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

ChEBI IDCHEBI:138440
ChEBI Name(3R,4R)-3-[(1S)-1-hydroxyalkyl]-4-(hydroxymethyl)oxolan-2-one
Stars
ASCII Name(3R,4R)-3-[(1S)-1-hydroxyalkyl]-4-(hydroxymethyl)oxolan-2-one
DefinitionA 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).
Last Modified21 September 2017
SubmitterKristian Axelsen
DownloadsMolfile
FormulaC7H11O4R
Net Charge0
Average Mass (excl. R groups)159.160
Monoisotopic Mass (excl. R groups)159.06573
SMILES*C[C@H](O)[C@]1([H])C(=O)OC[C@@]1([H])CO
ChEBI Ontology
Outgoing Relation(s)
(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  Source
a VB type γ-butyrolactoneSUBMITTER
virginiae butanolidesChEBI
virginiae butanolideChEBI
VB type γ-butyrolactonesChEBI
UniProt Name  Source
a (3R,4R)-3-[(1S)-1-hydroxyalkyl]-4-(hydroxymethyl)oxolan-2-oneUniProt
Manual XrefsDatabases
Virginiae-butanolidesMetaCyc
Citations