sirolimus   Click here for help

GtoPdb Ligand ID: 6031

Synonyms: AY-22989 | Fyarro® (sirolimus albumin-bound particles) | Rapamune® | rapamycin | WY-090217
Approved drug PDB Ligand Immunopharmacology Ligand
sirolimus is an approved drug (FDA (1999), EMA (2001))
Compound class: Synthetic organic
Comment: Sirolimus is a macrolide produced by the bacteria Streptomyces hygroscopicus. It has potent immunosuppressive and antiproliferative properties. Sirolimus is classified as a Type IV allosteric kinase inhibitor [10].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 14
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 195.43
Molecular weight 913.56
XLogP 4.32
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES COC1CC(CCC1O)CC(C1OC(=O)C2CCCCN2C(=O)C(=O)C2(O)OC(CCC2C)CC(OC)C(=CC=CC=CC(CC(C(=O)C(C(C(=CC(C(=O)C1)C)C)O)OC)C)C)C)C
Isomeric SMILES CO[C@@H]1C[C@@H](CC[C@H]1O)C[C@H]([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H](CC[C@H]2C)C[C@H](OC)/C(=C/C=C/C=C/[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C(=C/[C@H](C(=O)C1)C)/C)O)OC)C)C)/C)C
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
InChI Key QFJCIRLUMZQUOT-HPLJOQBZSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1999), EMA (2001))
International Nonproprietary Names Click here for help
INN number INN
7104 sirolimus
Synonyms Click here for help
AY-22989 | Fyarro® (sirolimus albumin-bound particles) | Rapamune® | rapamycin | WY-090217
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9678687
Reactome Reaction Reactome logo R-HSA-9679044
Other databases
CAS Registry No. 53123-88-9
ChEBI CHEBI:9168
ChEMBL Ligand CHEMBL413
DrugBank Ligand DB00877
DrugCentral Ligand 2446
GtoPdb PubChem SID 178102653
Immunopaedia Search sirolimus
LIPID MAPS LMPK06000003
PubChem CID 5284616
RCSB PDB Ligand RAP
Search Google for chemical match using the InChIKey QFJCIRLUMZQUOT-HPLJOQBZSA-N
Search Google for chemicals with the same backbone QFJCIRLUMZQUOT
Search PubMed clinical trials sirolimus
Search PubMed titles sirolimus
Search PubMed titles/abstracts sirolimus
SynPHARM 80549 (in complex with FK506 binding protein 1A)
UniChem Compound Search for chemical match using the InChIKey QFJCIRLUMZQUOT-HPLJOQBZSA-N
UniChem Connectivity Search for chemical match using the InChIKey QFJCIRLUMZQUOT-HPLJOQBZSA-N
Wikipedia Sirolimus

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