Ligand profile

CHEMBL58550

Bioactivity hit from ChEMBL on a similar protein.

Bound to: KP13_01960 — Dihydrofolate reductase

Via homolog UniProt P0ABQ4 Formula C₁₈H₂₄N₄O
pchembl 8.80 ~1.6 nM
Mol. weight 312.42 Da
Permeability High
PAINS Clean

Identifiers

Database identifiers and provenance.

Ligand ID
CHEMBL58550
UniProt (similar protein)
P0ABQ4
pchembl
8.800 (~1.6 nM)
Target protein
KP13_01960

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 312.42 Da
LogP (Crippen) 2.92
H-bond donors 2
H-bond acceptors 5
TPSA 87.05 Ų
Rotatable bonds 7
Aromatic rings 2 / 2
Heavy atoms 23
Fraction sp³ C 0.33
Formula C₁₈H₂₄N₄O

Drug-likeness

Descriptor-based ADME screening flags from SMILES. These are not experimental toxicity results.

Permeability proxy High

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 87.0
  • −1 ≤ LogP ≤ 5 2.92
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 312.4
  • LogP ≤ 5 2.92
  • H-bond donors ≤ 5 2
  • H-bond acceptors ≤ 10 5
Veber's rules Pass
  • Rotatable bonds ≤ 10 7
  • TPSA ≤ 140 Ų 87.0
PAINS Clean

No PAINS structural alerts detected.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
C=CCc1cc(Cc2cnc(N)nc2N)cc(CCC)c1OC
InChI 
InChI=1S/C18H24N4O/c1-4-6-13-8-12(9-14(7-5-2)16(13)23-3)10-15-11-21-18(20)22-17(15)19/h4,8-9,11H,1,5-7,10H2,2-3H3,(H4,19,20,21,22)
InChIKey 
VSESKFNACWACPG-UHFFFAOYSA-N

Provenance

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

Method
LigQ sequence
Source
ChEMBL
Binding sites
PF00186

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_01960.

PDB 34

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)