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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
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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Tocris
Rapamycin (links to external site)
Cat. No. 1292