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CHEBI:9168 - sirolimus

Default Structure
ChEBI IDCHEBI:9168
ChEBI Namesirolimus
Stars
DefinitionA 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.
Secondary ChEBI IDsCHEBI:45276, CHEBI:67812
Last Modified28 October 2021
DownloadsMolfile
FormulaC51H79NO13
Net Charge0
Average Mass914.187
Monoisotopic Mass913.55514
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
InChIInChI=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
InChIKeyQFJCIRLUMZQUOT-HPLJOQBZSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Streptomyces hygroscopicus (ncbitaxon:1912) - PubMed (21438579)
Roles Classification
Biological Roles:
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.
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.
anticoronaviral agent  Any antiviral agent which inhibits the activity of coronaviruses.
antifungal drug  Any antifungal agent used to prevent or treat fungal infections in humans or animals.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
Applications:
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.
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
antifungal drug  Any antifungal agent used to prevent or treat fungal infections in humans or animals.
ChEBI Ontology
Outgoing Relation(s)
sirolimus (CHEBI:9168) has role antibacterial drug (CHEBI:36047)
sirolimus (CHEBI:9168) has role anticoronaviral agent (CHEBI:149553)
sirolimus (CHEBI:9168) has role antineoplastic agent (CHEBI:35610)
sirolimus (CHEBI:9168) has role bacterial metabolite (CHEBI:76969)
sirolimus (CHEBI:9168) has role geroprotector (CHEBI:176497)
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 macrolide lactam (CHEBI:145565)
sirolimus (CHEBI:9168) is a organic heterotricyclic compound (CHEBI:26979)
sirolimus (CHEBI:9168) is a secondary alcohol (CHEBI:35681)
Incoming Relation(s)
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  Source
sirolimusWHO MedNet
sirolimusWHO MedNet
sirolimúsWHO MedNet
sirolimusumWHO MedNet
Synonyms  Source
(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-pentoneIUPAC
Antibiotic AY 22989DrugBank
rapamycinChEBI
(-)-RapamycinChemIDplus
SirolimusKEGG COMPOUND
Brand Name  Source
RapamuneDrugBank
Manual XrefsDatabases
2446DrugCentral
C00018055KNApSAcK
C07909KEGG COMPOUND
D00753KEGG DRUG
DB00877DrugBank
HMDB0015015HMDB
LMPK06000003LIPID MAPS
RAPPDBeChem
RapamycinWikipedia
Registry NumbersSources
Reaxys:5848501Reaxys
CAS:53123-88-9KEGG COMPOUND
CAS:53123-88-9ChemIDplus
Citations