Ligand profile

ZINC20663710

Virtual-screening candidate from ZINC.

Bound to: VK055_1548 — 3-phosphoshikimate 1-carboxyvinyltransferase

Via homolog UniProt P0A6D3 Formula C₂₃H₂₇NO₃
Tanimoto 0.54
Mol. weight 365.47 Da
Permeability High
PAINS Alert

Identifiers

Database identifiers and provenance.

Ligand ID
ZINC20663710
UniProt (similar protein)
P0A6D3
Tanimoto
0.544
Target protein
VK055_1548

Structure

2D representation rendered from SMILES.

Physicochemical properties

Computed with RDKit from SMILES.

Molecular weight 365.47 Da
LogP (Crippen) 4.97
H-bond donors 1
H-bond acceptors 4
TPSA 49.77 Ų
Rotatable bonds 6
Aromatic rings 2 / 3
Heavy atoms 27
Fraction sp³ C 0.35
Formula C₂₃H₂₇NO₃

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 49.8
  • −1 ≤ LogP ≤ 5 4.97
Lipinski's Rule of Five Pass 0 violations
  • MW ≤ 500 Da 365.5
  • LogP ≤ 5 4.97
  • H-bond donors ≤ 5 1
  • H-bond acceptors ≤ 10 4
Veber's rules Pass
  • Rotatable bonds ≤ 10 6
  • TPSA ≤ 140 Ų 49.8
PAINS Alert

Matches PAINS filter: mannich_A(296). May be a frequent false positive in HTS — review carefully.

Chemical representations

Canonical representations for cheminformatics workflows.

SMILES 
CCN(CC)Cc1c(O)ccc2c1O/C(=C\c1ccc(C(C)C)cc1)C2=O
InChI 
InChI=1S/C23H27NO3/c1-5-24(6-2)14-19-20(25)12-11-18-22(26)21(27-23(18)19)13-16-7-9-17(10-8-16)15(3)4/h7-13,15,25H,5-6,14H2,1-4H3/b21-13-
InChIKey 
PUXOHZIATMBXSH-BKUYFWCQSA-N

Provenance

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

Method
LigQ nearest_k
Query
CHEMBL334500
Homolog
P0A6D3

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_1548.

PDB 10

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

Ligand PDB entry

ChEMBL 14

Compounds with measured inhibitory activity on this target (higher pchembl = more potent).

Compound Potency (pchembl)

ZINC 49

Virtual screening candidates selected by structural similarity to known actives (Tanimoto ≥ 0.5).

Compound Similarity (Tanimoto)