pleuromutilin

CHEBI:8269 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

Pleuromutilin is a natural product antibiotic produced by Clitopilus passeckerianus. Related antibiotics of clinical significance, such as tiamulin and retapamulin, are semi-synthetic derivatives of this compound. — PMID:23589420

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

pleuromutilin antibioticARO:3000670

Strictly broader compounds or drug classes this molecule belongs to.

pleuromutilin antibiotic ARO:3000670

Chemical structure

Computed structure properties
Molecular formula	C22H34O5
Charge	0
Average mass	378.509 Da
Monoisotopic mass	378.24062 Da
Source	ChEBI
InChIKey	ZRZNJUXESFHSIO-ZXVYJXQESA-N

SMILES

[H][C@@]12C(=O)CC[C@]13CCC(C)[C@@]2(C)[C@H](OC(=O)CO)C[C@@](C)(C=C)[C@@H](O)[C@@H]3C

InChI

InChI=1S/C22H34O5/c1-6-20(4)11-16(27-17(25)12-23)21(5)13(2)7-9-22(14(3)19(20)26)10-8-15(24)18(21)22/h6,13-14,16,18-19,23,26H,1,7-12H2,2-5H3/t13?,14-,16+,18-,19-,20+,21-,22-/m0/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:3001317`	pleuromutilin	`antibioticmech:aro-ac69007b2b`	2026-08-30

Resistance mechanisms

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

ANTIBIOTIC_TARGET_PROTECTION 6

ANTIBIOTIC_TARGET_PROTECTION
Determinant	ARO ID	Organism	Gene families	Evidence
eatAv Evidence-scope review 2026-10-15-eatav-parent-compound-scope: The functional study tested tiamulin, a pleuromutilin derivative, not the parent pleuromutilin structure represented here. Its results do not establish resistance to this exact compound. Retain CARD's route-level assertion as database evidence only; no experimental allele, protein, organism or susceptibility observation is assigned. Qualification references, not an upgrade of the CARD assertion: DOI:10.1128/AAC.01030-13 (Results and discussion; Table 3 compound headers; publisher primary HTML text; table not visually verified; supplements not reviewed). Reviewed 2026-10-15 by Codex; curation/card_evidence_reviews.json SHA-256 584f3e32ce0122eb2315fe09bbe22e058539bef184ad2d75756a6f3016bf2687.	ARO:3003761	not organism-specific	—	ARO:3003761 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3001317 (pleuromutilin); database assertion, not a primary citation.)
lsaA	ARO:3000300	not organism-specific	—	ARO:3000300 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3001317 (pleuromutilin); database assertion, not a primary citation.)
lsaB	ARO:3003111	not organism-specific	—	ARO:3003111 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3001317 (pleuromutilin); database assertion, not a primary citation.)
lsaC	ARO:3003112	not organism-specific	—	ARO:3003112 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3001317 (pleuromutilin); database assertion, not a primary citation.)
lsaE	ARO:3003206	not organism-specific	—	ARO:3003206 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3001317 (pleuromutilin); database assertion, not a primary citation.)
tva(A)	ARO:3004730	not organism-specific	—	ARO:3004730 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3001317 (pleuromutilin); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 1

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
TaeA	ARO:3003986	not organism-specific	—	ARO:3003986 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3001317 (pleuromutilin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 1

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Mycoplasma gallisepticum 23S rRNA mutation conferring resistance to pleuromutilin antibiotics	ARO:3004159	not organism-specific	—	ARO:3004159 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3001317 (pleuromutilin); 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 2026-10-15 · seed_from_sources
Re-seeded; changed: resistance_mechanisms (CARD). Upstream retrieval date 2026-08-30, unchanged.
RESEEDED_FROM_SOURCES 2026-10-16 · seed_from_sources
Re-seeded; changed: resistance_mechanisms (CARD). Upstream retrieval date 2026-08-30, unchanged.
RESEEDED_FROM_SOURCES 2026-10-16 · seed_from_sources
Re-seeded; changed: resistance_mechanisms (CARD). Upstream retrieval date 2026-08-30, unchanged.

Provenance

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

Explore across X-Mech: MediaIngredientMech (pleuromutilin) · CultureMech · NaturalProductMech · PathwayMech · TraitMech