streptomycin

CHEBI:17076 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A amino cyclitol glycoside that consists of streptidine having a disaccharyl moiety attached at the 4-position. The parent of the streptomycin class — 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:26788 CHEBI:26788
CHEBI:87113 CHEBI:87113
CHEBI:87114 CHEBI:87114
ARO:0000016 ARO:0000016

Chemical structure

Computed structure properties
Molecular formula	C21H39N7O12
Charge	0
Average mass	581.58 Da
Monoisotopic mass	581.26567 Da
Source	ChEBI
InChIKey	UCSJYZPVAKXKNQ-HZYVHMACSA-N

SMILES

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

InChI

InChI=1S/C21H39N7O12/c1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35/h4-18,26,29,31-36H,3H2,1-2H3,(H4,22,23,27)(H4,24,25,28)/t5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+/m0/s1

Also called

Kantrex (BRAND_NAME)— chebi
N,N'''-[(1R,2R,3S,4R,5R,6S)-4-{5-deoxy-2-O-[2-deoxy-2-(methylamino)-α-L-glucopyranosyl]-3-C-formyl-α-L-lyxofuranosyloxy}-2,5,6-trihydroxycyclohexane-1,3-diyl]diguanidine (EXACT_SYNONYM)— chebi
2,4-Diguanidino-3,5,6-trihydroxycyclohexyl 5-deoxy-2-O-(2-deoxy-2-methylamino-alpha-L-glucopyranosyl)-3-C-formyl-beta-L-lyxopentanofuranoside (EXACT_SYNONYM)— chebi
SM (EXACT_SYNONYM)— chebi
STREPTOMYCIN (EXACT_SYNONYM)— chebi
[2-deoxy-2-(dimethylamino)-α-L-glucopyranosyl]-(1→2)-[5-deoxy-3-C-formyl-α-L-lyxofuranosyl]-(1→4)-{N',N'''-[(1,3,5/2,4,6)-2,4,5,6-tetrahydroxycyclohexane-1,3-diyl]diguanidine} (EXACT_SYNONYM)— chebi
streomycin (EXACT_SYNONYM)— chebi
streptomycin A sulfate (EXACT_SYNONYM)— aro
streptomycin A (EXACT_SYNONYM)— aro
streptomycin sulfate (EXACT_SYNONYM)— aro
streptomycin sulphate (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:0000040
cas:57-92-1
drugbank:DB01082
drugcentral:2481
hmdb:HMDB0015214
kegg.compound:C00413
kegg.drug:D08531
metacyc.compound:STREPTOMYCIN
pdb-ccd:SRY
pesticides:streptomycin
reaxys:74498
wikipedia.en:Streptomycin
chembl:CHEMBL372795
pubchem.compound:19649

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:36043 CHEBI:36043
CHEBI:36047 CHEBI:36047
CHEBI:86327 CHEBI:86327
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:0000040`	streptomycin	`antibioticmech:aro-26f72b86a6`	2026-08-30
CHEBI	`CHEBI:17076`	streptomycin	`antibioticmech:chebi-214ec2f677`	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:0000040 (streptomycin); database assertion, not a primary citation.)

antibiotic sensitive Ribosomal protein S12 (rpsL) PROTEIN DIRECT_BINDING_TARGET

ARO:3003431

CARD/ARO database assertion; target organism, strain, and assay are not specified. Ribosomal protein S12 is asserted as targeted and inhibited by streptomycin. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3003431 (CARD/ARO asserts targeted_by_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)

Mechanism summary

Mode of action: PROTEIN_SYNTHESIS_INHIBITION microbial target — CURATOR: Confirmed as bacterial 30S ribosomal decoding-site inhibition after primary streptomycin mechanism review. PMID:23322043; PMID:24820088.

