AntibioticMech

cerulenin

CHEBI:171741 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function. — ChEBI

Classification

antibiotic without defined classificationARO:3000003

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:29347 CHEBI:29347
• CHEBI:32955 CHEBI:32955
• ARO:3000003 ARO:3000003

Chemical structure

Computed structure properties

Molecular formula	C12H17NO3
Charge	0
Average mass	223.272 Da
Monoisotopic mass	223.12084 Da
Source	ChEBI
InChIKey	GVEZIHKRYBHEFX-NQQPLRFYSA-N

SMILES

[H][C@@]1(C(N)=O)O[C@]1([H])C(=O)CC/C=C/C/C=C/C

InChI

InChI=1S/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/b3-2+,6-5+/t10-,11-/m1/s1

Also called

• (2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide (EXACT_SYNONYM)— chebi
• (+)-cerulenin (EXACT_SYNONYM)— chebi
• (2R,3S)-3-((4E,7E)-Nona-4,7-dienoyl)-oxirane-2-carboxylic acid amide (EXACT_SYNONYM)— chebi
• (2R,3S)-3-((4E,7E)-nona-4,7-dienoyl)oxirane-2-carboxamide (EXACT_SYNONYM)— chebi
• Cerulenin (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• ARO:3009177
• beilstein:4807182
• cas:17397-89-6
• drugbank:DB01034
• drugcentral:578
• kegg.compound:C12058
• knapsack:C00018711
• chembl:CHEMBL45627
• pubchem.compound:5282054

Activity roles

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

• CHEBI:33281 CHEBI:33281
• 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
ARO	ARO:3009177	cerulenin	antibioticmech:aro-4511688145	2026-08-30
CHEBI	CHEBI:171741	cerulenin	antibioticmech:chebi-aec5174768	2026-08-30

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (ARO, CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. 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.