CHEBI:90239 - tiazofurine

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ChEBI Name tiazofurine
ChEBI ID CHEBI:90239
Definition A C-glycosyl compound that is 1,3-thiazole-4-carboxamide in which the hydrogen at position 2 has been replaced by a β-D-ribofuranosyl group. It is metabolised to thiazole-4-carboxamide adenine dinucleotide (TAD), a selective inhibitor of inosine monophosphate dehydrogenase (IMP dehydrogenase).
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C9H12N2O5S
Net Charge 0
Average Mass 260.268
Monoisotopic Mass 260.047
InChI InChI=1S/C9H12N2O5S/c10-8(15)3-2-17-9(11-3)7-6(14)5(13)4(1-12)16-7/h2,4-7,12-14H,1H2,(H2,10,15)/t4-,5-,6-,7-/m1/s1
InChIKey FVRDYQYEVDDKCR-DBRKOABJSA-N
SMILES O1[C@@H](C=2SC=C(N2)C(N)=O)[C@H](O)[C@H](O)[C@H]1CO
Roles Classification
Biological Role(s): EC 1.1.1.205 (IMP dehydrogenase) inhibitor
An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of IMP dehydrogenase (EC 1.1.1.205), so blocking de novo biosynthesis of purine nucleotides.
Application(s): prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing tiazofurine (CHEBI:90239) has functional parent β-D-ribose (CHEBI:47002)
tiazofurine (CHEBI:90239) has role antineoplastic agent (CHEBI:35610)
tiazofurine (CHEBI:90239) has role EC 1.1.1.205 (IMP dehydrogenase) inhibitor (CHEBI:53746)
tiazofurine (CHEBI:90239) has role prodrug (CHEBI:50266)
tiazofurine (CHEBI:90239) is a 1,3-thiazoles (CHEBI:38418)
tiazofurine (CHEBI:90239) is a C-glycosyl compound (CHEBI:20857)
tiazofurine (CHEBI:90239) is a monocarboxylic acid amide (CHEBI:29347)
IUPAC Name
(1R)-1,4-anhydro-1-(4-carbamoyl-1,3-thiazol-2-yl)-D-ribitol
INNs Sources
tiazofurina WHO MedNet
tiazofurine WHO MedNet
tiazofurine WHO MedNet
tiazofurinum WHO MedNet
Synonyms Sources
2-(β-D-ribofuranosyl)-4-thiazolecarboxamide ChEBI
2-β-D-ribofuranosyl-4-thiazolecarboxamide ChemIDplus
CI-909 ChemIDplus
riboxamide ChemIDplus
TCAR ChEBI
tiazofurin KEGG DRUG
Manual Xrefs Databases
D06130 KEGG DRUG
Tiazofurin Wikipedia
TIZ PDBeChem
View more database links
Registry Numbers Types Sources
1084555 Reaxys Registry Number Reaxys
60084-10-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11249583 PubMed citation Europe PMC
23764899 PubMed citation Europe PMC
2712550 PubMed citation Europe PMC
8667040 PubMed citation Europe PMC
Last Modified
05 November 2015