(E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid (CHEBI:167669)

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CHEBI:167669 - (E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid

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ChEBI ID	CHEBI:167669
ChEBI Name	(E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid
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ASCII Name	(E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid
Definition	A member of the class of 1,3-thiazoles that is 1,3-thiazole substituted by (2E)-2-(2-carboxybenzylidene)hydrazinyl and 2-chlorophenyl groups at positions 2 and 4, respectively. It is a potent inhibitor of human dihydroorotate dehydrogenase (hDHODH) with IC₅₀ of 32 nM. It exhibits antineoplastic activity and broad-spectrum antiviral activity against various RNA viruses including influenza A, Zika, Ebola, and SARS-CoV-2 viruses.
Last Modified	12 April 2021
Submitter	R. Stephan
Downloads	Molfile

Formula	C17H12ClN3O2S
Net Charge	0
Average Mass	357.822
Monoisotopic Mass	357.03388
SMILES	O=C(O)c1ccccc1/C=N/Nc1nc(-c2ccccc2Cl)cs1
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+
InChIKey	DDEIFUOYHWEWSS-DJKKODMXSA-N

Roles Classification

Chemical Role:	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:	EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor An EC 1.3.5.* (oxidoreductase acting on CH-CH of donor with a quinone or related compound as acceptor) inhibitor that interferes with the action of dihydroorotate dehydrogenase (quinone), EC 1.3.5.2. apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. antiviral agent A substance that destroys or inhibits replication of viruses. anticoronaviral agent Any antiviral agent which inhibits the activity of coronaviruses.
Application:	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	(E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid (CHEBI:167669) has role anticoronaviral agent (CHEBI:149553)
	(E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid (CHEBI:167669) has role antineoplastic agent (CHEBI:35610)
	(E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid (CHEBI:167669) has role antiviral agent (CHEBI:22587)
	(E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid (CHEBI:167669) has role apoptosis inducer (CHEBI:68495)
	(E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid (CHEBI:167669) has role EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor (CHEBI:77103)
	(E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid (CHEBI:167669) is a 1,3-thiazoles (CHEBI:38418)
	(E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid (CHEBI:167669) is a benzoic acids (CHEBI:22723)
	(E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid (CHEBI:167669) is a hydrazone (CHEBI:38532)
	(E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid (CHEBI:167669) is a monochlorobenzenes (CHEBI:83403)

IUPAC Name
2-[(E)-{2-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene}methyl]benzoic acid

Synonym	Source
S312	SUBMITTER

Manual Xrefs	Databases
3X2	PDBeChem

Citations