multiplolide B

CHEBI:66412 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

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

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:25000 CHEBI:25000
CHEBI:32955 CHEBI:32955
CHEBI:35681 CHEBI:35681

Chemical structure

Computed structure properties
Molecular formula	C14H18O6
Charge	0
Average mass	282.292 Da
Monoisotopic mass	282.11034 Da
Source	ChEBI
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

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

Also called

(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 (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:8847393

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:35718 CHEBI:35718

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:66412`	multiplolide B	`antibioticmech:chebi-5f2616ba1a`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.