AntibioticMech

apramycin

CHEBI:2790 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

An aminoglycoside that is 2-deoxystreptamine that is substituted on the oxygen at position 4 by an (8R)-2-amino-8-O-(4-amino-4-deoxy-α-D-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-D-glycero-α-D-allo-octodialdo-1,5:8,4-dipyranos-1-yl) group. — ChEBI

Classification

aminoglycoside antibioticARO:0000016

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:27171 CHEBI:27171
• CHEBI:47779 CHEBI:47779
• CHEBI:61800 CHEBI:61800
• ARO:0000016 ARO:0000016

Chemical structure

Computed structure properties

Molecular formula	C21H41N5O11
Charge	0
Average mass	539.583 Da
Monoisotopic mass	539.28026 Da
Source	ChEBI
InChIKey	XZNUGFQTQHRASN-XQENGBIVSA-N

SMILES

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

InChI

InChI=1S/C21H41N5O11/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31/h5-21,26-32H,2-4,22-25H2,1H3/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-/m1/s1

Also called

• apramicina (INN)— chebi
• apramycine (INN)— chebi
• apramycinum (INN)— chebi
• (2R,3S,4R,4aR,6S,7R,8aS)-7-amino-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}-4-hydroxy-3-(methylamino)octahydropyrano[3,2-b]pyran-2-yl 4-amino-4-deoxy-α-D-glucopyranoside (EXACT_SYNONYM)— chebi
• 4-O-((8R)-2-amino-8-O-(4-amino-4-deoxy-α-D-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-D-glycero-α-D-allo-octodialdo-1,5:8,4-dipyranos-1-yl)-2-deoxy-D-streptamine (EXACT_SYNONYM)— chebi
• 4-O-(3α-amino-6α-((4-amino-4-deoxy-α-D-glucopyranosyl)oxy)-2,3,4,5aβ,6,7,8,8aα-octahydro-8β-hydroxy-7β-(methylamino)pyrano(3,2-b)pyran-2α-yl)-2-deoxy-D-streptamine (EXACT_SYNONYM)— chebi
• APRAMYCIN (EXACT_SYNONYM)— chebi
• Apramycin (EXACT_SYNONYM)— chebi
• nebramycin II (EXACT_SYNONYM)— chebi
• nebramycin factor 2 (EXACT_SYNONYM)— chebi
• ambylan (EXACT_SYNONYM)— aro
• apralan (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

• ARO:0000037
• cas:37321-09-8
• drugbank:DB04626
• kegg.compound:C01555
• kegg.drug:D02322
• patent:US3691279
• pdb-ccd:AM2
• reaxys:4610404
• vsdb:1743
• chembl:CHEMBL1909452
• pubchem.compound:3081545

Activity roles

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

• CHEBI:33281 CHEBI:33281
• CHEBI:36047 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.

Upstream concepts merged into this record

Source	Native ID	Label	Minted CURIE	Version
ARO	ARO:0000037	apramycin	antibioticmech:aro-a893a1ab5d	2026-08-30
CHEBI	CHEBI:2790	apramycin	antibioticmech:chebi-a23bd5a077	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.

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:0000037 (apramycin); database assertion, not a primary citation.)

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_INACTIVATION 2

ANTIBIOTIC_INACTIVATION

Determinant	ARO ID	Organism	Gene families	Evidence
AAC(3)-IVa	ARO:3002539	not organism-specific	—	ARO:3002539 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000037 (apramycin); database assertion, not a primary citation.)
apmA	ARO:3003918	not organism-specific	—	ARO:3003918 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000037 (apramycin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 1

ANTIBIOTIC_TARGET_ALTERATION

Determinant	ARO ID	Organism	Gene families	Evidence
kamB	ARO:3004102	not organism-specific	—	ARO:3004102 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000037 (apramycin); database assertion, not a primary citation.)

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

Provenance

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