Ligand profile

CHEMBL4458393

Bioactivity hit from ChEMBL on a similar protein.

Bound to: KP13_02169 — D-3-phosphoglycerate dehydrogenase

Via homolog UniProt O43175 Formula C₂₁H₂₁N₃O₅S
pchembl 7.60 ~25.1 nM
Mol. weight 427.48 Da
Permeability Check
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL4458393
UniProt (similar protein)
O43175
pchembl
7.600 (~25.1 nM)
Target protein
KP13_02169

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 427.48 Da
LogP (Crippen) 2.44
H-bond donors 2
H-bond acceptors 6
TPSA 118.36 Ų
Rotatable bonds 7
Aromatic rings 3 / 3
Heavy atoms 30
Fraction sp³ C 0.19
Formula C₂₁H₂₁N₃O₅S

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 118.4
  • −1 ≤ LogP ≤ 5 2.44
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 427.5
  • LogP ≤ 5 2.44
  • H-bond donors ≤ 5 2
  • H-bond acceptors ≤ 10 6
Veber's rules Pass
  • Rotatable bonds ≤ 10 7
  • TPSA ≤ 140 Ų 118.4
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
C[C@@H](NC(=O)c1cc(-c2ccccc2)nn1C)c1ccc(S(=O)(=O)CC(=O)O)cc1
InChI 
InChI=1S/C21H21N3O5S/c1-14(15-8-10-17(11-9-15)30(28,29)13-20(25)26)22-21(27)19-12-18(23-24(19)2)16-6-4-3-5-7-16/h3-12,14H,13H2,1-2H3,(H,22,27)(H,25,26)/t14-/m1/s1
InChIKey 
JWRWQGAIWWMMBE-CQSZACIVSA-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
1160807
Curation
pdb_similarity_tanimoto
Binding sites
PF00389' 'PF02826

External resources

Open this ligand in third-party databases and cheminformatics tools.

Other ligands for this protein

Quick navigation to other ligands bound to KP13_02169.

PDB 20

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

Ligand PDB entry

ChEMBL 99

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)