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CHEBI:66043 - (3R,4S,1'R)-3-(1'-hydroxyethyl)-4-methyldihydrofuran-2(3H)-one

ChEBI IDCHEBI:66043
ChEBI Name(3R,4S,1'R)-3-(1'-hydroxyethyl)-4-methyldihydrofuran-2(3H)-one
Stars
ASCII Name(3R,4S,1'R)-3-(1'-hydroxyethyl)-4-methyldihydrofuran-2(3H)-one
DefinitionA γ-lactone that is dihydrofuran-2(3H)-one substituted by a hydroxyethyl group at position 3 and a methyl group at position 4 (the 3R,4S,1'R stereoisomer). Isolated from an edible mushroom Mycoleptodonoides aitchisonii, it exhibits protective activity against endoplasmic reticulum (ER) stress dependent cell death.
Last Modified26 February 2013
DownloadsMolfile
FormulaC7H12O3
Net Charge0
Average Mass144.170
Monoisotopic Mass144.07864
SMILES[H][C@@]1([C@@H](C)O)C(=O)OC[C@H]1C
InChIInChI=1S/C7H12O3/c1-4-3-10-7(9)6(4)5(2)8/h4-6,8H,3H2,1-2H3/t4-,5-,6-/m1/s1
InChIKeyPOKADFGKQLIDGO-HSUXUTPPSA-N
Species of MetaboliteComponentSourceComments
Mycoleptodonoides aitchisonii (ncbitaxon:1076280) - DOI (10.1016/j.tet.2008.10.068)
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
ChEBI Ontology
Outgoing Relation(s)
(3R,4S,1'R)-3-(1'-hydroxyethyl)-4-methyldihydrofuran-2(3H)-one (CHEBI:66043) has role metabolite (CHEBI:25212)
(3R,4S,1'R)-3-(1'-hydroxyethyl)-4-methyldihydrofuran-2(3H)-one (CHEBI:66043) has role neuroprotective agent (CHEBI:63726)
(3R,4S,1'R)-3-(1'-hydroxyethyl)-4-methyldihydrofuran-2(3H)-one (CHEBI:66043) is a secondary alcohol (CHEBI:35681)
(3R,4S,1'R)-3-(1'-hydroxyethyl)-4-methyldihydrofuran-2(3H)-one (CHEBI:66043) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(3R,4S)-3-[(1R)-1-hydroxyethyl]-4-methyldihydrofuran-2(3H)-one
Registry NumbersSources
Reaxys:18852552Reaxys