azidamfenicol

CHEBI:135238 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

Azidamfenicol is a water soluble derivative of chloramphenicol, sharing the same mode of action of inhibiting peptide synthesis by interacting with the 23S RNA of the 50S ribosomal subunit. — PMID:15539072

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

phenicol antibioticARO:3000387

Strictly broader compounds or drug classes this molecule belongs to.

phenicol antibiotic ARO:3000387

Chemical structure

Computed structure properties
Molecular formula	C11H13N5O5
Charge	0
Average mass	295.255 Da
Monoisotopic mass	295.09167 Da
Source	ChEBI
InChIKey	SGRUZFCHLOFYHZ-MWLCHTKSSA-N

SMILES

[N-]=[N+]=NCC(=O)N[C@H](CO)[C@H](O)c1ccc([N+](=O)[O-])cc1

InChI

InChI=1S/C11H13N5O5/c12-15-13-5-10(18)14-9(6-17)11(19)7-1-3-8(4-2-7)16(20)21/h1-4,9,11,17,19H,5-6H2,(H,14,18)/t9-,11-/m1/s1

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:3000382`	azidamfenicol	`antibioticmech:aro-215796a9db`	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 peptidyl transferase (23S rRNA) NUCLEIC_ACID DIRECT_BINDING_TARGET

ARO:3000754

CARD/ARO database assertion; target organism, strain, and assay are not specified. 23S rRNA peptidyl-transferase center is asserted as the target. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000754 (CARD/ARO asserts targeted_by_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)

Resistance mechanisms

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

ANTIBIOTIC_INACTIVATION 19

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
Bacillus pumilus cat86	ARO:3002672	not organism-specific	—	ARO:3002672 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
CatU	ARO:3003983	not organism-specific	—	ARO:3003983 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
Clostridium butyricum catB	ARO:3002674	not organism-specific	—	ARO:3002674 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
Limosilactobacillus reuteri cat-TC	ARO:3002671	not organism-specific	—	ARO:3002671 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
Plasmid-encoded cat (pp-cat)	ARO:3002689	not organism-specific	—	ARO:3002689 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
Pseudomonas aeruginosa catB6	ARO:3002678	not organism-specific	—	ARO:3002678 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
Pseudomonas aeruginosa catB7	ARO:3002679	not organism-specific	—	ARO:3002679 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
catA1	ARO:3002683	not organism-specific	—	ARO:3002683 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
catB10	ARO:3003110	not organism-specific	—	ARO:3003110 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
catB2	ARO:3002675	not organism-specific	—	ARO:3002675 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
catB3	ARO:3002676	not organism-specific	—	ARO:3002676 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
catB8	ARO:3002680	not organism-specific	—	ARO:3002680 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
catB9	ARO:3002681	not organism-specific	—	ARO:3002681 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
catD	ARO:3002682	not organism-specific	—	ARO:3002682 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
catII	ARO:3002684	not organism-specific	—	ARO:3002684 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
catIII	ARO:3002685	not organism-specific	—	ARO:3002685 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
catP	ARO:3002686	not organism-specific	—	ARO:3002686 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
catQ	ARO:3002687	not organism-specific	—	ARO:3002687 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
catS	ARO:3002688	not organism-specific	—	ARO:3002688 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 5

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
cfrA	ARO:3003441	not organism-specific	—	ARO:3003441 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
cipA	ARO:3003907	not organism-specific	—	ARO:3003907 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
clbA	ARO:3002814	not organism-specific	—	ARO:3002814 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
clbB	ARO:3002815	not organism-specific	—	ARO:3002815 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); database assertion, not a primary citation.)
clbC	ARO:3002816	not organism-specific	—	ARO:3002816 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000382 (azidamfenicol); 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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