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

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

antibiotic without defined classificationARO:3000003

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:29347
Label unavailable CHEBI:32955
antibiotic without defined classification 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

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Activity roles

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

antimicrobial agent CHEBI:33281
antifungal agent 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

Resistance mechanisms

2 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

ANTIBIOTIC_TARGET_ALTERATION 2

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Bacillus subtilis GS76 fabF3 resistance to cerulenin JH642 derivative. Source protein notation retained; nucleotide and protein numbering are not normalized. No strain-specific protein, strain TaxID or genome accession verified.	—	Bacillus subtilis `NCBITaxon:1423` strain GS76 fabF	fabF	PMID:24641521 (Characterization of bsFabF[I108M]; Tables 2, 4 and 5.) Cell-free enzyme assay and genetic complementation
Bacillus subtilis GS77 fabF1 resistance to cerulenin JH642 derivative. Reference protein O34340, sequence version 1, not a mutant-specific accession. Source I108F is retained; UniProt's GS77 annotation uses I109F. No coordinate conversion, strain TaxID or genome assignment. Expression regulation also contributes in this background.	—	Bacillus subtilis `NCBITaxon:1423` strain GS77 `UniProtKB:O34340` fabF	fabF	PMID:24641521 (Results; Table 2; Figure 2.) UniProtKB:O34340 (Reference crosswalk only: GS77 variant cites PMID:11325930; PDB 4LS6.) Biochemical inhibition and structural analysis

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, 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
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
CURATED_RESISTANCE_EVIDENCE 2026-10-08 · codex · LLM-assisted
Added two primary-supported strain-specific fabF claims; grounded species and the GS77 reference protein. Preserved numbering caveats; no AST, genome or strain TaxID inferred.

Provenance

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

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