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.

CHEBI:16385 CHEBI:16385
CHEBI:33308 CHEBI:33308
CHEBI:35681 CHEBI:35681
CHEBI:38032 CHEBI:38032
CHEBI:3992 CHEBI:3992
CHEBI:50996 CHEBI:50996
CHEBI:52557 CHEBI:52557
CHEBI:72588 CHEBI:72588
ARO:3000670 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

Equivalent identifiers for this same structure in other resources.

ARO:3000671
cas:55297-95-5
kegg.compound:C12065
kegg.drug:D06127
patent:DE2248237
patent:US3919290
pdb-ccd:MUL
reaxys:7348837
wikipedia.en:Tiamulin
chembl:CHEMBL1234521
pubchem.compound:656958

Activity roles

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

CHEBI:36047 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 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_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

Provenance

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