S312   Click here for help

GtoPdb Ligand ID: 11163

Synonyms: compound 19 [PMID: 26443076]
PDB Ligand
Compound class: Synthetic organic
Comment: S312 is an inhibitor of dihydroorotate dehydrogenase (DHODH) [2]. It was initially designed and reported for application as an anti-inflammatory agent [1] and was effective in a mouse rheumatoid arthritis model. S312 has most recently been explored for antiviral activity against RNA viruses, including influenza virus strains, Zika and Ebola viruses and SARS-CoV-2, based on the rationale that viruses depend on host pyrimidine synthesis to maintain their replication rate, and that therefore inhibiting a crucial step in this synthetic pathway has potential to limit viral replication. Mechanistically, S312 binds at the putative ubiquinone binding tunnel within the DHODH active site.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 102.82
Molecular weight 357.03
XLogP 5.41
No. Lipinski's rules broken 1
Click here for help
Canonical SMILES Clc1ccccc1c1csc(n1)N/N=C/c1ccccc1C(=O)O
Isomeric SMILES Clc1ccccc1c1csc(n1)N/N=C/c1ccccc1C(=O)O
InChI InChI=1S/C17H12ClN3O2S/c18-14-8-4-3-7-13(14)15-10-24-17(20-15)21-19-9-11-5-1-2-6-12(11)16(22)23/h1-10H,(H,20,21)(H,22,23)/b19-9+
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
2-[(Z)-[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid
Synonyms Click here for help
compound 19 [PMID: 26443076]
Database Links Click here for help
GtoPdb PubChem SID 434122223
PubChem CID 139033340
RCSB PDB Ligand 3X2
Search Google for chemical match using the InChIKey DDEIFUOYHWEWSS-DJKKODMXSA-N
Search Google for chemicals with the same backbone DDEIFUOYHWEWSS
UniChem Compound Search for chemical match using the InChIKey DDEIFUOYHWEWSS-DJKKODMXSA-N
UniChem Connectivity Search for chemical match using the InChIKey DDEIFUOYHWEWSS-DJKKODMXSA-N