tiamulin

CHEBI:44137 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A carbotricyclic compound that is pleuromutilin in which the hydroxyacetate group is replaced by a 2-{[2-(diethylamino)ethyl]sulfanyl}acetate group. An antibacterial drug, tiamulin is used in veterinary medicine (generally as its hydrogen fumarate salt) for the treatment of swine dysentery caused by Serpulina hyodysenteriae. — 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

pleuromutilin antibioticARO:3000670

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:16385
Label unavailable CHEBI:33308
Label unavailable CHEBI:35681
Label unavailable CHEBI:38032
Label unavailable CHEBI:3992
Label unavailable CHEBI:50996
Label unavailable CHEBI:52557
Label unavailable CHEBI:72588
pleuromutilin antibiotic ARO:3000670

Chemical structure

Computed structure properties
Molecular formula	C28H47NO4S
Charge	0
Average mass	493.754 Da
Monoisotopic mass	493.32258 Da
Source	ChEBI
InChIKey	UURAUHCOJAIIRQ-QGLSALSOSA-N

SMILES

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

InChI

InChI=1S/C28H47NO4S/c1-8-26(6)17-22(33-23(31)18-34-16-15-29(9-2)10-3)27(7)19(4)11-13-28(20(5)25(26)32)14-12-21(30)24(27)28/h8,19-20,22,24-25,32H,1,9-18H2,2-7H3/t19-,20+,22-,24+,25+,26-,27+,28+/m1/s1

Also called

tiamulina (INN)— chebi
tiamuline (INN)— chebi
tiamulinum (INN)— chebi
(3aS,4R,5S,6S,8R,9R,9aR,10R)-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-6-vinyldecahydro-3a,9-propanocyclopenta[8]annulen-8-yl {[2-(diethylamino)ethyl]sulfanyl}acetate (EXACT_SYNONYM)— chebi

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.

kegg.drug:D06127

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

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

antibacterial drug CHEBI:36047

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:3000671`	tiamulin	`antibioticmech:aro-3cd7dfcc47`	2026-08-30
CHEBI	`CHEBI:44137`	tiamulin	`antibioticmech:chebi-9d414fbd6e`	2026-08-30

Resistance mechanisms

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

ANTIBIOTIC_TARGET_PROTECTION 11

ANTIBIOTIC_TARGET_PROTECTION
Determinant	ARO ID	Organism	Gene families	Evidence
Neobacillus vireti vmlR2	ARO:3007646	not organism-specific	—	ARO:3007646 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000671 (tiamulin); database assertion, not a primary citation.)
lsaD	ARO:3005121	not organism-specific	—	ARO:3005121 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000671 (tiamulin); database assertion, not a primary citation.)
salA	ARO:3003749	not organism-specific	—	ARO:3003749 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000671 (tiamulin); database assertion, not a primary citation.)
salB	ARO:3007026	not organism-specific	—	ARO:3007026 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000671 (tiamulin); database assertion, not a primary citation.)
salC	ARO:3007027	not organism-specific	—	ARO:3007027 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000671 (tiamulin); database assertion, not a primary citation.)
salD	ARO:3007028	not organism-specific	—	ARO:3007028 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000671 (tiamulin); database assertion, not a primary citation.)
salE	ARO:3007029	not organism-specific	—	ARO:3007029 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000671 (tiamulin); database assertion, not a primary citation.)
vga(E) Staphylococcus cohnii	ARO:3004715	not organism-specific	—	ARO:3004715 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000671 (tiamulin); database assertion, not a primary citation.)
vgaC	ARO:3002831	not organism-specific	—	ARO:3002831 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000671 (tiamulin); database assertion, not a primary citation.)
vgaE	ARO:3002833	not organism-specific	—	ARO:3002833 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000671 (tiamulin); database assertion, not a primary citation.)
vmlR	ARO:3004476	not organism-specific	—	ARO:3004476 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000671 (tiamulin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 9

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Thermus thermophilus 23s rRNA conferring resistance to pleuromutilin antibiotics	ARO:3005083	not organism-specific	—	ARO:3005083 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000671 (tiamulin); database assertion, not a primary citation.)
Thermus thermophilus uL3 mutations conferring resistance to pleuromutilin antibiotics	ARO:3005081	not organism-specific	—	ARO:3005081 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000671 (tiamulin); database assertion, not a primary citation.)
cfrA	ARO:3003441	not organism-specific	—	ARO:3003441 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000671 (tiamulin); database assertion, not a primary citation.)
cfrE	ARO:3005023	not organism-specific	—	ARO:3005023 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000671 (tiamulin); database assertion, not a primary citation.)
cipA	ARO:3003907	not organism-specific	—	ARO:3003907 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000671 (tiamulin); database assertion, not a primary citation.)
clbA	ARO:3002814	not organism-specific	—	ARO:3002814 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000671 (tiamulin); database assertion, not a primary citation.)
clbB	ARO:3002815	not organism-specific	—	ARO:3002815 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000671 (tiamulin); database assertion, not a primary citation.)
clbC	ARO:3002816	not organism-specific	—	ARO:3002816 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000671 (tiamulin); database assertion, not a primary citation.)
clcD	ARO:3004599	not organism-specific	—	ARO:3004599 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000671 (tiamulin); 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 2026-09-10 · 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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