CHEBI:66412 - multiplolide B

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ChEBI Name multiplolide B
ChEBI ID CHEBI:66412
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C14H18O6
Net Charge 0
Average Mass 282.28910
Monoisotopic Mass 282.11034
InChI InChI=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
InChIKey MKNCRDRXKFGNDG-BGEOUFIESA-N
SMILES C\C=C\C(=O)O[C@@H]1C[C@@H](C)OC(=O)C2OC2\C=C\[C@@H]1O
Metabolite of Species Details
Xylaria multiplex (NCBI:txid323545) of strain BCC 1111 See: PubMed
Roles Classification
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
8847393 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
11473437 PubMed citation Europe PMC
Last Modified
02 October 2012