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

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

aminoglycoside antibioticARO:0000016

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:27171
Label unavailable CHEBI:47779
Label unavailable CHEBI:61800
aminoglycoside antibiotic 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

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.

Patents and articles

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

patent:US3691279

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.

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

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

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 2026-09-10 · 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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