kasugamycin

CHEBI:81419 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

An amino cyclitol glycoside that is isolated from Streptomyces kasugaensis and exhibits antibiotic and fungicidal properties. — 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.

CHEBI:22479 CHEBI:22479
CHEBI:22507 CHEBI:22507
CHEBI:35359 CHEBI:35359
CHEBI:63367 CHEBI:63367
CHEBI:87114 CHEBI:87114
ARO:0000016 ARO:0000016

Chemical structure

Computed structure properties
Molecular formula	C14H25N3O9
Charge	0
Average mass	379.366 Da
Monoisotopic mass	379.15908 Da
Source	ChEBI
InChIKey	PVTHJAPFENJVNC-MHRBZPPQSA-N

SMILES

C[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H](N)C[C@@H]1NC(=N)C(=O)O

InChI

InChI=1S/C14H25N3O9/c1-3-5(17-12(16)13(23)24)2-4(15)14(25-3)26-11-9(21)7(19)6(18)8(20)10(11)22/h3-11,14,18-22H,2,15H2,1H3,(H2,16,17)(H,23,24)/t3-,4+,5+,6-,7+,8+,9-,10+,11+,14-/m1/s1

Also called

(1S,2R,3S,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl 2-amino-4-{[carboxy(imino)methyl]amino}-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside (EXACT_SYNONYM)— chebi
3-O-[2-amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranosyl]-D-chiro-inositol (EXACT_SYNONYM)— chebi
Kasumin 2L (EXACT_SYNONYM)— chebi
Kasumin L (EXACT_SYNONYM)— chebi
kasugamicin (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3001296
bpdb:2195
cas:6980-18-3
kegg.compound:C17968
knapsack:C00018722
pdb-ccd:KSG
pesticides:kasugamycin
ppdb:2195
reaxys:1403823
wikipedia.en:Kasugamycin
chembl:CHEMBL1631109
pubchem.compound:65174

Activity roles

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

CHEBI:24127 CHEBI:24127
CHEBI:33281 CHEBI:33281
CHEBI:35718 CHEBI:35718
CHEBI:86328 CHEBI:86328

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:3001296`	kasugamycin	`antibioticmech:aro-939e110ffd`	2026-08-30
CHEBI	`CHEBI:81419`	kasugamycin	`antibioticmech:chebi-94c20c967b`	2026-08-30

Mechanism summary

Mode of action: PROTEIN_SYNTHESIS_INHIBITION host shared target — Assigned from ChEBI role CHEBI:48001 (protein synthesis inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.

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(2')-IIa	ARO:3004628	not organism-specific	—	ARO:3004628 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3001296 (kasugamycin); database assertion, not a primary citation.)
AAC(2')-IIb	ARO:3003988	not organism-specific	—	ARO:3003988 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3001296 (kasugamycin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 1

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Escherichia coli 16S rRNA (rrsC) mutation conferring resistance to kasugamicin	ARO:3003333	not organism-specific	—	ARO:3003333 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3001296 (kasugamycin); 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

Provenance

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