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.
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
Equivalent identifiers for this same structure in other resources.
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 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 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.