puromycin

CHEBI:17939 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

An aminonucleoside antibiotic, derived from the Streptomyces alboniger bacterium, that causes premature chain termination during translation taking place in the ribosome. — 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

nucleoside antibioticARO:3000034

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:26404
nucleoside antibiotic ARO:3000034

Chemical structure

Computed structure properties
Molecular formula	C22H29N7O5
Charge	0
Average mass	471.518 Da
Monoisotopic mass	471.22302 Da
Source	ChEBI
InChIKey	RXWNCPJZOCPEPQ-NVWDDTSBSA-N

SMILES

COc1ccc(C[C@H](N)C(=O)N[C@H]2[C@@H](O)[C@H](n3cnc4c(N(C)C)ncnc43)O[C@@H]2CO)cc1

InChI

InChI=1S/C22H29N7O5/c1-28(2)19-17-20(25-10-24-19)29(11-26-17)22-18(31)16(15(9-30)34-22)27-21(32)14(23)8-12-4-6-13(33-3)7-5-12/h4-7,10-11,14-16,18,22,30-31H,8-9,23H2,1-3H3,(H,27,32)/t14-,15+,16+,18+,22+/m0/s1

Also called

puromicina (INN)— chebi
puromycine (INN)— chebi
puromycinum (INN)— chebi
3'-deoxy-N,N-dimethyl-3'-(O-methyl-L-tyrosinamido)adenosine (EXACT_SYNONYM)— chebi
(S)-3'-((2-Amino-3-(4-methoxyphenyl)-1-oxopropyl)amino)-3'-deoxy-N,N-dimethyladenosine (EXACT_SYNONYM)— chebi
3'-(L-alpha-Amino-p-methoxyhydrocinnamamido)-3'-deoxy-N,N-dimethyladenosine (EXACT_SYNONYM)— chebi
3'-[[(2S)-2-amino-3-(4-methoxyphenyl)-1-oxopropyl]amino]-3'-deoxy-N,N-diemthyladenosine (EXACT_SYNONYM)— chebi
9-{3-deoxy-3-[(O-methyl-L-tyrosyl)amino]-β-D-xylofuranosyl}-N,N-dimethyl-9H-purin-6-amine (EXACT_SYNONYM)— chebi
Achromycin (EXACT_SYNONYM)— chebi
Puromycin (EXACT_SYNONYM)— chebi
Puromycin dihydrochloride (EXACT_SYNONYM)— aro
Puromycin hydrochloride (EXACT_SYNONYM)— aro
Stylomycin dihydrochloride (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.

wikipedia.en:Puromycin

Activity roles

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

nucleoside antibiotic CHEBI:25605
antimicrobial agent CHEBI:33281

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:0000047`	puromycin	`antibioticmech:aro-332ca24429`	2026-08-30
CHEBI	`CHEBI:17939`	puromycin	`antibioticmech:chebi-70c879b2c4`	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.

30S ribosomal subunit P-site RIBOSOMAL_SUBUNIT DIRECT_BINDING_TARGET

ARO:3000756

CARD/ARO database assertion; target organism, strain, and assay are not specified. The 30S P-site is asserted as the target site. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000756 (CARD/ARO asserts targeted_by_antibiotic ARO:0000047 (puromycin); database assertion, not a primary citation.)

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

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

ANTIBIOTIC_EFFLUX 4

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
MdtNOP	ARO:3004101	not organism-specific	—	ARO:3004101 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000047 (puromycin); database assertion, not a primary citation.)
bmr	ARO:3003007	not organism-specific	—	ARO:3003007 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000047 (puromycin); database assertion, not a primary citation.)
lmrAB Operon	ARO:3003027	not organism-specific	—	ARO:3003027 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000047 (puromycin); database assertion, not a primary citation.)
mdtM	ARO:3001214	not organism-specific	—	ARO:3001214 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000047 (puromycin); 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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