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Accession:CHEBI:138440 term browser browse the term
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).
Synonyms:related_synonym: Formula=C7H11O4R;   SMILES=[C@]1([C@@](C(OC1)=O)([C@H](C*)O)[H])(CO)[H];   VB type gamma-butyrolactones;   a (3R,4R)-3-[(1S)-1-hydroxyalkyl]-4-(hydroxymethyl)oxolan-2-one;   a VB type gamma-butyrolactone;   virginiae butanolide;   virginiae butanolides
 xref: MetaCyc:Virginiae-butanolides;   PMID:12193632 "SUBMITTER";   PMID:2621168 "Europe PMC";   PMID:3108224 "Europe PMC";   PMID:7744885 "Europe PMC"

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  CHEBI ontology 19716
    chemical entity 19714
      molecular entity 19711
        polyatomic entity 19627
          heteroatomic molecular entity 19535
            hydroxides 19013
              organic hydroxy compound 18571
                alcohol 14939
                  primary alcohol 13820
                    (3R,4R)-3-[(1S)-1-hydroxyalkyl]-4-(hydroxymethyl)oxolan-2-one 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19716
    subatomic particle 19712
      composite particle 19712
        hadron 19712
          baryon 19712
            nucleon 19712
              atomic nucleus 19712
                atom 19712
                  main group element atom 19598
                    p-block element atom 19598
                      carbon group element atom 19486
                        carbon atom 19480
                          organic molecular entity 19480
                            organic group 18407
                              organic divalent group 18397
                                organodiyl group 18397
                                  carbonyl group 18285
                                    carbonyl compound 18285
                                      carboxylic ester 13969
                                        lactone 5865
                                          gamma-lactone 1198
                                            butan-4-olide 291
                                              (3R,4R)-3-[(1S)-1-hydroxyalkyl]-4-(hydroxymethyl)oxolan-2-one 0
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.