multiplolide A

CHEBI:66411 ·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. Multiplolide A was first isolated from the fungus Xylaria multiplex BCC 1111. It shows antifungal activity against Candida albicans. — 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	C10H14O5
Charge	0
Average mass	214.217 Da
Monoisotopic mass	214.08412 Da
Source	ChEBI
InChIKey	GSXXKILAEILYRX-JRSSMJHLSA-N

SMILES

[H][C@]12/C=C/[C@H](O)[C@H](O)C[C@@H](C)OC(=O)[C@@]1([H])O2

InChI

InChI=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

Also called

(1S,4R,6R,7S,8E,10S)-6,7-dihydroxy-4-methyl-3,11-dioxabicyclo[8.1.0]undec-8-en-2-one (EXACT_SYNONYM)— chebi
(1S,2E,4S,5R,7R,10S)-4,5-dihydroxy-7-methyl-8,11-dioxabicyclo[8.1.0]undec-2-en-9-one (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:15836339

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:66411`	multiplolide A	`antibioticmech:chebi-aef65d7cb5`	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.