geneticin

CHEBI:42768 ·resolve ·ANTIPROTOZOAL ·EXACT SEEDED

An aminoglycoside antibiotic produced by Micromonospora rhodorangea. It blocks polypeptide synthesis by inhibiting the elongation step in both prokaryotic and eukaryotic cells. — 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

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:22507 CHEBI:22507

Chemical structure

Computed structure properties
Molecular formula	C20H40N4O10
Charge	0
Average mass	496.558 Da
Monoisotopic mass	496.27444 Da
Source	ChEBI
InChIKey	BRZYSWJRSDMWLG-CAXSIQPQSA-N

SMILES

CN[C@@H]1[C@@H](O)[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3O[C@H](C(C)O)[C@@H](O)[C@H](O)[C@H]3N)[C@@H](N)C[C@H]2N)OC[C@]1(C)O

InChI

InChI=1S/C20H40N4O10/c1-6(25)14-11(27)10(26)9(23)18(32-14)33-15-7(21)4-8(22)16(12(15)28)34-19-13(29)17(24-3)20(2,30)5-31-19/h6-19,24-30H,4-5,21-23H2,1-3H3/t6?,7-,8+,9+,10+,11-,12-,13+,14+,15+,16-,17+,18+,19+,20-/m0/s1

Also called

(1R,2S,3S,4R,6S)-4,6-diamino-3-[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyloxy]-2-hydroxycyclohexyl 2-amino-2,7-dideoxy-D-glycero-α-D-gluco-heptopyranoside (EXACT_SYNONYM)— chebi
G 418 (EXACT_SYNONYM)— chebi
G418 (EXACT_SYNONYM)— chebi
GENETICIN (EXACT_SYNONYM)— chebi
Geneticin (EXACT_SYNONYM)— chebi
antibiotic G 418 (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

beilstein:1669188
cas:49863-47-0
drugbank:DB04263
kegg.compound:C17703
pdb-ccd:GET

Activity roles

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

CHEBI:33281 CHEBI:33281
CHEBI:35818 CHEBI:35818
CHEBI:35820 CHEBI:35820

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
CHEBI	`CHEBI:42768`	geneticin	`antibioticmech:chebi-f6f4a5a0a0`	2026-08-30

Curation history

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

Provenance

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