Resistance mechanisms

62 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 43

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
ANT(3'')-II-AAC(6')-IId bifunctional protein	ARO:3002598	not organism-specific	—	ARO:3002598 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
ANT(3'')-IIa	ARO:3004089	not organism-specific	—	ARO:3004089 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
ANT(3'')-IIb	ARO:3004090	not organism-specific	—	ARO:3004090 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
ANT(3'')-IIc	ARO:3004091	not organism-specific	—	ARO:3004091 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
ANT(3'')-Ib	ARO:3005062	not organism-specific	—	ARO:3005062 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
ANT(6)-Ia	ARO:3002626	not organism-specific	—	ARO:3002626 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
ANT(6)-Ib	ARO:3002629	not organism-specific	—	ARO:3002629 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
APH(3'')-Ia	ARO:3002638	not organism-specific	—	ARO:3002638 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
APH(3'')-Ib	ARO:3002639	not organism-specific	—	ARO:3002639 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
APH(3'')-Ic	ARO:3002640	not organism-specific	—	ARO:3002640 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
APH(6)-Ia	ARO:3002657	not organism-specific	—	ARO:3002657 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
APH(6)-Ib	ARO:3002658	not organism-specific	—	ARO:3002658 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
APH(6)-Ic	ARO:3002659	not organism-specific	—	ARO:3002659 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
APH(6)-Id	ARO:3002660	not organism-specific	—	ARO:3002660 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aad(6)	ARO:3002628	not organism-specific	—	ARO:3002628 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA	ARO:3002601	not organism-specific	—	ARO:3002601 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA10	ARO:3004692	not organism-specific	—	ARO:3004692 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA11	ARO:3002611	not organism-specific	—	ARO:3002611 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA12	ARO:3002612	not organism-specific	—	ARO:3002612 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA13	ARO:3002613	not organism-specific	—	ARO:3002613 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA14	ARO:3002614	not organism-specific	—	ARO:3002614 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA15	ARO:3002615	not organism-specific	—	ARO:3002615 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA16	ARO:3002616	not organism-specific	—	ARO:3002616 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA17	ARO:3002617	not organism-specific	—	ARO:3002617 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA2	ARO:3002602	not organism-specific	—	ARO:3002602 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA21	ARO:3002618	not organism-specific	—	ARO:3002618 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA22	ARO:3002619	not organism-specific	—	ARO:3002619 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA23	ARO:3002620	not organism-specific	—	ARO:3002620 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA24	ARO:3002621	not organism-specific	—	ARO:3002621 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA25	ARO:3003197	not organism-specific	—	ARO:3003197 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA27	ARO:3004682	not organism-specific	—	ARO:3004682 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA3	ARO:3002603	not organism-specific	—	ARO:3002603 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA4	ARO:3002604	not organism-specific	—	ARO:3002604 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA5	ARO:3002605	not organism-specific	—	ARO:3002605 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA6	ARO:3002606	not organism-specific	—	ARO:3002606 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA6/aadA10	ARO:3002622	not organism-specific	—	ARO:3002622 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA7	ARO:3002607	not organism-specific	—	ARO:3002607 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA8	ARO:3002608	not organism-specific	—	ARO:3002608 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA8b	ARO:3004704	not organism-specific	—	ARO:3004704 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadA9	ARO:3002609	not organism-specific	—	ARO:3002609 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadK	ARO:3002627	not organism-specific	—	ARO:3002627 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aadS	ARO:3004683	not organism-specific	—	ARO:3004683 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
aphA15	ARO:3004675	not organism-specific	—	ARO:3004675 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 12

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Chlamydomonas reinhardtii 16S rRNA (rrnS) mutation conferring resistance to streptomycin	ARO:3003978	not organism-specific	—	ARO:3003978 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
Escherichia coli 16S rRNA (rrnB) mutation conferring resistance to streptomycin	ARO:3003406	not organism-specific	—	ARO:3003406 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
Escherichia coli 16S rRNA (rrsB) mutation conferring resistance to streptomycin	ARO:3003405	not organism-specific	—	ARO:3003405 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
Mycobacterium tuberculosis 16S rRNA mutation conferring resistance to streptomycin	ARO:3003480	not organism-specific	—	ARO:3003480 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
Mycobacterium tuberculosis Rv1258c mutations confer resistance to pyrazinamide, isoniazid, and streptomycin	ARO:3007186	not organism-specific	—	ARO:3007186 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
Mycobacterium tuberculosis Rv1258c mutations confer resistance to streptomycin	ARO:3004971	not organism-specific	—	ARO:3004971 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
Mycobacterium tuberculosis gidB mutation conferring resistance to streptomycin	ARO:3003470	not organism-specific	—	ARO:3003470 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
Mycobacterium tuberculosis rpsL mutations conferring resistance to streptomycin	ARO:3003395	not organism-specific	—	ARO:3003395 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
Mycobacterium tuberculosis tlyA mutations conferring resistance to aminoglycosides	ARO:3003445	not organism-specific	—	ARO:3003445 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
Mycobacterium tuberculosis whib7 mutation conferring resistance to streptomycin	ARO:3004968	not organism-specific	—	ARO:3004968 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
Mycolicibacterium smegmatis 16S rRNA (rrsB) mutation conferring resistance to streptomycin	ARO:3003541	not organism-specific	—	ARO:3003541 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
streptomycin resistant whib7	ARO:3004965	not organism-specific	—	ARO:3004965 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 5

