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CHEBI:90239 - tiazofurine

ChEBI IDCHEBI:90239
ChEBI Nametiazofurine
Stars
DefinitionA C-glycosyl compound that is 1,3-thiazole-4-carboxamide in which the hydrogen at position 2 has been replaced by a β-D-ribofuranosyl group.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).
Last Modified5 November 2015
SubmitterGareth Owen
DownloadsMolfile
FormulaC9H12N2O5S
Net Charge0
Average Mass260.271
Monoisotopic Mass260.04669
SMILESNC(=O)c1csc([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)n1
InChIInChI=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
InChIKeyFVRDYQYEVDDKCR-DBRKOABJSA-N
Wikipedia
Roles Classification
Biological Role:
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.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
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.
ChEBI Ontology
Outgoing Relation(s)
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 C-glycosyl compound (CHEBI:20857)
tiazofurine (CHEBI:90239) is a 1,3-thiazoles (CHEBI:38418)
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  Source
tiazofurinumWHO MedNet
tiazofurineWHO MedNet
tiazofurineWHO MedNet
tiazofurinaWHO MedNet
Synonyms  Source
2-β-D-ribofuranosyl-4-thiazolecarboxamideChemIDplus
TCARChEBI
CI-909ChemIDplus
2-(β-D-ribofuranosyl)-4-thiazolecarboxamideChEBI
riboxamideChemIDplus
tiazofurinKEGG DRUG
Manual XrefsDatabases
D06130KEGG DRUG
TIZPDBeChem
TiazofurinWikipedia
Registry NumbersSources
Reaxys:1084555Reaxys
CAS:60084-10-8ChemIDplus
Citations