cycloheximide

CHEBI:27641 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus. — 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.

CHEBI:35356 CHEBI:35356
CHEBI:35681 CHEBI:35681
CHEBI:3992 CHEBI:3992
CHEBI:48589 CHEBI:48589
CHEBI:49318 CHEBI:49318
CHEBI:87114 CHEBI:87114
ARO:3000003 ARO:3000003

Chemical structure

Computed structure properties
Molecular formula	C15H23NO4
Charge	0
Average mass	281.352 Da
Monoisotopic mass	281.16271 Da
Source	ChEBI
InChIKey	YPHMISFOHDHNIV-FSZOTQKASA-N

SMILES

[H][C@@]1([C@H](O)CC2CC(=O)NC(=O)C2)C[C@@H](C)C[C@H](C)C1=O

InChI

InChI=1S/C15H23NO4/c1-8-3-9(2)15(20)11(4-8)12(17)5-10-6-13(18)16-14(19)7-10/h8-12,17H,3-7H2,1-2H3,(H,16,18,19)/t8-,9-,11-,12+/m0/s1

Also called

cicloheximida (INN)— chebi
cicloheximide (INN)— chebi
cicloheximidum (INN)— chebi
4-{(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl}piperidine-2,6-dione (EXACT_SYNONYM)— chebi
3-((R)-2-((1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimide (EXACT_SYNONYM)— chebi
Cycloheximid (EXACT_SYNONYM)— chebi
Cycloheximide (EXACT_SYNONYM)— chebi
Zykloheximid (EXACT_SYNONYM)— chebi
naramycin (EXACT_SYNONYM)— chebi
naramycin A (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3009188
cas:66-81-9
kegg.compound:C06685
kegg.drug:D03625
knapsack:C00047211
lincs.smallmolecule:LSM-2791
pdb-ccd:3HE
ppdb:1680
reaxys:88868
wikipedia.en:Cycloheximide
chembl:CHEMBL123292
pubchem.compound:2900

Activity roles

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

CHEBI:149553 CHEBI:149553
CHEBI:24127 CHEBI:24127
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:3009188`	cycloheximide	`antibioticmech:aro-eb6ceb3794`	2026-08-30
CHEBI	`CHEBI:27641`	cycloheximide	`antibioticmech:chebi-122ccc7d98`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

ribosomal complex PROTEIN_COMPLEX DIRECT_BINDING_TARGET

ARO:3000729

CARD/ARO database assertion; target organism, strain, and assay are not specified. ARO asserts stabilization of the ribosomal complex by antibiotics. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000729 (CARD/ARO asserts targeted_by_antibiotic ARO:3009188 (cycloheximide); database assertion, not a primary citation.)

Mechanism summary

Mode of action: PROTEIN_SYNTHESIS_INHIBITION host shared target — Assigned from ChEBI role CHEBI:48001 (protein synthesis inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.

Resistance mechanisms

3 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_EFFLUX 1

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
Trychophyton rubrum MFS1 with mutations conferring resistance against cyclohexamide	ARO:3009291	not organism-specific	—	ARO:3009291 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3009188 (cycloheximide); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 1

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Saccharomyces cerevisiae ACT1 with mutations conferring resistance to cycloheximide	ARO:3009326	not organism-specific	—	ARO:3009326 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3009188 (cycloheximide); database assertion, not a primary citation.)

UNKNOWN 1

UNKNOWN
Determinant	ARO ID	Organism	Gene families	Evidence
STS1+ (wild type) [Overexpression] associated with resistance to cycloheximide This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Saccharomyces cerevisiae `NCBITaxon:4932` strain YPH501 `NCBITaxon:559292` `UniProtKB:P38637` YIR011C_mRNA `PHIPO:0000544`	—	PMID:8307980 (PHI-base primary-literature antimicrobial interaction PHIG:1805; joined to this record by exact ChEBI identifier.) Cell growth assay

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 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-02 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-02 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-03 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-03 · 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.