Item 1 of 1 (back to results) multiplolide B 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.

Current search: 03. Biological Effects of Specific Chemicals: biochemical uses [CHEBI:52206] > metabolite [CHEBI:25212] > secondary metabolite [CHEBI:26619] > multiplolide B [CHEBI:66412] × Select any link to see items in a related category. more general categories    information about this item 03. Biological Effects of Specific Chemicals  03. Biological Effects of Specific Chemicals  biochemical uses [CHEBI:52206] (3306)   metabolite [CHEBI:25212] (2692)   secondary metabolite [CHEBI:26619] (2225)   multiplolide B [CHEBI:66412] (1)  antimicrobial agent [CHEBI:33281] (927)   antifungal agent [CHEBI:35718] (130)   multiplolide B [CHEBI:66412] (1) 06. Name of Biological Source of Chemical  06. Name of Biological Source of Chemical  Fungi, Yeasts, Molds and Mildews (348)   Dikarya (97)   Ascomycota (82)   Pezizomycotina (82)   Sordariomycetes (72)   Xylariomycetidae (19)   Xylariales (19)   Xylariaceae (19)   Xylaria (19)   Xylaria multiplex (2) 07. Part of Biological Source of Chemical  07. Part of Biological Source of Chemical  unspecified structure [PO:0000004] (703) 08. Chemical Category  08. Chemical Category  main group molecular entity [CHEBI:33579] (25650)   s-block molecular entity [CHEBI:33674] (7287)   hydrogen molecular entity [CHEBI:33608] (6932)   hydroxides [CHEBI:24651] (5641)   organic hydroxy compound [CHEBI:33822] (3050)   alcohol [CHEBI:30879] (1371)   secondary alcohol [CHEBI:35681] (342)   multiplolide B [CHEBI:66412] (1)  p-block molecular entity [CHEBI:33675] (25343)   chalcogen molecular entity [CHEBI:33304] (15225)   oxygen molecular entity [CHEBI:25806] (14414)   hydroxides [CHEBI:24651] (5641)   organic hydroxy compound [CHEBI:33822] (3050)   alcohol [CHEBI:30879] (1371)   secondary alcohol [CHEBI:35681] (342)   multiplolide B [CHEBI:66412] (1)  organooxygen compound [CHEBI:36963] (11352)   ether [CHEBI:25698] (876)   cyclic ether [CHEBI:37407] (314)   epoxide [CHEBI:32955] (145)   multiplolide B [CHEBI:66412] (1)  carbonyl compound [CHEBI:36586] (5928)   carboxylic ester [CHEBI:33308] (1495)   lactone [CHEBI:25000] (516)   multiplolide B [CHEBI:66412] (1)  oxacycle [CHEBI:38104] (2002)   lactone [CHEBI:25000] (516)   multiplolide B [CHEBI:66412] (1)  cyclic ether [CHEBI:37407] (314)   epoxide [CHEBI:32955] (145)   multiplolide B [CHEBI:66412] (1)  organochalcogen compound [CHEBI:36962] (11874)   organooxygen compound [CHEBI:36963] (11352)   ether [CHEBI:25698] (876)   cyclic ether [CHEBI:37407] (314)   epoxide [CHEBI:32955] (145)   multiplolide B [CHEBI:66412] (1)  carbonyl compound [CHEBI:36586] (5928)   carboxylic ester [CHEBI:33308] (1495)   lactone [CHEBI:25000] (516)   multiplolide B [CHEBI:66412] (1)  oxacycle [CHEBI:38104] (2002)   lactone [CHEBI:25000] (516)   multiplolide B [CHEBI:66412] (1)  cyclic ether [CHEBI:37407] (314)   epoxide [CHEBI:32955] (145)   multiplolide B [CHEBI:66412] (1)  carbon group molecular entity [CHEBI:33582] (23847)   organic molecular entity [CHEBI:50860] (23769)   heteroorganic entity [CHEBI:33285] (15197)   organic heterocyclic compound [CHEBI:24532] (5243)   oxacycle [CHEBI:38104] (2002)   lactone [CHEBI:25000] (516)   multiplolide B [CHEBI:66412] (1)  cyclic ether [CHEBI:37407] (314)   epoxide [CHEBI:32955] (145)   multiplolide B [CHEBI:66412] (1)  organochalcogen compound [CHEBI:36962] (11874)   organooxygen compound [CHEBI:36963] (11352)   ether [CHEBI:25698] (876)   cyclic ether [CHEBI:37407] (314)   epoxide [CHEBI:32955] (145)   multiplolide B [CHEBI:66412] (1)  carbonyl compound [CHEBI:36586] (5928)   carboxylic ester [CHEBI:33308] (1495)   lactone [CHEBI:25000] (516)   multiplolide B [CHEBI:66412] (1)  oxacycle [CHEBI:38104] (2002)   lactone [CHEBI:25000] (516)   multiplolide B [CHEBI:66412] (1)  cyclic ether [CHEBI:37407] (314)   epoxide [CHEBI:32955] (145)   multiplolide B [CHEBI:66412] (1)  organic hydroxy compound [CHEBI:33822] (3050)   alcohol [CHEBI:30879] (1371)   secondary alcohol [CHEBI:35681] (342)   multiplolide B [CHEBI:66412] (1)  ester [CHEBI:35701] (3370)   lactone [CHEBI:25000] (516)   multiplolide B [CHEBI:66412] (1)  carboxylic ester [CHEBI:33308] (1495)   lactone [CHEBI:25000] (516)   multiplolide B [CHEBI:66412] (1)  organic molecule [CHEBI:72695] (11399)   organic cyclic compound [CHEBI:33832] (7633)   organic heterocyclic compound [CHEBI:24532] (5243)   oxacycle [CHEBI:38104] (2002)   lactone [CHEBI:25000] (516)   multiplolide B [CHEBI:66412] (1)  cyclic ether [CHEBI:37407] (314)   epoxide [CHEBI:32955] (145)   multiplolide B [CHEBI:66412] (1)  organic oxo compound [CHEBI:36587] (5932)   carbonyl compound [CHEBI:36586] (5928)   carboxylic ester [CHEBI:33308] (1495)   lactone [CHEBI:25000] (516)   multiplolide B [CHEBI:66412] (1)  polyatomic entity [CHEBI:36357] (18777)   molecule [CHEBI:25367] (11520)   cyclic compound [CHEBI:33595] (7817)   organic cyclic compound [CHEBI:33832] (7633)   organic heterocyclic compound [CHEBI:24532] (5243)   oxacycle [CHEBI:38104] (2002)   lactone [CHEBI:25000] (516)   multiplolide B [CHEBI:66412] (1)  cyclic ether [CHEBI:37407] (314)   epoxide [CHEBI:32955] (145)   multiplolide B [CHEBI:66412] (1)  heterocyclic compound [CHEBI:5686] (5275)   organic heterocyclic compound [CHEBI:24532] (5243)   oxacycle [CHEBI:38104] (2002)   lactone [CHEBI:25000] (516)   multiplolide B [CHEBI:66412] (1)  cyclic ether [CHEBI:37407] (314)   epoxide [CHEBI:32955] (145)   multiplolide B [CHEBI:66412] (1)  organic molecule [CHEBI:72695] (11399)   organic cyclic compound [CHEBI:33832] (7633)   organic heterocyclic compound [CHEBI:24532] (5243)   oxacycle [CHEBI:38104] (2002)   lactone [CHEBI:25000] (516)   multiplolide B [CHEBI:66412] (1)  cyclic ether [CHEBI:37407] (314)   epoxide [CHEBI:32955] (145)   multiplolide B [CHEBI:66412] (1)  organic oxo compound [CHEBI:36587] (5932)   carbonyl compound [CHEBI:36586] (5928)   carboxylic ester [CHEBI:33308] (1495)   lactone [CHEBI:25000] (516)   multiplolide B [CHEBI:66412] (1)  heteroatomic molecular entity [CHEBI:37577] (13672)   hydroxides [CHEBI:24651] (5641)   organic hydroxy compound [CHEBI:33822] (3050)   alcohol [CHEBI:30879] (1371)   secondary alcohol [CHEBI:35681] (342)   multiplolide B [CHEBI:66412] (1) ChEBI Compound Accession Identifier:   [CHEBI:66412] ChEBI Compound Description:   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. ChEBI Compound Identification Number:   66412 ChEBI InChI Value:   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 ChEBI InChIKey Value:   MKNCRDRXKFGNDG-BGEOUFIESA-N ChEBI Compound Name:   multiplolide B ChEBI SMILES Value:   C\C=C\C(=O)O[C@@H]1C[C@@H](C)OC(=O)C2OC2\C=C\[C@@H]1O ChEBI Substance ID:   160645292 ChEBI URL:   ChEBI:66412 ChemSpider ID:   9953199 Ontomatica Chemical Accession Key (OnChAKey):   MKNCRDRXKFGNDG_BGEOUFIESA_N_000_000000 PubChem Compound ID:   11778517