nM
Mol. weight 575.65 Da
Permeability Check
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL4299749
UniProt (similar protein)
P71716
pchembl
7.840 (~14.5 nM)
Target protein
VK055_5117

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 575.65 Da
LogP (Crippen) -0.41
H-bond donors 5
H-bond acceptors 13
TPSA 214.47 Ų
Rotatable bonds 8
Aromatic rings 4 / 5
Heavy atoms 40
Fraction sp³ C 0.46
Formula C₂₄H₃₃N₉O₆S

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 214.5
  • −1 ≤ LogP ≤ 5 -0.41
Lipinski's Rule of Five Fail 2 violations
  • MW ≤ 500 Da 575.7
  • LogP ≤ 5 -0.41
  • H-bond donors ≤ 5 5
  • H-bond acceptors ≤ 10 13
Veber's rules Fail
  • Rotatable bonds ≤ 10 8
  • TPSA ≤ 140 Ų 214.5
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
CCN(CC)CC.Nc1ncnc2c1ncn2[C@@H]1O[C@H](CNS(=O)(=O)c2n[nH]c3ccccc3c2=O)[C@@H](O)[C@H]1O
InChI 
InChI=1S/C18H18N8O6S.C6H15N/c19-15-11-16(21-6-20-15)26(7-22-11)18-14(29)13(28)10(32-18)5-23-33(30,31)17-12(27)8-3-1-2-4-9(8)24-25-17;1-4-7(5-2)6-3/h1-4,6-7,10,13-14,18,23,28-29H,5H2,(H,24,27)(H2,19,20,21);4-6H2,1-3H3/t10-,13-,14-,18-;/m1./s1
InChIKey 
ROGKYOIYPKHIAW-GCHWKPKDSA-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
Curation
pdb_similarity_tanimoto
Binding sites
PF00501' 'PF13193

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_5117.

PDB 7

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

Ligand PDB entry

ChEMBL 81

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)