Ligand profile

CHEMBL218023

Bioactivity hit from ChEMBL on a similar protein.

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

Via homolog UniProt P71716 Formula C₁₈H₂₀N₆O₇S

pchembl 8.64 ~2.3 nM

Mol. weight 464.46 Da

Permeability Check

PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID: CHEMBL218023
UniProt (similar protein): P71716
pchembl: 8.640 (~2.3 nM)
Target protein: VK055_5117

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 464.46 Da

LogP (Crippen) -0.91

H-bond donors 5

H-bond acceptors 12

TPSA 202.78 Å²

Rotatable bonds 6

Aromatic rings 3 / 4

Heavy atoms 32

Fraction sp³ C 0.33

Formula C₁₈H₂₀N₆O₇S

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 Å² and −1 ≤ LogP ≤ 5 are treated as a favorable small-molecule permeability screen.

TPSA ≤ 90 Å² 202.8
−1 ≤ LogP ≤ 5 -0.91

Lipinski's Rule of Five Pass 1 violation

MW ≤ 500 Da 464.5
LogP ≤ 5 -0.91
H-bond donors ≤ 5 5
H-bond acceptors ≤ 10 12

Veber's rules Fail

Rotatable bonds ≤ 10 6
TPSA ≤ 140 Å² 202.8

PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES

Nc1ncnc2ncn([C@@H]3C[C@H](COS(=O)(=O)NC(=O)c4ccccc4O)[C@@H](O)[C@H]3O)c12

InChI

InChI=1S/C18H20N6O7S/c19-16-13-17(21-7-20-16)22-8-24(13)11-5-9(14(26)15(11)27)6-31-32(29,30)23-18(28)10-3-1-2-4-12(10)25/h1-4,7-9,11,14-15,25-27H,5-6H2,(H,23,28)(H2,19,20,21)/t9-,11-,14-,15+/m1/s1

InChIKey

BTIHYYWXCLTVAO-VGKMCQHDSA-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.

ChEMBL ChEMBL compound CHEMBL218023 →
UniProt UniProt P71716 (homolog) →
PubChem PubChem (by InChIKey) →
Cheminformatics SwissADME prediction →
Cheminformatics SwissTargetPrediction →
Web Google Scholar (search “CHEMBL218023”) →

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)