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
Acinetobacter baumannii AbuO	ARO:3004578	not organism-specific	—	ARO:3004578 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
Klebsiella pneumoniae KpnEF	ARO:3004585	not organism-specific	—	ARO:3004585 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
Klebsiella pneumoniae KpnGH-TolC	ARO:3004598	not organism-specific	—	ARO:3004598 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
Staphylococcus aureus LmrS	ARO:3004572	not organism-specific	—	ARO:3004572 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)
ykkCD	ARO:3003062	not organism-specific	—	ARO:3003062 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_REPLACEMENT 1

ANTIBIOTIC_TARGET_REPLACEMENT
Determinant	ARO ID	Organism	Gene families	Evidence
dfrL	ARO:3007456	not organism-specific	—	ARO:3007456 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)

REDUCED_PERMEABILITY 1

REDUCED_PERMEABILITY
Determinant	ARO ID	Organism	Gene families	Evidence
Escherichia coli mipA	ARO:3004127	not organism-specific	—	ARO:3004127 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000040 (streptomycin); database assertion, not a primary citation.)

Causal graphs

Evidence-backed mechanism graphs: how the compound reaches its target, what the target does, and how the effect propagates to growth inhibition or death.

Streptomycin perturbs the bacterial 30S decoding site MECHANISTIC

Streptomycin binds the bacterial 30S ribosomal decoding site formed by 16S rRNA and ribosomal protein S12, distorts 16S rRNA helix 44, and lowers translational decoding accuracy.

Nodes — streptomycin_30s_decoding_site_misreading
Node	Label	Type	Grounding
`streptomycin`	streptomycin	COMPOUND	`CHEBI:17076`
`rrna_16s`	bacterial 16S rRNA	RNA	`ARO:3000755`
`ribosomal_protein_s12`	ribosomal protein S12	GENE_OR_PROTEIN	`ARO:3003431`
`streptomycin_30s_binding_site`	streptomycin binding site in the 30S ribosomal subunit	STATE	REVIEWED_LABEL_ONLY
`distorted_decoding_site`	streptomycin-distorted decoding site	STATE	REVIEWED_LABEL_ONLY
`decoding_accuracy`	bacterial translational decoding accuracy	QUALITY	REVIEWED_LABEL_ONLY
`protein_synthesis`	bacterial protein synthesis	BIOLOGICAL_PROCESS	REVIEWED_LABEL_ONLY

Edges — streptomycin_30s_decoding_site_misreading
Subject	Predicate	Object	Evidence
`rrna_16s`	participates in	`streptomycin_30s_binding_site`	PMID:24820088 (Demirci and colleagues resolved streptomycin-bound Thermus thermophilus 30S subunits and described 16S rRNA contacts in the streptomycin site.)
`ribosomal_protein_s12`	participates in	`streptomycin_30s_binding_site`	PMID:24820088 (The 16S rRNA resistance-structure study placed S12 next to streptomycin in the bacterial 30S subunit.)
`streptomycin`	binds	`streptomycin_30s_binding_site`	PMID:23322043 (Demirci and colleagues used X-ray crystallography to locate streptomycin in the Thermus thermophilus 30S decoding region.)
`streptomycin_30s_binding_site`	promotes	`distorted_decoding_site`	PMID:23322043 (Streptomycin-bound 30S structures showed local distortion of 16S rRNA and bases involved in codon recognition.)
`distorted_decoding_site`	decreases	`decoding_accuracy`	PMID:23322043 (Cognate and near-cognate mRNA-tRNA crystal structures explained how streptomycin promotes misreading of the genetic code.)
`decoding_accuracy`	supports	`protein_synthesis`	PMID:11340196 (Ogle and colleagues resolved 30S ribosomal subunit complexes that define the conserved A-site bases used to recognize cognate tRNA.)

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
CURATED_CAUSAL_GRAPH 2026-09-04 · codex · LLM-assisted
Added a PMID-supported causal graph for streptomycin binding to the bacterial 30S decoding site and marked the coarse target scope as curator-reviewed.

Provenance

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