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 ID CHEBI:138440 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 Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search 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 View more database links 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