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

CHEBI:167669 ·resolve ·ANTIVIRAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:22723 CHEBI:22723
CHEBI:38418 CHEBI:38418
CHEBI:38532 CHEBI:38532
CHEBI:83403 CHEBI:83403

Chemical structure

Computed structure properties
Molecular formula	C17H12ClN3O2S
Charge	0
Average mass	357.822 Da
Monoisotopic mass	357.03388 Da
Source	ChEBI
InChIKey	DDEIFUOYHWEWSS-DJKKODMXSA-N

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+

Also called

2-[(E)-{2-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene}methyl]benzoic acid (EXACT_SYNONYM)— chebi
S312 (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

pdb-ccd:3X2

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:149553 CHEBI:149553
CHEBI:22587 CHEBI:22587

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:167669`	(E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid	`antibioticmech:chebi-8403b20400`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.