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.
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2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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+
InChI Key DDEIFUOYHWEWSS-DJKKODMXSA-N
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
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