CHEBI:9168 - sirolimus

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ChEBI Name sirolimus
ChEBI ID CHEBI:9168
Definition A macrolide 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45276, CHEBI:67812
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Formula C51H79NO13
Net Charge 0
Average Mass 914.17190
Monoisotopic Mass 913.555
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
InChIKey QFJCIRLUMZQUOT-HPLJOQBZSA-N
SMILES [H][C@]1(CC[C@@H](O)[C@@H](C1)OC)C[C@@H](C)[C@]1([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](C[C@]2([H])CC[C@@H](C)[C@@](O)(O2)C(=O)C(=O)N2CCCC[C@@]2([H])C(=O)O1)OC
Metabolite of Species Details
Streptomyces hygroscopicus (NCBI:1912) See: PubMed
Roles Classification
Biological Role(s): immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
antibacterial drug
A drug used to treat or prevent bacterial infections.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
mTOR inhibitor
A protein kinase inhibitor of the mammalian target of rapamycin (mTOR), a protein that regulates cell growth, cell proliferation, cell motility, cell survival, protein synthesis and transcription. mTOR inhibitors are used to prevent transplant rejection and in treatment of cancer.
antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
(via antibiotic antifungal drug )
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
(via antibiotic antifungal agent )
Application(s): immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antibacterial drug
A drug used to treat or prevent bacterial infections.
antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
(via antibiotic antifungal drug )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing sirolimus (CHEBI:9168) has role antibacterial drug (CHEBI:36047)
sirolimus (CHEBI:9168) has role antineoplastic agent (CHEBI:35610)
sirolimus (CHEBI:9168) has role bacterial metabolite (CHEBI:76969)
sirolimus (CHEBI:9168) has role immunosuppressive agent (CHEBI:35705)
sirolimus (CHEBI:9168) has role mTOR inhibitor (CHEBI:68481)
sirolimus (CHEBI:9168) is a antibiotic antifungal drug (CHEBI:87113)
sirolimus (CHEBI:9168) is a cyclic acetal (CHEBI:59770)
sirolimus (CHEBI:9168) is a cyclic ketone (CHEBI:3992)
sirolimus (CHEBI:9168) is a ether (CHEBI:25698)
sirolimus (CHEBI:9168) is a lactam (CHEBI:24995)
sirolimus (CHEBI:9168) is a macrolide (CHEBI:25106)
sirolimus (CHEBI:9168) is a organic heterotricyclic compound (CHEBI:26979)
sirolimus (CHEBI:9168) is a secondary alcohol (CHEBI:35681)
Incoming everolimus (CHEBI:68478) has functional parent sirolimus (CHEBI:9168)
ridaforolimus (CHEBI:82677) has functional parent sirolimus (CHEBI:9168)
IUPAC Name
(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
INNs Sources
sirolimus WHO MedNet
sirolimús WHO MedNet
sirolimus WHO MedNet
sirolimusum WHO MedNet
Synonyms Sources
(-)-Rapamycin ChemIDplus
(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 IUPAC
Antibiotic AY 22989 DrugBank
rapamycin ChEBI
Sirolimus KEGG COMPOUND
Brand Name Source
Rapamune DrugBank
Database Links Databases
2446 DrugCentral
C00018055 KNApSAcK
C07909 KEGG COMPOUND
D00753 KEGG DRUG
DB00877 DrugBank
HMDB0015015 HMDB
LMPK06000003 LIPID MAPS
RAP PDBeChem
Rapamycin Wikipedia
View more database links
Registry Numbers Types Sources
53123-88-9 CAS Registry Number KEGG COMPOUND
53123-88-9 CAS Registry Number ChemIDplus
5848501 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
22960739 PubMed citation Europe PMC
22981852 PubMed citation Europe PMC
22984623 PubMed citation Europe PMC
Last Modified
22 February 2017