oleandomycin

CHEBI:16869 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

Oleandomycin is a 14-membered macrolide produced by Streptomyces antibioticus. It is ssimilar to erythromycin, and contains a desosamine amino sugar and an oleandrose sugar. It targets the 50S ribosomal subunit to prevent protein synthesis. — PMID:13425352

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

macrolide antibioticARO:0000000

Strictly broader compounds or drug classes this molecule belongs to.

macrolide antibiotic ARO:0000000

Chemical structure

Computed structure properties
Molecular formula	C35H61NO12
Charge	0
Average mass	687.868 Da
Monoisotopic mass	687.41938 Da
Source	ChEBI
InChIKey	RZPAKFUAFGMUPI-QESOVKLGSA-N

SMILES

CO[C@H]1C[C@H](O[C@H]2[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3O)[C@@H](C)C[C@@]3(CO3)C(=O)[C@H](C)[C@@H](O)[C@@H](C)[C@@H](C)OC(=O)[C@@H]2C)O[C@@H](C)[C@@H]1O

InChI

InChI=1S/C35H61NO12/c1-16-14-35(15-43-35)32(40)19(4)27(37)18(3)22(7)46-33(41)21(6)31(47-26-13-25(42-11)28(38)23(8)45-26)20(5)30(16)48-34-29(39)24(36(9)10)12-17(2)44-34/h16-31,34,37-39H,12-15H2,1-11H3/t16-,17+,18-,19+,20+,21+,22+,23-,24-,25-,26-,27-,28-,29+,30-,31-,34-,35+/m0/s1

Also called

Amimycin (EXACT_SYNONYM)— aro
Matromycin (EXACT_SYNONYM)— aro

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.

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:3000867`	oleandomycin	`antibioticmech:aro-4ec68d2906`	2026-08-30

Resistance mechanisms

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

ANTIBIOTIC_TARGET_ALTERATION 23

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Erm(33)	ARO:3000599	not organism-specific	—	ARO:3000599 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
Erm(34)	ARO:3000600	not organism-specific	—	ARO:3000600 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
Erm(35)	ARO:3000604	not organism-specific	—	ARO:3000604 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
Erm(36)	ARO:3000605	not organism-specific	—	ARO:3000605 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
Erm(37)	ARO:3000392	not organism-specific	—	ARO:3000392 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
Erm(38)	ARO:3000601	not organism-specific	—	ARO:3000601 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
Erm(39)	ARO:3000602	not organism-specific	—	ARO:3000602 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
Erm(41)	ARO:3000603	not organism-specific	—	ARO:3000603 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
ErmA	ARO:3000347	not organism-specific	—	ARO:3000347 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
ErmB	ARO:3000375	not organism-specific	—	ARO:3000375 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
ErmC	ARO:3000250	not organism-specific	—	ARO:3000250 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
ErmD	ARO:3000495	not organism-specific	—	ARO:3000495 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
ErmE	ARO:3000326	not organism-specific	—	ARO:3000326 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
ErmF	ARO:3000498	not organism-specific	—	ARO:3000498 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
ErmG	ARO:3000522	not organism-specific	—	ARO:3000522 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
ErmH	ARO:3002823	not organism-specific	—	ARO:3002823 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
ErmN	ARO:3000592	not organism-specific	—	ARO:3000592 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
ErmQ	ARO:3000593	not organism-specific	—	ARO:3000593 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
ErmR	ARO:3000594	not organism-specific	—	ARO:3000594 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
ErmT	ARO:3000595	not organism-specific	—	ARO:3000595 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
ErmV	ARO:3002824	not organism-specific	—	ARO:3002824 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
ErmX	ARO:3000596	not organism-specific	—	ARO:3000596 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
ErmY	ARO:3002825	not organism-specific	—	ARO:3002825 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)

