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Substrate Report for: 1,5-Seco-vibralactone

Name Class
1,5-Seco-vibralactoneTypeNatural
Lactone
Other_Name(1S)-1,5-secovibralactone
3beta-(3-Methyl-2-butenyl)-5-hydroxymethyloxepin-2(3H)-one
Chemical_Nomenclature(3S)-5-(hydroxymethyl)-3-(3-methylbut-2-enyl)-3H-oxepin-2-one
FormulaC12H16O3
MW208.25
PaperFeng_2020_Angew.Chem.Int.Ed.Engl_59_7209
CommentVibralactone is isolated from the basidiomycete fungus Boreostereum vibrans as one of the strongest lipase inhibitors. Its unusual beta-lactone-fused bicycle is derived from an aryl ring moiety via an oxidative ring-expansion prior to an intramolecular cyclization. VibC stehr-Sh.112560 performs the carbocycle formation of an oxepinone to a fused bicyclic beta-lactone
Gene_locusstehr-Sh.112560
CID102473702
FamilyHormone-sensitive_lipase_like
InChIKeyGBGOKTDQCPDZMS-NSHDSACASA-N
CanonicalSMILESCC(=CCC1C=C(C=COC1=O)CO)C
InChIInChI=1S/C12H16O3/c1-9(2)3-4-11-7-10(8-13)5-6-15-12(11)14/h3,5-7,11,13H,4,8H2,1-2H3/t11-/m0/s1

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Mail to: Nicolas Lenfant, Thierry Hotelier, Yves Bourne, Pascale Marchot and Arnaud Chatonnet.
Please cite: Lenfant 2013 Nucleic.Acids.Res. or Marchot Chatonnet 2012 Prot.Pept Lett.
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