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CHEBI:66412 - multiplolide B

ChEBI IDCHEBI:66412
ChEBI Namemultiplolide B
Stars
DefinitionA 10-membered lactone obtained from 10-methyl-9,10-dihydro-2H-oxecin-2-one by the epoxidation of the double bond at position 3-4 and cis-dihydroxylation of the double bond at position 7-8, with further acylation of the hydroxy group at position 8 by a but-2-enoyl group. Multiplolide B was first isolated from the fungus Xylaria multiplex BCC 1111. It shows antifungal activity against Candida albicans. The epoxide group has cis-configuration, but its configuration relative to the other substituents was not established.
Last Modified2 October 2012
DownloadsMolfile
FormulaC14H18O6
Net Charge0
Average Mass282.292
Monoisotopic Mass282.11034
SMILESC/C=C/C(=O)O[C@@H]1C[C@@H](C)OC(=O)C2OC2/C=C/[C@@H]1O
InChIInChI=1S/C14H18O6/c1-3-4-12(16)19-11-7-8(2)18-14(17)13-10(20-13)6-5-9(11)15/h3-6,8-11,13,15H,7H2,1-2H3/b4-3+,6-5+/t8-,9+,10?,11-,13?/m1/s1
InChIKeyMKNCRDRXKFGNDG-BGEOUFIESA-N
Species of MetaboliteComponentSourceComments
Xylaria multiplex (ncbitaxon:323545) - PubMed (11473437) Strain: BCC 1111
Roles Classification
Biological Roles:
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
multiplolide B (CHEBI:66412) has role antifungal agent (CHEBI:35718)
multiplolide B (CHEBI:66412) has role metabolite (CHEBI:25212)
multiplolide B (CHEBI:66412) is a epoxide (CHEBI:32955)
multiplolide B (CHEBI:66412) is a lactone (CHEBI:25000)
multiplolide B (CHEBI:66412) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(4R,6R,7S,8E)-7-hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl (2E)-but-2-enoate
Registry NumbersSources
Reaxys:8847393Reaxys
Citations