(−)-anisomycin

CHEBI:338412 ·resolve ·ANTIVIRAL ·EXACT SEEDED

An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system. — 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.

organonitrogen heterocyclic antibiotic CHEBI:25558
Label unavailable CHEBI:46777

Chemical structure

Computed structure properties
Molecular formula	C14H19NO4
Charge	0
Average mass	265.309 Da
Monoisotopic mass	265.13141 Da
Source	ChEBI
InChIKey	YKJYKKNCCRKFSL-RDBSUJKOSA-N

SMILES

[H][C@]1(Cc2ccc(OC)cc2)NC[C@H](O)[C@H]1OC(C)=O

InChI

InChI=1S/C14H19NO4/c1-9(16)19-14-12(15-8-13(14)17)7-10-3-5-11(18-2)6-4-10/h3-6,12-15,17H,7-8H2,1-2H3/t12-,13+,14+/m1/s1

Also called

(2R,3S,4S)-4-hydroxy-2-(4-methoxybenzyl)pyrrolidin-3-yl acetate (EXACT_SYNONYM)— chebi
1,4,5-Trideoxy-1,4-imino-5-(p-methoxyphenyl)-D-xylo-pentitol 3-acetate (EXACT_SYNONYM)— chebi
2-(p-Methoxybenzyl)-3,4-pyrrolidinediol 3-acetate (EXACT_SYNONYM)— chebi
2-p-Methoxyphenylmethyl-3-acetoxy-4-hydroxypyrrolidine (EXACT_SYNONYM)— chebi
Anisomycin (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.

drugbank:DB07374

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

wikipedia.en:Anisomycin

Activity roles

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

anticoronaviral agent CHEBI:149553
antimicrobial agent CHEBI:33281

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:338412`	(−)-anisomycin	`antibioticmech:chebi-0bda73c132`	2026-08-30

Mechanism summary

Mode of action: MULTIPLE host shared target — Assigned from ChEBI roles CHEBI:48001 (protein synthesis inhibitor), CHEBI:59517 (DNA synthesis inhibitor), which map to NUCLEIC_ACID_SYNTHESIS_INHIBITION, PROTEIN_SYNTHESIS_INHIBITION. ChEBI asserts these roles on the compound; a curator should decide whether one is primary. 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

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

ANTIBIOTIC_TARGET_ALTERATION 1

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Laboratory RPL3-associated anisomycin resistance Context-dependent association in JD1090 derivatives; responses differ among tested contexts. This is not a species-wide phenotype. Experimental allele, protein and genome unresolved; no standardized MIC or clinical category inferred.	—	Saccharomyces cerevisiae `NCBITaxon:4932` RPL3	—	https://doi.org/10.1093/nar/gkn642 (Results, Table 1 and native Figure 2D. Qualitative anisomycin result only; source concentration-unit discrepancy is not resolved or imported.) https://www.uniprot.org/uniprotkb/P14126/entry (Reference-only UniProtKB:P14126, entry version 233, sequence version 4, release 2026_03; RPL3 in S288c (NCBITaxon:559292). Not an exact experimental derivative or resistance allele.) Comparative growth susceptibility

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
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
CURATED_RESISTANCE_EVIDENCE 2026-10-13 · codex · LLM-assisted
Added a qualified laboratory yeast RPL3 association from inspected primary results. UniProt remains reference-only; no experimental allele, protein, genome or numeric AST assigned. Preserved existing owners and left whole-record review open.

Provenance

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

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