isepamicin

antibioticmech:aro-3116ad4253 ·ANTIBACTERIAL ·MINTED SEEDED

A semi-synthetic derivative of gentamicin B (hydroxyamino propionyl genamicin B). It is modified to combat microbial inactivation and has a slightly larger spectrum of activity compared to other aminoglycosides, including Ser marcescens, Enterobacteria, and K pneumoniae. — PMID:8622111

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.

aminoglycoside antibiotic ARO:0000016

Chemical structure

Computed structure properties
Molecular formula	C22H43N5O12
Charge	0
Average mass	569.6 Da
Monoisotopic mass	569.29082182 Da
Source	PubChem · retrieved 2026-08-29
InChIKey	UDIIBEDMEYAVNG-ZKFPOVNWSA-N

SMILES

C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@@H]2O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)O)N)NC(=O)[C@H](CN)O)O

InChI

InChI=1S/C22H43N5O12/c1-22(35)6-36-20(15(33)18(22)26-2)39-17-8(27-19(34)9(28)4-23)3-7(25)16(14(17)32)38-21-13(31)12(30)11(29)10(5-24)37-21/h7-18,20-21,26,28-33,35H,3-6,23-25H2,1-2H3,(H,27,34)/t7-,8+,9-,10+,11+,12-,13+,14-,15+,16+,17-,18+,20+,21+,22-/m0/s1

Also called

isepamicine (EXACT_SYNONYM)— aro
isepamicinum (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:3000652`	isepamicin	`antibioticmech:aro-3116ad4253`	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:3000652 (isepamicin); database assertion, not a primary citation.)

Resistance mechanisms

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

ANTIBIOTIC_INACTIVATION 10

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
AAC(6')-29a	ARO:3002583	not organism-specific	—	ARO:3002583 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000652 (isepamicin); database assertion, not a primary citation.)
AAC(6')-29b	ARO:3002584	not organism-specific	—	ARO:3002584 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000652 (isepamicin); database assertion, not a primary citation.)
AAC(6')-31	ARO:3002585	not organism-specific	—	ARO:3002585 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000652 (isepamicin); database assertion, not a primary citation.)
ANT(4')-IIa	ARO:3002624	not organism-specific	—	ARO:3002624 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000652 (isepamicin); database assertion, not a primary citation.)
ANT(4')-IIb	ARO:3002625	not organism-specific	—	ARO:3002625 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000652 (isepamicin); database assertion, not a primary citation.)
ANT(4')-Ia	ARO:3002623	not organism-specific	—	ARO:3002623 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000652 (isepamicin); database assertion, not a primary citation.)
ANT(4')-Ib	ARO:3003905	not organism-specific	—	ARO:3003905 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000652 (isepamicin); database assertion, not a primary citation.)
APH(3')-IIIa	ARO:3002647	not organism-specific	—	ARO:3002647 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000652 (isepamicin); database assertion, not a primary citation.)
APH(3')-VIa	ARO:3002652	not organism-specific	—	ARO:3002652 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000652 (isepamicin); database assertion, not a primary citation.)
APH(3')-VIb	ARO:3002653	not organism-specific	—	ARO:3002653 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000652 (isepamicin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 5

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
armA	ARO:3000858	not organism-specific	—	ARO:3000858 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000652 (isepamicin); database assertion, not a primary citation.)
rmtA	ARO:3000859	not organism-specific	—	ARO:3000859 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000652 (isepamicin); database assertion, not a primary citation.)
rmtB	ARO:3000860	not organism-specific	—	ARO:3000860 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000652 (isepamicin); database assertion, not a primary citation.)
rmtC	ARO:3000861	not organism-specific	—	ARO:3000861 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000652 (isepamicin); database assertion, not a primary citation.)
sgm	ARO:3000862	not organism-specific	—	ARO:3000862 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000652 (isepamicin); database assertion, not a primary citation.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO)
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

Provenance

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

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