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

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ChEBI Name (3R,4S,1'R)-3-(1'-hydroxyethyl)-4-methyldihydrofuran-2(3H)-one
ChEBI ID CHEBI:66043
ChEBI ASCII Name (3R,4S,1'R)-3-(1'-hydroxyethyl)-4-methyldihydrofuran-2(3H)-one
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C7H12O3
Net Charge 0
Average Mass 144.16840
Monoisotopic Mass 144.07864
InChI InChI=1S/C7H12O3/c1-4-3-10-7(9)6(4)5(2)8/h4-6,8H,3H2,1-2H3/t4-,5-,6-/m1/s1
InChIKey POKADFGKQLIDGO-HSUXUTPPSA-N
SMILES [H][C@]1([C@@H](C)O)[C@H](C)COC1=O
Metabolite of Species Details
Mycoleptodonoides aitchisonii (NCBI:txid1076280) See: DOI
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (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 γ-lactone (CHEBI:37581)
(3R,4S,1'R)-3-(1'-hydroxyethyl)-4-methyldihydrofuran-2(3H)-one (CHEBI:66043) is a secondary alcohol (CHEBI:35681)
IUPAC Name
(3R,4S)-3-[(1R)-1-hydroxyethyl]-4-methyldihydrofuran-2(3H)-one
Registry Number Type Source
18852552 Reaxys Registry Number Reaxys
Last Modified
26 February 2013
General Comment
2013-02-26 Tetrahedron (2009), 65(1), 221-224.