ANTIBIOTIC_INACTIVATION 7

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
gimA	ARO:3000463	not organism-specific	—	ARO:3000463 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
mphA	ARO:3000316	not organism-specific	—	ARO:3000316 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
mphB	ARO:3000318	not organism-specific	—	ARO:3000318 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
mphC	ARO:3000319	not organism-specific	—	ARO:3000319 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
oleD biochemical glycosylation of oleandomycin Biochemical inactivation route, not a measured whole-cell resistance or clinical susceptibility call. The donor species Streptomyces antibioticus (reference NCBITaxon:1890, species rank) is distinct from the heterologous expression host Streptomyces lividans. Donor and reference taxonomy do not identify an organism tested for resistance here. No experimental allele, protein accession, strain TaxID or genome is assigned. Reference-only protein entries: UniProtKB:Q53685, UniProtKB:Q3HTL6. OleR-mediated reactivation is a different direction, not another inactivation determinant. No class-wide substrate claim is inferred.	—	not organism-specific	oleD	PMID:9680207 (Results, expression/activity sections and Figure 4A/6 legends: qualitative glycosylation evidence with a negative expression-host control. Results on in vitro protein synthesis support reduced activity of the glycosylated product. Publisher-indexed text inspected; figures not visually inspected.) PMID:17376874 (Table 3, wild-type oleandomycin row; biochemical activity with oleandomycin, not an MIC. Author-hosted paper, Figure 2 and cited table visually inspected. Correction DOI:10.1073/pnas.0704090104 changes author-contribution credit. Supplementary material was not inspected; no claim depends on it.) UniProtKB:Q53685 (Reference identity only; UniProtKB release 2026_03, retrieved 2026-10-09, entry version 100, sequence version 1. Separate deposits are not collapsed into one experimental allele.) UniProtKB:Q3HTL6 (Reference identity only; UniProtKB release 2026_03, retrieved 2026-10-09, entry version 69, sequence version 2. Separate deposits are not collapsed into one experimental allele.)
oleI	ARO:3000866	not organism-specific	—	ARO:3000866 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)
oleI biochemical glycosylation of oleandomycin Biochemical inactivation route, not a measured whole-cell resistance or clinical susceptibility call. The donor species Streptomyces antibioticus (reference NCBITaxon:1890, species rank) is distinct from the heterologous expression host Streptomyces lividans. Donor and reference taxonomy do not identify an organism tested for resistance here. No experimental allele, protein accession, strain TaxID or genome is assigned. Reference-only protein entries: UniProtKB:O68841, UniProtKB:Q3HTL7. OleR-mediated reactivation is a different direction, not another inactivation determinant. No class-wide substrate claim is inferred.	—	not organism-specific	oleI	PMID:9680207 (Results, expression/activity sections and Figure 4A/6 legends: qualitative glycosylation evidence with a negative expression-host control. Results on in vitro protein synthesis support reduced activity of the glycosylated product. Publisher-indexed text inspected; figures not visually inspected.) PMID:17376874 (Table 1, wild-type row; biochemical activity with oleandomycin, not an MIC. Author-hosted paper, Figure 2 and cited table visually inspected. Correction DOI:10.1073/pnas.0704090104 changes author-contribution credit. Supplementary material was not inspected; no claim depends on it.) UniProtKB:O68841 (Reference identity only; UniProtKB release 2026_03, retrieved 2026-10-09, entry version 77, sequence version 1. Separate deposits are not collapsed into one experimental allele.) UniProtKB:Q3HTL7 (Reference identity only; UniProtKB release 2026_03, retrieved 2026-10-09, entry version 79, sequence version 2. Separate deposits are not collapsed into one experimental allele.)

ANTIBIOTIC_EFFLUX 1

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
oleC	ARO:3003748	not organism-specific	—	ARO:3003748 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_PROTECTION 1

ANTIBIOTIC_TARGET_PROTECTION
Determinant	ARO ID	Organism	Gene families	Evidence
oleB	ARO:3003036	not organism-specific	—	ARO:3003036 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000867 (oleandomycin); database assertion, not a primary citation.)

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
CURATED_RESISTANCE_EVIDENCE 2026-10-09 · codex · LLM-assisted
Added two qualitative primary-paper biochemical inactivation assertions for oleI and oleD, retaining separate UniProt references and donor/host context. Preserved all 30 CARD assertions. No experimental allele, protein or organism identifier, whole-cell phenotype, or quantitative AST assigned.

Provenance

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

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