spectinomycin

CHEBI:9215 ·resolve ·ANTIBACTERIAL ·EXACT REVIEWED

A pyranobenzodioxin and antibiotic that is active against gram-negative bacteria and used (as its dihydrochloride pentahydrate) to treat gonorrhea. It is produced by the bacterium Streptomyces spectabilis. — ChEBI

Classification

aminoglycoside antibioticARO:0000016

Strictly broader compounds or drug classes this molecule belongs to.

• Label unavailable CHEBI:146295
• Label unavailable CHEBI:35681
• Label unavailable CHEBI:3992
• Label unavailable CHEBI:50995
• Label unavailable CHEBI:59770
• Label unavailable CHEBI:59780
• aminoglycoside antibiotic ARO:0000016

Chemical structure

SMILES

[H][C@]12O[C@@H]3[C@@H](O)[C@H](NC)[C@H](O)[C@H](NC)[C@H]3O[C@@]1(O)C(=O)C[C@@H](C)O2

InChI

InChI=1S/C14H24N2O7/c1-5-4-6(17)14(20)13(21-5)22-12-10(19)7(15-2)9(18)8(16-3)11(12)23-14/h5,7-13,15-16,18-20H,4H2,1-3H3/t5-,7-,8+,9+,10+,11-,12-,13+,14+/m1/s1

Also called

• espectinomicina (INN)— chebi
• spectinomycine (INN)— chebi
• spectinomycinum (INN)— chebi
• (2R,4aR,5aR,6S,7S,8R,9S,9aR,10aS)-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)decahydro-4H-pyrano[2,3-b][1,4]benzodioxin-4-one (EXACT_SYNONYM)— chebi
• Antibiotic 2233wp (EXACT_SYNONYM)— chebi
• Actinospectacin (EXACT_SYNONYM)— aro
• Spectam (EXACT_SYNONYM)— aro
• Togamycin (EXACT_SYNONYM)— aro
• Trobicin (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.

• spectinomycinARO:0000039
• cas:1695-77-8
• hmdb:HMDB0015055
• kegg.compound:C02078
• lincs.smallmolecule:LSM-5298
• pdb-ccd:SCM
• reaxys:2171701
• chembl:CHEMBL1167
• pubchem.compound:15541

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:DB00919
• drugcentral:2468
• kegg.drug:D08526

Patents and articles

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

• patent:US4203903
• patent:WO2005041984
• wikipedia.en:Spectinomycin

Activity roles

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

• antimicrobial agent CHEBI:33281
• antibacterial drug CHEBI:36047

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.

Molecular targets

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

antibiotic sensitive 16S rRNA NUCLEIC_ACID DIRECT_BINDING_TARGET

ARO:3000755

CARD/ARO database assertion; target organism, strain, and assay are not specified. 16S rRNA is asserted as the target. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

• ARO:3000755 (CARD/ARO asserts targeted_by_antibiotic ARO:0000039 (spectinomycin); database assertion, not a primary citation.)

30S ribosomal head domain RIBOSOMAL_SUBUNIT DIRECT_BINDING_TARGET

Spectinomycin-bound E. coli 70S structures directly showed the drug trapping a distinct small-subunit head-swivel state; in-vitro reverse-translocation assays measured the corresponding kinetic disruption. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2007-08 (retrieved 2026-09-02).

Escherichia coli NCBITaxon:562

• PMID:17696316 (Primary spectinomycin-bound E. coli ribosome structure and translocation study (DOI:10.1021/cb700100n).)

Mechanism summary

Mode of action

PROTEIN_SYNTHESIS_INHIBITION host shared target — CURATOR: PMID:17696316 combined Escherichia coli 70S crystal structures and reverse-translocation assays. Spectinomycin binds the small subunit, traps a distinct 30S-head swivel state, and sterically blocks head motion required for mRNA/tRNA translocation, thereby disrupting the translation cycle.

Resistance mechanisms

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

Record-level evidence

• PMID:17696316 (Primary exact-spectinomycin ribosome structure and translocation-mechanism study.)

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

4. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

5. REVIEWED 2026-09-03 · codex · LLM-assisted

   Verified exact ChEBI/CARD identity, structure, antibiotic role, class, and provenance of 48 retained CARD resistance assertions; added protein-synthesis inhibition and the directly observed 30S head-swivel mechanism.

6. RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

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