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CHEBI:233586 - thiamet G

ChEBI IDCHEBI:233586
ChEBI Namethiamet G
Stars
DefinitionA pyranothiazole that is (3aR,7aR)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole substituted by an ethylamino, hydroxymethyl, hydroxy, and hydroxy groups at positions 2, 5R, 6S, and 7R. It is a potent and selective inhibitor of O-GlcNAcase (Ki = 21 nM).
Last Modified15 April 2025
SubmitterFlyBase
DownloadsMolfile
FormulaC9H16N2O4S
Net Charge0
Average Mass248.304
Monoisotopic Mass248.08308
SMILES[H][C@]12O[C@H](CO)[C@@H](O)[C@H](O)[C@@]1([H])N=C(NCC)S2
InChIInChI=1S/C9H16N2O4S/c1-2-10-9-11-5-7(14)6(13)4(3-12)15-8(5)16-9/h4-8,12-14H,2-3H2,1H3,(H,10,11)/t4-,5-,6-,7-,8-/m1/s1
InChIKeyPPAIMZHKIXDJRN-FMDGEEDCSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
chemosensitiser  Any compound that can sensitise tumour cells to chemotherapy.
EC 3.2.1.169 (protein O-GlcNAcase) inhibitor  An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of protein O-GlcNAcase (EC 3.2.1.169).
Application:
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
ChEBI Ontology
Outgoing Relation(s)
thiamet G (CHEBI:233586) has role chemosensitiser (CHEBI:233442)
thiamet G (CHEBI:233586) has role EC 3.2.1.169 (protein O-GlcNAcase) inhibitor (CHEBI:234036)
thiamet G (CHEBI:233586) has role neuroprotective agent (CHEBI:63726)
thiamet G (CHEBI:233586) is a pyranothiazole (CHEBI:48880)
thiamet G (CHEBI:233586) is a secondary amino compound (CHEBI:50995)
IUPAC Name 
(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol
Synonyms  Source
2-(ethylamino)-3aR,6S,7R,7aR-tetrahydro-5R-(hydroxymethyl)-5H-pyrano[3,2-d]thiazole-6,7-diolChEBI
thiamet-GChEBI
Registry NumbersSources
CAS:1009816-48-1SUBMITTER
Citations