sirolimus

CHEBI:9168 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A macrolide lactam isolated from Streptomyces hygroscopicus consisting of a 29-membered ring containing 4 trans double bonds, three of which are conjugated. It is an antibiotic, immunosupressive and antineoplastic agent. — 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

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:145565
Label unavailable CHEBI:25698
Label unavailable CHEBI:26979
Label unavailable CHEBI:35681
Label unavailable CHEBI:3992
Label unavailable CHEBI:59770
antibiotic antifungal drug CHEBI:87113

Chemical structure

Computed structure properties
Molecular formula	C51H79NO13
Charge	0
Average mass	914.187 Da
Monoisotopic mass	913.55514 Da
Source	ChEBI
InChIKey	QFJCIRLUMZQUOT-HPLJOQBZSA-N

SMILES

[H][C@@]1(C[C@@H](C)[C@]2([H])CC(=O)[C@H](C)/C=C(\C)[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)/C=C/C=C/C=C(\C)[C@@H](OC)C[C@]3([H])CC[C@@H](C)[C@@](O)(O3)C(=O)C(=O)N3CCCC[C@@]3([H])C(=O)O2)CC[C@@H](O)[C@H](OC)C1

InChI

InChI=1S/C51H79NO13/c1-30-16-12-11-13-17-31(2)42(61-8)28-38-21-19-36(7)51(60,65-38)48(57)49(58)52-23-15-14-18-39(52)50(59)64-43(33(4)26-37-20-22-40(53)44(27-37)62-9)29-41(54)32(3)25-35(6)46(56)47(63-10)45(55)34(5)24-30/h11-13,16-17,25,30,32-34,36-40,42-44,46-47,53,56,60H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12+,31-17+,35-25+/t30-,32-,33-,34-,36-,37+,38+,39+,40-,42+,43+,44-,46-,47+,51-/m1/s1

Also called

Rapamune (BRAND_NAME)— chebi
sirolimusum (INN)— chebi
sirolimús (INN)— chebi
(3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,27-dihydroxy-3-{(2R)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl}-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro-3H-23,27-epoxypyrido[2,1-c][1,4]oxazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone (EXACT_SYNONYM)— chebi
(-)-Rapamycin (EXACT_SYNONYM)— chebi
(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-{(2S)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl}-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone (EXACT_SYNONYM)— chebi
Antibiotic AY 22989 (EXACT_SYNONYM)— chebi
Sirolimus (EXACT_SYNONYM)— chebi
rapamycin (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.

Patents and articles

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

wikipedia.en:Rapamycin

Activity roles

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

anticoronaviral agent CHEBI:149553
antifungal agent CHEBI:35718
antibacterial drug CHEBI:36047
antifungal drug CHEBI:86327

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
CHEBI	`CHEBI:9168`	sirolimus	`antibioticmech:chebi-6b754382a1`	2026-08-30

Mechanism summary

Clinical status: APPROVED

Resistance mechanisms

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

UNKNOWN 2

UNKNOWN
Determinant	ARO ID	Organism	Gene families	Evidence
Laboratory FPR1-associated rapamycin resistance Qualified association in the source-selected laboratory comparisons, not all perturbations of FPR1 or a species-wide or clinical phenotype. Distinct background and drug-free growth controls remain separate. Molecular binding effects are not directly measured by these growth comparisons; reference proteins are not exact experimental allele or genome assignments.	—	Saccharomyces cerevisiae `NCBITaxon:4932` strain YKK207 laboratory derivatives FPR1	—	DOI:10.1371/journal.pgen.1008865 (Kasahara et al. (2020), Results / Characterization of Fpr1 function; native Figure 5B and S1 Table host labels. Qualitative association only; no numeric AST or exact variant specification imported.) https://www.uniprot.org/uniprotkb/P20081/entry (Reference-only UniProtKB:P20081, reviewed entry 220, sequence version 2, release 2026_03; YNL135C, SGD:S000005079. S288c reference lineage supports species NCBITaxon:4932; reference strain NCBITaxon:559292 is not assigned to the tested derivatives.) Comparative growth spot assay
Laboratory TOR2-associated rapamycin resistance Qualified association in the source-selected laboratory comparisons, not all perturbations of TOR2 or a species-wide or clinical phenotype. Distinct background and drug-free growth controls remain separate. Molecular binding effects are not directly measured by these growth comparisons; reference proteins are not exact experimental allele or genome assignments.	—	Saccharomyces cerevisiae `NCBITaxon:4932` strain YKK1081 laboratory derivatives TOR2	—	DOI:10.1371/journal.pgen.1008865 (Kasahara et al. (2020), Results / Characterization of Fpr1 function; native Figure 6 and S1 Table host labels. Qualitative association only; no numeric AST or exact variant specification imported.) https://www.uniprot.org/uniprotkb/P32600/entry (Reference-only UniProtKB:P32600, reviewed entry 214, sequence version 3, release 2026_03; YKL203C, SGD:S000001686. S288c reference lineage supports species NCBITaxon:4932; reference strain NCBITaxon:559292 is not assigned to the tested derivatives.) Comparative growth spot assay

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (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 2026-08-31 · 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
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
CURATED_RESISTANCE_EVIDENCE 2026-10-13 · codex · LLM-assisted
Added two qualified laboratory rapamycin gene associations from primary growth comparisons and source strain-table review. Molecular routes remain UNKNOWN and UniProt proteins reference-only. No exact experimental allele, genome or numeric AST assigned; whole-record review remains open.

Provenance

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

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