CHEBI:138440 - (3R,4R)-3-[(1S)-1-hydroxyalkyl]-4-(hydroxymethyl)oxolan-2-one

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ChEBI Name (3R,4R)-3-[(1S)-1-hydroxyalkyl]-4-(hydroxymethyl)oxolan-2-one
ChEBI ASCII Name (3R,4R)-3-[(1S)-1-hydroxyalkyl]-4-(hydroxymethyl)oxolan-2-one
Definition A butan-4-olide in which the lactone skeleton is substituted at positions 3pro-R and 4pro-R by 1-hydroxyalkyl and hydroxymethyl groups, respectively, in which the secondary alcohol has moiety has S configuration. Originally isolated from Streptomyces virginiae, where they control virginiamycin production, they are also known as virginiae butanolides (VB compounds).
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Download Molfile XML SDF
Formula C7H11O4R
Net Charge 0
Average Mass (excl. R groups) 159.160
Monoisotopic Mass (excl. R groups) 159.06573
SMILES [C@]1([C@@](C(OC1)=O)([C@H](C*)O)[H])(CO)[H]
ChEBI Ontology
Outgoing (3R,4R)-3-[(1S)-1-hydroxyalkyl]-4-(hydroxymethyl)oxolan-2-one (CHEBI:138440) is a butan-4-olide (CHEBI:22950)
(3R,4R)-3-[(1S)-1-hydroxyalkyl]-4-(hydroxymethyl)oxolan-2-one (CHEBI:138440) is a primary alcohol (CHEBI:15734)
(3R,4R)-3-[(1S)-1-hydroxyalkyl]-4-(hydroxymethyl)oxolan-2-one (CHEBI:138440) is a secondary alcohol (CHEBI:35681)
Synonyms Sources
a (3R,4R)-3-[(1S)-1-hydroxyalkyl]-4-(hydroxymethyl)oxolan-2-one UniProt
a VB type γ-butyrolactone SUBMITTER
VB type γ-butyrolactones ChEBI
virginiae butanolide ChEBI
virginiae butanolides ChEBI
Manual Xref Database
Virginiae-butanolides MetaCyc
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Citations Waiting for Citations Types Sources
12193632 PubMed citation SUBMITTER
2621168 PubMed citation Europe PMC
3108224 PubMed citation Europe PMC
7744885 PubMed citation Europe PMC
Last Modified
21 September 2017