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CHEBI:66411 - multiplolide A

ChEBI IDCHEBI:66411
ChEBI Namemultiplolide A
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. Multiplolide A was first isolated from the fungus Xylaria multiplex BCC 1111. It shows antifungal activity against Candida albicans.
Last Modified23 October 2012
DownloadsMolfile
FormulaC10H14O5
Net Charge0
Average Mass214.217
Monoisotopic Mass214.08412
SMILES[H][C@]12/C=C/[C@H](O)[C@H](O)C[C@@H](C)OC(=O)[C@@]1([H])O2
InChIInChI=1S/C10H14O5/c1-5-4-7(12)6(11)2-3-8-9(15-8)10(13)14-5/h2-3,5-9,11-12H,4H2,1H3/b3-2+/t5-,6+,7-,8+,9+/m1/s1
InChIKeyGSXXKILAEILYRX-JRSSMJHLSA-N
Species of MetaboliteComponentSourceComments
Xylaria multiplex (ncbitaxon:323545) - PubMed (11473437) Strain: BCC 1111
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
ChEBI Ontology
Outgoing Relation(s)
multiplolide A (CHEBI:66411) has role antifungal agent (CHEBI:35718)
multiplolide A (CHEBI:66411) has role metabolite (CHEBI:25212)
multiplolide A (CHEBI:66411) is a epoxide (CHEBI:32955)
multiplolide A (CHEBI:66411) is a lactone (CHEBI:25000)
multiplolide A (CHEBI:66411) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(1S,4R,6R,7S,8E,10S)-6,7-dihydroxy-4-methyl-3,11-dioxabicyclo[8.1.0]undec-8-en-2-one
Synonym  Source
(1S,2E,4S,5R,7R,10S)-4,5-dihydroxy-7-methyl-8,11-dioxabicyclo[8.1.0]undec-2-en-9-oneChEBI
Registry NumbersSources
Reaxys:15836339Reaxys
Citations